Windermere Homes with Deed Restrictions Community Features

Windermere Homes with Deed Restrictions Community Features

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County, where charm meets luxury in a serene lakeside setting. Known for its stunning landscapes and vibrant community, Windermere offers a unique blend of small-town warmth and modern amenities. With its close proximity to Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping, while still savoring the tranquility of suburban living.

Windermere is renowned for its beautiful homes, many of which are located in deed-restricted communities. These neighborhoods are designed to maintain the area’s aesthetic appeal and ensure a cohesive living environment. Homeowners benefit from well-maintained streets, lush landscaping, and a sense of pride in their community. The deed restrictions often include guidelines that protect property values and enhance the overall quality of life.

In addition to its stunning residences, Windermere boasts a variety of community features that cater to an active lifestyle. Enjoy the scenic beauty of the Butler Chain of Lakes, perfect for boating, fishing, and leisurely strolls along picturesque waterfronts. The town also offers parks, playgrounds, and recreational facilities, making it ideal for families and outdoor enthusiasts alike.

Windermere is not just a place to live; it’s a community where neighbors become friends and every day feels like a getaway. Discover your dream home in this enchanting town, where luxury meets comfort, and embrace a lifestyle filled with adventure and relaxation. Come experience Windermere—your perfect Florida retreat awaits!

Newest Windermere Homes with Deed Restrictions Community Features

11209 Macaw Court, Windermere
$2,695,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
An extraordinary expression of craftsmanship and architectural distinction, this custom Unnerstall residence was originally conceived as the builder's personal home, where exceptional attention to detail and thoughtful design are evident throughout. Beautifully positioned along the 4th hole of the Golden Bear Club's Jack Nicklaus Signature Golf Course, the estate captures sweeping fairway and tranquil water views within the guard-gated community of Keene's Pointe. Spanning 6,105 square feet of air-conditioned living space, the thoughtfully designed floor plan offers 5 bedrooms, 6 full bathrooms, 1 half bath, and an impressive collection of spaces tailored to today's luxury lifestyle. Soaring ceilings, elegant travertine flooring, exquisite Venetian plaster finishes, and distinctive architectural details create an atmosphere of timeless sophistication, while expansive windows invite natural light and showcase the picturesque surroundings. At the heart of the home, a beautifully appointed gourmet kitchen features rich custom cabinetry, stone countertops, professional-style appliances, and an expansive center island. Opening to a dramatic two-story family room, this inviting space creates a seamless flow for everything from intimate gatherings to grand-scale entertaining. Two dedicated offices, including a richly appointed executive study with custom built-ins and a fireplace, has exceptional flexibility, while a private fitness room and sun-filled bonus/game room provide additional spaces for recreation and relaxation. The expansive main-level primary suite is a sanctuary of comfort and elegance, featuring generous dual walk-in closets and a remarkable spa-inspired bathroom with a soaring two-story ceiling, architectural detailing, dual vanities, and a luxurious soaking tub. A second main-floor bedroom suite offers an ideal retreat for extended-stay guests, while three additional en-suite bedrooms provide beautifully appointed accommodations and privacy throughout the upper level. Beyond the interiors, the home's outdoor living spaces rival those of a private resort. An expansive covered lanai with automated retractable screens transitions effortlessly to a sparkling pool and spa, surrounded by lush, mature landscaping that creates a sense of seclusion while preserving the stunning golf course views. A distinctive copper-roofed gazebo, complete with a summer kitchen and bar, provides an unforgettable setting for alfresco dining, entertaining, and enjoying Florida's beautiful year-round climate. Additional appointments include an expansive paver driveway, a three-car garage with a dedicated golf cart entrance, and an array of custom finishes that reflect the home's exceptional quality and craftsmanship. Set amid the natural beauty of Keene's Pointe, with its winding streets, mature trees, and picturesque golf and water views, this remarkable residence offers an exceptional combination of architectural character, versatile living spaces, and the effortless elegance of the Windermere lifestyle.

11209 Macaw Court, Windermere

703 E 6th Avenue, Windermere
$3,450,000
4 Beds ⋅ 5 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterranean architecture meets the elegance of refined Florida living. Ideally along the shores of Lake Down, part of the desired Butler Chain of Lakes, this exceptional residence offers a rare opportunity to experience breathtaking water views, sophisticated interiors and an unparalleled boating lifestyle. From moment you arrive, exquisite stone detailing and custom wrought-iron double entry doors establish a sense of architectural distinction. Beyond the grand entrance, soaring ceilings, expansive living spaces, and thoughtfully curated design elements create an atmosphere of understated elegance and effortless sophistication. Designed for grand-scale entertaining and intimate gatherings, the home's gracious formal dining room provides an elegant setting for memorable occasions. At the heart of the residence, an expansive great room seamlessly integrates a gourmet kitchen, casual dining area, custom bar and inviting natural gas fireplace. Framed by captivating waterfront views, this exceptional gathering space offers the ideal balance of luxury, comfort and functionality. The main-level primary suite serves as a private sanctuary, offering serene views of Lake Down and a beautifully appointed en-suite bath featuring dual vanities, two spacious walk-in closets, a luxurious jetted soaking tub and an oversized travertine shower. An additional main-level bedroom provides exceptional versatility, ideally suited for guest accommodations, a private executive office, fitness studio or creative retreat. Upstairs, two generously proportioned bedrooms provide additional privacy and comfort. Thoughtfully reconfigured from the home's original three-bedroom upper-level layout, one of these bedrooms has been transformed into an exceptionally spacious retreat, complete with its private balcony. Abundant storage throughout the residence, a spacious laundry room with a recently updated washer and dryer, and a three-car garage further enhance the home's everyday convenience. Beyond the interiors, an extraordinary outdoor oasis awaits. An expansive covered and screened lanai, custom swimming pool, lush, mature landscaping and picturesque waterfront surroundings create a private resort-inspired setting. Whether hosting elegant outdoor gatherings, enjoying a leisurely afternoon poolside, or simply taking in the tranquil beauty of the lake, every moment invites relaxation and enjoyment. For boating enthusiasts, the property's enclosed boathouse offers a distinctive waterfront amenity, featuring a protected boat area and an inviting screened retreat. With direct access to the 13 interconnected lakes of the Butler Chain, an exceptional lifestyle of boating, waterskiing, wakeboarding, paddleboarding and waterfront exploration awaits just beyond your doorstep. Adding to its appeal is the timeless charm of Windermere itself. Enjoy the town's celebrated weekly farmers market, boutique shops, inviting restaurants, local brewery, wine market and cherished community events. All this is complemented by convenient access to Orlando's premier shopping, acclaimed dining destinations, world-renowned attractions and Orlando International Airport.

703 E 6th Avenue, Windermere

8325 Vivaro Isle Way, Windermere
$799,900
4 Beds ⋅ 3 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Virtually Staged. **POND VIEWS & DISNEY FIREWORKS!** Prepare to be impressed by this beautifully appointed 4-bedroom, 3-bath home in sought-after Windermere Isle, offering an inviting blend of stylish living, thoughtful upgrades, and a picturesque pond backdrop with a fountain and conservation views. Designed for both everyday comfort and entertaining, the open floor plan is enhanced by a decorative coffered ceiling in the dining room and a custom built-in entertainment feature that adds architectural interest and a polished focal point to the family room. The kitchen is equally impressive with granite countertops, tile backsplash, stainless steel appliances, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A first-floor bedroom with a full bath nearby provides wonderful flexibility for guests, while a creative nook beneath the stairs features a built-in desk, storage, and chalkboard wall, offering a fun space for homework, crafts, or play. Upstairs, **laminate flooring** extends throughout the stairs and entire second floor, where a spacious loft provides another inviting gathering space. The primary suite offers a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a freestanding soaking tub, and glass-enclosed shower. The outdoor setting truly sets this home apart. A screened lanai with summer kitchen overlooks the fenced backyard and tranquil pond with fountain, creating the perfect backdrop for dining, entertaining, or simply unwinding while enjoying Disney fireworks in the distance. The home is also equipped with solar panels, while the two-car garage features an EV charger and overhead storage. Upgraded landscaping enhances the home’s curb appeal. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, beautiful pond setting, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

8325 Vivaro Isle Way, Windermere

5021 Carillon Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm trees, and a covered front porch create a warm welcome. Inside, the foyer opens to a formal dining room with an elegant chandelier and a home office enclosed by glass French doors. Neutral tones, arched walkways, and wood laminate flooring are found throughout the main living areas. The spacious, open floor plan flows into the kitchen featuring shaker cabinets, granite countertops, a decorative backsplash, stainless steel appliances, a wine rack, and a large custom pantry with built-in storage. A dedicated laundry area with folding space adds convenience. The light-filled living room opens to a breakfast nook with a stylish rattan light fixture, bay window seating, and sliding glass doors leading to the pool. The private primary suite features double-door entry, a custom walk-in closet with extensive built-ins, and a spa-inspired bathroom with dual vanities, a large soaking tub, and a separate glass-enclosed shower. Three additional bedrooms and two full guest bathrooms with tub/shower combinations provide plenty of space for family and guests. Step outside to your own tropical retreat, complete with a screened-in pool, shaded gazebo, and vinyl fencing for added privacy. Updates include HWT 2023, HVAC 2019, and roof replacement in 2020. Conveniently located near entertainment, shopping and dining at Winter Garden Village, Walt Disney World, and major roadways including Florida's Turnpike, this home offers both comfort and accessibility. Schedule your private showing today!

5021 Carillon Lane, Windermere

8516 Danforth Drive, Windermere
$350,000
2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere - Lake Reams Townhomes SubDv. ⋅ 34786 Zip Code
Live Where the Magic Happens! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2.5-bath Townhome is located in the coveted Windermere area, perfectly situated just minutes from DISNEY’S BACKYARD!! A quiet placement towards the rear of the community, this unit provides peaceful views of the conservation and walking trail surrounded by majestic oak-lined streets that capture the charm and serenity of this sought-after community. Step inside to an inviting open-concept layout with tile flooring throughout the main level and a seamless flow between the Living, Dining and Kitchen areas, perfect for everyday living or entertaining. Stunningly renovated Kitchen features Granite countertops, Stainless Steel Appliances, Island, Stone Backsplash and Dinette space. Upstairs, all bedrooms provide comfort and privacy with newer carpet. The Primary Bedroom boasts a walk-in closet and ensuite Bathroom with garden tub/shower combo. The second Bedroom also features an ensuite bathroom. Relax outdoors in your private, fenced courtyard with artificial turf, the perfect spot for morning coffee or evening gatherings, leading to your detached 2-car rear entry garage. Have complete peace of mind with the big-ticket expenses that have been recently taken care of: Roof 2021, Hot Water Heater 2021, AC 2021 and new Plumbing shut off valves and main water pressure reducer valve 2024. Low HOA includes a sparkling Community Pool and walking trails throughout! Zoned for top-rated Schools and conveniently close to major Theme Parks, and fantastic Shopping and Dining in Lakeside Village and Winter Garden Village. Experience the best of Florida living: Quiet Nature, Disney Magic and Windermere Charm - all in one!

8516 Danforth Drive, Windermere

9601 Ambleside Drive, Windermere
$1,160,000
4 Beds ⋅ 3 Baths ⋅ Lake Down Shores Rep SubDv. ⋅ 34786 Zip Code
Virtually Staged. Move in. Reimagine. Or build new. Welcome to the Lake Down Shores lifestyle, where one-acre homesites and private community access to the Windermere Chain of Lakes offer a special opportunity. Set on a beautiful corner lot just a few homes from the lake, 9601 Ambleside Drive offers something increasingly difficult to find: a move-in-ready home today, an exceptional amount of land, and the flexibility to imagine something entirely different for the future. Situated on a full, flat acre, the property offers a generous front yard while still leaving an enormous backyard with incredible possibilities. Offering more than 3,000 square feet of single-story living, 4 bedrooms, 2.5 baths, and garage parking for four vehicles, the home has been refreshed with a roof replaced in 2021, one of two HVAC systems replaced in 2022, new interior and exterior paint, lighting and fixtures, updated bathrooms, new door hardware, new front door, new carpet in many rooms, plumbing updates, new water softener, and new water heater. Generously sized rooms and an interconnected floor plan make this a wonderful home for entertaining. Wood flooring complements the main gathering areas, while expansive near-floor-to-ceiling windows and Solatubes bring in abundant natural light. The family room connects to the kitchen and air-conditioned Florida room, which features casement windows and plantation shutters. Updated in 2020, the kitchen features abundant cabinetry with wood pull-out drawers, a large island, quartz countertops, stainless-steel Samsung and LG appliances, and a glass-top convection range. The spacious primary suite features an ensuite bath and walk-in closet, plus French doors leading to a flexible bonus room ideal for a home office, nursery, or sitting room. Three additional bedrooms are also generously sized, and a large laundry room provides additional storage. What truly distinguishes this property is the opportunity it presents. Enjoy the beautifully refreshed residence today, reimagine the existing home through a comprehensive transformation, or create an entirely new custom residence on this exceptional one-acre homesite. Additional features include a 2-car attached garage plus a separate 2-car detached garage, dedicated irrigation well, and septic system pumped in April 2026. Lake Down Shores residents enjoy access to the community’s private HOA boat ramp onto the Windermere Chain of Lakes. The seller, an experienced luxury home builder, has already developed concepts specifically for the property, including plans for both a complete renovation of the existing residence and new construction. These concepts offer a compelling vision of what this remarkable homesite could become while letting the next owner choose the path that best reflects their lifestyle. Conceptual plans are available for review and are presented for inspiration only; future improvements and construction are subject to applicable governmental and HOA approvals. To experience the builder’s design aesthetic, finishes, and portfolio of completed residences, please ask to view Web Link 1.

9601 Ambleside Drive, Windermere

8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere

7231 Sangalla Drive, Windermere
$1,348,000
5 Beds ⋅ 5 Baths ⋅ Casa Del Lago-Replat SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of interior space with a private pool and a location remarkably connected to the destinations that define Southwest Orlando. Recently refreshed, the residence features newly painted interiors and new light white oak luxury vinyl flooring throughout the home, excluding the bathrooms. The result is a lighter, more contemporary palette that carries naturally from room to room and gives the home an entirely new point of view. At the center of the main level, the kitchen combines granite countertops, an oversized island, stainless steel appliances, gas cooking and generous cabinetry and pantry storage. It opens to the living and breakfast areas, creating one continuous space for daily living and entertaining. A formal dining room and dedicated office add definition to the floor plan without interrupting its openness. The first-floor primary suite offers a spacious retreat with a walk-in closet, dual vanities and oversized walk-in shower. Additional bedrooms provide flexibility for guests, work or creative space, while the approximately 448-square-foot upstairs bonus room adds another layer of versatility for a media lounge, game room, fitness space or secondary living area. Outside, the architecture gives way to a distinctly Florida setting. A screened swimming pool, covered lanai and expansive paver deck extend the living space outdoors, complemented by low-maintenance turf and additional backyard space. A three-car garage completes the residence. Casa Del Lago is positioned within Windermere’s Lake Burden area, placing the home near Lakeside Village, Hamlin, Downtown Windermere, Golden Oak, Four Seasons Resort Orlando, Walt Disney World Resort and the Sand Lake Road dining district known as Restaurant Row. The location offers convenient access to shopping, dining, entertainment and major roadways while maintaining the privacy of a gated residential setting. A refreshed interior, private outdoor living and a Windermere address positioned at the center of it all.

7231 Sangalla Drive, Windermere

8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere

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