Refine Search
Sort by
$3,900,000
5 Beds 5 Baths Windermere Town SubDv. 34786 Zip Code
Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000

212 W 1st Avenue, Windermere

$2,190,000
4 Beds 5 Baths Reserve At Lake Butler Sound SubDv. 34786 Zip Code
RARE, ONE-OF-A-KIND FULLY RENOVATED LUXURY CONTEMPORARY ESTATE IN WINDERMERE – OVER HALF AN ACRE WITH PRIVATE POND VIEW Welcome to 6550 Cartmel Ln, located in the exclusive Reserve at Lake Butler Sound — one of Windermere’s most prestigious gated communities. Completely and extensively renovated from top to bottom, this exceptional modern-contemporary residence offers the perfect blend of luxury, sophistication, and privacy. Situated on an oversized lot of more than half an acre, the property showcases serene private pond views and extraordinary outdoor living spaces. This stunning two-story home features 4 bedrooms, 4 full bathrooms, and 1 half bath, with a spacious open-concept layout designed for both comfortable living and elegant entertaining. Every detail has been thoughtfully updated, creating a truly move-in-ready luxury residence. The interior showcases high ceilings, abundant natural light, premium finishes throughout, and luxury vinyl flooring with no carpet anywhere in the home. The gourmet kitchen has been beautifully updated and features stainless steel appliances, quartz countertops, custom cabinetry, and ample space for gathering with family and guests. Step outside to your private backyard retreat, complete with a covered lanai, outdoor kitchen and grill area, sparkling pool, and expansive pond-front setting. Whether relaxing or entertaining, this outdoor space delivers the ultimate Florida lifestyle. Exterior furniture is included, making the home even more turnkey. Additional highlights include a 3-car garage and partially furnished interiors. Residents of Reserve at Lake Butler Sound enjoy an unparalleled lifestyle with 24-hour guard-gated security, private access to the Butler Chain of Lakes, and beautifully maintained community grounds. Ideally located just minutes from: • Walt Disney World Resort • Downtown Winter Garden • The Mall at Millenia • Top-rated schools, fine dining, shopping, and major highways Opportunities like this are rare—a fully renovated luxury home on an oversized waterfront-view lot in one of Central Florida’s premier communities. Schedule your private showing today and experience this extraordinary property firsthand.

6550 Cartmel Lane, Windermere

$6,000,000
6 Beds 6 Baths Rosser Reserve Rep SubDv. 34786 Zip Code
UNDER CONTRACT ACCEPTING BACKUP OFFERS! Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment you arrive, the home captivates with its contemporary architecture, expansive paver driveway, and striking façade. Clean lines, refined finishes, and manicured landscaping create an unforgettable first impression. Inside, soaring ceilings, exposed wood beams, and designer lighting enhance the open-concept layout. Oversized sliding glass doors frame breathtaking panoramic lake views while creating a seamless indoor-outdoor flow filled with natural light. The gourmet kitchen serves as the heart of the home, featuring an oversized quartz island, custom cabinetry, and premium stainless steel appliances — perfectly designed for both intimate gatherings and grand-scale entertaining. With 6 spacious bedrooms, 5 full bathrooms, and 1 powder room, the residence offers comfort and privacy for family and guests. Beyond the main living areas, this home delivers an exceptional lifestyle experience with a private gym, dedicated cinema room, game room, and playroom — thoughtfully designed for wellness, entertainment, and family enjoyment. Step outside into your private lakeside retreat. The resort-style pool with integrated spa is complemented by sleek glass railings that preserve unobstructed water views. The covered outdoor living area is a masterpiece, featuring a wood-paneled ceiling, oversized ceiling fan, stone fireplace, mounted TV, and a fully equipped summer kitchen with professional-grade stainless steel grill and hood — ideal for year-round entertaining. The private covered dock accommodates boats and jet skis and provides direct access to all 12 lakes of the Butler Chain, making this property a true paradise for boating enthusiasts. Additional features include: Whole-house water filtration system High-capacity generator capable of powering the entire residence Located within an exclusive gated community with meticulously maintained infrastructure Offering privacy, security, expansive outdoor space, and one of Windermere’s most coveted lakefront settings, this is more than a residence — it is a lifestyle defined by elegance, recreation, and exclusivity. Schedule your private showing and experience lakefront living at its finest.

1002 Down Reserve Court, Windermere

$4,500,000
6 Beds 8 Baths Lake Down Reserve SubDv. 34786 Zip Code
Welcome to a rare modern estate in an intimate gated enclave. Imagine 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom-built masterpiece was designed for those who value privacy, prestige and perfection. Go inside to discover European white oak flooring, soaring ceilings and designer-curated finishes that define understated elegance. The chef’s kitchen features Wolf appliances, an oversized island, and custom cabinetry that flows seamlessly into open-concept living and dining spaces, ideal for entertaining or effortless daily living. The first-floor primary suite is a sanctuary of its own, with a two-story boutique-style dressing room and a spa-inspired bath showcasing dual vanities, a freestanding soaking tub and a double rainfall shower beneath a skylight. Upstairs, each bedroom offers its private en suite, including a flexible Jack and Jill layout. Additional highlights include a private theater, executive office, and a detached casita ideal for guests or multigenerational living. Outdoors, experience your resort retreat, a negative-edge pool with cascading waterfalls, spa jacuzzi, covered lanai, and fully equipped outdoor kitchen built for year-round entertaining. Even the garage is a masterpiece, designed to house six cars and a boat, or up to fifteen vehicles with lifts. In a small, exclusive gated community, this property delivers a balance of modern sophistication and timeless comfort. Homes of this caliber rarely become available. Schedule your private showing today and experience why this estate stands in a class of its own.

1003 Down Reserve Court, Windermere

$2,750,000
6 Beds 8 Baths Casabella Ph 2 SubDv. 34786 Zip Code
$75,000 credit towards pool with acceptable offer! This exceptional 2019-built home has been transformed with nearly a full interior remodel, making it one of the most distinctive properties in the sought-after Windermere community of Casabella. As the largest model in the neighborhood, this home offers a rare blend of space, style, and function. Inside, thoughtful upgrades abound. A dramatic 24-foot fireplace with imported porcelain slabs is a stunning centerpiece in the main living area. The main level features oversized imported porcelain tile, upgraded baseboards, and enhanced door designs that elevate the overall aesthetic. Multiple recessed ceilings with integrated LED lighting and modern spotlights create a warm, inviting ambiance throughout. Curtains with built-in lighting add a subtle, sophisticated touch. The first-floor primary retreat offers double doors, a backlit tray ceiling, abundant closet space, a raised soaker tub, dual sinks, and clean linen finishes. The kitchen stands out with a sleek, modern design made entirely of imported cabinetry, paired with top-of-the-line appliances—including a Sub-Zero fridge, Wolf double oven, gas stove, microwave, and hood, plus a JennAir dishwasher. Quartz countertops flow through the kitchen and all bathrooms, which are finished with imported porcelain tile, linear drains, and LED-lit niches. Upstairs, you'll find a blend of wood accents that bring warmth to the bedrooms, loft, and theatre. The home theater is also prewired for LED lighting and motorized seating. Outside, the large covered lanai is prepped for a summer kitchen, paired with plenty of yard space to create your own private escape. Modern, refined, and built to impress—this is Windermere living at its finest. Call today to set up a tour!

4047 Isabella Circle, Windermere

$1,650,000
4 Beds 3 Baths Windermere SubDv. 34786 Zip Code
Now priced at $1,995,000, this expansive lakefront property presents an extraordinary value on the Butler Chain of Lakes. Whether you’re seeking a private waterfront retreat, a renovation project, or a rare opportunity to build new on Lake Down, 4108 Downeast Lane is an offering not to be missed. This rare lakefront estate is on Lake Down, part of the prestigious Butler Chain of Lakes and spans approximately 3.31 total acres, including 1.2 acres of high and dry land, with 225 feet of pristine sandy beach shoreline perfectly positioned on the west side of the property, offering breathtaking sunset views. Nestled at the end of a long, private driveway, the home provides a serene and secluded retreat. Built in 1979 by the loving family bringing it to the market today, this two-story, four-bedroom, three-bathroom home presents an incredible opportunity to embrace a lakeside lifestyle or reimagine the property to suit your vision. The first floor features an inviting open floor plan with a casual foyer, spacious family and dining areas, a kitchen, and a large Florida room that seamlessly connects to expansive outdoor entertaining spaces running the width of the home on both levels. The first-floor interior space is completed by a flex room, full bathroom, and laundry room, located between the general living area and the oversized two-car garage. Upstairs, the private retreat consists of a spacious primary suite with an en-suite bathroom and walk-in closet, two additional bedrooms with sliding glass doors opening onto the second-floor deck, a fourth bedroom, and a shared hall-entry full bathroom. Notable property features include sizable rooms within a desirable floor plan, double-pane windows, a new roof (2023), a storage shed, perfect for lake and boating gear, and a paver-covered walkway leading to Lake Down, which spans approximately 900 acres and is part of the Butler Chain of Lakes—a network of 13 interconnected lakes known for their clear waters, sandy bottoms, and luxury waterfront properties. The chain offers exceptional opportunities for boating, fishing, and water sports, with access via scenic canals and public boat ramps. Zoned for top-rated schools, including Windermere Elementary, Chain of Lakes Middle, and Olympia High School, the property is conveniently located near Apopka Vineland Road and Conroy Windermere Road, with easy access to The Vineyard shopping and dining, major highways, and Orlando’s world-renowned attractions.  This is a rare opportunity to build your dream lakefront estate and own a slice of paradise in Windermere. Schedule your private tour today!

4108 Downeast Lane, Windermere

$2,800,000
5 Beds 5 Baths Summerport Beach SubDv. 34786 Zip Code
The Lakehouse.....Built in 1966 and kept in original condition this mid-century modern home embodies timeless design and a seamless connection with nature. Set on over an acre of prime waterfront property with 200 feet of shoreline, this single-story residence offers 5 bedrooms, including two primary suites. The wide-open floor plan flows effortlessly, showcasing iconic terrazzo floors and expansive floor-to-ceiling windows bathing the interiors in natural light while exposing panoramic lake views. A cozy library with a fireplace provides a quiet retreat for reading or relaxation. Adorned with inspired wallpaper accents that reflect the era’s character, the home also features separate living quarters with a kitchenette—ideal for multi-generational living. Step outside to the patio, surrounded by lush landscaping, where you can enjoy the serene surroundings and lakefront views. Located just west of the Town of Windermere, this lakefront gem offers tranquility while being conveniently close to major roadways, shops, dining, and area attractions. NO HOA restrictions. Situated along the Butler Chain, one of Florida’s Outstanding Waterways with 13 interconnected freshwater lakes, this home is a rare opportunity to experience the best of Central Florida’s lakefront living. Being sold by the original owners.

12334 Summerport Lane, Windermere

$825,000
3 Beds 2 Baths Windermere Town SubDv. 34786 Zip Code
Welcome to Historic Downtown Windermere. This stunning, fully remodeled mid-century-modern home is ready to welcome its new owner into a life like none other. Located in the golf cart district, you have convenient access to a private boat ramp and two public boat ramps, community parks, tennis courts, and a downtown district that boasts charm and exclusivity. Besides an idyllic lifestyle, this home offers something that many do not, completely renovated and move in ready. With no detail forgotten, every aspect of this home has been masterfully updated and upgraded. Upon entering you are greeted by immaculate new landscaping, new sod, new trees, and shrubbery - giving fantastic curb appeal. This concrete block home has been completely repainted, along with the addition of a new garage door. Your smart front door swings open to towering high Ceilings, floor to ceiling windows, and a stunning bright home. Centered in the middle of the home is a mid-century fireplace with dark porcelain tile offsetting your bright porcelain tile flooring and new interior paint. This chef's kitchen has been completely remodeled, and redesigned. With designer cabinets, beautiful quartz countertops, luxury cafe appliances, and a beautiful butcher block island, your hosting desires are a reality with additional bar top seating. From your kitchen you have a large open family room, walk in pantry and walk in laundry room. In your main living space, you have an optional formal sitting area along with a potential formal dining room that leads to a covered outdoor patio. This home offers several different potential room layouts depending on your needs. Off of this space you have two guest rooms with new lighting, new fans, and a completely new bathroom. Up the new staircase, you have your private master suite. Complete with new lighting, new fans, new his and her vanities, new shower, new stand-alone tub, and new walk-in closet. The theme of this home is modern mid-century modern with the added convenience brand new finishes, technology, and features. Apart from the brand-new interior, this home offers a new AC, new electrical fuses, a new well tank, a new well pump, new irrigation, new gravel, a 2022 roof, and new hot water heater. Windermere is a town nestled along the lakes. Peace and tranquility at every turn, 4 Chase Road is the perfect home for anyone looking for luxury living in this historic waterfront town.

4 Chase Road, Windermere

$3,500,000
4 Beds 7 Baths Gotha SubDv. 34786 Zip Code
Under Construction. Welcome to the ideal of luxury living in this brand-new construction home, set to be completed in the first few months of 2024. This exceptional residence stands on over half an acre, offering solid block construction, a supreme location nearby for shopping and dining. As you approach this architectural masterpiece, the exterior sets the tone for what awaits inside. A private fence surrounds the property, highlighting the private modern outdoor heated pool, featuring Stromboli Anti-slip pavers and a Caribbean Blue pebble surface that adds a touch of opulence to the outdoor oasis. Add in the outdoor kitchen, and expand your entertaining. This two-story marvel boasts a sleek and contemporary design that captures the essence of modern living. The rear three-car garage ensures ample parking space, while the expansive double lot allows for a generous landscape that complements the architectural beauty. Step inside, and a seamless blend of form and function will greet you. The chef's kitchen is a culinary dream, equipped with top-of-the-line appliances from renowned brands such as Sub Zero, Wolf, Zephyr, and Bosch. Using natural gas adds an extra layer of efficiency to this culinary haven. European Valley cabinets and esteemed brands like Pavonazzo, Pfister, Toto, Myers, Koehler, and Berenson adorn the interiors, elevating the aesthetic to unparalleled heights. The interior layout is designed with both style and practicality in mind. With four bedrooms, including two spacious suites on each floor, this home provides the perfect setting for in-law accommodations or guest suites. Each bedroom boasts a private bath, ensuring comfort and convenience for every resident. Entertain with flair in the open separate formal areas, unwind in the large family room off the kitchen, or create a cinematic experience in the dedicated media room. A dedicated office space offers a tranquil environment for work or study, while the mudroom and dual laundry areas add a touch of everyday practicality. The five full baths and two half baths are adorned with luxurious Italian tile, adding a touch of timeless elegance to the home. The attention to detail extends to the balcony at the top of the glass and natural wood stairway, providing a breathtaking view overlooking the front yard's landscape. In terms of education, this residence falls within the popular school system of Thornbrooke Elementary, Gotha Middle, and Olympia High School. This home is not just a place but a statement of affluence and contemporary living. With its meticulous design, premium finishes, and an array of high-end amenities, this residence is poised to redefine your notion of luxury living in the heart of 2024. Secure your place in this exclusive haven and experience opulence in every detail.

9950 6th Street, Windermere

$715,000
3 Beds 2 Baths Windermere Town SubDv. 34786 Zip Code
DISTINGUISHED LOCATION!!! ALL REMODELED modern concept home, with massive UPGRADES!! Property is being sold AS IS, not finished. AC 2015, BRAND NEW ROOF, Entire house made of BLOCK! This desirable property is located in Olde Windermere across from Lake Butler. All the rooms are located on the first floor with the exception of the primary bedroom suite accessed via granite stairs on the 2nd level. From the dining area, glass sliders open to a covered screened lanai. Beautiful and private in its natural state or manicured to enhance magnificent flora. Windermere is a golf cart friendly town shaded by old oaks and accessed by sand roads with no HOA. World’s apart, yet minutes from fine dining, premium shopping, area attractions and International airport. The surrounding Butler Chain consists of 11 interconnecting lakes offering pleasure and sports for all water enthusiasts. Prefer golf….choice golf courses are nearby. So check this property out, bring a hammer, hatchet and elbow grease and uncover a true hidden gem! Enjoy all that the Town of Windermere has to offer with weekly farmer’s market, local shops, restaurants, brewery, and seasonal events.

4 Chase Road, Windermere

$2,550,000
4 Beds 4 Baths Aladar On Lake Butler SubDv. 34786 Zip Code
Welcome to Second Avenue…a quiet peninsula in the heart of Old Windermere. This ¾ acre waterfront property boasts 125 feet of sandy shoreline, concrete seawall and sweeping views of Wauseon Bay. Ultra two story boathouse includes sundeck, boat lift and double jetski lifts. There is a 600 sf building lakeside with potential to become your cabana, office, game room or whatever you can imagine. This structure is grandfathered and could not be built today! Existing single story, mid century 3,000 sf home has not been lived in since 2017. Restore, renovate or build new. Property has access to natural gas and Orange County water. Windermere affords a small town lifestyle yet close to major roadways, fine dining, renowned golf and area attractions. Residents enjoy the security of having their own respected police department. Walking distance to local restaurants, shops, brewery and seasonal events. Golf carts welcome and no HOA dues or restrictions. The Butler Chain is designated as one of Florida’s Outstanding Waterways. There are 11 pristine, interconnecting lakes sure to please all water enthusiasts.

803 W 2nd Avenue, Windermere