Windermere Homes with Courtyard Exterior Features

Windermere Homes with Courtyard Exterior Features

Welcome to Windermere, Florida – a charming lakeside town nestled in the heart of Orange County! Known for its picturesque landscapes and serene atmosphere, Windermere offers a perfect blend of natural beauty and suburban living. With its stunning views of the Butler Chain of Lakes, this vibrant community is ideal for those who appreciate outdoor activities, from boating and fishing to hiking and biking along scenic trails.

Windermere is not just about its breathtaking surroundings; it boasts a tight-knit community with a rich history and a commitment to preserving its unique character. The town is dotted with quaint shops, delightful eateries, and lush parks, making it a wonderful place to call home.

One of the standout features of homes in Windermere is their elegant courtyard exterior designs. These charming homes often showcase inviting courtyards that serve as private retreats, perfect for enjoying the beautiful Florida weather. Imagine sipping your morning coffee surrounded by lush greenery or hosting evening gatherings under the stars in your own secluded oasis. The courtyard designs not only enhance the aesthetic appeal of the properties but also provide a seamless transition between indoor and outdoor living.

With a variety of architectural styles and sizes, Windermere's homes cater to diverse lifestyles and preferences. Whether you are a growing family seeking space or a couple looking for a cozy retreat, you will find the perfect home that reflects your unique taste. Come explore Windermere, where you can enjoy the tranquility of lakeside living while being just a short drive from the excitement of Orlando!

Newest Windermere Homes with Courtyard Exterior Features

$799,500
5 Beds ⋅ 5 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code
Welcome to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulously maintained 5-bedroom, 4.5-bathroom residence offers 3,036 square feet of elegant living space designed for comfort, functionality, and entertaining. A long private driveway and charming front courtyard create a grand first impression. Inside, you'll discover spacious living and entertaining areas filled with natural light, soaring ceilings, and an inviting floor plan that flows effortlessly from room to room. Whether hosting holiday gatherings or enjoying quiet evenings at home, every space has been thoughtfully designed for comfortable living. The gourmet kitchen serves as the heart of the home and features abundant cabinetry, generous counter space, and premium appliances. Included with the sale are the kitchen refrigerator, stove/range, built-in wine refrigerator, built-in espresso machine, washer, and dryer, allowing the next owner to move in with ease. One of this home's most distinctive features is its private detached suite, located separately from the main residence with its own private entrance and full bathroom. This versatile space is ideal as an in-law suite, private guest quarters, executive home office, fitness studio, creative workspace, or media room, offering endless possibilities while maintaining privacy from the main living areas. The second story offers generously sized bedrooms and comfortable accommodations for family and guests. The staircase and upstairs bedroom carpeting were replaced approximately 1.5 years ago, while one upstairs bedroom showcases beautiful hardwood flooring, adding warmth and character. Step outside into your own private backyard retreat. The fully fenced backyard provides both privacy and security while creating the perfect setting for outdoor entertaining, pets, or simply relaxing in your own personal oasis. The sparkling swimming pool offers exceptional flexibility, as it can be operated as either a traditional chlorine pool or converted to saltwater, depending on the owner's preference. Recent upgrades include a new pool motor and complete pool filter assembly installed in 2025, and all existing pool equipment is included with the sale. The existing wicker patio furniture also conveys, allowing the next owner to begin enjoying the outdoor living space immediately. The property has been meticulously maintained, with all HVAC units receiving regular service, one HVAC unit replaced, and the tile roof professionally maintained annually, including semiannual soft washing, tile replacement, and recementing as needed to preserve both appearance and longevity. The garage features epoxy flooring, an insulated garage door, its own air-conditioning unit, built-in shelving, and a workbench, while a backyard storage shed provides additional storage. Conveniently located just minutes from top-rated schools, championship golf courses, world-class dining, upscale shopping, Disney, and the Butler Chain of Lakes, this exceptional home offers the perfect blend of luxury, flexibility, and everyday convenience. Whether you're looking for multigenerational living, a private home office, or simply an impeccably maintained luxury residence, this Windermere gem is truly move-in ready.

11434 Rapallo Lane, Windermere
$5,999,000
5 Beds ⋅ 5 Baths ⋅ Aladar On Lake Butler SubDv. ⋅ 34786 Zip Code
Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates.

800 W 2nd Avenue, Windermere
$2,960,000
5 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Located within the prestigious guard gated community of Keene’s Pointe, this extraordinary estate offers a rare combination of luxury, privacy, and breathtaking views. Positioned on a premier lot with combined water and golf course frontage, this one-of-a-kind residence captures stunning vistas from every angle. On arrival, the expansive, multi-car, circular driveway provides ample parking for all, blending grand scale with ultimate convenience and estate-style privacy. Enter through custom wrought-iron gates into a private courtyard oasis, which makes for an unforgettable first impression. Boasting nearly 6,000 square feet of thoughtfully designed living space, the home features 5 bedrooms, including a detached casita/in-law suite with separate entrance, full bathroom, fridge and microwave. In addition, there is an equipped media room with half bathroom, also with microwave and fridge. A bonus room that can be used as a home office or gym is located off the downstairs primary suite. The gourmet kitchen is the heart of the home, showcasing custom cabinetry, granite countertops, premium appliances including a built-in Miele coffee machine, Wolf range, double oven, an incredible center island, wine cellar and generous gathering spaces. Expansive living and dining areas, with soaring ceilings, exquisite features such as, Venetian plaster, travertine floors, wood beams and custom built ins. The luxurious primary suite offers a private sanctuary with elegant finishes, dual custom closets, one with an additional washer and dryer set, a beautifully designed bathroom and private access to the office/gym/bonus rm. Three 2nd floor guest rooms include a potential second primary suite which provides exceptional accommodations for multigenerational living or visiting guests. Recently remodeled, this spacious suite has a full bathroom, walk-in closet and double door access to the balcony with its glorious golf course and water views. Outside, an oasis awaits. Floor to ceiling glass sliders in the living room offer uninterrupted views and provide access to the resort-style screened lanai featuring an expansive pool, sauna and outdoor fireplace. Indoor/outdoor speakers, security cameras, app controlled pool system with multi light show. A private sports court further enhances the lifestyle offered by this exceptional property. Keene’s Pointe is in the heart of Windermere and offers 24-hour manned security, access to the community boat ramp and optional membership to the Golden Bear Golf & Country Club, where golf, tennis, pickleball, gym, restaurant and events are included in the membership fee. Close to state-of-the-art medical facilities, theme parks, shopping, restaurants and high achieving schools, this exceptional estate represents a rare opportunity to own one of Windermere's most distinctive luxury residences.

6417 Lake Burden View Drive, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ Carrington SubDv. ⋅ 34786 Zip Code
Beautiful 3-bedroom, 2.5-bath townhome located in the highly desirable Carrington community. This well-maintained home features an open-concept floor plan, granite countertops, and a combination of tile and carpet flooring throughout. Enjoy your own private courtyard, perfect for relaxing, outdoor dining, or entertaining guests.Residents have access to community amenities including a sparkling pool and scenic walking paths. Conveniently situated near shopping, dining, major highways, and world-famous theme parks, this property offers both comfort and convenience. Whether you're looking for a primary residence or an investment opportunity, this exceptional townhome is a must-see and won't last long!

12357 Via Derna Place, Windermere
$424,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph I SubDv. ⋅ 34786 Zip Code
Welcome home to Lake Burden, one of Windermere's most peaceful and welcoming neighborhoods. This beautifully maintained 3-bedroom, 2.5-bath townhouse — built in 2013 — is move-in ready, waiting for you with the BEST PRICE in the area! Start your mornings on the charming front porch, where you can sip your coffee and watch the neighborhood come to life. Inside, the main floor covered with beautiful laid tiles features an open and airy layout. Cozy living room complete with built-in surround sound flows naturally into the heart of the home — the kitchen. You'll love the oversized island with quartz countertops, tall 42" espresso cabinetry, walk-in pantry and brand-new stainless steel appliances. A sunny dining room rounds out this inviting space, perfect for everyday meals or weekend brunches. A convenient powder room is also located downstairs for you and your visitors. Head upstairs to find the spacious primary bedroom, accentuated with tray ceiling, complete with walk-in closets and a private bath that includes a relaxing garden tub - perfect for unwinding after a long day. A dedicated laundry room is also conveniently located on the second floor. Two additional guest bedrooms are comfortable and share a well-appointed full bathroom. The two-car garage is detached, tucked at the rear, giving the front of the home clean curb appeal. With coated surface and a large driveway, it is connected to the home through a private courtyard with brick pavers — a lovely little outdoor space that's all yours. One of the best perks of life in Lake Burden? The HOA takes care of the outside — from the roof down to the neatly trimmed lawn — so you can spend your time enjoying the community pool and clubhouse instead. Tile roof just replaced at the end of 2025 along with fresh coat of exterior paint. Ground maintenance upkeep the neighborhood beautifully. Many other amenities also offered here, from clubhouse and beautiful community pool, children playground, even tennis courts. Take a walk around the neighborhood, especially along the lakeside path, and you'll discover a quiet, nature-filled setting where wild birds and local wildlife are regular visitors. Nightly fireworks display from Disney theme parks are also visible from this water's edge. Zoned for top-rated A schools at every level, this home truly has it all — great location with plenty of conveniences nearby, low maintenance, and a neighborhood that feels like home from day one. This is Florida living at its finest.

7435 Ripplepointe Way, Windermere
$1,090,000
4 Beds ⋅ 3 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code
Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor living. One of the greatest advantages of this property is that it has NO HOA, allowing you the freedom to enjoy your property without restrictive association rules or expensive monthly fees. Whether you are looking for a primary residence, vacation home, or investment property, this home offers endless possibilities. The property features a beautiful swimming pool and stunning water views, creating the perfect atmosphere to relax, entertain guests, and enjoy the Florida lifestyle all year round. The oversized lot provides plenty of space for family gatherings, outdoor activities, parking, or future improvements.

1407 Hempel Avenue, Windermere
$449,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph I SubDv. ⋅ 34786 Zip Code
Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Lake Burden South, where this immaculately maintained 3-bedroom, 2.5-bath END UNIT townhome delivers the space, style and location you have been searching for in the perfect Windermere location! Formerly the MODEL HOME for the community, this residence showcases UPGRADED FINISHES, TIMELESS DESIGN elements and a thoughtful layout that feels both functional and elevated from the moment you step inside. Crown molding, abundant natural light and move-in ready condition create a polished feel throughout, while the walkable community setting puts shopping, dining and everyday conveniences just moments away. The main floor offers defined yet connected living and dining spaces, creating a natural flow for both entertaining and daily living. The UPGRADED KITCHEN feels classic and refined with sleek granite countertops, 42” cabinetry topped with crown molding, STAINLESS STEEL APPLIANCES, pantry storage and a large ISLAND with bar seating. A wall of windows keeps the entire space light and bright, while the adjacent breakfast nook and direct access to the PRIVACY FENCED PAVER PATIO make indoor/outdoor living effortless. A convenient half bath for guests, plus a rear-facing 2-car garage, add even more functionality. Upstairs, the spacious PRIMARY SUITE is privately positioned on one side of the home and features a WALK-IN CLOSET along with a beautifully upgraded en-suite bath complete with dual sinks, a SOAKING TUB and a WALK-IN SHOWER with CUSTOM TILE SURROUND. Two additional bedrooms are situated on the opposite side of the second floor and share a full bath, while the LOFT area includes a built-in desk for added flexibility and storage. Residents of Lake Burden South enjoy access to a COMMUNITY POOL and an unbeatable Windermere location with easy access to Winter Garden Vineland Road, nearby lakes, shopping, dining, entertainment and area attractions including Disney parks. Whether you are searching for a beautiful primary residence, a vacation home near Central Florida’s top destinations or a strong investment opportunity, this townhome checks every box. Call today to schedule a tour!

7330 Brightland Street, Windermere
$440,000
3 Beds ⋅ 3 Baths ⋅ Windermere Sound Ph 2 SubDv. ⋅ 34786 Zip Code
Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool, tennis and basketball courts, playgrounds, and scenic ponds, all with lawn care included. Ideally situated just minutes from Disney World, premium shopping, fine dining, and top-rated schools such as Windermere High School, this home perfectly blends comfort, convenience, and luxury living in one of Orlando's most sought-after areas.

7612 Fairgrove Avenue, Windermere
$2,250,000
5 Beds ⋅ 4 Baths ⋅ Waterford Pointe Ph 02 Rep SubDv. ⋅ 34786 Zip Code
Virtually Staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**

2068 Roberts Point Drive, Windermere
$1,825,000
4 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
The Ultimate Entertainer’s Dream Home. Welcome to this exceptional custom-built courtyard estate by Bill Sauerwine, offering 4 bedrooms, 4.5 bathrooms, and 4,549 square feet of luxurious living in the highly sought-after Windermere area. Designed for both grand entertaining and everyday comfort, this stunning residence centers around a private courtyard pool, creating a true indoor-outdoor lifestyle. The expansive outdoor patio overlooks the sparkling pool, providing the perfect setting for hosting guests or enjoying peaceful Florida evenings in your own private retreat. Inside, the home showcases spacious, thoughtfully designed living areas, including a dedicated movie theater for an elevated at-home experience and a versatile separate living space complete with a full bathroom—ideal for guests, in-laws, or multi-generational living. A generously sized loft adds flexibility for a home office, game room, or additional lounge space. At the heart of the home, the gourmet kitchen is a true chef’s delight. Featuring a premium Sub-Zero refrigerator, gas cooktop, and built-in oven and microwave, this space blends high-end functionality with timeless design. Abundant counter space, a spacious breakfast bar, and soaring two-story ceilings create an open and inviting atmosphere perfect for both entertaining and everyday living. The luxurious primary suite serves as a private sanctuary, offering ample space and a spa-like bathroom designed for ultimate relaxation and comfort. Combining custom craftsmanship, elegant design, and resort-style amenities, this one-of-a-kind home delivers an unparalleled lifestyle in Windermere, just moments from premier dining, shopping, and convenient access to major roadways. Opportunity awaits in the highly coveted guard-gate community of Keenes Pointe. Expansive W.J. Sauerwine custom home offering the best value in the community.

11226 Macaw Court, Windermere
$2,950,000
5 Beds ⋅ 4 Baths ⋅ Down Point Sub SubDv. ⋅ 34786 Zip Code
Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.

4301 Down Point Lane, Windermere
$750,000
4 Beds ⋅ 4 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code
Unique opportunity to own a stunning Mediterranean-style home FOR AN INCREDIBLE PRICE, with WATER VIEWS and a PRIVATE COURTYARD, located in the highly sought-after, gated Belmere community. This exceptional residence truly checks all the boxes. Upon entry, you are welcomed by a WINDING STAIRCASE featuring decorative WROUGHT IRON DETAILS. Natural light fills the home, enhancing the thoughtfully designed split floor plan that offers both comfort and privacy. The home showcases a NEW spacious kitchen, a RENOVATED primary bathroom, and a RENOVATED en-suite bathroom in the second bedroom. The oversized primary suite is a true retreat, complete with a sitting area and private BALCONY overlooking WATER VIEWS. The en-suite master bath features dual vanities, a soaking tub, and a separate shower. Designed for both everyday living and entertaining, the home offers multiple gathering spaces including a spacious family room, formal living room, and an open loft area. SIGNIFICANT recent upgrades include the installation of TWO BRAND NEW high efficiency RUUD model A/C units (APRIL 2026), enhanced for modern comfort, peace of mind and delivering superior climate control throughout the home. This home has been freshly painted inside and out, offering a crisp, modern aesthetic. Enjoy the best of Florida living in your own backyard with water views, perfect for relaxing or entertaining. Additional highlights include a dual 3-car garage, brick paver driveway, and charming courtyard entry. This home would cost over $1,000,000 to build new—making it an incredible value. In three words: functionality, tranquility, and serenity. Located in a gated community with low HOA fees and excellent amenities, this home is zoned for top-rated schools and is conveniently close to dining, shopping, entertainment, and world-renowned theme parks. Experience the home anytime with our 24-hour 3D interactive tour. Showings are available for pre-approved buyers only—schedule yours today, as this home will not last!

910 Lascala Drive, Windermere
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