34786 Homes with Golf Carts OK Community Features

34786 Homes with Golf Carts OK Community Features

Welcome to the charming community of Windermere, Florida, nestled within the picturesque Orange County and boasting the coveted zip code 34786. Renowned for its lush landscapes and serene lakes, Windermere is a hidden gem that offers a unique blend of suburban tranquility and vibrant community life.

One of the standout features of this delightful area is its welcoming atmosphere for golf cart enthusiasts. Many homes in Windermere are part of communities where golf carts are not just accepted but encouraged! Imagine cruising through tree-lined streets, enjoying the gentle Florida breeze as you make your way to the local shops, parks, or the nearby golf courses. This lifestyle promotes a sense of community, where neighbors greet each other while taking leisurely rides in their golf carts.

The homes in Windermere are as diverse as they are beautiful, ranging from elegant single-family residences to luxurious estates. Many properties boast stunning views of the surrounding lakes and golf courses, creating a serene backdrop for your everyday life. The community also offers a plethora of amenities, including parks, walking trails, and access to top-rated schools, making it an ideal place for families and retirees alike.

With its rich blend of recreational activities, community spirit, and scenic beauty, the 34786 zip code is more than just a place to live—it's a lifestyle. Experience the charm of Windermere and discover how living here can elevate your everyday life. Come see why so many are proud to call this vibrant community home!

Newest 34786 Homes with Golf Carts OK Community Features

$19,500,000
6 Beds ⋅ 10 Baths ⋅ Isleworth Amd 03 SubDv. ⋅ 34786 Zip Code
Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

5192 Vardon Drive, Windermere
$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
$650,000
Windermere Town Rep SubDv. ⋅ 34786 Zip Code
A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone. Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas and county water already available. With no HOA, you have the freedom to design and build exactly the home you envision. Just a short walk to downtown shops, restaurants, and community events, this homesite combines small-town charm with unbeatable convenience. Opportunities like this don't last long — bring your builder and make it yours! Lots approx. 100' x 167'. Lots 19-22: $650,000 each | Lot 18: $700,000 | Lot 29: $750,000 | Lot 30: $800,000. Multiple offers on lots 29 & 30. Highest and best by Friday, 9/18 at 5:00 pm.

618 Ridgewood Drive, Windermere
$7,200,000
5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, 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 golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere
$3,189,000
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
$1,395,000
5 Beds ⋅ 4 Baths ⋅ Town Of Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

101 Lee Street, Windermere
$1,895,000
4 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, 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
$6,900,000
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
$6,650,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with a fully modernized media display featuring handmade wooden slats and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zero appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. Offering an impressive sense of scale, the expansive covered lanai features soaring volume ceilings and beautiful new oversized stone tile flooring that elevate the space's timeless architecture. A fully equipped summer kitchen overlooks the custom swimming pool and spa, while generous areas for lounging and dining create an inviting extension of the home's beautifully reimagined interiors. Together, they create the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise Drive, Windermere
$2,250,000
5 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of the most peaceful cul-de-sacs in the Keene's Pointe community. Perfectly positioned on a stunning water-view homesite with an expansive backyard and exceptional privacy, this home offers an incredibly flexible floor plan rarely found in today's market. The thoughtfully designed layout places the main living areas, private office, and spacious primary suite all on the first floor, creating the perfect setup for everyday living. Upstairs, three generously sized bedrooms and a large bonus room are tucked away, providing an ideal retreat for family or guests. Adding even more versatility, a completely separate detached in-law suite features a spacious bedroom and full bath, making it perfect for extended family, guests, a private home office, or live-in accommodations. Major updates provide peace of mind for years to come, including a brand-new roof, new glass sliders and windows, new septic system and drain field, A/C in 2024, and 2021 water heater. Keene's Pointe is one of Central Florida's premier 24-hour guard-gated communities, set along the pristine Butler Chain of Lakes. Residents enjoy beautifully maintained parks, playgrounds, walking trails, private boat launch access to Lake Burden, fishing piers, and a vibrant community atmosphere. Optional membership to the renowned Golden Bear Club provides access to a Jack Nicklaus Signature golf course, tennis and pickleball courts, a resort-style swimming pool, fitness center, and more. Families will also appreciate the community's proximity to top-rated schools, upscale shopping, fine dining, world-famous attractions, and Orlando International Airport.

9904 Brentford Court, Windermere
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