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$5,900,000
5 Beds ⋅ 4 Baths ⋅ Alabama Oaks SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets. Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy. Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you'll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake. The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you'll find three additional bedrooms, each offering spacious comfort and ample storage. A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home's fifth bedroom, providing a wonderful haven for guests. Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!

1530 Alabama Drive, Winter Park
$4,750,000
5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

2525 Temple Drive, Winter Park
$4,250,000
4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park
$3,999,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Designed to evoke the timeless architecture of Olde Winter Park, this exceptional modern Tudor home features character, craftsmanship, and presence rarely found in today's market. Perfectly positioned on an expansive 0.37-acre homesite in the highly coveted Park Grove neighborhood, the residence offers the rare privilege of walking to Park Avenue while still having immense privacy. A soaring 20-foot foyer creates an unforgettable first impression and immediately establishes the home's sense of grandeur. Beyond the entry, the expansive great room is defined by dramatic exposed wood beams, a sleek electric fireplace, and a custom-built entertainment wall accented with subtle LED underlighting. At the heart of the home, the chef's kitchen is equal parts statement and workspace. Custom cabinetry is paired with a full Thermador appliance suite, including a paneled built-in refrigerator, while striking Taj Mahal quartzite countertops complete the space. Just beyond, an oversized butler's pantry dramatically expands the kitchen's functionality. Outfitted with extensive cabinetry, generous prep space, a secondary refrigerator, sink, and dishwasher, it is designed to support everything from intimate dinners to large-scale entertaining. The adjacent dining room is equally refined, featuring a custom dry bar complete with a built-in wine refrigerator. One of the home's most exceptional attributes is its floor plan. Offering two luxurious primary suites, a rarity in Winter Park, the residence provides remarkable flexibility for multigenerational living or extended guests. Both suites feature custom Idelli closet systems and spa-inspired baths appointed with marble mosaic tile, expansive walk-in showers, freestanding soaking tubs, and dual vanities. Every additional bedroom is designed as a private ensuite with its own walk-in closet. Two guest suites are conveniently located on the main level, while upstairs you'll find a spacious game room, a dedicated study nook for kids, and a second laundry room to complement the main-level laundry. The outdoor living experience is equally impressive. An expansive backyard, rarely found in Winter Park, creates a private setting for everyday living and entertaining alike. A covered lanai with a fully equipped summer kitchen overlooks the resort-style pool and spa, while upgraded landscaping and generous green space complete the grounds. An oversized motor court and a three-car garage with soaring 12-foot ceilings provide an uncommon level of parking and storage for the car enthusiast. Positioned just moments from Park Avenue, Winter Park Village, and Hannibal Square, this is far more than another luxury home. It is a thoughtfully crafted masterpiece that captures the timeless character of Olde Winter Park while delivering the scale, amenities, and craftsmanship expected of a modern home. Opportunities to own a property of this caliber, in a location this desirable, are exceptionally rare. Don't miss out!

1417 Williams Drive, Winter Park
$3,750,000
4 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by Steve & Jodie Konold of Scout & Co., the 3,826-sf residence offers 4 beds & 5.5 baths, w/ a layout thoughtfully arranged to provide the intentional privacy of a luxury retreat. Beyond its terraced walkway—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer featuring a woven rattan chandelier, sourced & designed in London, leads to a sculptural stairwell positioned just off the main living spaces. The great room includes soaring ceilings, a sleek, custom plaster fireplace & walls of glass doors & windows. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. The kitchen is appointed w/ a Thermador dual-fuel range, matching plaster hood, full refrigerator & freezer columns & a large island with seating topped in honed black quartzite. The surrounding cabinetry features hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces line the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balances the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The main floor primary suite is accessed through antique doors that open to a light-filled gallery overlooking the rear courtyard & pool. The primary bath features an extended vanity w/ dual sinks, matte black fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink paired w/ a handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby bedroom suite is marked by an antique door entry. Each guest bedroom features an en-suite bath introduced by a hand-painted tile threshold, complemented by designer lighting, distinctive mirrors & continuous European oak flooring. The rooftop terrace is accessed from the second-floor hallway. The detached casita opens to the pool courtyard through accordion glass doors on two walls & includes a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Other outdoor spaces include 2 garden courtyards, a heated saltwater pool & a newly constructed outdoor kitchen designed to accommodate a built-in grill & Big Green Egg. A spacious gravel courtyard is ideal for dining or relaxing and is enveloped by mature bamboo that creates exceptional privacy. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle within one of Winter Park’s most exclusive enclaves.

1150 Via Salerno, Winter Park
$2,800,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Under Construction. A timeless expression of modern luxury, this exceptional new residence by LUIH Luxury Homes brings together thoughtful architecture, designer finishes, and refined craftsmanship in one of Winter Park’s most desirable neighborhoods. Situated on an oversized homesite along a quiet, tree-lined street, the home offers approximately 4,018 square feet of beautifully designed living space with five bedrooms, four-and-a-half bathrooms, and an open floor plan created for both everyday living and effortless entertaining. Natural light fills the interior, highlighting wide-plank wood flooring, custom millwork, curated designer lighting, and a warm, neutral palette that creates an inviting atmosphere throughout. The main living areas transition seamlessly from one space to the next, anchored by a spacious family room featuring a sleek linear electric fireplace and expansive sliding glass doors that open to the outdoor living area. Designed to be both functional and beautiful, the chef’s kitchen serves as the centerpiece of the home. Custom shaker cabinetry, waterfall-edge quartz countertops, a designer tile backsplash, and an oversized island are complemented by a premium Thermador appliance package, including a gas cooktop, built-in refrigerator, microwave and oven combination, dishwasher, wine refrigerator, and designer vent hood. A generous walk-in pantry and an adjacent wet bar further enhance the space, while the dining area offers an elegant setting for everything from casual family meals to formal entertaining. The first-floor primary suite provides a peaceful retreat with direct access to the covered lanai and pool. The adjoining bath is designed with a spa-inspired aesthetic, featuring a freestanding soaking tub, an oversized glass-enclosed shower, dual vanities with quartz countertops, designer fixtures, and a spacious custom walk-in closet. Also on the main level are a private office and an additional bedroom with an en suite bath, offering flexibility for guests, multigenerational living, or a dedicated workspace. Upstairs, a generous loft creates an ideal secondary gathering area, while three additional bedrooms and well-appointed bathrooms provide comfortable accommodations for family and visitors. Outdoor living is thoughtfully integrated into the home’s design. The covered lanai includes a fully equipped summer kitchen overlooking the resort-style pool and spa, creating an inviting setting for year-round entertaining. A spacious backyard offers additional room to relax, play, or personalize the outdoor experience. Located just minutes from the renowned shopping, dining, and cultural attractions of Park Avenue, residents can enjoy favorites including Prato, AVA Mediterranean, Boca Winter Park, Hillstone, The Ravenous Pig, Choulala Fine Pastries, and Barnie’s Coffee & Tea Co. Nearby outdoor destinations include Mead Botanical Garden, Kraft Azalea Garden, Central Park, Cady Way Park, Dinky Dock Park, and the Winter Park Golf Course. Rollins College, AdventHealth Winter Park, and Winter Park High School are also conveniently located nearby. Combining timeless architecture, thoughtfully selected finishes, and an exceptional location, this residence presents a rare opportunity to own a newly constructed luxury home in the heart of Winter Park. Renderings are artistic interpretations. Features and finishes may vary from final construction.

609 S Phelps Avenue, Winter Park
$2,750,000
4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh, refined feel throughout. Just off the entry, a stately office/den with a wood-burning fireplace offers a handsome, versatile space for a home office, library or sitting room, while a formal dining room provides an elegant setting for entertaining. At the heart of the home is the beautifully updated kitchen, featuring new cabinetry and hardware, marble countertops and an expansive center island with generous seating. Luxury appliances include a striking induction range, integrated refrigerator and convenient beverage refrigeration drawer, while a dedicated coffee bar adds function and style. A sunny breakfast nook provides casual dining space, and the kitchen opens seamlessly to the spacious great room, where French doors lead to the covered lanai and fill the interiors with natural light. A cleverly concealed doorway in the kitchen provides access to the garage and a large bonus room above, complete with a custom wet bar and under-counter beverage refrigerator, an exceptional space for entertaining, recreation or media. Privately on the first floor, the primary suite offers direct access to the covered lanai, an ample custom walk-in closet and spa-inspired bath with dual vanities, soaking tub and glass-enclosed shower. A laundry room with custom cabinetry and powder bath with outdoor access complete the main level. Upstairs, a bright and spacious family room accompanies three additional bedrooms. One features a private en-suite bath, while the remaining two share a Jack-and-Jill bath. All closets feature custom organizational systems. Outdoor living is equally impressive. Accessible from the great room and primary suite, the covered lanai overlooks the newly refinished heated saltwater pool and spa, surrounded by new non-slip pool deck pavers. Wi-Fi-enabled pool and spa equipment provides convenient app-based control. Redesigned by Signature Landscape, the backyard features a turf area for loungers, dedicated firepit space and new fence installed in 2023, creating a wonderful setting for outdoor entertaining. A professionally installed Mist and More mosquito misting system adds another level of comfort, while a gas line from the street supplies the pool and firepit. Extensive upgrades include three HVAC systems installed in 2024 and 2025, a new water heater, whole-home water filtration system and Ecobee smart thermostats. The interior and exterior were repainted in 2025, complemented by new flooring, baseboards and crown molding, custom window treatments, wallpaper and carefully selected designer finishes. Interiors by nationally recognized designer Jaime Garnet of WYC Designs create a polished, cohesive aesthetic throughout. Ideally just minutes from downtown Winter Park, the home offers convenient access to exceptional dining, shopping and cultural amenities, along with major roadways for easy connectivity throughout Central Florida. With extensive updates, flexible living spaces, sophisticated interiors and a beautifully redesigned outdoor setting, this exceptional residence is move-in ready.

948 Poinciana Lane, Winter Park
$2,495,000
5 Beds ⋅ 6 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Under Construction. Experience exceptional craftsmanship and timeless design in this brand-new luxury custom home being built by FG Schaub Custom Homes. This residence will feature 5 bedrooms, 5.5 bathrooms, and 3,656 square feet of thoughtfully designed living space, blending modern architecture with everyday comfort. The open-concept floor plan highlights a gourmet chef’s kitchen equipped with a premium Wolf/Sub-Zero appliance package, custom cabinetry, a walk-in pantry, and a large center island overlooking the spacious great room. Expansive sliding glass doors lead to a covered outdoor living area complete with a summer kitchen, roll-away screen, and mini-split A/C—perfect for year-round entertaining. The outdoor space also includes a private pool, creating a seamless indoor–outdoor flow ideal for the Florida lifestyle. The first floor offers a primary suite with a spa-inspired bath and a generous walk-in closet, along with a private guest suite—ideal for visitors or multigenerational living. Upstairs, 3 additional bedrooms each include en-suite baths and walk-in closets, providing comfort and privacy for family or guests. Additional features include a two-car garage with epoxy flooring and an EV charger, premium landscaping, and vinyl fencing for added beauty and privacy. Conveniently located and zoned for Audubon K-8 and Winter Park High School, this home offers exceptional access to top-rated schools, local parks, and the vibrant shops and dining of Downtown Winter Park. **Estimated completion: October 2026.**

2812 Mulford Avenue, Winter Park
$2,460,000
4 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved street-front home winds around century-old oaks while overlooking Lake Howard, creating the kind of property you will love coming home to. Many rooms inside the home are designed to incorporate the outdoor spaces. These artfully designed exterior areas feel like an extension of the interior, making the home feel even larger and more luxurious. The first floor welcomes you and your guests through the 5’ wide steel pivot door near the private office. The extra-large kitchen, open pantry, and breakfast nook are framed by warm natural oak floor-to-ceiling cabinetry and Thermador appliances while overlooking the exterior raised garden bed. This beautiful kitchen flows seamlessly into the living room, which features a modern floating-hearth fireplace. The living room opens to the outdoor living space, summer kitchen, pool, and hot tub. The primary bathroom has a modern natural feel, featuring a glass sauna room that opens to a private outdoor spa with hot and cold plunge tub. The first-floor laundry room is located just off the two-car garage and includes a drop zone for additional organization. Another bonus feature is the inclusion of two laundry rooms—one on each floor. Upstairs, the kids’ lounge is surrounded by three bedrooms and a secret media room. One bedroom is en-suite, while the other two bedrooms share a common bathroom with dual vanity areas. The exterior of the home utilizes every area like a thoughtfully designed park, creating usable space around every corner. The driveway accommodates several vehicles and includes a side drive for additional parking and storage behind the gate and garage. When you do leave your beautiful home, you are surrounded by the best that Winter Park and Orlando have to offer. This neighborhood is zoned for top-rated schools, where kids walk and ride their bikes to school daily, and is surrounded by amazing parks, restaurants, shops, and nature. Your home can feel like a perfect balance of natural and modern architecture, both inside and out. Call us to see how this home delivers that truly unique feeling.

2228 Howard Drive, Winter Park
$2,394,500
5 Beds ⋅ 7 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.

2412 Chantilly Avenue, Winter Park
$2,390,000
4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.

645 Pansy Avenue, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

140 E Morse Boulevard Unit J, Winter Park
$1,950,000
32792 Zip Code
Rare opportunity to acquire an established church property on 6.21 acres with outstanding frontage and visibility along one of the area's busiest corridors. The existing sanctuary, ample parking, and expansive grounds provide an excellent opportunity for a growing congregation to establish or expand its ministry. For investors and developers, the property's Future Land Use designation for multifamily offers exceptional long-term redevelopment potential in a high-demand location. A unique offering with immediate functionality and future possibilities.

3075 N Goldenrod Road, Winter Park
$1,875,000
3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Set along the brick-lined streets of Charmont, one of Winter Park’s most coveted and established neighborhoods, 1661 Laurel Road presents a rare opportunity to own a home in an exceptional location just three houses from Lake Virginia. From the front yard, enjoy beautiful lake views and the timeless character of a neighborhood defined by mature trees, gracious homes, and a true sense of place. The current owners have cherished this property since 1972, and after more than five decades, the home is ready for its next chapter. Situated on an impressive 0.43-acre corner lot (18,802 square feet), the property offers flexibility that is increasingly difficult to find in Winter Park. The existing home can be thoughtfully remodeled and the floor plan reimagined while preserving the architectural charm and character that make the property special. Or, for those looking to create something entirely their own, the generous lot offers the potential to build a new home in one of Winter Park’s most desirable settings. Inside, a welcoming foyer introduces a floor plan filled with opportunity. To the right, the grand living room features abundant windows and natural light, beautiful proportions, and a wood-burning fireplace, with the space extending into a bright sunroom overlooking the grounds. A hallway off the living room leads to two bedrooms, each with its own ensuite bathroom. To the left of the foyer, a third bedroom offers a dedicated bathroom and walk-in closet. Straight ahead, the dining room features charming corner cabinetry and leads into the existing kitchen. Beyond the dining room, an additional sunroom and sitting area presents one of the home's many opportunities for transformation. Envision opening this space to create a more expansive kitchen with room for a built-in breakfast banquette, coffee bar, and functional drop zone—a gathering space designed around the way today's families live while retaining the home's original charm. A breezeway connects the main house to the two-car garage, while the space above offers a separate one-bedroom, one-bath apartment. Ideal for visiting guests, a private playroom or teen retreat, an office, or potential rental income, this additional living space adds another layer of flexibility to the property. Additional features include an irrigation well and 2018 HVAC system. Beyond the property itself, the location is what makes 1661 Laurel Road truly special. Enjoy Park Avenue, where Winter Park's beloved restaurants, boutiques, galleries, cafés, and cultural institutions create one of Central Florida's most distinctive lifestyles. Rollins College, Hannibal Square, Central Park, Mead Botanical Garden, and the Winter Park Chain of Lakes are all close by, while the neighborhood's tree-canopied streets offer a peaceful retreat just minutes from the energy of downtown. Zoned for Audubon Park K-8 and Winter Park High School, this is an opportunity to put down roots in one of Winter Park's most sought-after locations. Whether you envision restoring and reimagining the existing home or creating a new residence from the ground up, the possibilities at 1661 Laurel Road are truly exceptional. Some properties are defined by their finishes; others are defined by their location, land, history, and potential. This one offers all four.

1661 Laurel Road, Winter Park
$1,825,000
2 Beds ⋅ 2 Baths ⋅ Whispering Waters/Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square feet in the heart of downtown Winter Park. Located on the second floor of Building 1, this light-filled residence was extensively remodeled in 2023 with an open floor plan and raised ceiling heights that give the home an airy, comfortable feel throughout. The spacious living room and kitchen take full advantage of the breathtaking views of Lake Osceola, while two fireplaces—one in the living room and another in the primary bedroom—add warmth and character to the space. The kitchen has been updated with white cabinetry, stainless steel appliances, double ovens, induction cooktop, tile backsplash, center island, and wine/beverage refrigerator. Formal living and dining spaces offer plenty of room for entertaining, and the oversized entertainment room off the primary bedroom features a closet and separate entry, making it a great option for a third bedroom, media room, or home office. The primary suite offers a walk-in closet and en-suite bathroom with a shower and dual sinks. The secondary bedroom includes two closets along with a separate alcove ideal for a reading nook or office space. A Florida room, currently used as a storage room, features brick flooring. Other highlights include plantation shutters throughout, beautiful exposed beams, additional storage closet in the garage, and two designated parking spaces in the covered garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. A rare opportunity to enjoy spacious lakefront living in one of Winter Park’s most desirable communities.

311 E Morse Boulevard Unit 1-3, Winter Park
$1,824,000
4 Beds ⋅ 4 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Timeless charm meets thoughtful investment in the heart of Park Grove, Winter Park's most coveted enclave. Set on one of the neighborhood's largest lots beneath a canopy of mature oaks, this home offers something increasingly rare this close to Park Avenue: room to breathe, inside and out. Behind that charm is a home that has been genuinely looked after. A new roof in 2021, a complete replumb in 2023, and new air conditioning in 2025 mean the unglamorous work is finished. There is nothing here waiting on you. Move in, unpack, and simply enjoy it. Out front, a newly remodeled courtyard sets the tone. It is a gracious welcome and an unexpectedly versatile entertaining space, equally suited to morning coffee, an evening glass of wine, or a gathering that spills comfortably outdoors. Inside, the floor plan rewards daily living. Generous proportions, abundant natural light, and storage of a kind that simply is not built anymore, with closets throughout that are uncommonly deep and plentiful. The kitchen is anchored by custom cabinetry, thoughtfully designed and beautifully executed, while handsome built-ins and a wine refrigerator remain with the home. Two recently remodeled guest bathrooms carry the same restraint, finished in a timeless, traditional style that flows seamlessly with the rest of the home rather than competing with it. The primary suite is a genuine retreat, opening to a private sitting room that has served as both a nursery and a home office over the years and stands ready to become whatever the next chapter requires: a study, a reading room, a nursery once again, or a quiet place to close the door on the day. Beyond the back doors, the grounds unfold deep and green, framed by established landscaping and shaded by mature oaks. The rear of the property faces west, so evening light spills generously across the patio and the lawn beyond. There is ample room to add the pool of your dreams, an increasingly uncommon luxury on lots of this size so near the heart of Winter Park. Park Grove itself needs little introduction. Treasured for its oversized lots and unusually wide, oak-lined streets, the neighborhood delivers the quiet residential character that draws one to Winter Park in the first place, with an enviable position moments from the shops, restaurants and galleries of Park Avenue and effortless access to I-4, downtown Orlando and the airport. Homes here rarely come available, and for good reason.

631 Williams Drive, Winter Park
$1,800,000
Sharon Place SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. A rare opportunity to create your own vision in the heart of Winter Park. This exceptional 17,624-square-foot (0.40-acre) oversized corner lot offers approximately 112' x 145' of space and is ideally situated on a quiet, dead-end street just steps from the Winter Park Racquet Club. Opportunities to acquire a homesite of this size in Winter Park are increasingly rare. Majestic oak trees canopy the street, creating a beautiful and established setting for your future dream home. The property is being offered for land value, providing an outstanding opportunity to build a custom residence tailored to your lifestyle. Enjoy a prime location just minutes from Park Avenue's renowned shopping, dining and cultural offerings, as well as Interlachen Country Club, the YMCA and Phelps Park. Zoned for excellent “A” rated schools, this is a truly special opportunity to secure a substantial homesite in one of Winter Park's most desirable locations.

1220 Sharon Place, Winter Park
$1,795,000
4 Beds ⋅ 4 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.

1230 Sunset Drive, Winter Park
$1,795,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one. Step through the custom pivot front door into a home that immediately announces its intentions. Soaring 10-ft ceilings throughout rise to a dramatic 22-ft volume in the great room, framed by sliding glass walls that dissolve the line between interior living and the private outdoor retreat beyond. Level 5 smooth drywall finish — the standard reserved for the finest custom builds — runs throughout, while wide-plank hardwood flooring flows across every living area. Italian porcelain tile anchors all bathrooms and the laundry room with precision and permanence. Every window and exterior door is imported from Germany — Unilux® precision-engineered for thermal performance, acoustic excellence, and longevity that no domestic product can match. Grohe® plumbing fixtures, also made in Germany, carry that same philosophy through every bathroom. Countertops are Cambria or Silestone® quartz with a thickened 3cm mitered edge throughout. Custom solid wood cabinetry is built to plan in the kitchen, laundry, and all bathrooms, finished with Emtek® hardware and 8-ft solid core architectural doors with 7" baseboard throughout. The Winter Park Chain of Lakes — 12 interconnected lakes spanning 2,781 acres of pristine Florida waterways — is moments away, offering boating, paddleboarding, and the beloved Winter Park Scenic Boat Tour. Over 70 parks, Kraft Azalea Gardens, Mead Botanical Garden, and more than a dozen walkable green spaces define the outdoor lifestyle. The Winter Park Farmers' Market, held every Saturday at the historic train station, is a community institution. Rollins College, one of the South's most respected liberal arts institutions, sits lakeside just minutes away, bringing cultural programming, the Bach Festival, and vibrant intellectual energy to the neighborhood year-round. Families are served by highly rated Orange County public schools, with Winter Park High School renowned for its academic rigor and championship programs, as well as exceptional private options, including Trinity Preparatory School and St. Margaret Mary. New construction in 32789 is genuinely rare — historic preservation standards and limited land availability make it so. For international buyers, Orlando International Airport is 30 minutes south. Disney, Universal, and the theme park corridor are under 30 minutes via I-4. Atlantic beaches are under an hour away. This is not a production home dressed up with upgrades. It is a ground-up, custom-built, German-engineered, the most coveted zip code in Central Florida. Schedule your private showing today.

2501 Lafayette Avenue, Winter Park
$1,795,000
3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

106 S Interlachen Avenue Unit 518, Winter Park
$1,690,000
4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Available furnished or unfurnished, lease-to-own or straight lease (6-12 months). On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home’s clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef’s kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home’s entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park’s desirable settings.

1420 Magnolia Avenue, Winter Park
$1,649,000
3 Beds ⋅ 3 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Picturesque and beautifully appointed, this three-bedroom, three-bath residence is ideally situated along the sought-after Vias of Winter Park, a charming brick-paved street framed by mature landscaping and distinguished residences. Meticulously maintained grounds surround the home, with brick-paver walkways and inviting side and rear courtyards creating a seamless connection between the indoors and outdoors. Inside, gorgeous wood floors extend throughout the first level, complimented by soaring ceilings and an abundance of windows that fill the home with natural light. The spacious living room features a striking wood-burning fireplace and an impressive ceiling height, creating an inviting setting for both everyday living and entertaining. The well-designed kitchen offers an island, stainless steel appliances and excellent functionality, while an adjacent breakfast nook features a custom built-in bar and beverage center with under-counter refrigerator. The elegant dining room has a set of French doors overlooking lush greenery and the home's beautifully landscaped backyard. Thoughtfully renovated by the current owners, the first floor was reconfigured to create a luxurious primary suite with soaring ceilings and French doors opening to tranquil courtyard views. The spacious walk-in closet and newly added ensuite bath complete this private retreat. A second bedroom, a full bath, and a dedicated laundry room round out the main level. Upstairs, an open loft provides versatile additional living space, while a generously sized third bedroom suite offers exceptional privacy and flexibility. With a spacious walk-in closet and spa-inspired bath, this expansive suite could easily serve as a secondary primary retreat. Beyond the remote-controlled driveway gate, a detached two-car garage provides exceptional convenience and storage, while the upstairs loft/flex space of 480 sq ft (NOT included in main house heated SF) offers endless possibilities for a fitness studio, yoga retreat, creative space or home office. The location is truly exceptional, with the Winter Park Racquet Club and Kraft Azalea Garden just a short walk or bike ride away. Park Avenue's renowned shopping, dining, sidewalk cafés and cultural attractions are only minutes from home, along with everything downtown Winter Park has to offer. Convenient access to highly regarded public and private schools further enhances the appeal of this special property. A rare combination of thoughtful renovation, timeless character, exceptional outdoor spaces and an enviable Winter Park location, this beautifully presented residence offers a refined yet comfortable lifestyle in one of the area's most coveted settings.

1200 Woodmere Drive, Winter Park
$1,649,000
5 Beds ⋅ 4 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

2501 Winter Park Road, Winter Park
$1,395,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Pointe SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137- acre spring-fed lake, this stunning estate-like property sits on more than half an acre and is surrounded by lush landscaping, mature trees and beautifully maintained grounds. From the moment you arrive, the long, newly paved driveway sets the tone for what awaits. Meticulously maintained, this impressive home offers 4 bedrooms, 4 full bathrooms, a dedicated office and a spacious upstairs loft/bonus room. The dramatic entry features soaring ceilings, expansive windows and sliding glass doors that draw your attention to the pool and picturesque backyard. The formal dining room, accented by coffered ceilings, flows seamlessly into the beautifully appointed kitchen through a wet bar and wine closet. Completely reimagined down to the studs in 2016, the kitchen features gorgeous marble countertops, custom cabinetry with built-in drawers, a brand-new gas cooktop, double wall ovens, Sub-Zero refrigerator, generous breakfast nook and a large picture window overlooking the pool. The kitchen opens directly to the spacious family room, where soaring ceilings, floor- to-ceiling windows, a gas fireplace and custom built-in cabinetry create an inviting gathering space. A secondary bedroom and full bathroom are conveniently located just off the family room. The expansive downstairs primary suite is a true retreat, featuring tall ceilings, abundant windows and a French door providing direct access to the pool and lanai. Completely remodeled in 2019, the luxurious primary bath offers two separate vanities with dual sinks, a spacious shower with dual shower heads, a beautiful soaking tub and a custom walk-in closet. Just beyond the primary suite is a dedicated office and convenient pool bath. Upstairs, a separate living area provides exceptional flexibility with a generous loft/bonus room, two spacious bedrooms and a full bath featuring dual sinks, a soaking tub and separate shower. Designed with entertaining in mind, the home’s indoor and outdoor spaces blend effortlessly together. The heated pool and spa are surrounded by a covered, screened lanai and a lush backyard oasis complete with mature trees and charming walking paths—creating a private setting for relaxing or entertaining. Bear Gully Pointe offers sidewalks throughout the community, a tennis court, playground and a brand-new gazebo overlooking Bear Lake. Ideally located just minutes from downtown Winter Park, Trinity Preparatory School, Winter Springs and Oviedo. Additional updates include a 2021 roof, 2022 gas water heater, 2024 re-pipe, 2016 pool resurfacing, 2025 driveway, 2022 exterior paint and hardwood flooring downstairs added in 2013.

2873 Old Castle Drive, Winter Park
$1,325,000
6 Beds ⋅ 4 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot with beautiful water views, this impressive Kerrville II by Meritage Homes combines sophisticated design, generous living spaces, and an incredible outdoor lifestyle. Offering 6 bedrooms, 4.5 bathrooms, and a 3-car garage, this thoughtfully designed residence provides the flexibility today's buyers are looking for. The light-filled interior features an open and inviting layout with upgraded finishes throughout, creating the perfect setting for both everyday living and entertaining. At the center of the home, the gourmet kitchen is designed to impress with premium cabinetry, quartz countertops, a large center island, and high-end appliances. The kitchen opens seamlessly to the main living and dining spaces, making it easy to gather with family and friends. The outdoor living area truly sets this home apart. Step through to the extended lanai and enjoy your own private Florida retreat featuring a heated saltwater, self-cleaning pool and spa, outdoor kitchen, and an impressive screened enclosure enhanced with color-changing lighting for a dramatic evening atmosphere. Solar panels add an additional energy-efficient benefit to the home. The first floor offers exceptional versatility with formal living and dining spaces along with a private guest suite featuring its own en-suite bathroom and convenient access toward the pool area—ideal for guests, extended family, or multi-generational living. Upstairs, the owner's retreat provides a peaceful escape with views overlooking the pool and water. The spa-inspired primary bathroom, upscale finishes, and generous walk-in closets complete the space. Additional bedrooms and flexible living areas offer endless possibilities for a media room, home office, fitness space, playroom, or additional guest accommodations. The 3-car garage includes convenient overhead storage shelving, providing even more functionality and organization. Residents of Hawks Crest enjoy access to outstanding amenities, including a resort-style community pool, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. Spend your weekends kayaking, canoeing, paddleboarding, fishing, or simply enjoying the lakefront setting. Ideally located in Winter Park with convenient access to Park Avenue, shopping, dining, entertainment, and cultural attractions, this home offers the perfect combination of luxury, lifestyle, location, and flexibility. Schedule your private showing today and experience everything this exceptional Hawks Crest residence has to offer.

1117 Wading Waters Circle, Winter Park
$1,300,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
beautiful home

1434 Via Sangro Pl, Winter Park
$1,295,000
4 Beds ⋅ 4 Baths ⋅ Hamilton Place SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Now offered at an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest. This remarkable home represents one of the best opportunities in today’s Winter Park luxury market, featuring exquisite finishes, modern design, and an unmatched lifestyle just moments from Park Avenue. Built in 2018, this custom-designed 4-bedroom, 3.5-bath residence offers 2,843 square feet of thoughtfully crafted living space, just a short walk from Park Avenue and the historic Winter Park Golf Course. Distinctive architectural details—including shiplap ceilings in the living room and kitchen, decorative ceiling treatments, and a dramatic tile staircase feature illuminated by natural light—create a home that is both elegant and inviting. At the heart of the home is a chef-inspired kitchen featuring Wolf and Sub-Zero appliances, custom cabinetry, Kohler fixtures, and an open-concept layout that flows effortlessly into the living and dining spaces, making it ideal for everyday living and entertaining alike. The primary suite serves as a peaceful retreat with a spa-inspired marble bathroom, while the upstairs bonus room offers flexible space for a media room, home office, or playroom. Outside, enjoy your own backyard oasis complete with a sparkling pool and spa combo—perfect for relaxing or hosting family and friends. Located just minutes from Park Avenue’s renowned restaurants, boutiques, and year-round events, this home delivers one of Central Florida’s most sought-after lifestyles. Schedule your private showing today.

802 Hamilton Place Court, Winter Park
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Mrs L A Dennis Sub SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Incredibly charming Craftsman style home that's been artfully renovated and is located in the heart of Winter Park’s sought-after College Quarter, just footsteps from Rollins, restaurants, and Park Avenue! The owners thoughtfully renovated this three-bedroom, two-bath bungalow in 2022/2023. The home underwent a comprehensive transformation with all major systems and components fully updated or replaced, including the electrical, plumbing, HVAC, roof, siding, walls, spray foam insulation, appliances and more, offering a turnkey residence where modern functionality complements timeless character. Inside, gorgeous "antique heart of pine" wood floors lend warmth and character, while abundant windows/glass doors fill the home with natural light. The welcoming living room features a vaulted ceiling and French doors opening to an expansive deck and private, fenced backyard, creating an effortless connection between indoor and outdoor living. The beautiful new classic kitchen is designed for both everyday living and entertaining, with a generous island with seating and a gas range and hood. The serene primary suite is enhanced by custom built-ins and two separate closets outfitted with thoughtfully designed organization systems, providing exceptional storage. The renovated primary bath features dual vanities and a spacious walk-in shower. Two additional bedrooms offer flexibility for guests, work or personal space, with one currently utilized as a comfortable office/den. A beautifully remodeled second bath and convenient interior laundry closet complete the well-designed floor plan. Additional storage is found in the spacious attic, which has been thoughtfully improved with added flooring for ease of access and a new pull-down ladder system, creating a highly functional area for seasonal belongings and household storage. Outside, the sunny backyard is framed by bamboo and features a detached utility shed for additional outdoor storage (note: well for irrigation system). A picturesque setting and an enviable location further distinguish this delightful residence. From here, stroll along Holt Avenue to Rollins College, enjoy the scenic Lake Virginia walking trail, or walk to Park Avenue’s acclaimed restaurants, boutique shops and sidewalk cafés. Central Park and the Winter Park Farmers’ Market are close by, as is the Winter Park 9 Golf Course. This exceptional location places the best of Winter Park within easy reach while offering the comfort, character and peace of a beautifully renewed bungalow.

393 Holt Avenue, Winter Park
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Lords Sub SubDv. ⋅ 32789 Zip Code
Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

632 Country Club Drive, Winter Park
$999,000
3 Beds ⋅ 4 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

1120 Wisconsin Avenue, Winter Park