Winter Park Homes with Sidewalk Exterior Features

Winter Park Homes with Sidewalk Exterior Features

Welcome to Winter Park, Florida, a picturesque city renowned for its enchanting landscapes, vibrant arts scene, and historic charm. Nestled just north of Orlando, Winter Park is a haven for those seeking a perfect blend of suburban tranquility and urban excitement. With its tree-lined streets, stunning lakes, and an array of boutiques and cafes, this city offers a delightful lifestyle that appeals to families, professionals, and retirees alike.

One of the standout features of Winter Park is its commitment to walkability. Many homes in this enchanting city boast beautiful sidewalk exterior features, encouraging residents to step outside and explore the neighborhood. Imagine taking a leisurely stroll along the charming streets, where you can wave hello to friendly neighbors, enjoy the fresh Florida air, and marvel at the lush landscaping that adorns the area. Sidewalks not only enhance the aesthetic appeal of the community but also promote a healthy and active lifestyle, making it easy to enjoy morning jogs or evening walks with loved ones.

Winter Park is also home to a variety of parks, including the serene Central Park, where you can relax under the shade of ancient oaks or enjoy a picnic by the lake. The city’s rich cultural offerings, from the renowned Rollins College to the vibrant Winter Park Art Festival, provide endless opportunities for enrichment and entertainment.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Park’s diverse real estate market, complemented by its inviting sidewalks, makes it the perfect place to call home. Embrace the charm of Winter Park and discover a lifestyle that is both enchanting and fulfilling!

Newest Winter Park Homes with Sidewalk Exterior Features

$3,500,000
5 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Under Construction. Situated on a prominent corner lot in one of Winter Park's most desirable neighborhoods, this exceptional new construction residence makes an unforgettable first impression with its commanding architecture, refined craftsmanship, and remarkable attention to detail. Every element of the home has been designed to deliver a level of luxury rarely found at this price point, creating a residence that is both visually striking and exceptionally functional. A dramatic entry sets the tone from the moment you step inside, where a custom paneled feature wall and ceiling with integrated lighting create an architectural statement. Beyond the foyer, the expansive great room unfolds beneath soaring ceilings, anchored by a stunning entertainment wall featuring custom millwork, integrated LED lighting, and a sleek electric fireplace that serves as the centerpiece of the home's main gathering space. Oversized glass doors invite natural light throughout while seamlessly connecting the interior to the outdoor living areas. Designed for both everyday living and effortless entertaining, the chef's kitchen is as beautiful as it is functional. Custom cabinetry provides an abundance of storage, complemented by quartz countertops, an oversized center island, and a complete suite of premium Thermador appliances, including a built-in coffee system and paneled refrigerator. Just beyond, a spacious walk-in pantry offers extensive additional cabinetry, generous prep space, and a second dishwasher, making hosting on any scale effortless. The first-floor primary suite offers a private retreat with direct access to the backyard and resort-style pool. Its spa-inspired bath features dual vanities, an expansive walk-in shower, and a freestanding soaking tub, while the extraordinary custom closet by Hommes Design elevates everyday living with integrated LED lighting, a center island, and meticulously designed storage. A second downstairs bedroom, a highly sought-after feature rarely found in Winter Park, provides exceptional flexibility for guests, extended family, or a private home office. Upstairs, a spacious bonus room creates an additional living space complete with its own custom entertainment center, integrated LED lighting, and electric fireplace. A second primary suite, two additional generously sized bedrooms, and a private balcony complete the upper level, offering an ideal layout for large families and guests alike. The outdoor living experience is equally impressive. A covered lanai with a full summer kitchen overlooks a striking L-shaped pool with a raised spillover spa, while the oversized backyard and expansive side yard provide an exceptional amount of green space. The home also features a dedicated pool bath for functionality. Located just minutes from Cady Way Park, the Winter Park YMCA, and the boutiques and restaurants of Park Avenue, this residence also benefits from one of Winter Park's fastest-transforming corridors, where significant investment and redevelopment continue to enhance the area's long-term appeal. Combining exceptional architecture, thoughtful design, and an outstanding package of upgrades, this is a rare opportunity to own one of the most impressive new homes available in Winter Park today.

1901 Loch Berry Road, Winter Park
$675,000
4 Beds ⋅ 3 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gated Hawks Crest community – and offers buyers a turn-key opportunity to crack into the Winter Park market. With 1,770 square feet of thoughtfully designed living space, this home strikes the perfect balance between functionality and flow, featuring a living/dining combination anchored by the kitchen in the heart of the home. The central dining configuration is equally suited for quiet evenings or effortless entertaining, while the living room offers versatility as a spacious indoor retreat, or an indoor-outdoor oasis, complimented by the glass sliders. Before entering the primary suite, find three secondary rooms - two guest bedrooms and an office - along with a full guest bathroom and a powder bath, making every day living hassle-free and providing ample privacy. In the primary en-suite, unwind and enjoy the pleasures of a spacious retreat featuring an over-sized walk-in shower. This home is only 4 years young, so newer appliances and core components provide peace of mind, and an upgraded Tesla level 2 charger makes it fully equipped to suit every homeowner's needs. This home is just a short walk to the community amenities which include a clubhouse, pool, fitness center, turf lawn with a putting green, playground, dog park, and a private community dock on to Lake Howell. The 24-hour gated community provides peace of mind, all within easy reach of A-rated Seminole County schools (Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High), major employment corridors, the Orlando International Airport, and everything that Orlando has to offer. This is the kind of opportunity that doesn't come along often. Contact us to schedule your private tour today!

1122 Wildmeadow Run, Winter Park
$354,999
3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code
Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park
$229,900
3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 01 SubDv. ⋅ 32792 Zip Code
Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park
$1,775,000
4 Beds ⋅ 5 Baths ⋅ Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code
Charming and Sophisticated, this single-story home combines the old with the new in such a seamless manner, you will walk through the etched glass front door and immediately have the desire to sit down with a glass of wine, listen the player piano, and you will never want to leave. Welcome to this Completely Renovated Custom Home in the highly coveted area of Winter Park, just a few blocks from Phelps Park, the YMCA, and a beautiful walk to the Park Avenue shops and restaurants. Walking up the paver drive, over the travertine front patio and stepping into this gorgeous home, you are greeted with the formal living room featuring a player piano, a beautiful marble wood burning fireplace, and hardwood floors that flow throughout the home. Turning to your right you will find 3 large bedrooms, 2 full bathrooms and 1 half bath. You will note one of these secondary bedrooms presents as an en-suite with a full bathroom. The other 2 bedrooms share a full bathroom, along with an auxiliary half bath. Moving forward through the living room you step into the stunning oversized dining room, complete with a wall-bar custom made in Italy along with a wine dispensing machine (picture the Wine Room) which conveys with the sale. From the dining room we step down into a chef's kitchen like no other. Stunning 42"white wood cabinets, quartz countertops, white subway tile backsplash, a 6-burner natural GAS RANGE, double oven, and the largest center island with a microwave and beverage cooler on either end. This magnificent kitchen opens up to a large family room with French doors, surround sound speakers and large sunlit windows. Walking through the family room you will find the primary suite tucked away in the back of the house for the ultimate private sanctuary. Along with the generously sized bedroom with French doors giving access to the backyard and pool, you will be in absolute awe of the incredible primary bathroom, featuring his and hers sinks, a standalone tub, and a double-sided walk-in shower with 2 showerheads and storage benches. The on-demand hot water heater servicing this bathroom means you will never run out of hot water! Oversized His and Hers closets are the proverbial icing on the cake to this primary retreat ("Hers" is the size of a bedroom!). Stepping outside to the cozy covered patio, you will be drawn to the heated, saltwater pool built new in 2023, along with a summer kitchen, electric fireplace, and outdoor TV entertainment, also featuring the cutest pool half bath (no more dripping wet indoor bathroom trips!). Complementing the pool area is a fully fenced backyard for the 2-legged and/or 4-legged kiddos, large privacy hedges, and NO REAR NEIGHBORS. This home comes complete with a whole house Sonos system and speakers playing music throughout the house, even on the back patio, along with a whole house security system including 2 cameras and a Ring doorbell through Vivint. The 2-car garage easily fits both of your vehicles and has amble overhead storage along with attic access. Freshly painted exterior in 2026! Roof is 2018, AC's are 2018, hot water heater is 2026, and an updated irrigation system supported by a private well. Zoned for the BEST SCHOOLS, you can walk to Lakemont Elementary! Middle school is Maitland Middle, and of course, Winter Park High School. Only one lucky family will be able to call this turn-key custom Winter Park home theirs. Make an appt today so that lucky family is yours!

890 N Phelps Avenue, Winter Park
$495,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code
Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park
$145,000
2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo 02 SubDv. ⋅ 32792 Zip Code
Welcom Home to your second/top floor 2-bedroom, 2 bathroom condo with brand new beautiful luxury vinyl floors throughout. This property has been a rental the last few years and is now ready for an owner or investor to make it their own. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options. Schedule your showing today!

7340 Swallow Run Unit 7340, Winter Park
$635,000
2 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Luxury Meets Timeless Design in the Heart of Winter Park. Welcome to this beautifully renovated 2-bedroom, 2-bath residence where thoughtful design and exceptional craftsmanship come together to create a truly move-in ready home. Located just minutes from the shops and restaurants of Park Avenue, this home offers a rare combination of modern luxury and classic Winter Park charm. The light-filled open floor plan is anchored by a stunning chef's kitchen featuring Taj Mahal quartz countertops, custom cabinetry, premium stainless steel appliances, and a dramatic waterfall island that serves as the centerpiece of the home. Wide-plank wood flooring flows throughout, while recessed lighting, designer fixtures, and carefully selected finishes add warmth and sophistication to every room. The spacious primary suite is designed as a private retreat with custom-built closet systems and a beautifully appointed en-suite bath showcasing dual vanities, designer tile, quartz countertops, and a custom frameless glass shower. The guest bedroom also features custom closet cabinetry and easy access to an equally impressive second bathroom finished with high-end materials and elegant fixtures. From the welcoming covered front porch to the abundance of natural light throughout the home, every detail has been carefully considered to create a space that is both inviting and functional. Whether you're looking for a full-time residence or a low-maintenance luxury home in one of Central Florida's premier communities, this exceptional Winter Park property delivers style, quality, and an unbeatable location.

531 W Swoope Avenue, Winter Park
$2,390,000
4 Beds ⋅ 5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
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
$4,750,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the product of meticulous vision, extraordinary craftsmanship, and an unwavering commitment to quality. Every space has been curated to create one of the most refined and meticulously executed homes to ever come to market in Winter Park. Situated on an expansive 15,000-square-foot homesite in the coveted Park Grove neighborhood, just moments from the boutiques and acclaimed dining of Park Avenue, the home immediately captivates with its striking architectural presence and a sweeping double-entry driveway. Beyond the front doors, a breathtaking foyer unfolds beneath soaring 22-foot ceilings, where an elegant, curved staircase, intricate marble mosaic flooring, oversized windows, and meticulous millwork establish a level of craftsmanship rarely found in today's market. Chevron-pattern engineered hardwood flooring extends throughout, complemented by exquisite natural marble and thoughtfully curated designer finishes at every turn. Designed to impress while remaining effortlessly livable, the grand living room features illuminated tray ceilings, a custom-built entertainment wall, and a sleek electric fireplace. The chef's kitchen is a true showpiece, anchored by dramatic Calacatta Viola marble countertops and backsplash, a complete Thermador appliance suite with paneled refrigerator and freezer, and a stunning ILVE range. An expansive butler's pantry with a second sink, double oven, warming drawer, dishwasher, and abundant preparation space elevates both entertaining and everyday functionality, while formal and casual dining spaces provide the perfect setting for gatherings of any scale. The primary suite is a private sanctuary designed for ultimate comfort, featuring its own coffee bar, an extraordinary custom dressing room. The primary also features a spa-caliber bath appointed with striking marble finishes, a dramatic illuminated walk-in shower, freestanding soaking tub, and Perrin & Rowe fixtures. A first-floor guest suite or dedicated office offers exceptional flexibility, while upstairs, three spacious en-suite bedrooms with walk-in closets are complemented by a hidden bonus room. Pocketing glass doors create a seamless transition to an exceptional outdoor retreat complete with a covered lanai featuring retractable screens, a fully equipped summer kitchen, resort-style pool and spa, expansive backyard, and professionally curated landscaping. Located just minutes from Park Avenue and surrounded by top-rated schools, this residence is more than a luxury home, it is a statement of artistry, craftsmanship, and timeless design that redefines what luxury new construction can be in Winter Park.

1525 Granville Drive, Winter Park
$2,099,990
4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury living. Defined by its striking architecture and refined contemporary design, the home makes an unforgettable first impression with a dramatic two-story foyer featuring soaring ceilings, a statement staircase with custom millwork, designer lighting, and LED accent illumination. Just beyond, a custom wine display with Dekton surfaces and integrated lighting, creates a sophisticated focal point while introducing the exceptional finishes found throughout the home. Designed for both everyday living and effortless entertaining, the expansive great room is anchored by a floor-to-ceiling custom millwork feature wall with integrated LED lighting and a sleek electric fireplace. Oversized sliding glass doors create a seamless connection to the outdoor living spaces, while the chef's kitchen serves as the heart of the home with custom cabinetry, quartz countertops, extensive under-cabinet LED lighting, a premium appliance package, and an oversized walk-in pantry. Located on the main level, the primary suite offers a peaceful retreat with direct access to the lanai and pool. The spa-inspired bath features dual vanities with backlit mirrors, a freestanding soaking tub, an expansive walk-in shower, and a custom walk-in closet. Upstairs, a spacious loft provides an ideal secondary gathering space complete with a stylish dry bar and built-in wine refrigerator. Three additional bedrooms offer generous accommodations for family and guests, each finished with the same exceptional attention to detail. Outdoor living is equally impressive with a massive covered lanai featuring a fully equipped summer kitchen, an additional electric fireplace, and generous space for dining and relaxation. Beyond, a resort-style pool with a spillover spa is complemented by an expansive backyard and side yard. Ideally located just minutes from Cady Way Park, AdventHealth Winter Park, and the shopping, dining, and charm of Park Avenue, this exceptional residence offers the perfect blend of luxury, convenience, and lifestyle. With craftsmanship and design rarely found at this price point, this is a home that is both timeless and unforgettable.

525 S Lakemont Avenue, Winter Park
$115,000
1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, Winter Park
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