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$620,000
4 Beds 4 Baths Preston Square SubDv. 34786 Zip Code
Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago,New Roof, an exceptional offering in a premier Windermere community. Owner relocated .motivated seller. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.

6840 Helmsley Circle, Windermere

$455,000
3 Beds 3 Baths Vineyards/Horizons West Ph 4 SubDv. 34786 Zip Code
Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a playground area. The Vineyards of Horizon West community offers easy access to SR-429, SR-535, and US-192 and area employers, including Walt Disney World®, Orange County National Golf Center and Lodge, and Universal Orlando® Resort. The community is also close to several excellent dining and shopping options, including Winter Garden Village and downtown Windermere.

13733 Bressler Alley, Windermere

$426,000
3 Beds 3 Baths Wickham Park 04 05 06 09 10 11 12 01 SubDv. 34786 Zip Code
Welcome to this well-maintained 3-bedroom, 2.5-bath home offering 1,583 square feet of comfortable living space in the well established Wickham Park community. The home is in excellent condition and has been thoughtfully cared for, making it truly move-in ready. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting, and landscaping. Residents also have access to a community pool and clubhouse. Conveniently located approximately 5 miles from the Disney Parks and close to Winter Garden Village, this home offers easy access to shopping, dining, and entertainment while still providing a quiet residential setting.

12944 Garridan Avenue, Windermere

$3,450,000
4 Beds 6 Baths Casa Del Lago Rep SubDv. 34786 Zip Code
One or more photo(s) has been virtually staged. Experience elevated lakefront luxury living in Windermere with this professionally designed former model home ideally positioned on the shores of Lake Burden. Showcasing 4 bedrooms, 4 full baths, and 2 half baths — including a dedicated pool bath and club room bath — this stunning estate blends timeless architecture, designer finishes, and resort-style outdoor living. Inside, the palatial great room is framed by rich millwork, intricate ceiling details, wood flooring, a circular wet bar, and a stone-accented wine room, while dramatic 10-foot pocket sliding glass doors open completely to the expansive lanai for seamless indoor-outdoor entertaining. The chef’s gourmet kitchen impresses with a massive waterfall-edge island, chef-grade appliances, and two oversized walk-in pantries, flowing effortlessly into the formal dining room highlighted by a statement mirrored ceiling and the light-filled morning room. The first-floor primary suite offers tranquil lake views and a spa-inspired bath with a freestanding soaking tub and oversized walk-in shower. A private den and guest bedroom complete the main level. Upstairs, enjoy a spacious club room with wet bar, dedicated media room/home theater, two additional bedrooms, generous storage space, and a covered balcony overlooking the pool and Lake Burden. Step outside to your private backyard oasis featuring a custom resort-style pool and spa, sunken fire pit lounge, and a fully equipped outdoor kitchen with gas grill, sink, beverage center, and “L”-shaped bar seating — perfect for entertaining or relaxing while enjoying nightly sunset views and Disney fireworks over the water. Recent updates provide peace of mind, including exterior paint (2021), interior paint (2021 & 2025), new carpet (2021), and tankless water heater (2024). A rare opportunity to own a luxury waterfront estate in Windermere, this exceptional home delivers elegance, comfort, and unforgettable views in one of Central Florida’s most desirable lakefront communities.

12120 Montalcino Circle, Windermere

$1,699,000
4 Beds 5 Baths Providence SubDv. 34786 Zip Code
Experience refined lakefront living in this exceptional Windermere residence, ideally positioned on Little Lake Sawyer.  Set on an oversized homesite, this property offers a rare combination of privacy, natural beauty, and everyday luxury in one of Central Florida’s most desirable communities – Windermere.  The home features an open, light-filled floor plan with expansive windows, sleek flooring, and soaring cathedral-style ceilings, creating an inviting environment for both everyday living and entertaining. Thoughtful updates throughout include fresh interior paint, updated luxury bathrooms, and energy-efficient LED lighting.  Floorplan showcases 4 bedrooms plus an office ( could be 5th bedroom ) PLUS a rare and highly desirable feature, the attached in-law suite includes a private bedroom, full kitchen, and sun-filled living area, offering an elegant and flexible solution for guests, multigenerational living, or a secluded private retreat.  At the center of the home is a well-appointed chef’s kitchen with custom cabinetry, stainless steel appliances, solid surface countertops, and a walk-in pantry. Designed with entertaining in mind, the kitchen also offers granite countertops, dual dishwashers, and a wet bar complete with a wine refrigerator, ice maker, and refrigerated drawers.  The primary suite serves as a private retreat, featuring a balcony with sweeping lake views—perfect for enjoying morning coffee or unwinding in the evenings with distant Disney fireworks.  Additional highlights include surround sound wiring with built-in speakers in the main living area and the convenience of washer and dryer sets located on both the main and upper levels.  Outdoor living is elevated with a private boat dock and electrical lift, providing effortless access to boating and waterfront enjoyment on Lake Sawyer. The home has a very large yard and ready for a pool offering the opportunity to further customize your outdoor space.  Residents enjoy a well-maintained community with a pool and scenic walking paths, all while being just minutes from Windermere’s top-rated schools, dining, shopping, major highways, and world-class attractions.  This is more than a home—it’s a lakefront lifestyle defined by comfort, elegance, and the timeless appeal of living on the water in Windermere.

13120 Zori Lane, Windermere

$1,210,000
4 Beds 4 Baths Lake Cawood Estates SubDv. 34786 Zip Code
NEW PRICE - SELLER MOTIVATED! Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a three-car garage and exceptional privacy. A long driveway and inviting covered front porch create a warm welcome, while soaring ceilings and tranquil pool views greet you the moment you step inside. The open floor plan is ideal for entertaining and everyday living, featuring a grand living room with gas fireplace, formal dining room with wet bar, expansive family room, and a versatile game or bonus room perfect for a media space, home office, or guest retreat. The gourmet kitchen opens seamlessly to the breakfast nook and family room and is beautifully appointed with granite countertops, stainless steel appliances, built-in double ovens, and a large center island. The luxurious primary suite offers tray ceilings, a private fireplace, sitting area, and abundant natural light, along with a spa-inspired ensuite featuring dual vanities, a jacuzzi tub and two spacious walk-in closets. Three additional bedrooms are generously sized with large closets and a convenient cabana bath provides direct access to the outdoor living area. Step outside to your private resort-style retreat featuring a screened heated pool and spa, expansive paver patio, and a fully equipped summer kitchen designed for year-round Florida living and entertaining. Large sliding doors provide seamless indoor-outdoor flow, enhancing the home’s open and airy feel. Built in 2004 and extensively upgraded for modern comfort and peace of mind, this move-in-ready home features a brand-new roof (2024), new A/C system (2024), new well system (2025), new water filtration system, new saltwater pool system (2025), fresh interior paint (2025), updated lighting and fans (2024), and new kitchen and laundry appliances including a GE Café refrigerator and dishwasher and Samsung washer and dryer. The property operates on well and septic, providing efficiency and long-term value. Ideally located near top-rated dining, shopping, and everyday conveniences, this exceptional home is approximately 15 minutes from Walt Disney World and less than 30 minutes from Orlando International Airport. This rare opportunity combines luxury, space, and major system upgrades in one of Central Florida’s most desirable communities. Schedule your private showing today and experience the lifestyle you’ve been dreaming of.

13734 Lake Cawood Drive, Windermere

$1,550,000
5 Beds 5 Baths Keenes Pointe SubDv. 34786 Zip Code
Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect blend of elegance and modern convenience. Home Features: • Total 4 suites Bedrooms, 5 Baths, a Gym & a Office. • 3 spacious suites on the first floor. • 1 converted in-law suite on the second floor. • Dedicated office space for work-from-home convenience. • 3 Car garage with a huge driveway/ parking. • Open-Concept Living with high-end finishes throughout including plantation shutters. Home also features a whole Home Water Filtration System. • Gourmet Kitchen: • Expansive granite island with seating. • Built-in appliances & wine bar. • Double-door dishwasher & trash compactor. • Touchless faucet & instant filtered boiling water. • Natural gas cooktop & pantry. Recent Replacements: • New Gas Water Heater (November 2024). • New Roof (September 2023). • Fairly New Air Conditioning Units (September/2019). Outdoor Oasis – Perfect for Entertaining! • Lanai with unobstructed picture screen for breathtaking views. • Heated pool with built-in bench & jets. • Full Summer Kitchen: • Ice maker, dishwasher, BBQ grill. • Hibachi Japanese grill & pizza oven. • Built-in Gas Fire Pit – perfect for cozy evenings • 5-Person Infrared Jacuzzi Sauna. • Outdoor Bath & Shower for convenience. Prime Location & Community Perks: • A-rated school zone. • Close to theme parks, fine dining, and shopping. • Keene’s Pointe Amenities: • Guarded gate, parks, trails, and clubhouse. • Optional Membership to The Golden Bear Club: • Championship golf course, tennis courts, gym, pool, restaurant & more. Stop searching—this home has it all! Experience luxury, privacy, and resort-style living in one of Windermere’s most exclusive communities. Schedule your private showing today! ****Feel free to Text Listing Agent asking the video of the property****

6001 Caymus Loop, Windermere

$2,745,000
5 Beds 6 Baths Isleworth West SubDv. 34786 Zip Code
Nestled within the private gates of Isleworth West, a secluded enclave within the prestigious Isleworth community, this five-bedroom residence offers serenity and privacy against a backdrop of tranquil preserve views. Encompassing more than 6,200 square feet of thoughtfully designed living space, the home showcases elegant French country architectural styling, soaring volume ceilings, and exceptional custom finishes throughout. At the heart of the home, an inviting central gathering area seamlessly connects the center-island kitchen, casual dining space, and a warm, light-filled family room—ideal for both everyday living and effortless entertaining. The kitchen is appointed with custom light-toned cabinetry, granite countertops, and a full suite of Viking and Sub-Zero appliances, combining timeless design with exceptional functionality. Formal living and dining rooms provide graceful settings for more elevated occasions. The home office serves as a true standout, featuring a dramatic cathedral ceiling accented by exposed wood beams and richly crafted built-in cabinetry—an inspiring retreat for work or study. The expansive primary suite on the main level offers a serene escape complete with pool access, an expansive walk-in closet, and an elegant bath highlighted by exquisite dual vanities. Upstairs, a spacious bonus room currently configured as a home theater provides a versatile space for entertainment or relaxation, opening to a large balcony featuring picturesque views of the surrounding nature preserve. Designed to embrace Florida living, the screened and covered lanai features a summer kitchen and fireplace and opens effortlessly to a sparkling open-air pool and spa. Completing the residence is a three-car garage, offering ample space for vehicles and storage. An exceptional offering in one of Isleworth’s most private settings, this residence blends architectural character, refined interiors, and resort-style outdoor living in a truly distinguished environment.

6248 Louise Cove Dr, Windermere

$1,750,000
4 Beds 5 Baths Harbor Isle SubDv. 34786 Zip Code
Under contract-accepting backup offers. Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of amenities, right at home. Through the grand entrance, the formal living room is bright and chic, with ceiling niche lighting and picturesque windows to enhance the details of this beautifully-crafted estate. Formal living, wine bar, and fabulous chef’s kitchen with breakfast nook with built-ins, plus generously-sized family room enhance your largest gatherings and everyday living. The chef’s kitchen with island and preparation sink feature gas cooktop with hood, stainless appliances, and double ovens. The vast owner’s retreat spans the entire south wing of the house and includes a lovely sitting area, French doors to the patio, large walk-in closets, and a spa-like bath with double vanities, jetted tub, and large shower. Two additional bedrooms are located on the opposite side of the house on the first floor with a Jack and Jill bath and a secondary bed and bath are upstairs off a large game room. The resort-style pool and spa with mammoth paver patio decking and summer kitchen offers a private outdoor retreat under a large screen enclosure. New carpeting and new Plantation shutters just installed. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.

3013 Seigneury Drive, Windermere

$1,535,000
2 Beds 2 Baths Kelso On Lake Butler SubDv. 34786 Zip Code
Experience refined, low-maintenance lakefront living in this 2-bedroom, 2-bathroom custom home with dedicated office, built in 2016 and offering approximately 2,034 square feet of thoughtfully designed space. The open-concept layout features a bright great room, stylish kitchen, and flexible dining area that create an effortless flow for both everyday living and entertaining. The private primary suite includes a spacious bedroom, generous closet space, and a well-appointed ensuite bath, while the secondary bedroom and full guest bath provide comfortable accommodations for family or visitors. A separate office offers the perfect quiet space for working from home, hobbies, or a potential guest area. Outdoor living shines with a large patio ideal for dining, lounging, and gatherings, along with a private boat dock equipped with a boat lift for easy access to the water. A 2-car garage with dedicated golf cart parking adds convenience and extra storage, making this home as practical as it is inviting. Call today for a private viewing in-person or virtually of this amazing property.

1134 Kelso Boulevard, Windermere

$710,000
4 Beds 4 Baths Windermere Trls Ph 5a SubDv. 34786 Zip Code
Beautiful 4 Bedroom, 4 Bathroom Home in Highly Sought-After Windermere Trails ! Welcome to this exceptional single-family residence located in the desirable Windermere Trails community. This well-appointed two-story home offers a functional and spacious layout with all four bedrooms located on the main floor, plus an expansive second-floor loft with a full bathroom and walk-in closet, perfect as a bonus room, media room, or private guest suite. The open-concept main living area features a bright and inviting living room with built-in display cabinetry, a gourmet kitchen, and a cozy breakfast nook, complemented by a separate formal dining room ideal for gatherings. The kitchen is a chef’s delight with granite countertops, double ovens, a butler’s pantry, and a large central island. The primary suite, conveniently located on the main level, includes an ensuite bath with upgraded finishes. Three additional guest bedrooms and two full bathrooms complete the main floor. All bathrooms feature granite countertops for a cohesive upscale look. Built in 2014, this home showcases a tile roof for added durability and curb appeal. The garage includes a built-in sink, an accessibility ramp, refrigerator providing excellent storage and utility options. As an added bonus, the home is being offered fully furnished, including living room furniture, bedroom sets, side tables, and even a patio swing—making this truly a move-in-ready opportunity. Located in a top-rated school zone from elementary through high school, this home is not one to miss. Experience the beauty and convenience of Windermere Trails living—schedule your private showing today!

9047 Reflection Pointe Drive, Windermere

$305,000
3 Beds 2 Baths Lakeside/Lks/Windermere SubDv. 34786 Zip Code
One or more photo(s) has been virtually staged. Step into this beautifully maintained second -floor unit in the sought-after Lakeside at Lakes of Windermere community. Ideally located Directly across from the community pool and clubhouse. Offering 1,455 square feet, this 3-bedroom, 2-bathroom home is designed for effortless Florida living—with timeless details and upscale finishes throughout. The spacious kitchen features granite countertops, ample cabinetry, and a custom walk-in pantry, while the open-concept layout seamlessly connects the living and dining areas. Relax on your screened-in balcony, overlooking the sparkling community pool. Your primary suite offers a private retreat with dual vanities, separate shower, and a custom walk-in closet. Two additional bedrooms are filled with natural light, ideal for guests or a home office. Includes appliances, new Laundry Machines (2026), new AC Condenser (2026), New Range (2026) 2 parking spaces (1 assigned + guest), and valet trash. HOA covers water, sewer, security, and amenities. Convenient Windermere location near Disney and Winter Garden Village.

8168 Boat Hook Loop Unit 207/714, Windermere

$2,895,000
4 Beds 5 Baths Lake Down Estates SubDv. 34786 Zip Code
Under contract-accepting backup offers. Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.

10870 Bayshore Drive, Windermere

$1,274,000
5 Beds 4 Baths Westside Village SubDv. 34786 Zip Code
This exceptional residence offers a rare combination of contemporary design, smart technology, functionality, and lifestyle. Fully renovated and thoughtfully planned with meticulous attention to detail, the home showcases a high level of craftsmanship and a cohesive modern aesthetic throughout. Luxury vinyl flooring extends throughout the entire home, providing durability, comfort, and a refined contemporary look. Custom millwork is a defining feature of the property, present in the fully planned kitchen, custom bathroom vanities, TV feature wall, and architectural wood paneling that adds warmth, texture, and visual continuity across all living spaces. Imported Italian wallpaper enhances every room, elevating the interior with a sophisticated and curated finish. The gourmet kitchen is professionally designed with bespoke cabinetry, a spacious waterfall island, premium stone countertops and backsplash, and a complete Samsung appliance package, seamlessly blending performance, technology, and modern design. Custom window treatments are installed throughout the home and integrated with smart home automation, offering voice control via Alexa for effortless daily living. The functional and highly desirable layout features five bedrooms, with the primary suite conveniently located on the main level, providing privacy and ease of access. All bedrooms include custom-designed walk-in closets, fully built out with tailored cabinetry for optimal storage, organization, and functionality. Bathrooms offer a spa-inspired experience with custom millwork vanities, large-format tile, frameless glass showers, rainfall showerheads, body jets, and modern matte-black fixtures. A striking custom staircase serves as both a design statement and architectural feature, enhanced with motion-activated LED lighting that illuminates each step. The dramatic double-height entry is highlighted by a contemporary chandelier and glass railing, allowing natural light to flow seamlessly between levels and creating a strong first impression. Designed for entertaining and elevated living, the home includes a dedicated wine bar, complete with built-in wine storage, wall-mounted racks, custom cabinetry, and a temperature-controlled wine refrigerator perfect for hosting guests or enjoying intimate gatherings. The outdoor living area completes the lifestyle experience with a heated pool, clean architectural lines, and low-maintenance landscaping. A private patio features a custom mini putting green, offering a resort-style atmosphere ideal for relaxation and entertainment, complemented by tranquil water views. Located in the desirable Town of Windermere, the home is situated within one of Central Florida’s most sought-after communities, known for its scenic lakes, family-friendly environment, and convenient access to shopping, dining, and major roadways. The area is served by highly regarded public schools and is close to prestigious private institutions such as Windermere Preparatory School. This move-in-ready residence stands out for its design, quality, technology, and location—an exceptional opportunity for buyers seeking a refined and thoughtfully curated home.

12779 Westside Village Loop, Windermere

$716,000
4 Beds 4 Baths Enclave At Berkshire Park SubDv. 34786 Zip Code
Beautifully updated home with peaceful pond views from the front creates an idyllic setting to call home. High end finishes can be found throughout including: engineered white oak hardwood floors, designer light fixtures, fully remodeled transitional kitchen with quartz counters and stainless steel appliances, luxuriously updated baths, laundry room, and family room with custom built ins and electric fireplace for added warmth and ambiance. Major upgrades provide peace of mind: new roof (2021), new HVAC systems for both levels (2023 & 2025), and a fully re-screened lanai (2025). Backyard landscaping refreshed in 2024 with a low-smoke fire pit, perfect for outdoor entertaining. This home will accommodate any style of living with it’s modern updates, thoughtful improvements, and scenic water views. You’re Home!

13912 Darchance Road, Windermere

$750,000
3 Beds 3 Baths Summerport Ph 03 SubDv. 34786 Zip Code
Welcome to 5018 River Gem Avenue, an exceptional one-story pool estate with serene pond views in the prestigious Summerport community of Windermere, perfectly positioned for luxury living, convenience, and resort-style enjoyment — only 20 minutes from the Disney Theme Parks, Disney Springs, premier shopping, dining, and major roadways. This 3-bedroom, 2.5-bath, 2,379 sq ft showpiece features a refined split floor plan with 10- and 12-foot ceilings, abundant natural light, and new tile and marble flooring throughout (no carpet). Custom interior finishes elevate the living spaces, while tranquil water views grace multiple rooms. Recent high-end improvements include a new pool screen enclosure (Jan 2025), vinyl/iron fencing (2023), roof (2018), tankless water heater (2017), HVAC (2017), and Kinetico water softener & reverse osmosis system (2023). A natural gas line is in place for future chef-ready upgrades. The gourmet kitchen boasts granite countertops, stainless steel appliances, wood cabinetry, a raised breakfast bar, and a cozy nook overlooking the great room and pool. Designed for effortless entertaining, the interior flows to the travertine-finished, screen-enclosed lanai, extended patio, and solar-heated saltwater pool with a new pool pump (2025) and salt cell (2024, with warranty) — all framed by calming pond vistas. The primary suite is a private sanctuary with a tray ceiling, dual walk-in closets, garden tub, electronic window treatments, and direct access to outdoor living. Additional highlights include a pool-access half bath, oversized split garage with high ceilings and deep storage, and impeccably landscaped, low-maintenance grounds with mature fruit trees (lemon, lime, avocado, guava and papaya). Living in Summerport means enjoying an unparalleled lifestyle. Residents have access to the community’s exclusive clubhouse and pool complex with fitness center and social spaces at Summerport Residential POA Clubhouse. Meandering walking and biking trails, parks, and green spaces provide daily opportunities for outdoor recreation just steps from home. The nearby Summerport Neighborhood Park offers playgrounds, picnic areas, and scenic paths for all ages. For everyday convenience, Cornerstone at Summerport village-style shopping is just around the corner, providing groceries, cafés, services, and more. Downtown Windermere and Winter Garden’s vibrant boutiques, specialty dining, and lifestyle retail are also moments away, with premier destinations like Winter Garden Village and The Grove reachable in under 15–20 minutes. This remarkable home blends luxury, comfort, and lifestyle — ideal as a primary residence, second home, or Florida retreat with everything you want just minutes away.

5018 River Gem Avenue, Windermere

$3,195,000
6 Beds 6 Baths Kelso On Lake Butler SubDv. 34786 Zip Code
Under contract-accepting backup offers. Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated access to Kelso's private boat ramp on the prestigious Butler Chain of Lakes. This convergence of private waterfront with chain-of-lakes connectivity creates unparalleled boating and recreational opportunities found in few lakefront estates. The expansive grounds and recent outdoor enhancements create an entertainer's paradise that is second to none! A newly upgraded outdoor bar and grill area, resort-caliber pool and spa, and sweeping lawn frame breathtaking sunset views over the water. Boasting 6 bedrooms, 6 bathrooms, 3 car garage, and more than 6,000 square feet of living space, this custom estate offers privacy, scale, and unforgettable lakefront views from nearly every room. From the moment you arrive, the chic coastal architecture, circular drive, and sprawling presence command attention. Step inside to dramatic 25-foot ceilings in the living room with a two story stacked stone fireplace and walls of glass that dissolve the boundary between interior luxury and lakefront beauty. An adjacent sun-filled flex room provides tranquil views of Lake Davis, while the completely remodeled chef's kitchen, with its oversized island, custom cabinetry, high end appliances, adjacent indoor bar and generous family room, is designed for both intimate moments as well as large scale entertaining. The main level's thoughtfully designed primary suite offers serene seclusion with a private sitting area, spa-inspired bathroom, and expansive walk-in closet, complemented by a convenient main-floor office. Upstairs, five additional oversized bedrooms, a versatile loft, dedicated gym, and stunning rooftop deck provide space for every lifestyle need. Recent upgrades give you the ultimate peace of mind, including upgraded lighting throughout, a new roof with GAF Golden Pledge 20 year workmanship warranty, three newer A/C units, updated water heater, Hayward pool heater, new dock motor, new sprinkler system with a lake-fed pump, and a transferable Massey termite bond. Minutes from Disney's back gates, top-tier schools, and Windermere's celebrated shopping and dining, yet completely private and serene—this is lakefront living without sacrifice. Your Kelso compound awaits!

5538 W Lake Butler Road, Windermere

$3,350,000
4 Beds 4 Baths Lakes SubDv. 34786 Zip Code
Under contract-accepting backup offers. Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.

10577 Down Lakeview Circle, Windermere

$830,000
4 Beds 3 Baths Westover Club Ph 01 44/139 SubDv. 34786 Zip Code
Welcome home to modern luxury living in the gated community of Westover Club. This impressive residence, situated on a generous 1/3-acre parcel, has been COMPLETELY updated, top to bottom/front to back with NO expense spared to offer a fresh, neutral, contemporary, move-in ready experience. The interior has NO CARPET and features NEW/2024 European white oak engineered wood flooring that flows seamlessly throughout the main living areas and the wet areas have NEW/2024 porcelain tile. The home also feels light, bright and expansive thanks to the installation of NEW/2024... FAS energy efficient and hurricane rated windows and sliding doors that flood the space with natural light. The floor plan also includes a formal living and dining room, the latter adorned with decorative wainscoting. At the heart of the home, the kitchen and family room have an eat-in area that maximizes space and offers uninterrupted views of the beautiful pool area. The kitchen features NEW/2024/2026 stainless steel appliances, NEW/2024 solid wood Wellborn cabinetry, Lemurian blue granite countertops, and a breakfast bar that serves as the social hub of the house. The split floor plan ensures ultimate privacy, anchored by a large primary suite with direct access to the pool, a connected private office, and two walk-in closets. The primary bath and all guest bathrooms have been updated with NEW/2024 modern tile work and flooring, NEW/2024 vibrant white cabinetry (Primary has NEW/2024 solid wood Wellborn cabinetry) with Lemurian blue granite or marble countertops, elevating the spa-like atmosphere. Upstairs, a versatile bonus room awaits your vision...perfect as a 5th bedroom, gym, or media room. Outside, enjoy the Florida lifestyle on the expansive lanai featuring a fully screened-in and NEWLY/2024 resurfaced pool and spa, surrounded by a fully fenced backyard that offers total tranquility, garden space and many fruit trees. Other recent updates include the Roof, AC, and water heater. For peace of mind and convenience the home also has a 5-room generator connection and fiber U-verse Cat 6 technology. Located minutes from top-rated schools, fine dining, and major thoroughfares, this move-in-ready home is the one you’ve been looking for. Schedule your showing today!

9495 Westover Club Circle, Windermere

$692,000
4 Beds 2 Baths Enclave SubDv. 34786 Zip Code
New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and durability. The layout includes 4 bedrooms and 2 bathrooms, plus a large dedicated office, ideal for working from home or for those seeking a quiet, flexible space. Designed for comfortable single-level living, this home is perfect for buyers who appreciate the convenience of no stairs while still enjoying an open and grand feel. Located in the heart of Windermere, the property offers outstanding accessibility, with shopping, dining, and daily amenities just minutes away. AC WAS INSTALLED IN 2022,3.5 TONS. The primary suite is a true retreat, featuring an elegant tray ceiling, serene pond views with screen patio, and direct access to the backyard, allowing you to step outside and enjoy the peaceful water scenery at any time. Both the primary bedroom and the living room overlook the pond, bringing nature and calm into everyday living. This is an ideal home for those seeking privacy, convenience, and refined single-story living in a prime Windermere location.

17514 Black Rail Street, Windermere

$990,000
4 Beds 4 Baths Palms At Windermere SubDv. 34786 Zip Code
One or more photo(s) has been virtually staged. Welcome to the Arlington with Bonus a stunning 4-bedroom, 4-bathroom home offering 3,123 square feet of beautifully designed living space. Thoughtfully crafted with an open-concept layout, this home is perfect for both everyday living and entertaining. Step inside to find soaring 10-foot ceilings on the first floor and durable laminate flooring throughout, creating a seamless and modern feel. The gourmet kitchen is a true centerpiece, featuring elegant quartz countertops, a large center island, and abundant cabinet space—ideal for hosting and meal preparation alike. The spacious floor plan includes a versatile second-floor bonus room complete with a full bath, perfect for a guest suite, media room, or home office. The elegant primary bathroom offers a spa-like retreat, featuring a spacious walk-in shower with a luxurious rain shower head and a dual vanity with ample counter space. Situated on a desirable conservation homesite, this property offers added privacy and serene natural views. The oversized garage provides ample room for vehicles, storage, or even a workshop. This home effortlessly combines style, functionality, and comfort.

14285 Crest Palm Avenue, Windermere

$599,000
4 Beds 3 Baths Summerport SubDv. 34786 Zip Code
Welcome home to this beautiful residence situated on a quiet cul-de-sac along a tree-lined street in the highly desirable Windermere community of Summerport. Perfectly positioned within the neighborhood, this beautifully maintained and updated 4-bedroom, 3-bath POOL home offers a thoughtfully designed floor plan, exceptional flexibility, and abundant storage throughout—every bedroom features a walk-in closet. From the moment you arrive, the inviting front porch sets the tone for relaxed Florida living. Inside, the expansive open-concept layout is enhanced by crown molding, laminate wood flooring, upgraded light fixtures, and abundant natural light, creating a warm and welcoming atmosphere. Upon entering the home, you are immediately greeted with views of the pool, creating a seamless connection between indoor and outdoor living spaces. The centrally located kitchen serves as the heart of the home and features quartz countertops, stainless steel appliances, 42-inch cabinetry, generous cabinet and counter space, and a walk-in pantry. The open layout provides clear views of the living room, kitchen, dining, and pool areas, making it easy to stay connected while cooking, hosting, or spending time together. The primary suite is a private retreat, offering two walk-in closets and a spacious en-suite bathroom with dual vanities, a walk-in shower, and a soaking garden tub. Downstairs are two additional bedrooms—each with walk-in closets—and a full bathroom, creating a functional layout. Adding to the home’s versatility, the fourth bedroom and third full bathroom are located upstairs above the garage, offering a flexible space ideal for a guest suite, mother-in-law suite, home office, media room, or playroom. With its separation from the main living areas and its own walk-in closet, this space offers privacy rarely found in similar homes. Step outside to enjoy the screened private pool with an electric heater, allowing for year-round outdoor living. Whether relaxing poolside, entertaining guests, or enjoying morning coffee on the front porch, this home is designed to embrace all that Florida living has to offer. Additional highlights include a laundry room with cabinetry for storage, overhead garage storage racks, a dedicated storage closet in the garage, and the main A/C replaced in 2021. The home is ideally located near the community bike path at the beginning of the street, offering easy access to schools, the community center, playgrounds, and resort-style amenities—perfect for walking or biking throughout Summerport. Summerport is known for its numerous amenities, including a clubhouse, fitness center, community pool, tennis and pickleball courts, basketball and volleyball courts, playgrounds, a lakeside beach area with fishing docks, and miles of walking and biking trails. The community also features on-site conveniences such as a coffee shop, pizzeria, and ice cream parlor, with additional local favorites nearby. Zoned for Keene’s Crossing Elementary, Bridgewater Middle, and Windermere High School, and conveniently located near Hamlin Town Center, Winter Garden Village, Publix, historic downtown Winter Garden and Windermere, Disney, Universal, and major roadways including SR 429, SR 408, and CR 535. This home combines a prime Windermere location, a flexible layout, and an amenity-rich community—making it a standout opportunity!

5463 Gemgold Court, Windermere

$560,000
4 Beds 4 Baths Lakes/Windermere-Peachtree SubDv. 34786 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3.5-bath residence located in the sought-after, gated Lakes of Windermere community. This two-story home offers peace of mind with a brand-new roof installed in 2025 and features a light-filled, open-concept layout designed for both everyday living and entertaining. The main level includes formal living and dining spaces, a generous family room, a well-appointed kitchen, breakfast nook, and a convenient half bath. The kitchen overlooks the family room and is highlighted by Corian countertops, abundant cabinetry, a large pantry, and a breakfast bar with additional seating. Upstairs, the expansive primary suite features elegant French door entry and a private en-suite bath complete with a soaking garden tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. Three additional well-sized bedrooms, all with new carpet installed in 2025, and an upstairs laundry room provide comfort and functionality for the entire household. Enjoy outdoor living in the backyard with a covered lanai, perfect for relaxing or entertaining. Additional highlights include a two-car garage and the rare bonus of nightly fireworks views from the front porch. Lakes of Windermere offers a welcoming, small-town atmosphere with resort-style amenities including a fishing dock, junior Olympic-size community pool, and organized recreational activities. Ideally situated in the heart of Windermere, this home is just minutes from Disney attractions, I-4, SR 408, the Florida Turnpike, and Winter Garden Village shopping and dining. Not a short sale or foreclosure, this move-in-ready home has been meticulously cared for and is ready for its next owner.

8650 Abbotsbury Drive, Windermere

$1,250,000
7 Beds 5 Baths Enclave SubDv. 34786 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering 4,563 square feet of thoughtfully designed space created for both effortless entertaining and everyday comfort. Featuring 7 bedrooms plus a dedicated office (with flexibility for a second office or bonus use), 4.5 bathrooms, and an open-concept layout, the home flows seamlessly from room to room—and even better, from indoors to out. The heart of the home opens directly to a massive covered lanai, creating a true indoor-outdoor lifestyle that Florida living is known for. Step outside to your custom resort-style pool with sun shelf, recessed table, and tranquil waterfall. The space is anchored by a fully equipped outdoor kitchen and bar complete with bar seating, keg, grill, smoker, and sink—ideal for hosting game days, celebrations, or quiet evenings at home. Inside, the primary suite on the main level serves as a private retreat, featuring a spa-inspired bath and a custom walk-in closet with built-ins. A secondary primary suite upstairs provides exceptional flexibility for guests or multigenerational living, while the remaining bedrooms and bonus spaces offer endless options for work, play, or relaxation. A rare bonus, the 3-car garage features an 18,000 BTU Bluetooth-controlled AC, making it ideal for a climate-controlled home gym, hobby space, or car enthusiast’s workshop. A three-car garage, beautifully maintained finishes throughout, and access to the community neighborhood park complete the offering. Located in Enclave, you’ll enjoy tree-lined streets, a strong sense of community, and proximity to everything Windermere has to offer—including access to the Butler Chain of Lakes. This is more than a home, it’s a lifestyle.

11658 Hampstead Street, Windermere

$930,000
5 Beds 4 Baths Windstone SubDv. 34786 Zip Code
RARE PRIVACY IN WINDERMERE — 5 BEDROOMS + 2 BONUS ROOMS WITH NO REAR, FRONT-FACING, OR LEFT-SIDE NEIGHBORS Welcome to a rare Windermere opportunity offering the space, privacy, and lifestyle buyers dream about. This expansive 5-bedroom, 4-bath home features two additional bonus rooms, including a large movie/media room, giving you incredible flexibility for work, entertaining, guests, fitness, play, or multi-generational living. Set in a uniquely private location with no rear neighbors, no front-facing neighbors, and no neighbor on the left side, this home offers a peaceful setting that is hard to find in Windermere. Behind the home, an oversized backyard provides the perfect canvas for your future outdoor oasis, whether you envision a resort-style pool, summer kitchen, garden retreat, or spacious play area. Inside, the open-concept floor plan is designed for connection and everyday comfort. At the heart of the home, the gourmet-style kitchen flows seamlessly into the main living spaces and offers the option for a gas stove connection, making it ideal for those who love to cook, gather, and entertain. The home also features a living room, family room, and generous light-filled spaces that create a warm and functional layout. The bedroom design offers privacy and comfort for everyone. All four main bedrooms feature walk-in closets, while the private guest suite includes its own en-suite bathroom and walk-in closet, making it ideal for visitors, extended family, or a luxurious secondary retreat. When the day winds down, escape to the spacious primary suite, a peaceful sanctuary designed for rest, relaxation, and renewal. With multiple living areas, oversized bedrooms, flexible bonus spaces, and an exceptional outdoor setting, this home offers the space to live, work, host, and grow with ease. Ideally located in Windermere, just minutes from Disney, Central Florida attractions, dining, shopping, and everyday conveniences, this home offers the rare combination of privacy, space, location, and possibility. This is more than a home — it’s a lifestyle designed for comfort, connection, and the dream of living beautifully in Windermere.

6752 Trellis Vine Loop, Windermere

$2,948,000
5 Beds 6 Baths Keenes Pointe Ut 06 50 95 SubDv. 34786 Zip Code
Set within the guard-gated community of Keene’s Pointe, this golf course front residence offers sweeping views across the fairway to Lake Burden just beyond, creating one of the rarest and uninterrupted backdrops in all of Windermere. Walls of glass draw in natural light and keep the scenery front and center throughout the home. In the evenings, the sun settles over the lake, casting warm reflections across the water and fairway, creating an ever changing backdrop enjoyed from both inside and out. As night falls, Disney fireworks complete the view. Designed for modern living, the home features two full bedroom suites on the main level, ideal for multi-generational living, guests, or options for office space. The open kitchen anchors the home and flows seamlessly into the family room and lanai, making it equally suited for entertaining and everyday life. Viking appliances, dual farmhouse sinks, a pot filler, and a generous center island create a chef-driven layout without sacrificing style. Indoor and outdoor living blend effortlessly as sliding glass doors open to a resort style setting. The backyard is anchored by a custom pool with sun shelf, spillover spa, fire features, and water elements, all surrounded by expansive pavers and lush landscaping. A covered lanai offers multiple lounge zones, a summer kitchen with built in grill and beverage refrigerator, ceiling fans, and an open air shower, all positioned to maximize sunset views over the lake. The upper level serves as a private retreat. Enjoy elevated views of the golf course and Lake Burden from your second story primary bedroom which includes a spa inspired bath with freestanding tub, oversized shower, dual vanities, and a boutique style closet. Two additional bedroom en-suites, massive media room with fireplace, and extended balcony provide flexibility for relaxation or work from home living. A split four car garage offers epoxy flooring, EV charging, and climate control adds modern convenience, while thoughtful upgrades throughout make the home truly turnkey. This is a rare opportunity to own a lake and golf front home in Windermere where the view, the floor plan, and the lifestyle align.

11255 Macaw Court, Windermere

$825,000
4 Beds 3 Baths Windermere Downs 1st Add SubDv. 34786 Zip Code
Located in the peaceful setting of oak-lined streets of the sought after Windermere Downs community, this well-maintained home offers recent upgrades, generous living spaces, and access to the renowned Butler Chain of Lakes. The home features a fully fenced, large backyard with privacy fencing and a large 35’+ pool with expansive deck area—ideal for outdoor living and entertaining. Inside, the family room includes a wood-burning fireplace, while the formal living room provides flexible space for an office or additional sitting area. The formal dining room is accented with chair rail and an elegant tray ceiling. The kitchen offers granite countertops, bar seating, upgraded appliances, abundant cabinetry, and a built-in desk area. Wood-style flooring highlights the formal areas, while new carpet runs throughout the second floor. All bedrooms are located upstairs, including the spacious primary suite with a soaking tub, walk-in shower, two separate granite-topped vanities, and a large walk-in closet. The secondary bathroom features a double-sink granite vanity and a shower/tub combination. Recent major improvements include a new A/C in 2025 and new windows, stucco, and exterior paint in 2024. Additional features include an oversized 2-car garage with extra storage space, a circular drive plus a separate driveway. Windermere Downs residents enjoy access to the Butler Chain of Lakes with a private boat ramp, covered dock, beach and swim area, along with playgrounds, tennis, and pickleball courts. Conveniently located near theme parks, fine dining, shopping, the airport, and Downtown Orlando.

1735 Maple Leaf Drive, Windermere