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$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

$352,155
3 Beds 3 Baths Oasis Cove I/Lakeside Village Ph 01 SubDv. 34786 Zip Code
Elegant 3-Bedroom Townhome in Gated Windermere Community — Minutes from Disney World Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhouse nestled in one of Windermere’s most sought-after gated communities. Boasting a spacious open layout and thoughtful upgrades throughout, this home perfectly blends style, comfort, and convenience. The primary suite is conveniently located downstairs, offering privacy and ease of access, while the upstairs bonus room and flex space provide the ideal setup for a home office, media room, or guest retreat. The gourmet kitchen is a chef’s dream, featuring modern appliances, ample counter space, and elegant finishes — perfect for cooking and entertaining. Relax on the screened porch, a peaceful retreat to enjoy morning coffee or evening breezes. Recent updates include a newer roof and air conditioning system, adding extra peace of mind. Residents enjoy access to exceptional community amenities, including a resort-style pool, clubhouse, and well-maintained grounds — all within a secure gated neighborhood. Located just 5 minutes from Walt Disney World, this home offers unmatched convenience to world-class attractions, shopping, dining, and top-rated schools.

14008 Luminous Lane Unit 802, Windermere

$3,100,000
5 Beds 7 Baths Sawyer Sound SubDv. 34786 Zip Code
Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A welcoming entrance showcases style and elegance with a massive Great Room as the lake and massive saltwater pool beckons beyond. An impressive chef’s kitchen with island and stainless appliances are perfectly fitted for entertaining family and friends. Highlights include rich hardwood floors throughout plus Thermador appliances including 6-burner plus griddle stove and hood, custom-built cabinetry, hidden walk-in pantry, expansive built-in China cabinet, and an especially large dining room with picturesque window. Opposite is a primary retreat with sitting room, spa-like bath with soaking tub, walk-in shower, toilet closet, and separate den. Bathrooms just updated. Upstairs are four bedrooms, each with a private full bath, plus gathering room and separate gaming room. Distinct outdoor spaces are crafted for year-round enjoyment: covered cabana with bar and gas grill plus dining space, mammoth saltwater pool with hot tub, and outdoor family room with fireplace and disappearing screens. Boat house with boat lift puts your water toys within reach and offers easy access to Little Lake Sawyer. Also, enjoy nightly Disney World fireworks viewing from the dock. Boat, trailer, kayaks, and all furniture available for purchase separately. Home is fitted with automatic Generac generator plus 3-car garage (one single and one double). Home may be sold furnished if desired.

5024 Sawyer Cove Way, Windermere

$470,000
3 Beds 2 Baths Preston Square SubDv. 34786 Zip Code
One or more photo(s) has been virtually staged. *** Multiple offers received, deadline for highest and best is Monday 10/13/2025 @ 6pm *** Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after Preston Square community of Windermere. This single-story residence offers 1,609 sq. ft. of open living space and fresh updates throughout. The heart of the home is the kitchen with granite countertops, stainless steel appliances (including a 2024 dishwasher), ample cabinet storage, and breakfast bar, which seamlessly connects to the dining space and great room. Fresh interior paint, new carpet, and updated landscaping add a move-in ready appeal. The private primary suite features a tray ceiling, walk-in closet, dual vanities, soaking tub, and separate shower. Two additional bedrooms and a full bath are tucked away on the opposite side of the home, perfect for guests, family, or office use. Major updates bring peace of mind, including a new roof (2025), A/C (2024), water heater (2024), exterior paint (2024), interior paint (Sep 2025) and new carpets (Sep 2025). Enjoy Florida living with a covered front porch, rear-entry garage, fenced yard, and paver patio. Preston Square offers resort-style amenities including a pool, playground, and basketball court. Conveniently located near top-rated schools, shopping, dining, and major highways, this home is the perfect blend of comfort, convenience, and style.

6864 Helmsley Circle, Windermere

$9,000,000
6 Beds 10 Baths Isleworth SubDv. 34786 Zip Code
It’s more than a home, it’s a story waiting to be lived. The light that spills across the kitchen feels like an invitation to linger a little longer. The staircase carries the rhythm of celebrations, and the open spaces invite moments that turn into memories. Long after the boxes are unpacked, you’ll realize it wasn’t just the marble, the quartz, or the soaring ceilings that made you fall in love; it was the way this home makes every day feel radiant. Introducing an exquisitely remodeled, fully furnished three-level Isleworth estate on Lake Butler, part of the prestigious Butler Chain of Lakes. With over 11,100 sq. ft. of refined living space, this home features 6 suites, 7 full bathrooms, and 3 half baths. Every detail has been curated for both comfort and indulgence: from the wellness sanctuary with a sauna, gym, and golf simulator, to the leisure lounge complete with 2 full bars, your own pub, theater, direct access to the outdoor retreat, and an elevator for your convenience. Step outside to your private oasis, an expansive pool and hot tub overlooking the water, paired with a fully refurbished dock and brand-new boat lift. Inside, timeless craftsmanship shines in the intricate millwork, crown molding, grand soapstone fireplace, and premium quartz and marble finishes. An elevator and breathtaking lakefront vistas ensure both elegance and convenience. This is where mornings begin with light spilling through wide windows like hope, and evenings unwind in spaces designed for connection and calm. Welcome to a residence where luxury and life blend seamlessly.

9832 Laurel Valley Drive, Windermere

$1,890,000
5 Beds 4 Baths Windermere Pointe SubDv. 34786 Zip Code
Back on the market. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage. Lake Roper is renowned for its water sports, water skiing, jet skiing and fishing only acceded by the surrounding houses (No Public Ramps). This is one of the largest lots in the community. Location: Only minutes from Winter Garden Village and Downtown Windermere, minutes from main roads like 429 and 408 and a short distance from Theme Parks and Shopping Areas. Great School District. Kitchen: Totally renewed, custom-built cabinetry, high-end stainless still appliances, built in induction cook top, built in microwave and oven, huge island built with one piece of quartz, no sims. Pop-out outlets, touchless faucet and built in hood. Bathrooms: Contemporary look with porcelain tiles, quartz tops, custom made cabinetry and modern metals. Pool area: The pool was resurfaced, surrounded by new pavers overviewing the lake and a brand-new equipped summer kitchen just built. Dock: Wood dock and fishing pier with Electric Boat lift. The house was completely renovated from top to bottom including new engineering hardwood floors, 3 new A/Cs, new water heater, new irrigation system, fresh painted and new roof installed in 2020. Important Notice: "Seller is willing to accept a smaller house as part of the payment".

13048 Lake Roper Ct., Windermere

$1,775,000
3 Beds 3 Baths Lake Butler Estates SubDv. 34786 Zip Code
Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere. Surrounded by multi-million-dollar residences, and just moments from the famed Butler Chain of Lakes, this property offers a rare opportunity to enjoy luxury living in one of Central Florida’s most desirable communities. Step inside and be greeted by natural light pouring through every room, highlighting fresh interior paint (2025) and warm wood flooring. The open-concept floor plan creates an effortless flow between living, dining, and entertaining spaces, anchored by a cozy wood-burning fireplace. Offering incredible flexibility, the home features two primary suites—perfect for multi-generational living or guest accommodations—along with a dedicated flex room to adapt to your lifestyle. Designed for both relaxation and recreation, the home’s outdoor living spaces are a true highlight. A screen-enclosed pool and spa, expansive covered lanai, and lush surroundings create the perfect backdrop for year-round Florida living. For those with a passion for travel or hobbies, the oversized 48x20 recreational garage provides exceptional space for a motor coach, RV, or boat. With a brand-new roof (2025), freshly painted exterior (2025), and durable block construction, this home is move-in ready while still offering room for expansion. Located within the coveted A-rated school district, close to charming downtown Windermere, world-class golf, and renowned shopping and dining, this residence offers not just a home, but a lifestyle. Owner finance options available. Don’t miss your chance to own a piece of Windermere luxury — where contemporary elegance, everyday comfort, and premier location meet.

12001 Lake Butler Boulevard, Windermere

$560,000
3 Beds 2 Baths Windermere Sound SubDv. 34786 Zip Code
NOW AVAILABLE! This beautiful move-in-ready home in Windermere, FL features 3 bedrooms, 2 bathrooms, and a den in a sought-after school district, just minutes from Walt Disney World and Orlando’s best entertainment. Blending modern finishes with a practical open layout, this one-story property is a perfect fit for families, professionals, and relocation buyers. Enjoy modern luxury details throughout, including 32x32” polished ceramic tile, elegant 5 ¼” crown molding and baseboards, and smart Alexa-enabled LED lighting. Designed with style and convenience in mind, the kitchen features quartz countertops, designer backsplash, and a dramatic waterfall island. With ample cabinet storage, a walk-in pantry, and upgraded pendant lighting, this space blends elegance and everyday function. Enjoy the privacy of a rear-positioned primary suite with a walk-in closet and spa-like bathroom. Two well-sized bedrooms and a second full bath provide comfort for family or guests, while a bright den/office at the front of the home creates space for work or hobbies. Step outside to a front covered patio or the lanai overlooking a fenced backyard — perfect for barbecues, gatherings, or quiet evenings under the Florida sky. A brick paver driveway leads to a finished 2-car garage with epoxy flooring. This community offers resort-style amenities, including a pool, tennis courts, basketball courts, and a playground — all beautifully landscaped and HOA-maintained. Lawn care is included, giving you more time to enjoy the lifestyle. This property offers comfort, upgrades, and lifestyle convenience — an ideal home for families seeking to live near Disney and within a top-rated school district. Call today to schedule a showing!

7266 Penkridge Lane, Windermere

$515,000
3 Beds 2 Baths Silver Woods Ph 03a SubDv. 34786 Zip Code
Located in the highly sought-after Silver Woods community in Windermere, this beautifully updated single-story home features 3 bedrooms, 2 bathrooms, and a 2-car garage, highlighted by an open and airy oversized great room that flows seamlessly into the dining area and kitchen, enhanced by skylights that fill the space with natural light and improve energy efficiency. The spacious backyard offers a private pool perfect for relaxing or entertaining, while recent upgrades include a Tesla charger, vinyl fencing, double-pane windows throughout, a 2021 A/C, and fresh interior and exterior paint in 2023. Ideally situated just half a mile from The Grove, 5 miles from Universal Studios, and 9 miles from Disney World—with easy access to Dr. Phillips and Restaurant Row—this home is zoned for top-rated schools and offers a low annual HOA fee of only $363.83, making it the perfect blend of comfort, convenience, and prime location.

9485 Woodbreeze Boulevard, Windermere

$1,099,995
6 Beds 5 Baths Westover Club Ph 02 47/71 SubDv. 34786 Zip Code
Welcome to Westover Club, a sought-after gated community in Windermere known for its tree-lined streets and excellent location. This well-maintained 6-bedroom, 4.5-bathroom pool home sits on a spacious 0.34-acre lot and offers a thoughtfully designed layout ideal for comfortable living and entertaining. Inside, you'll find an inviting open foyer, formal dining room, and dedicated office with custom built-in shelving and file drawers. The heart of the home is the kitchen, featuring a built-in double oven, 36” commercial-style column refrigerator, cooktop, breakfast bar, built-in desk, and breakfast nook—flowing into a light-filled family room with electric fireplace and crown molding. Enjoy outdoor living in the screened and covered lanai with a pool, summer kitchen with infrared grill, outdoor refrigerator, sink with storage, outdoor speakers with Sonos and an oversized fenced backyard with tall viburnum hedges and covered seating area—perfect for relaxation or entertaining. The first-floor primary suite features lanai access, a sitting area, dual walk-in closets, and a spacious en suite bath with dual vanities, soaking tub, and walk-in shower. Upstairs offers additional bedrooms, a Jack-and-Jill bathroom, a guest room with private balcony, a versatile game room (ideal as a playroom, or secondary master with its own bath and walk-in closet), and a media room equipped with custom raised platform seating, screen, new projector, surround sound, noise-proof walls, and blackout curtains. Additional highlights include a large under-stairs storage room (perfect as a second pantry), new roof (2023), new A/C units (2022 and 2020), new dishwasher (2022), generator with hookup, and prewiring for electric car charging. Community amenities include a park, playground, basketball court, and tennis courts. Located minutes from Sand Lake’s Restaurant Row, Winter Garden Village, Downtown Winter Garden, Mall at Millenia, and Walt Disney World. Zoned for Thornebrooke Elementary and Olympia High. Don’t miss the opportunity to own this exceptional home in one of Windermere’s premier neighborhoods.

9439 Westover Club Circle, Windermere

$385,000
3 Beds 3 Baths Windermere Trls Prcl 3 SubDv. 34786 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly desirable Windermere Trails community! This spacious two-story home features a bright open floor plan and fresh interior paint throughout. The kitchen offers a chef kitchen, granite countertops, stainless steel appliances, and a large center island ideal for both everyday living and entertaining. Upstairs, you'll find all three bedrooms, including a generous primary suite with a walk-in closet and dual vanities. Additional highlights include a 2-car garage and a private patio, perfect for relaxing or hosting gatherings. Enjoy resort-style community amenities just steps away: pool, dog park, playground, and scenic walking trails. This home is also zoned for top-rated schools, making it an exceptional choice for families and investors alike.

8625 Coventry Park Way, Windermere

$1,025,000
4 Beds 3 Baths Willows At Lake Rhea Ph 01 SubDv. 34786 Zip Code
Stunning Remodeled Executive Home in The Willows at Lake Rhea. Welcome to 11401 Willow Stowe Lane, a beautifully renovated 4-bedroom, 3-bath executive home located in the prestigious Windermere community of The Willows at Lake Rhea. This move-in-ready residence seamlessly blends luxury, energy efficiency, and modern upgrades—perfectly positioned in one of Central Florida’s most desirable neighborhoods. Step inside through custom wooden entry doors to an open and airy layout, flooded with natural light and accented by engineered hardwood floors. The formal living and dining rooms are ideal for entertaining, while 12-foot sliding glass doors provide seamless access from the living room to the covered patio and pool—perfect for indoor-outdoor living. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances including double convection ovens, Bosch induction cooktop, built-in prep island, custom wood cabinetry, and a sunlit breakfast nook overlooking the backyard oasis. The east wing of the home is a private retreat, offering a large primary suite with walk-in closet, an updated en-suite bathroom, and a flexible space currently used as a home office, plus private access to the pool. An adjacent guest bedroom and full pool bath are ideal for guests or multi-generational living. The west wing includes two additional guest bedrooms with a shared bath. This home has been extensively upgraded with over $100,000 in recent improvements, including: New solar panels (Sept 2023) – offering over $25,000 in savings over 15 years (averaging $2,500+ per year) Shallow water well for irrigation – resulting in water bills averaging under $20/month saving nearly $100 per month Trane 19.5 SEER HVAC system with smart thermostat, upgraded ducts and vents Updated electrical system and all-new outlets throughout the home Designer ceiling fans installed in the primary bedroom, office, living room, kids’ room, and patio Pool resurfacing, tongue-and-groove patio ceiling with built-in speakers Tesla charging stations (2), MyQ smart garage system, Ring doorbell and security system, and Schlage smart locks Newer roof, gutters, and hot water heater Custom built-in cabinetry in the family room and a full-home water softener system Hurricane protection belts and lightning rods for added security and peace of mind Located within the town limits of Windermere, this home offers quick access to major highways including the 408, 429, and Florida’s Turnpike. Enjoy a 30-minute commute to Orlando International Airport, Walt Disney World, and downtown Orlando. Spend your weekends exploring Winter Garden Village or the shops and restaurants of historic Plant Street. This is more than just a home—it’s a fully upgraded, energy-efficient lifestyle in a prime location. Don’t miss your opportunity to own this rare gem. Schedule your private tour today!

11401 Willow Stowe Lane, Windermere

$670,000
4 Beds 3 Baths Creeks Run SubDv. 34786 Zip Code
Welcome Home, one of the best floorplans in all of Summerport, this 4 bedroom plus office, 3 full bath plus 3 car garage home is all one story. With a large screened in patio that overlooks your immense, fully fenced yard right next to one of the several community maintained ponds. Featuring newer roof (2018), Newer HVAC (2023), fresh interior repaint, new carpet, this home is ready to me moved into today. Walking through the front door you have a formal dining room to the left and spacious office to the right. The home quickly opens up to the living room, overlooked by the kitchen breakfast bar/island featuring all stainless appliances with gas range. A butler pantry with prep counter and wine fridge across from the walk-in pantry is right off the kitchen. Plus eat-in space off the kitchen next to the secluded 4th bedroom in the back of the home with it's own full bath. The split floorplan features a spacious primary bedroom with huge closet and bathroom with dual vanities, garden tub, roomy stand up shower and separate water closet. Across the home are two additional bedrooms another full bathroom and secluded laundry room. Not to mention the oversixed 3 car garage too! This property is just waiting for the next person to call it home and enjoy all it and the community has to offer. Including huge clubhouse, gym, pool, playgrounds, tennis, basketball, and volleyball. Minutes to the Winter Garden Village, Hwy 429, Downtown Winter Garden and Windermere High School.

13943 Caywood Pond Drive, Windermere

$2,250,000
5 Beds 8 Baths Keenes Pointe SubDv. 34786 Zip Code
BACK ON THE MARKET - BUYERS' FINANCE FELL THROUGH. Welcome to a home that isn’t just designed—it’s curated. Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the second floor. Every detail intentional. Every space elevated. Set on almost three-quarters of an acre, this Stonebridge-built masterpiece merges classic elegance with the kind of indoor-outdoor living that defines Florida luxury. Think: expansive travertine floors, warm wood textures, and a seamless flow from light-filled interiors to an outdoor oasis made for entertaining. The heart of the home? A chef’s kitchen worthy of its name—Sub-Zero, Thermador, Electrolux—all the names you expect, plus a breakfast bar for eight that says, this is where weekends begin. Around the corner, a wine cellar, a card/media room, a game room with built-in bar... this house plays just as hard as it lives. But the showstopper? Step outside. A custom bird-shaped saltwater pool, sprawling screened-in terrace, and a fully loaded summer kitchen—full-size fridge, grill, range, dishwasher, bar seating—all under cover and designed to entertain year-round. Whether it’s cocktails at sunset or brunch after golf, the vibe is effortless sophistication. The layout is thoughtful, too: five bedrooms, all on the main level, separated for privacy. The primary suite is its own retreat with a wet bar, built-in workstation, and a spa-like en-suite bath that feels more five-star resort than residential. With an oversized 4-car garage, a large driveway, and a golf cart bay in the garage, there's planty of space for your toys. Located in Keenes Pointe, with 24-hour guard-gated security, private access to the Golden Bear Club’s Jack Nicklaus-designed course, and the Butler Chain of Lakes just minutes away, this home offers not only privacy—but prestige. Downtown Orlando, world-class dining, top private schools, and theme parks are all within easy reach. But when you’re here, you might just forget you’re anywhere near the city. This isn’t just a home. It’s a statement. Elegant. Iconic. Effortless.

9905 Lanai View Court, Windermere

$350,000
3 Beds 3 Baths Wickham Park 04 05 06 09 10 11 12 01 SubDv. 34786 Zip Code
BIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Rear entry 2 car garage. All stainless-steel fridge, stove, microwave and dishwasher with solid surface counter tops. Versatile all ceramic tiled 1st floor plan with formal dining room or use as front office. Open kitchen to rear great room that opens to covered screened private patio and fenced yard. All bedrooms up. Primary bedroom features ceramic tile floor, ceiling fan, 8'x5' walk-in closet, dual sinks and garden tub in en-suite bath, secondary bedrooms have carpet. Energy efficient double pane windows. Community pool and clubhouse, playground, and trails nearby all at affordable HOA fees. Convenient to shopping and attractions and no neighbors across the street. One or more photos has been virtually staged with AI technology.

7462 Bentonshire Ave, Windermere

$562,500
3 Beds 2 Baths Lakes Windermere Ph 01 49 108 SubDv. 34786 Zip Code
Beautiful 3 bed 2 bath, 2-car Pool Home in Prime Location – Move-In Ready!Welcome to your dream home! Nestled in a vibrant, family-friendly neighborhood, this meticulously maintained residence offers comfort, style, and unbeatable convenience. Step inside to find 9-foot ceilings that create a spacious and airy atmosphere throughout the home. The interior has been recently repainted adding a fresh, modern feel. The kitchen is a chef’s delight, featuring all-new Samsung appliances (2019), an island with new kitchen sink, whole house water softener from Rainsoft and ample space for entertaining. Stay comfortable year-round with a brand-new AC system (May 2022) with upgraded humidity control and rest easy knowing the roof was just replaced in September 2024. Stay safe with the Simplisafe home security system on all doors and windows plus interior and exterior motion detection. Note the spacious master suite with 9'3 by 10'4 closet. Enjoy Florida living at its finest with a screened-in pool surrounded by privacy landscaping—perfect for relaxing or hosting friends. The pool deck was also repainted in 2024, giving it a crisp, clean look. Located in a wonderful community boasting a basketball court, tennis court, volleyball court, two playgrounds, a soccer field, Community pool, fishing and community dock, plus sidewalks perfect for scooters and skateboards. All this comes with a low HOA of just $70/month. You’re just minutes from major highways, family services, numerous shopping options and world-class attractions: 15 minutes to Magic Kingdom, 25 minutes to Universal, and 20 minutes to SeaWorld—making this home ideal for both everyday living and enjoying all that Central Florida has to offer.

12641 Arley Dr, Windermere

$670,000
4 Beds 4 Baths Lakes/Windermere Ph 3 SubDv. 34786 Zip Code
Prime Location – Resort-Style Living! Perfectly situated just minutes from Orlando’s world-famous attractions and vibrant downtown, this spacious 4-bedroom, 3.5-bath home offers unbeatable convenience with schools, shopping, dining, and major roadways all close by. Inside, enjoy a private living room, formal dining room, butler’s pantry, a dedicated office, and a large kitchen that opens to a bright family room—perfect for everyday living and entertaining. The upstairs features a generous primary suite with a large walk-in closet, a secondary bedroom with its own private bath, and a Jack & Jill bath shared by the remaining two bedrooms, NEW ROOF. Step outside to your own backyard oasis with a sparkling pool. The community offers incredible amenities including a pool, tennis court, sand volleyball, and sports field. Plus, just next door, enjoy a county park with two dog parks, a large playground, and picnic pavilions with grills.

13055 Overstreet Road, Windermere

$934,500
5 Beds 4 Baths Westover Reserve Ph 02 SubDv. 34786 Zip Code
Welcome to luxury living in the distinguished, gated community of Westover Reserve in Windermere. This custom-built estate home has been meticulously maintained and thoughtfully upgraded, blending timeless elegance with modern convenience. At the heart of the home is a brand new, custom kitchen (2024), showcasing 42” cabinets with crown molding, stunning quartz countertops, a double oven, an expansive island, abundant cabinetry, and a beautifully tiled backsplash—crafted for both function and entertaining. The open kitchen and family room layout offers a seamless flow, perfect for gatherings, and features a cozy gas fireplace that adds warmth and charm to the space. The formal dining room is enhanced by an elegant coffered ceiling, perfect for hosting special occasions. Throughout the main living areas, you’ll find luxury wood-look porcelain tile flooring, offering durability with high-end style. Rich wood flooring adds warmth and character to the staircase, private office, and upstairs bonus room, creating an elevated yet comfortable feel throughout the home. The spacious primary suite and cabana pool bath both feature custom shutters, adding a refined finishing touch and enhancing privacy and light control. Additional notable upgrades include a new roof (2018), a full exterior repaint (2021), a main A/C system replaced in 2022, and a Jandy-brand hot tub heater installed in 2022. Step outside into your own private retreat featuring a sparkling pool and generous covered seating area—perfect for relaxing or entertaining year-round. The Jack and Jill bathroom was fully renovated in 2022, with beautiful new cabinetry, quartz countertops, stylish mirrors, and a modern walk-in shower. Located near top-rated schools, major highways, and within 30 minutes of Orlando’s world-class theme parks and attractions, this exceptional home offers not only luxurious design and quality craftsmanship, but also unbeatable convenience and lifestyle. Don’t miss your opportunity to own this one-of-a-kind Windermere estate.

2046 Westover Reserve Boulevard, Windermere

$5,150,000
6 Beds 7 Baths Kelso On Lake Butler SubDv. 34786 Zip Code
Discover 11,699 sqft of total luxury at 1455 Kelso Blvd, a stunning lakefront estate in Windermere’s Kelso on Lake Butler community. Set on nearly an acre with 119 feet of frontage on Lake Butler, this fully renovated 6-bedroom, 6.5-bath home offers over 6,448 sqft of living square footage. Features include a gourmet kitchen, first-floor primary suite with lake views, an attached in-law suite with private entrance, formal and family rooms, and multiple bonus spaces. Enjoy a saltwater pool and spa, beach, boathouse with lift, summer kitchen, and breathtaking lakefront views. Extensive upgrades include new roofing, plumbing, electrical, windows, and solar panels. A 4-car garage with EV charging and golf cart parking complete this exceptional offering. Community boat ramp access to the Butler Chain of Lakes.

1455 Kelso Boulevard, 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

$365,000
3 Beds 3 Baths Oasis Cove I/Lakeside Village Ph 01 SubDv. 34786 Zip Code
MOTIVATED SELLER! Welcome to the GATED Windermere Community of Oasis Cove a first class community in Central Florida, founded in 2007, where residents live amidst the tranquil magic of our adventurous surroundings. 2 stories, 3-bedroom, 2.5-bath, and features a Loft and Flex Room Upstairs with the Primary Suite Downstairs. Downstairs, you will find an inviting Open Floor Plan with tile and bamboo flooring. The kitchen shines with stainless steel appliances, elegant wood cabinetry, and a convenient breakfast bar.The kitchen features granite counters, upgraded backsplash, and a pantry. The downstairs also features the 1st Floor Master Bedroom, Private Large Luxurious Bathroom (1/2 bath downstairs to share), and a walk-in closet! Two additional bedrooms, full bathroom and a laundry room complete the upstairs space. Enjoy the large living area on the first floor or head out back through the sliding doors to your fenced in back patio, that is perfect for entertaining. This lovely property backs up to the preserve, has a fenced in patio area. This home also includes a spacious two-car garage for added convenience. The gated community offers fantastic amenities, including a resort-style pool, playground, and clubhouse, creating the perfect balance of relaxation and recreation. Scenic trails around the community. Plus, with Walt Disney World just 5 minutes away and Horizon West nearby for all your shopping and dining needs, you’ll have everything at your fingertips. Conveniently located close to hotspots of Downtown Windermere and Downtown Winter Garden. Offering comfort, style, and a peaceful setting, this condo is a must-see -- don't hesitate to schedule a showing today!

8031 Enchantment Drive Unit GE, Windermere

$490,000
3 Beds 2 Baths Wickham Park SubDv. 34786 Zip Code
Beautiful home with park views offering maintenance free living with HOA dues covering roof replacement, exterior painting and front lawn/shrub maintenance. The interior has fresh paint, vinyl wood plank flooring was just installed, and the exterior has been painted recently. You'll love the open layout with a large great room opening out from the gourmet island kitchen with granite and stainless steel appliances. A split plan, covered lanai in the front and rear, security system, walking to distance to schools, and community pool makes this home an exceptional opportunity for a single family home in Windermere at a value rich price. A new park/play area is under construction to accommodate just about any style of living. This home has so much to offer. You're home!

12751 Calderdale Avenue, Windermere

$710,000
4 Beds 3 Baths Belmere Village G3 48 70 SubDv. 34786 Zip Code
Expect to be impressed with this beautifully appointed water view home in Windermere’s Belmere community. Room for everyone and everything – abundant common living space with 4 bedrooms (3 way split layout) and 3 full baths. Step inside to open formal living/dining rooms. Notice the architectural elements here – tray and coffered ceilings add elegance, and transom windows keep the space bright. In the heart of the home, you’ll find a stunning contemporary kitchen which is open to a spacious family room – each making a great gathering space. Kitchen boasts abundant raised panel cabinetry, attractive tile backsplash, under the counter lighting, plenty of counter space, breakfast bar and eat-in nook with direct access to the covered patio. Primary suite is on one side of the home – ideal for privacy. The bedroom is large enough for a sitting area or private desk, has direct access to the patio, and features a walk-in closet and ensuite bath w/soaker tub, separate shower and dual sink vanity. Two generous sized bedrooms share an ensuite bath, and a third bedroom/full bath are off the family room in the back, making an ideal guest suite. You will love all that you have out back – expansive paver patio with covered and open space overlooking the community lake – great spot for relaxing or entertaining. Overall ideal location – Belmere is a secure gated community in an A rated school district. Easy access to essential shopping/dining (1 mile to Publix, 3 miles to Winter Garden Village) and major roadways (3 miles to SR 50, SR 429, Turnpike). Community features pool, fitness center, tennis, play area and more. This home and community SHINE, and you’ll love living here. Come see all that makes this home so special.

1027 Algare Loop, Windermere

$387,000
2 Beds 3 Baths Summerport Ph 04 C E F & G SubDv. 34786 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2.5-bathroom townhome located in the highly sought-after Summerport neighborhood in Windermere! This home offers a perfect blend of comfort, style, and functionality. Step inside to find laminate flooring on the first floor and hardwood stairs, adding a touch of elegance, while the second floor features durable vinyl flooring for easy upkeep. The open-concept living and dining areas flow seamlessly into a well-equipped kitchen with a gently used refrigerator, stove, and microwave—perfect for entertaining or everyday living. Enjoy the freshly painted interior and exterior plus the comfort of a newer AC system (replaced just 2 years ago). Smart home features include a Nest thermostat, smart doorbell, and garage camera for added convenience and security. Outside, you'll love the paved backyard, ideal for relaxing or hosting gatherings. A detached 2-car garage offers plenty of storage and parking space. As part of the Summerport community, you'll have access to a host of amenities including a community pool, fitness center, playgrounds, and sports courts for tennis, basketball, and volleyball. This home is walking distance to Keene’s Crossing Elementary (A-rated school), and just a short drive from Bridgewater Middle and Windermere High School. Don’t miss this opportunity to own a well-appointed home in a prime location close to schools, parks, shopping, and dining! Schedule your private showing today and discover the lifestyle waiting for you in Summerport!

14233 Confetti Drive, Windermere

$1,655,000
4 Beds 3 Baths Kelso On Lake Butler SubDv. 34786 Zip Code
Welcome to 1424 Kelso Boulevard, a stunning luxury waterfront estate that seamlessly blends elegance and modern comfort. This 4-bedroom, 2.5 bathroom masterpiece offers unparalleled craftsmanship and breathtaking water views, creating the perfect sanctuary for refined living. Upon approaching the home you are greeted by the recently brick paved circular driveway with ample parking for all the future events you can host. As you enter the home through the solid wood custom built double front doors the brick foyer offers a warm welcome as does the formal living room with expansive vaulted ceiling and dining room with built in bar separated by the double sided fireplace. Onto the magnificent kitchen with custom cabinets and drawers including the cabinet faced refrigerator, Bosch built in oven and microwave, cooktop, and dishwasher. Expansive 15' exotic granite center island with 2 sinks and a glass backsplash to reflect the one of a kind amazing views to the back. Additional room off the kitchen can be used for a breakfast nook and or additional family room. Upstairs you will find the 4 bedrooms including the master suite with vaulted ceilings, double sink vanity and walk in closet, 3 of the 4 rooms offer a sliding door out to the full length balcony overlooking the aforementioned views of the backyard and lake. Full bath with double sink vanity, frameless glass shower and custom tile. Additional interior features include half bath with copper sink and spacious laundry room with built in cabinets, counter and sink. Back downstairs you find the 8" sliders leading out to the recently added heated and salt water pool with fiber optic color changing. When your finished playing in the pool take a quick stroll don the brick paver path to the custom built weather resistant dock with lift and jump in your boat and or jet ski and live the lake life! When the day is done, choose your location either in the pool, on the balcony or on the dock and watch the magnificent glow of the sunset disappear beyond the lake. Additional exterior features include solid storage shed, tile roof, along with a side rear entry garage. The private community of Kelso on Lake Butler is situated on its own little peninsula nestled between Lake Cypress and Lake Butler and offers deeded access to the famous "Butler Chain of Lakes." Location benefits include easy access to Downtown Windermere and Winter Garden where you will find local farmers markets, easy access to Disney, The Florida Turnpike, SR 408 and Downtown Orlando.

1424 Kelso Boulevard, Windermere

$700,000
5 Beds 5 Baths Sanctuary/Lks/Windermere SubDv. 34786 Zip Code
Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration.

13106 Orange Isle Drive, Windermere

$2,000,000
4 Beds 6 Baths Sawyer Sound SubDv. 34786 Zip Code
Experience luxury living in this new contemporary home, located in exclusive gated community of Sawyer Sound featuring only 20 private estates. Set on half and acre, this 4 Bedroom, 4 full Bathroom and 2 half bathroom residence offers modern elegance with an open floor plan designed for living and entertainment. The first floor boasts a spacious living area that flows into a large Kitchen, complete with premium appliances, custom cabinetry and a oversized island. A full laundry room with sink and cabinetry, formal dinning room, guest bedroom with private bathroom, home office, a large game room that conects with the screnned patio with retractable door panels. On the Second floor, a large loft for entertainment. A primary suite features a walk in custom made closet, balcony and bathroom. Additionaly, bedroom 2 and 3 features a walk in custom made closets and private bathrooms for each bedroom.The Exterior features a spacious patio with retractable screens that conects with the pool. Just minutes from top rated schools, shopping, dinning and world class attractions.

6106 Marleon Drive, Windermere

$900,000
4 Beds 4 Baths Windsor Hill SubDv. 34786 Zip Code
Welcome to this charming one-owner, custom-built Windsor Hill estate, perfectly situated on a peaceful half-acre lot along a cul-de-sac. With nearly 4,000 square feet of thoughtfully designed living space, this spacious 4-bedroom, 4-bathroom home offers incredible potential to make it your own.Step inside to find a grand formal living room with beautiful wood floors that extend throughout the main living areas and bedrooms. The formal dining room provides an inviting space for memorable gatherings, while the expansive family room, complete with a cozy fireplace, opens to a large pool deck—ideal for relaxation and entertaining.The well-appointed kitchen offers abundant cabinetry to meet all your culinary needs. Dishwasher is not warranted. Upstairs, you’ll discover a massive 26 x 38 bonus room featuring built-in cabinets, a closet, and a full bathroom, providing endless possibilities for a home office, media room, or guest suite.This home has been lovingly maintained by its original owners and includes valuable updates such as a new roof in 2021, a 2013 AC system with an electric filter, a dedicated 2010 AC unit for the bonus room, and stylish paver driveways installed in 2019. The exterior showcases a convenient side-entry garage, and an elegant paver circular driveway, offering ample parking and enhanced curb appeal. The white vinyl fencing provides privacy and frames the spacious backyard, where a sparkling pool awaits your personal touch.This property offers a unique opportunity to bring your creative vision and transform it into the home of your dreams. Located in the desirable Windsor Hill community, residents enjoy amenities such as tennis courts and a playground, enhancing the neighborhood’s appeal.Don’t miss your chance to create something truly special in this highly sought-after community. Schedule your private tour today!

9548 Crown Prince Lane, Windermere

$2,250,000
5 Beds 5 Baths Windermere Town SubDv. 34786 Zip Code
BACK ON MARKET! Financing fell through. Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family. The open living and dining room features built-ins with floating shelves, and the gourmet kitchen is sure to impress with custom cabinetry, waterfall quartz countertops, luxury appliances, a natural gas cooktop, and a walk-in pantry—everything you need for everyday living or hosting. Your primary suite feels like a retreat with two walk-in closets, a spa-like bath with a freestanding tub, and sleek custom cabinets. Upstairs, two bedrooms include built-in desks and charming corner windows—perfect for a reading nook or window seat. You’ll also find a first-floor guest suite, a private office with pool views, a 3-car garage, and a spacious attic for storage. The resort style backyard was designed for fun and relaxation. Enjoy the heated pool and spa, an entertainer’s bar, and even space to park your boat. The poolside casita with kitchenette is the ultimate bonus space—ideal as an in-law suite, game room or man cave. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.

409 W 2nd Avenue, Windermere

$2,900,000
5 Beds 6 Baths Keenes Pointe SubDv. 34786 Zip Code
Get ready to enjoy the lake lifestyle in your custom estate poised on a cul-de-sac lot with 110 feet of pristine shoreline on Lake Burden. Recently underwent a $1 million remodel. This masterpiece of a home has it all with 5 bedrooms, 5.5 bathrooms, spacious great room, office, and a large 5 car garage! Your timeless Mediterranean home with contemporary finishes was designed to enjoy the breathtaking panoramic views of sunsets and Disney fireworks over Lake Burden with the utmost comfort and privacy. The grand façade has its own gated courtyard includes lush tropical landscaping complimented with a long driveway, balcony, and large custom double entry door. Upon entry you will immediately notice 12’ soaring high ceilings in the foyer with chic porcelain floors throughout. Sit back, relax, and take in your beautiful lake views from the great room which is open to the kitchen and casual dining space. The chef’s kitchen is a dream come true with a large center island, breakfast bar seating, marble backsplash, Viking refrigerator and dishwasher, Dacor 6 burner range with a vented hood and a walk-in pantry. The elegant dining room is perfect for those formal occasions with its own private courtyard and temperature controlled 1,000+ bottle wine cellar. Work from home in peace with your own office away from the living areas. The primary suite has its own seating area with amazing lake views including two large built-in walk-in closets, spa like bathroom including a glass shower, tub, and dual vanities. All secondary bedrooms are spacious en-suites with plenty of closet space. Relax and enjoy captivating lake views within the serenity of the expansive outdoor living area that is fully screened with your heated pool and water features with premium stone deck pavers. The covered lanai includes an amazing fully equipped summer kitchen for those perfect summer barbeques and get-togethers with loved ones. Gather around the massive sunken firepit for those beautiful star gazing nights. The wooden dock includes a jet ski lift to enjoy all 129 acres of Lake Burden. Your home was built by award-winning builder Campbell Custom Homes and features one-of-a-kind finishes throughout. Additionally, Keene’s Pointe is a 24-hour guard gated community, includes plenty of parks, playgrounds, with access to The Butler Chain of Lakes, The Golden Bear Country Club with amenities that include a gym, pool, golf, tennis courts, and neighborhood boat/RV storage. Close to Orlando’s best attractions including Walt Disney World, shopping, and “A” schools including Windermere Elementary, Bridgewater Middle, and the newer Windermere High School. Don’t miss out on this extraordinary lakefront property. Be sure to click on the virtual tour links.

8336 Boyla Court, Windermere