Windermere Real Estate

Windermere Real Estate

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and charming small-town vibe, Windermere offers a unique blend of natural beauty and modern living. This vibrant community is surrounded by the serene waters of the Butler Chain of Lakes, making it a haven for water enthusiasts and nature lovers alike.

Windermere boasts an inviting atmosphere that is perfect for families, retirees, and young professionals seeking a tranquil lifestyle without sacrificing access to urban amenities. The town is characterized by its beautiful tree-lined streets, historic homes, and a strong sense of community. Residents enjoy a variety of recreational activities, from boating and fishing on the lakes to exploring the numerous parks and trails that wind through the area.

The local economy is thriving, with a range of shops, dining options, and services that cater to the needs of its residents. Windermere is also conveniently located near major highways, providing easy access to the bustling city of Orlando, renowned theme parks, and cultural attractions.

Education is a priority in Windermere, with highly-rated schools that serve the community, ensuring that families have access to quality education for their children.

Whether you are looking to settle down in a peaceful neighborhood or searching for a vacation home in a scenic locale, Windermere offers a welcoming community filled with charm and opportunity. Discover the beauty of Windermere, where every day feels like a vacation!

Newest Listings in Windermere

13578 Gorgona Isle Drive, Windermere
$799,999
5 Beds ⋅ 4 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
It's here~ this rare floor plan that was a former model and beautifully appointed 5-bedroom, 3.5-bath home in sought-after Windermere Isle offers a unique blend of stylish living and useful upgrades with views of the night time fireworks. Designed with an open floor plan and enhanced decorative features, like upscale wall coverings, a coffered ceiling in the dining room (which is currently being used as an at-home office/den) and a custom built-in entertainment feature that adds useful storage, while being visually appealing. The kitchen is finished with granite countertops, tile backsplash, stainless steel double oven, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A large downstairs bedroom equipped with a full bath provides wonderful flexibility for guests or multi-generational living. Upstairs you will find a spacious loft, providing another inviting gathering space. A cute reading nook is positioned just outside the the private primary suite. Inside the primary bedroom you'll find a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a soaking tub, and glass-enclosed shower. The outdoor setting has a large screened lanai with artificial turf for easy maintenance. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways.

13578 Gorgona Isle Drive, Windermere
9253 Sabal Palm Cir, Windermere
$479,000
3 Beds ⋅ 2 Baths ⋅ Silver Woods SubDv. ⋅ 34786 Zip Code
Welcome home to this 3 bedroom, 2 bathroom home at 9253 Sabal Palm Circle in Windermere’s Silver Woods community! This meticulously maintained home has had the big updates done, so you can move right in. The split floor plan puts the primary suite on its own side, away from the other two bedrooms. The kitchen has a breakfast bar and its own eating area, which works well for quick meals and for having people over. Both bathrooms were recently remodeled, and the primary bath has a walk-in shower. New windows and new flooring run throughout the home. Out back, the screened rear porch is a comfortable spot for morning coffee or an evening outside without the bugs. It overlooks a fully fenced backyard, good for pets, play or relaxing outdoors. The major systems have been updated too: plumbing replaced 5 years ago, a new septic field, a newer roof, A/C installed in 2019 with new ductwork, and a water heater that is 3 years old. The home is also on city water. The location is hard to beat, with The Grove at Isleworth just minutes away and Dr. Phillips’ famous Restaurant Row a short drive. Upgrades like these don’t come along often, so schedule your showing today! *Click on VIRTUAL TOUR LINK 1 for a 3-D walkthrough of this home*

9253 Sabal Palm Cir, Windermere
7906 Brofield Avenue, Windermere
$560,000
3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South SubDv. ⋅ 34786 Zip Code
*Video Tour Available* Welcome to Brofield Avenue that’s tucked away in Lake Sawyer South. This quiet loop has no through traffic and this home sits on a conservation lot across from community greenspace. There aren’t any neighbors in the front or back of this property! The front porch with it’s ceiling fan invites you in. You’ll find the formal living and dining space at the front of the home and the open family and kitchen towards the back. The eat-in kitchen has granite countertops, solid wood cabinetry, stainless-steel appliances and a spacious pantry. The large family room has triple slider doors that allow the living space to open to the outdoors. Enjoy the screened patio that overlooks the fenced-in backyard and conservation land. Back inside, you’ll find the primary bedroom with a large walk-in closet, en-suite bathroom with double sinks, garden tub, shower and linen closet. The secondary bedrooms share a hall bathroom with a bathtub and shower. This home is turnkey, used as a vacation home and has been well cared for by the original owners and can be sold furnished. Addition upgrades include a new roof (2025), newer motor in the AC handler (2024), newer light fixtures, and ceiling fans. The HOA includes access to the community pool and playground. Lake Sawyer South is minutes from Disney, restaurants, shopping and great schools.

7906 Brofield Avenue, Windermere
13755 Bravante Alley, Windermere
$460,000
3 Beds ⋅ 3 Baths ⋅ Vineyards/Horizons West Ph 2b SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to Windermere! This beautiful 3-bedroom, 2.5-bath end-unit townhome offers a spacious, thoughtfully designed floor plan with comfortable living spaces both indoors and out. The open-concept great room flows seamlessly into the kitchen, featuring a large island with breakfast bar seating, solid surface countertops, stainless steel appliances, and plenty of room for gathering and entertaining. Upstairs, the primary suite is joined by two additional bedrooms and a spacious loft, offering flexible space for a media room, home office, game room, or second living area. Ceiling fans in the bedrooms add everyday comfort, and the washer and dryer are included. Step outside to the screened-in lanai, complete with a ceiling fan, and enjoy the adjoining paver patio, perfect for relaxing or outdoor entertaining. A *rare fenced and gated side yard provides additional outdoor space, an exceptional feature for townhome living. The 2-car rear-facing garage adds convenience while maintaining the home's attractive streetscape. Shopping, dining, and entertainment are just minutes away at Summerport, Windermere Village, Winter Garden Village, and Horizon West. Plus, enjoy convenient access to Central Florida's world-famous theme parks and attractions. With its end-unit location, versatile floor plan, inviting outdoor spaces, and convenient Windermere setting, this townhome offers a wonderful combination of comfort and convenience!

13755 Bravante Alley, Windermere
6808 Duncaster Street, Windermere
$481,500
3 Beds ⋅ 2 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
"Close by December 31 to take full advantage of Amendment 3 Homestead Exemptions." Welcome to the quiet, tree-lined community of Lakes of Windermere! This amazing home has 2094 heated SF with 3 Bd/2 BA & 2 car garage. As you enter the home the Living room / Dining room is on the right with beautiful Wood Floors. A very open kitchen with center island, 42 inch Cabinetry, Storage Galore including a Large Pantry and a large wraparound bar to the Family Room. The Family room has a gas fireplace and direct access to the covered Porch. The Primary bedroom has a trey ceiling and a large walk in closet. The Primary bathroom has dual vanities, walk in shower & separate garden tub. Interior laundry room with washer & dryer will remain. New roof, New Interior Paint & New Carpet Nov 2026 Located in a wonderful community of Lakes of Windermere, 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 $245/quarter. 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.

6808 Duncaster Street, Windermere
14551 Yellow Butterfly Road, Windermere
$784,900
5 Beds ⋅ 4 Baths ⋅ Stillwater Xings Prcl Sc-13 1 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained and thoughtfully updated home, ideally situated along a quiet bend of Yellow Butterfly Road in the desirable Summerport community. Backing to a peaceful natural setting with trees, a scenic walking path, and pond views, this property combines privacy, comfort, and convenience. Step outside and enjoy the fenced backyard, attractive landscaping, young orange and mango trees, and an expansive brick-paver patio—an inviting setting for relaxing, entertaining, or simply enjoying Florida's beautiful weather. Inside, the home features spacious living areas, including a versatile first-floor den that can serve as a home office, study, or flex space. Imagine coming home for the holidays, gathering with loved ones, and enjoying the warm glow of the fireplace at the flick of a switch—a cozy touch that makes this home especially inviting. The attached three-car tandem garage offers generous parking capacity and additional flexibility for storage. Upstairs, five generously sized bedrooms are thoughtfully arranged for comfort and privacy. The expansive primary suite features two walk-in closets, while two additional bedrooms share a Jack-and-Jill bathroom with separate vanities. Another bedroom features its own en-suite bathroom, and the oversized fifth bedroom, overlooking the trees and pond, provides endless possibilities as a playroom, game room, or additional living space. Conveniently located near SR 535, Hamlin's shopping and dining destinations, scenic walking trails, and Summerport's community amenities, this home provides easy access to the area's finest shopping, dining, recreation, and everyday conveniences. Keene's Crossing Elementary School is within easy reach via the walking path behind the home. Bridgewater Middle School, Windermere High School, Windermere Preparatory School, Foundation Academy, and other educational options are also nearby. Lovingly cared for by its owners, this home is being presented for sale due to a family relocation out of state. A wonderful opportunity to make this exceptional Summerport property your own! Seller is open to considering flexible buyer credits toward closing costs or a mortgage rate buydown for purchase proposals at or near the asking price.

14551 Yellow Butterfly Road, Windermere
104 E 11th Avenue, Windermere
$862,500
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Photos coming soon! Welcome to your new home in the historic, golf-cart-friendly Town of Windermere! Nestled on a 0.29-acre corner lot shaded by mature trees, this charming 1-story block home offers 3 bedrooms, 2 bathrooms, and 1,834 square feet of flexible living space on one of Windermere’s beloved dirt roads. Step inside to find an open-concept floor plan designed for effortless entertaining. The oversized main living room serves as a blank canvas, highlighted by a cozy fireplace that anchors the gathering area. Transition seamlessly into the expansive kitchen—a chef’s dream packed with extensive prep space. The hallway in the center of the house leads to the bedrooms and a full guest bathroom, while the rear primary suite serves as a quiet retreat complete with an en-suite bathroom. The entire home is fully wired for AT&T high-speed fiber internet, making remote work a breeze. Your private oasis awaits outside. Enjoy a dedicated 36’ x 40' sports court equipped with a basketball hoop, ping pong table, and pickleball net — the ultimate setup for weekend matches and entertaining. Afterward, unwind on your screened back porch. Experience additional peace of mind with an extensive list of structural and mechanical updates: Water Treatment & Softener System (08/2026, incl. transferable warranty) Well Pump (07/2024) Exterior Paint (01/2023) New Attic Insulation (2023) Electric Water Heater (03/2022) New Electric Panel ( 03/2023) Metal Roof (11/2017) HVAC System (06/2014) Double Pane Windows (2012) ?Living in the heart of Windermere means you are just a short walk or golf-cart ride from boutique shopping, weekly farmers markets, and local dining. Best of all, residents enjoy exclusive access to private neighbourhood boat ramps to launch into the pristine Butler Chain of Lakes, as well as nearby tennis courts and waterfront parks. Zoned for top-rated public schools including Windermere Elementary. ?Don't miss this rare opportunity to live the ultimate lake-community lifestyle! Seller offers up to 2% buyer credit or towards rate buy-down!!!

104 E 11th Avenue, Windermere
8133 Enchantment Drive Unit 1307, Windermere
$399,000
4 Beds ⋅ 3 Baths ⋅ Oasis Cove I/Lakeside Village Ph 01 SubDv. ⋅ 34786 Zip Code
Welcome to this BEAUTIFULLY UPDATED 4-Bedroom, 2.5-Bath Condo in the GATED Oasis Cove at Lakeside Village community in Windermere! Offering the spacious layout and FEEL OF A TOWNHOME, this two-story residence combines modern updates including NEWER AC (2023), flexible living spaces and the convenience of LOW-MAINTENANCE condo living. A paver driveway leads to the TWO-CAR GARAGE, featuring an attractive CARRIAGE-STYLE GARAGE DOOR, while the welcoming exterior sets the stage for all that's waiting inside. Step through the front door and you'll immediately appreciate the FRESH, CONTEMPORARY LOOK, highlighted by NEWER WOOD-LOOK LAMINATE FLOORING throughout the main living areas. The SPACIOUS OPEN LAYOUT allows the Kitchen, Dining Area and Living Room to flow together beautifully, creating an inviting space for everyday living or entertaining. The Living Room is filled with NATURAL LIGHT and features sliding glass doors that open to a COVERED REAR PATIO and fenced backyard—a lovely spot to enjoy your morning coffee or relax outdoors with a little green space of your own.The UPDATED KITCHEN is both stylish and functional, featuring STONE COUNTERTOPS, an abundance of cabinetry, STAINLESS STEEL APPLIANCES and a classic subway tile backsplash. A BREAKFAST BAR offers additional seating and creates a natural gathering spot for casual meals or conversation. The spacious FIRST-FLOOR PRIMARY SUITE provides a comfortable retreat, complete with an EN SUITE BATH featuring dual sinks and a step-in shower, and includes a LARGE WALK-IN CLOSET. A CONVENIENT HALF BATH on the first floor is perfect for guests and everyday living.Upstairs, a GENEROUS LOFT adds wonderful flexibility and makes an ideal family room, media space, game room or home office. ARCHITECTURAL ARCHWAYS and distinctive cutouts add character, while NEWER LAMINATE FLOORING and a sleek, modern ceiling fan give the space a fresh contemporary feel. Two additional Bedrooms, each with NEWER CARPETING, provide comfortable accommodations for family or guests, and both offer WALK-IN CLOSETS. A full Bath nearby, serves the upstairs Bedrooms, while an additional FLEX SPACE can be used as a FOURTH BEDROOM, office, hobby room or whatever best suits your needs. Enjoy the ease of LOW-MAINTENANCE LIVING in this GATED COMMUNITY, where amenities include a clubhouse, COMMUNITY POOL and playground, as well as exterior and grounds maintenance, cable, internet, trash and water, giving you more time to enjoy your home and the surrounding area. Oasis Cove is conveniently situated near LAKESIDE VILLAGE CENTER, where you'll find Publix, restaurants and everyday services, and for even more shopping and dining, WINTER GARDEN VILLAGE offers a wide variety of popular retailers and eateries. Outdoor enthusiasts can explore the trails and natural beauty of TIBET-BUTLER PRESERVE, enjoy lakeside recreation at R.D. KEENE PARK or spend an afternoon at WEST BEACH PARK. And with WALT DISNEY WORLD, Disney Springs and the many attractions of Central Florida nearby, there's always something fun to enjoy.The home is also zoned for A-Rated schools—BAY LAKE ELEMENTARY, HORIZON WEST MIDDLE and WINDERMERE HIGH SCHOOL. With its MODERN UPDATES, spacious loft, flexible living spaces and GREAT LOCATION, this Oasis Cove condo offers a WONDERFUL OPPORTUNITY to enjoy the best of Windermere living. Welcome Home!

8133 Enchantment Drive Unit 1307, Windermere
8736 Peachtree Park Court, Windermere
$875,000
4 Beds ⋅ 3 Baths ⋅ Peachtree Park SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully updated home in the desirable Windermere area, just minutes from Walt Disney World! Featuring a convenient downstairs bedroom and full bathroom. The main living area showcases a stunning custom fireplace, while the kitchen features high-end Café appliances, including an induction range, and a custom pantry. Additional upgrades include all new hurricane-impact windows, automatic shades throughout, a water softener, and fresh interior and exterior paint. Upstairs, you'll find the spacious primary suite with a custom California Closet, 2 additional bedrooms, a loft with a custom glass half wall. The garage features epoxy flooring and EV charging. Enjoy a fenced backyard with no rear neighbors and beautiful natural surroundings, plus a neighborhood playground. Conveniently located near Disney, shopping, dining, and major roadways, this home offers an incredible combination of upgrades, comfort, and location!

8736 Peachtree Park Court, Windermere
9100 Palm Tree Drive, Windermere
$579,000
3 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 01 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this inviting 3-bedroom, 2-bathroom pool home, situated on a corner lot with a circular driveway in the established community of Silver Woods. A spacious foyer opens into the living room, flowing seamlessly into the adjoining dining area for easy everyday living and entertaining. The conveniently located kitchen connects to the family room, where wood-look tile and vaulted ceilings create a warm, open gathering space. The split-bedroom floor plan offers privacy for the primary suite, complete with a walk-in closet and attached bathroom. Two additional bedrooms and a full bathroom are located on the opposite side of the home, providing flexibility for guests, a home office, or everyday needs. French doors from the family room open to the patio and in-ground pool, creating a welcoming setting for outdoor dining, weekend gatherings, or simply relaxing in the Florida sunshine. A fenced backyard completes the outdoor space. Recent updates - New Porcelain Tile floor throughout, New Hurricane strength garage door, New cabinetry in garage and laundry room, Custom closets in Primary, Roof 2021, Windows 2020, HVAC 2019. Silver Woods offers low HOA fees and community tennis courts, along with a convenient Windermere location near shopping, dining, and Dr. Phillips’ Restaurant Row. Enjoy access to major roadways and popular Central Florida destinations, including Universal Orlando Resort and Walt Disney World. This home brings together comfortable living, outdoor enjoyment, and everyday convenience!

9100 Palm Tree Drive, Windermere
10628 Reams Road, Windermere
$479,000
4 Beds ⋅ 3 Baths ⋅ Windermere Trls Ph 1c SubDv. ⋅ 34786 Zip Code
Welcome to Windermere Trails! This beautiful 4-bedroom, 2.5-bath, two-story home offers the perfect combination of comfort, style, and convenience in one of Central Florida's most desirable locations. Step inside to discover a spacious, open-concept floor plan designed for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, ample cabinetry, and a seamless flow into the living and dining areas. Wood flooring enhances the main living spaces, while generously sized bedrooms provide plenty of room to unwind. Enjoy the convenience of an attached two-car garage, interior laundry, and a private outdoor patio perfect for relaxing after a long day. Ideally located just minutes from Walt Disney World, Disney Springs, shopping, dining, and entertainment, with convenient access to major roadways and everything the growing Horizon West area has to offer. This home delivers the space, location, and lifestyle you've been looking for. Schedule your private showing today!

10628 Reams Road, Windermere
7129 Thicket Branch Alley, Windermere
$450,000
3 Beds ⋅ 3 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code
A kitchen that makes you stop scrolling. A Windermere address that makes you want to stay. This beautifully upgraded 3-bedroom, 2.5-bath townhome in Ashlin Park offers 1,588 square feet of inviting living space, fresh paint, and distinctive contemporary finishes. The centerpiece is the kitchen: brand-new countertops with a dramatic waterfall edge, decorative wood-slat accents, two-tone cabinetry, stainless steel appliances, and sleek architectural lighting. An open layout connects the kitchen, dining, and living areas—perfect for hosting friends or enjoying a quiet evening at home. Wood-look flooring and stylish bathroom finishes carry the contemporary feel beyond the kitchen. Upstairs, the primary bedroom offers a comfortable retreat, with two additional bedrooms providing room for guests or a home office. A welcoming front porch and two-car garage complete the home. Enjoy Ashlin Park’s community pool, playground, and sidewalks, with shopping, dining, and Disney nearby. Schedule your showing and see what makes this home stand out.

7129 Thicket Branch Alley, Windermere
Start Your Search

How much is your home worth?

Get instant property value now!