Windermere Homes with Deed Restrictions Community Extras

Windermere Homes with Deed Restrictions Community Extras

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its enchanting lakes and lush landscapes, Windermere offers a serene retreat from the hustle and bustle of nearby urban centers while still providing easy access to the vibrant attractions of the Orlando area. This charming town boasts a rich history, friendly neighborhoods, and a strong sense of community, making it an ideal place to call home.

Windermere is renowned for its stunning homes, many of which are situated within deed-restricted communities. These neighborhoods are designed to maintain the aesthetic appeal and value of properties, ensuring that residents enjoy a well-kept environment. With regulations in place to uphold community standards, homeowners can take pride in their surroundings, fostering a sense of unity and pride among residents.

The homes in Windermere are as diverse as its residents, ranging from elegant waterfront estates to cozy family residences. Many properties feature luxurious amenities such as private pools, expansive outdoor spaces, and breathtaking views of the surrounding lakes. The community extras in these deed-restricted neighborhoods often include access to recreational facilities, parks, and walking trails, providing ample opportunities for outdoor activities and social gatherings.

Life in Windermere is enriched by its close-knit community spirit, where neighbors become friends and local events bring everyone together. With top-rated schools, vibrant shopping districts, and an array of dining options, Windermere offers a lifestyle that balances tranquility with convenience. Discover the charm of Windermere and find your dream home in this idyllic Florida oasis!

Newest Windermere Homes with Deed Restrictions Community Extras

$18,750,000
6 Beds ⋅ 9 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe Drive, Windermere
$327,000
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
$2,685,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

8142 Tibet Butler Drive, Windermere
$639,500
4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere
$1,500,000
5 Beds ⋅ 7 Baths ⋅ Lake Cawood Ests Rep SubDv. ⋅ 34786 Zip Code
5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool and Spa, Outdoor Kitchen hookup, granite Counter tops, built in double stainless-steel Oven, built in range. Master Bedroom 1st floor. This house also contains 2 suites, 1 on 1st Floor and another located at the 2nd floor with large screen enclosed balcony leading to the bonus room above the garage. 2nd floor also contain 2 open view lofts and theatre room. New roof in June 2023. Great location with easy access to Hwy 429, 408 and Florida Turnpike, with Schools, Supermarket, and Shopping Centers nearby. This property is also available for rent. Call today to schedule a viewing.

13503 Lake Cawood Drive, Windermere
$2,500,000
5 Beds ⋅ 5 Baths ⋅ Lake Davis Reserve A & B SubDv. ⋅ 34786 Zip Code
A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive five-bedroom residence spans over 4,600 square feet, offering a remarkable sense of privacy and seclusion while remaining right in the heart of Windermere. From the moment you enter through the custom iron doors, the craftsmanship and attention to detail are unmistakable. Expansive living spaces, beautiful wood-look porcelain flooring, custom millwork and thoughtfully designed lighting create a home that feels luxurious yet exceptionally comfortable. Custom-designed fireplaces throughout the home provide striking focal points and give each living space its own sense of character and warmth. The chef's kitchen features abundant cabinetry, generous counter space, a large prep island, granite countertops, water softener and a vented cooktop, all opening seamlessly to the main living areas. The spacious primary suite is conveniently located on the first floor and offers a true private retreat, complete with its own custom fireplace, oversized walk-in shower and soaking tub. Additional generously sized bedrooms ensure everyone enjoys ample space, while upstairs, a large flex room with custom built-in cabinetry provides an ideal setting for entertaining, relaxing or movie nights. A dedicated gym adds even more versatility to the floor plan. Outside, the home's sense of privacy becomes even more apparent. A covered lanai, with wiring for remote-controlled screens, opens to a secluded backyard retreat framed by mature tropical landscaping. Completed in 2022, the heated saltwater pool features a PebbleTec finish, multicolor LED lighting, dual sun shelves and an illuminated pergola waterfall. An extended pool deck, outdoor audio, summer kitchen with natural gas, exterior bathroom and app-controlled pool and landscape lighting create an exceptional environment for entertaining or simply enjoying the Florida lifestyle in complete comfort. As evening approaches, the west-facing backyard provides beautiful sunset views in front of your patio gas fireplace. That feeling of seclusion is what makes Lake Davis Reserve so special. Despite its peaceful, private setting, the home sits in the heart of Windermere, with Windermere Preparatory School, Windermere High School and zoning for Windermere Elementary all close by. Disney, SR-429 and premier shopping and dining are just minutes away. Opportunities to purchase in Lake Davis Reserve are exceedingly rare, with only 18 custom estate homes behind its gates. Beautiful in photographs and even better in person, this is a home that simply needs to be experienced. The privacy, scale, custom finishes and atmosphere are difficult to fully capture in photographs. If your buyers are looking for luxury, security and seclusion without sacrificing the convenience of Windermere living, 5526 Marleon Drive deserves to be at the top of their viewing list.

5526 Marleon Drive, Windermere
$519,000
3 Beds ⋅ 2 Baths ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code
Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no carpet, providing a clean, stylish, and low-maintenance living environment. The kitchen is equipped with a natural gas stove, perfect for those who enjoy cooking with gas. Recent improvements include a newer roof, newer A/C system, and freshly painted exterior, offering added comfort and peace of mind. From the moment you enter the welcoming foyer, you’ll appreciate the bright and open floor plan. Two secondary bedrooms are conveniently located toward the front of the home, providing separation and privacy from the primary suite. Continue down the hallway to the spacious formal living room and flexible additional living space, perfect for adapting to your family’s needs. The private primary suite offers a relaxing retreat with a walk-in closet, dressing area, and ensuite bathroom featuring dual sinks and a spacious standing glass shower. The kitchen seamlessly connects to the bright family and dining areas, creating an inviting space filled with natural light and perfect for everyday living and entertaining. The natural gas stove adds an extra touch of convenience for the home chef. Sliding glass doors open to the covered porch, extending the living space outdoors and overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the Florida lifestyle. Summerport offers an impressive array of resort-style amenities, including a community pool, fitness center, parks, playgrounds, fishing pier, and scenic walking trails. The community’s desirable location provides easy access to Windermere, Winter Garden, and Clermont, with an abundance of shopping, dining, entertainment, recreation, and highly rated schools nearby. Commuters will appreciate the convenient access to major roadways, including Highway 429, the Florida Turnpike, SR 408 (East-West Expressway), and I-4, making it easy to travel throughout Central Florida. Walt Disney World and many of Orlando’s world-renowned attractions are also just a short drive away. For Disney enthusiasts, enjoy the added bonus of being just minutes from Walt Disney World, with the opportunity to catch the nightly fireworks from select areas within the community. With vinyl flooring throughout and no carpet, a natural gas stove, a newer roof, newer A/C, freshly painted exterior, flexible living spaces, spacious backyard, desirable location, and exceptional community amenities, this home offers an outstanding opportunity in Summerport. Schedule your private showing today and come see all this home has to offer!

4844 Flint Road, Windermere
$410,000
3 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere Lake Reams Townhomes Phase 3 SubDv. ⋅ 34786 Zip Code
Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere
$445,000
3 Beds ⋅ 3 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code
Get ready to move into one of the best homes and areas right now! Located in the thriving, serene, and highly sought-out Windermere, this dream home is one of a kind! One would never believe it, but this home is an end-unit turnkey luxury town home! Just being able to see the stunning fireworks from Disney from your beautiful home is a dream come true! The schools in Windermere are all outstanding as well, be grateful for the fact that you are living in a tranquil area with some of the best schools in Florida! Filled with several upgrades such as siding all over the garage, a summer kitchen completely fenced with vinyl fence, a filter for the water system throughout the whole house, and this is only for outside the house! This is a dream home through and through! Now entering the newly painted dream home, one will notice the wide-open floor plan with ceramic tile throughout the first floor. The kitchen has granite countertops with splash backs and stainless-steel appliances while being surrounded by several windows, take in the natural light as you cook and enjoy some great meals. Having a separate laundry room as well as a half bathroom on the first floor, enjoy the peacefulness the home brings! Going upstairs to the second floor, see the three bedrooms and two bathrooms! Both bathrooms have granite countertops as well! The master bedroom has a walk-in closet and lots of room! Don’t let this opportunity pass by, a luxurious home located in an excellent area could be yours today!

11734 Water Run Alley, Windermere
$354,900
2 Beds ⋅ 3 Baths ⋅ Wickham Park 04 05 06 09 10 11 12 01 SubDv. ⋅ 34786 Zip Code
Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community of Windermere! This desirable END UNIT 2-bedroom, 2.5-bath townhome offers CAREFREE, LOW-MAINTENANCE LIVING with the added benefit of its end-unit location and an outstanding setting directly across the street from expansive OPEN GREEN SPACE and an ORANGE COUNTY COMMUNITY PARK. Designed for easy Florida living, the home features a recently painted interior and a comfortable, functional floor plan with two bedrooms, each offering its own private full bath. Step outside to the PRIVATE COURTYARD connecting the home to a DETACHED TWO-CAR GARAGE—creating an inviting outdoor space with added privacy and versatility. Major improvements have already been completed, making this home truly MOVE-IN READY: HVAC replaced in 2021, NEW ROOF in 2023, exterior painted in 2024, recently painted interior, and all toilets replaced in 2026. Wickham Park residents enjoy desirable COMMUNITY AMENITIES, including a COMMUNITY POOL and CLUBHOUSE, along with a sought-after Windermere location convenient to Walt Disney World, Orlando theme parks and attractions, shopping, dining, entertainment, schools, and major Central Florida roadways. Enjoy the best of the FLORIDA LIFESTYLE with the convenience and ease of low-maintenance townhome living. Whether you're searching for a PRIMARY RESIDENCE, SECOND HOME, or simply a low-maintenance Windermere home close to Disney and Orlando's world-famous attractions, this END-UNIT townhome delivers LOCATION, CONVENIENCE, OUTDOOR SPACE, and CAREFREE LIVING. With the big-ticket updates already completed, all that's left to do is move in and enjoy. Schedule your private showing today!

7430 Bentonshire Avenue, Windermere
$420,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph 2 SubDv. ⋅ 34786 Zip Code
Location, lifestyle, and move-in-ready convenience come together in this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Windermere/Lake Burden community. Perfectly positioned directly across from the community pool, this home offers the ideal combination of comfort, style, and resort-inspired living. A charming covered front porch welcomes you inside, where you'll find a bright, open floor plan featuring tile flooring throughout the main level and a versatile flex room that makes the perfect home office, study, playroom, or additional living space. The spacious living room is filled with natural light and features elegant French doors that open to your private outdoor retreat. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing solid surface countertops, stainless steel appliances, abundant cabinetry, and a large center island with breakfast bar that overlooks the main living area. Step outside to your own private, fenced brick-paver courtyard, an ideal space for morning coffee, evening gatherings, or relaxing outdoors. The detached two-car garage provides ample parking and additional storage. Living in Lake Burden means enjoying an exceptional lifestyle with amenities just moments from your door, including a resort-style community pool, clubhouse with kitchen and lounge, tennis courts, trails, fishing pier, boardwalk, playground, softball field, picnic areas, and beautiful Lake Burden. Whether you enjoy an active lifestyle or peaceful evenings by the water, this community truly has something for everyone. Conveniently located just minutes from Disney, Winter Garden Village, Downtown Windermere, top-rated schools, shopping, dining, and major highways, this home is ideal as a primary residence, second home, or investment property. Offering prime location, flexible living space, a private courtyard, two-car garage, this is a rare opportunity to own a move-in-ready home in one of Central Florida's most sought-after communities. Schedule your private showing today!

11425 Brownstone Street, Windermere
$2,240,000
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
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