Windermere Homes with Association Recreation - Owned Community Features

Windermere Homes with Association Recreation - Owned Community Features

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County that perfectly blends small-town charm with modern conveniences. Known for its stunning lakes and lush landscapes, Windermere boasts a vibrant community that is as welcoming as it is beautiful. With its rich history and a commitment to preserving its natural surroundings, this enchanting town offers residents a serene lifestyle surrounded by the breathtaking scenery of Florida's renowned lakes.

Windermere is not just about beautiful views; it’s a community that thrives on connection and recreation. Many homes in this area are part of Association Recreation - Owned Communities, which means residents enjoy exclusive access to a variety of top-notch amenities. Imagine unwinding by the sparkling community pool, playing a friendly game of tennis, or enjoying leisurely strolls along scenic walking paths—all within the comfort of your neighborhood. These communities foster a sense of belonging, making it easy to forge lasting friendships with your neighbors.

Families will appreciate the top-rated schools and an array of parks that offer playgrounds, picnic areas, and sports facilities. Windermere is also conveniently located near major highways, providing easy access to the bustling city of Orlando, world-class dining, shopping, and entertainment options.

Whether you’re seeking a peaceful retreat or an active lifestyle, Windermere has something for everyone. Discover the charm of this delightful town and find your perfect home in a community that truly feels like family. Welcome to Windermere—your new home awaits!

Newest Windermere Homes with Association Recreation - Owned Community Features

3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Windermere community. Offering a perfect blend of comfort, style, and convenience, this move-in-ready home is an exceptional opportunity in one of Central Florida’s most sought-after areas. Step inside to discover a thoughtfully designed interior featuring no carpet throughout, making everyday living and maintenance a breeze. The well-appointed kitchen showcases stainless steel appliances, stone countertops, a stylish backsplash, and abundant cabinet space. Ceiling fans throughout the home, including on the private balcony, add an extra level of comfort and convenience. A washer and dryer are also included. Residents of Lakeside at Lakes of Windermere enjoy an array of resort-style amenities, including a sparkling community pool, spacious fitness center, and beautifully maintained grounds—creating a welcoming environment to relax, entertain, and enjoy the Florida lifestyle. The location is truly hard to beat! Lakeside Village Center is directly across the street, putting everyday conveniences just steps from your front door. Just minutes from Walt Disney World, major highways, highly regarded schools, shopping, dining, and the charming community of Windermere, this condo offers an incredible combination of lifestyle and location. Whether you're searching for a primary residence, vacation home, or investment property, this exceptional condo checks all the boxes. Come see why this Lakeside at Lakes of Windermere gem deserves to be at the top of your list!

8156 Boat Hook Loop Unit 623, Windermere

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

4 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Welcome to Keene’s Pointe - 24-hour gated/attended golf community situated around The Golden Bear Club, an 18-hole Jack Nicklaus golf course featuring golf, tennis, fitness, dining and swimming. This custom home positioned on a private lot overlooking the sixth hole offers single-story living with a split floor plan. Designed with function in mind, the primary suite and office are situated on one side for added privacy, while three additional bedroom en-suites and the laundry room are located on the opposite side. A double-door invites you into the formal living and dining room with wet bar. Quality finishes throughout, including 8-foot interior doors, custom woodwork and detailed ceiling designs, custom drapes and power blinds, camera system, and much more. The kitchen is equipped with stainless appliances, granite countertops, cooking island, spacious breakfast bar, a hidden walk-in pantry, and a built-in desk area. The family room features a stone gas fireplace with built-in cabinetry and flows naturally into the bonus room with half bath boasting beautiful wood paneled walls, perfect for use as a media room, playroom, or game room. The primary suite includes a sitting area, a 16x13 custom closet, and a well-appointed bathroom with jetted tub, walk-in shower, and dual vanities with makeup area. The office features built-in cabinetry and classic wood detailing. Outdoor living is designed for entertaining and functionality, with heated pool and spa with rock waterfall and fountains and summer kitchen with grill, sink and an area for a beverage refrigerator. The fenced back yard is private with a putting green, mosquito misting system and fire pit. Enjoy nightly Disney fireworks visible from the living room, primary bedroom, kitchen, and outdoor living space. The low-maintenance exterior combines stucco and stone finishes, complemented by a paver driveway and a three-car side-entry garage. Conveniently located to shopping, dining, expressways, tourist attractions and top-rated public and private schools, this highly desired community has it all!

6102 S Hampshire Ct, Windermere

6 Beds ⋅ 7 Baths ⋅ Lake Burden South Ph 2 SubDv. ⋅ 34786 Zip Code

Welcome to lakefront living in Windermere! Set along the shores of Lake Burden, this impressive 6-bedroom, 6.5-bath home offers more than 5,100 square feet of living space, a 3-car garage, and a flexible layout designed for both everyday living and entertaining. Featuring the builder’s major upgrades and owned by just one owner since purchased directly from the builder, this home has been exceptionally well maintained. Inside, soaring ceilings and generous living spaces create an immediate sense of openness, while expansive sliding doors bring the beautiful lake views right into the heart of the home. The spacious kitchen is ready for everything from quiet family dinners to a full house of guests. With two primary suites — one downstairs and one upstairs — plus an additional first-floor bedroom, the floor plan offers great flexibility for guests, multigenerational living, or a home office setup. Upstairs, oversized bedrooms, a large bonus room, and private balconies provide even more room to spread out and enjoy the views. The outdoor space is just as special, featuring an extended covered lanai, outdoor kitchen, mature landscaping, and a peaceful lakefront backdrop. Morning coffee by the water, weekend barbecues, sunset dinners — this home was made for Florida living. Located in Lake Burden South, in the heart of Windermere, this home offers a peaceful residential setting with convenient access to shopping, dining, entertainment, and everything the area has to offer. Big home, beautiful setting, fantastic layout — and a lake view that never gets old. Come see this one in person!

7467 Lake Albert Drive, Windermere

5 Beds ⋅ 6 Baths ⋅ Isleworth West SubDv. ⋅ 34786 Zip Code

Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere

6 Beds ⋅ 5 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. Under Construction. SWEETWATER H - Our beautiful huge 2 story home, located on a conservation lot, with 6 Bedrooms and 4.5 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. The living area has an extension to the room, 9' hidden sliding glass doors and a huge lanai that runs the width of the home. Downstairs flex room works well as an office or study. Upstairs, find 5 large bedrooms most with walk in closets, 3 full baths, and a second laundry room,(that's right! 1 upstairs, and 1 downstairs). Common areas upstairs include a spacious bonus room with wet bar, and a second flex room that works well as a theatre room. SAMPLE IMAGES

14213 Crest Palm Avenue, Windermere

4 Beds ⋅ 7 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code

Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious guard-gated community of Keene’s Pointe in Windermere. Completely reimagined with exceptional attention to detail, this residence seamlessly blends timeless architecture with sophisticated contemporary design. From the moment you enter, soaring ceilings accented by exposed wood beams, expansive porcelain flooring, designer lighting, custom millwork, and walls of glass create an atmosphere of understated elegance and warmth. Designed for both everyday living and grand-scale entertaining, the impressive great room is anchored by a striking floor-to-ceiling porcelain fireplace with custom illuminated built-ins. The gourmet kitchen is beautifully appointed with premium Viking appliances, custom European-style cabinetry, quartz countertops, an oversized center island, and a separate catering kitchen that makes hosting effortless. The luxurious primary suite offers a peaceful private retreat featuring custom-designed walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, a walk-in shower, and exceptional designer finishes throughout. Spacious guest suites provide comfort and privacy for family and visitors alike. One of the home’s most remarkable features is the expansive climate-controlled lanai, thoughtfully designed as a true extension of the interior living space. Complete with a fully equipped summer kitchen, multiple gathering areas, and panoramic golf course views, it offers the perfect setting for year-round indoor-outdoor living and unforgettable entertaining. One of the very few homes on Valhalla Drive to feature a four-car garage, this residence provides exceptional space for automobiles, golf carts, and additional storage. The pool and spa overlook the beautifully manicured fairways, creating a tranquil backdrop that captures the beauty and serenity of one of Central Florida’s premier private golf communities. Located in one of Windermere’s most sought-after addresses, Keene’s Pointe offers 24-hour guarded security, picturesque tree-lined streets, and an exceptional lifestyle centered around the renowned Golden Bear Club. Residents enjoy convenient access to top-rated schools, upscale shopping, fine dining, world-class attractions, and Orlando International Airport. This is more than a luxury home. It is an exceptional opportunity to own a beautifully renovated residence in one of Windermere’s most distinguished private golf communities.

6719 Valhalla Way, Windermere

3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt Disney World! This beautiful 3 Bed + 2 Bath top-floor unit is located in the highly sought-after Horizon West area of Windermere, where comfort, convenience, and an exceptional location come together. Perfectly situated directly across from the clubhouse with easy elevator access, this bright and spacious home offers relaxing views from the private screened balcony overlooking the community's extensive amenities. The open, split floor plan features tile flooring throughout the main living areas, carpet in the bedrooms, and gorgeous crown molding. The lovely kitchen has granite countertops, 42" maple cabinetry, quality appliances, upgraded fixtures, and a large walk-in pantry. Lakeside's amenities include two resort-style pools, fitness center, volleyball courts, and a spacious clubhouse. Located just minutes from Disney, Lake Side Shoppes, Hamlin Town Center, tons of restaurants and top-rated schools! Call today to schedule a viewing!

8168 Boat Hook Loop Unit 724, Windermere

2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks SubDv. ⋅ 34786 Zip Code

Discover comfort and convenience in this well-appointed first-floor condo located in the heart of Windermere. Unit 109 offers a functional split-bedroom layout with inviting living spaces, generous natural light, and easy ground-level access. The kitchen opens seamlessly to the main living area, creating a welcoming flow that works equally well for everyday living or entertaining guests. The primary suite features a spacious walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or family living. Step outside to enjoy the covered patio — a perfect spot for morning coffee or winding down at the end of the day. Situated within a gated community with resort-style amenities, residents enjoy access to a pool, fitness center, playground, walking areas, and more. Conveniently located near shopping, dining, major roadways, and Central Florida attractions, this property combines low-maintenance living with an unbeatable location.

8180 Boat Hook Loop Unit 109, Windermere

4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This furnished former model home with many extras and amenities features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and garden tub. Enjoy peaceful evenings in the private back yard with spacious lanai, screened oversized pool and large yard. The fourth bedroom is currently being used as a den with French doors. NEW ROOF IN 2022, WATER HEATER 2020, two car garage with storage, and much more. Discover all this community has to offer, including The Golden Bear Club, a private 18-hole golf course designed by Jack Nicklaus offering golf, tennis, swimming, dining and clubhouse. Located close to shopping, dining, expressways and top-rated public and private schools, this home is perfect as a primary home or vacation home. Call today for you private viewing.

8525 Bowden Way, Windermere

4 Beds ⋅ 3 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. The Arlington perfectly blends luxury, functionality, and comfort. This brand new 2,740 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in. Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.3 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, a large center island, upgraded cabinetry, quartz countertops, a walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living. 2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden—ideal for entertaining or relaxing.

14353 Crest Palm Avenue, Windermere

3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.

9144 Isleworth Gardens Drive, Windermere

Start Your Search