Location: Windermere
Do Not Show Listings
12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786
$1,490,0007 Days on yellowkey MLS ID: O6399958
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3487 Built: 1997Monthly Fee: $130 Tax: $6,661 (2025)Community: Isles WindermereSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,661
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The outdoor living area is designed for true Florida living, featuring a sparkling pool and spa, perfect for relaxing or entertaining. Adding to the sense of tranquility, one side of the property has no direct neighbors—only beautifully maintained green space and a scenic bridge, creating gorgeous views and a rare feeling of serenity. Inside, the home features generously sized rooms filled with comfort and charm, including an oversized family room with a wood-burning fireplace. The primary suite is a private retreat, complete with a luxurious bath featuring dual sinks, a jetted garden tub, a large walk-in shower, and a full vanity area. Every detail has been thoughtfully updated with style and functionality in mind. Additional highlights include a three-car garage with ample space for parking and storage, as well as a prime location within a top-rated public school district, just minutes from Windermere’s premier shopping, dining, and recreation. A rare opportunity to own a beautifully updated home in one of Central Florida’s most desirable communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Patricia Zimath, Llc (321-318-1050)
4226 DOWNEAST LN, WINDERMERE, FL 34786
$10,500,000181 Days on yellowkey MLS ID: O6355233
REDUCED by $1,300,000 (11.0%) on 04/08/2026
Bed: 5 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 5316 Built: 1980 Tax: $10,926 (2024)Community: NaSingle Family
Taxes:$10,926
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: DRAMATIC PRICE IMPROVEMENT. Exceptional DEVELOPMENT OPPORTUNITY, currently R-CE zoning should allow for 3 Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, part of the coveted BUTLER CHAIN of Lakes. This is a rare chance to create a premier LAKEFRONT ESTATE or subdivide to create three ideally sized lots with water frontage. At present, the property includes an older 5,000 sq ft home (5 bedrooms, 3.1 baths) and an oversized four car garage, which can serve as a temporary residence or teardown to make way for your vision. Why this property stands out, Unmatched location: Situated on the east side of Windermere, with convenient access from Conroy Windermere Road and Apopka Vineland. Windermere prestige, Offers the cachet of a WINDERMERE ADDRESS and proximity to luxury amenities. Prime access: Minutes to Isleworth Country Club, Bay Hill, and downtown Windermere. Development upside: Ready canvas for luxury estates in one of Central Florida’s most desirable waterfront corridors. Whether you’re a developer, custom builder, or investor, this is your opportunity explore and deliver truly exceptional homes in a highly sought-after market. Property is also listed as vacant land on MLS #O6367852.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thad Czapka (407-257-4253)
6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786
$970,00090 Days on yellowkey MLS ID: O6376318
REDUCED by $30,000 (3.0%) on 04/22/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3820 Built: 2018Monthly Fee: $200 Tax: $10,983 (2024)Community: WindstoneSingle Family
Taxes:$10,983
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: ONLY APPROXIMATELY 7 YEARS NEW, THIS HOME OFFERS MODERN DESIGN AND PEACE OF MIND. MAJOR PRICE DROP - $80,000 OFF! Designed for those who crave space, privacy, and elevated living, this exceptional newer home offers 5 BEDROOMS PLUS TWO BONUS ROOMS, including ALL 4 MAIN BEDROOMS with WALK-IN CLOSETS and a private guest suite featuring an EN-SUITE and WALK-IN CLOSET—all complemented by NO REAR NEIGHBORS and NO FRONT NEIGHBORS, creating extraordinary flexibility for refined living, entertaining, and everyday comfort. Have you ever dreamt of living close to Disney in an upscale neighborhood—where modern luxury meets peaceful surroundings? This is where that dream becomes reality. At the heart of the home, a gourmet kitchen that chefs will love anchors the OPEN-CONCEPT design. A Gas line is available for the stove. flowing effortlessly into the main living areas. Whether hosting celebrations or enjoying quiet evenings at home, the thoughtfully designed layout includes a living room, a family room, and expansive, light-filled spaces designed for connection. One of the large bonus rooms is currently being used as a MOVIE ROOM, offering a private, theater-style retreat ideal for entertaining or cozy nights in. The bedroom layout is equally impressive, offering space and privacy for everyone. ALL 4 MAIN BEDROOMS include WALK-IN CLOSETS, while the guest bedroom’s EN-SUITE and WALK-IN CLOSET create the perfect setup for visitors, multi-generational living, or a luxurious secondary retreat. Step outside to a truly rare outdoor setting—AN OVERSIZED BACKYARD with NO REAR NEIGHBORS and NO FRONT NEIGHBORS, where privacy and tranquility take center stage. This expansive space is ready to become your personal oasis, whether that includes a resort-style pool, outdoor kitchen, or serene garden escape. When the day winds down, retreat to the MASTER SUITE, an impressively spacious sanctuary designed for rest, relaxation, and renewal. Every detail throughout the home reflects thoughtful design, modern elegance, and effortless functionality. Ideally located VERY, VERY CLOSE TO DISNEY and ALL ATTRACTIONS in CENTRAL FLORIDA, this home offers the rare balance of privacy, space, and proximity—placing world-class entertainment, dining, and lifestyle experiences just minutes away. This is more than a home—it’s a lifestyle defined by luxury, location, and possibility.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Candice Liceaga (407-861-7303)
11486 MISTY OAK ALY, WINDERMERE, FL 34786
$549,0002 Days on yellowkey MLS ID: S5148331
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1950 Built: 2016Monthly Fee: $107 Tax: $7,492 (2025)Community: Ashlin Park Ph 1Single Family
Taxes:$7,492
Remarks: Beautiful two-story single-family home with a pond view in the Ashlin Park neighborhood of Windermere. Open floor plan includes large living room, dining, and kitchen, with ceramic tile throughout the first floor. Kitchen has quartz countertops, stainless steel appliances, large island, and ample cabinet space. Living room faces pond and peaceful walking trail with lovely indoor or porch water view. First floor also has a half bathroom and a large storage room, as well as an attached two-car-garage. All three bedrooms on second floor with carpet flooring, along with two full bathrooms and a spacious laundry room. Ashlin Park is quiet neighborhood located between the world-famous Walt Disney World and FL535, with great access to theme parks, a variety of restaurants and shops, major highways, golf courses, etc., Minutes’ walk to the community clubhouse and pool. Make this lovely home yours and enjoy Central Florida living.
Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)
Listing Agent: Kikuko Moribe, Pa (321-246-0066)
1028 LASCALA DR, WINDERMERE, FL 34786
$749,0001 Day on yellowkey MLS ID: O6400649
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2208 Built: 2002Monthly Fee: $140 Tax: $8,185 (2025)Community: Belmere Village G2 48 65Spa: YesSingle Family
Taxes:$8,185
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Introducing an EXCEPTIONAL opportunity to own a RENOVATED WATERFRONT POOL residence in the prestigious, GATED community of Belmere. Meticulously maintained, this elegant single-story home embodies refined living with a seamless blend of comfort, style, and tranquility. Designed with a desirable split floor plan, the home offers both privacy and effortless flow. The heart of the home is a newly designed chef’s kitchen featuring a generous island, integrated WINE REFRIGERATION, designer hardware, and a sleek touchless faucet—perfectly suited for both intimate gatherings and upscale entertaining. The adjoining living spaces are enhanced by luxury vinyl plank flooring, while the bedrooms offer newer carpeting for added comfort. The primary suite is a private retreat, complete with a sitting area and an en-suite bath featuring dual vanities, a soaking tub, a separate glass-enclosed shower, and a custom walk-in closet with built-ins. Through elegant Pella French doors, step into your own FLORIDA sanctuary. A SCREENED-IN SALTWATER POOL with a NEW PUMP, expansive PAED DEK, and serene water views create an atmosphere of peace and exclusivity—ideal for embracing the Florida lifestyle. Additional enhancements include a whole-home Reme Halo UV air purification system and thoughtfully included built-ins such as a TV console and mount. Set within a sought-after community offering low HOA fees, exceptional amenities, and access to top-rated schools, this residence is ideally located near fine dining, upscale shopping, and world-renowned attractions. This is more than a home—it is a lifestyle of sophistication, comfort, and serenity. Private showings available for pre-qualified buyers. Experience the home anytime through the immersive 24-hour 3D
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Petra Bukalo Pa (407-484-0685)
910 LASCALA DR, WINDERMERE, FL 34786
$770,00013 Days on yellowkey MLS ID: O6397847
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2742 Built: 2003Monthly Fee: $140 Tax: $6,213 (2025)Community: Belmere Village G2 48 65Single Family
Taxes:$6,213
Remarks: Unique opportunity to own a stunning Mediterranean-style home with WATER VIEWS and a PRIVATE COURTYARD, located in the highly sought-after, gated Belmere community. This exceptional residence truly checks all the boxes. Upon entry, you are welcomed by a WINDING STAIRCASE featuring decorative WROUGHT IRON DETAILS. Natural light fills the home, enhancing the thoughtfully designed split floor plan that offers both comfort and privacy. The home showcases a NEW spacious kitchen, a RENOVATED primary bathroom, and a RENOVATED en-suite bathroom in the second bedroom. The oversized primary suite is a true retreat, complete with a sitting area and private BALCONY overlooking WATER VIEWS. The en-suite master bath features dual vanities, a soaking tub, and a separate shower. Designed for both everyday living and entertaining, the home offers multiple gathering spaces including a spacious family room, formal living room, and an open loft area. SIGNIFICANT recent upgrades include the installation of TWO BRAND NEW A/C units (APRIL 2026), enhanced for modern comfort, peace of mind and delivering superior climate control throughout the home. This home has been freshly painted inside and out, offering a crisp, modern aesthetic. Enjoy the best of Florida living in your own backyard with water views, perfect for relaxing or entertaining. Additional highlights include a dual 3-car garage, brick paver driveway, and charming courtyard entry. This home would cost over $1,000,000 to build new—making it an incredible value. In three words: functionality, tranquility, and serenity. Located in a gated community with low HOA fees and excellent amenities, this home is zoned for top-rated schools and is conveniently close to dining, shopping, entertainment, and world-renowned theme parks. Experience the home anytime with our 24-hour 3D interactive tour. Showings are available for pre-approved buyers only—schedule yours today, as this home will not last!
13525 GORGONA ISLE DR, WINDERMERE, FL 34786
$1,120,00066 Days on yellowkey MLS ID: O6377789
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4625 Built: 2018Monthly Fee: $268 Tax: $9,351 (2025)Community: Windermere IsleSpa: NoSingle Family
Taxes:$9,351
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: One or more photo(s) has been virtually staged. Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space. Seller is providing a credit towards a 2-1 RATE BUY DOWN with full price offer. Inquire for more details.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Roo Klaers (407-493-5615)
81 OAKDALE ST, WINDERMERE, FL 34786
$2,300,000157 Days on yellowkey MLS ID: S5138567
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4284 Built: 2001 Tax: $24,940 (2025)Community: Davis ShoresSingle Family
Taxes:$24,940
Middle School: Gotha Middle
Remarks: Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step inside to an open, grand gathering space framed with natural wood beams, a gas fireplace, and a seamless flow into a chef-inspired kitchen. Featuring state-of-the-art GE Monogram appliances, a Taj Mahal quartzite island, restaurant-quality crushed ice, a 100+ bottle wine cooler, a full bar and coffee lounge, and a spacious walk-in kitchen pantry—this home invites effortless entertaining. Throughout, new wide-plank laminate wood floors set a refined, cohesive tone. Additional highlights include professional designer wallpaper in the dining room and powder bath, smart bidet in the primary bath, and a fully integrated smart-home lighting, shade, and security system. The primary suite is a private sanctuary, complete with a fully reimagined spa bath wrapped in marble and porcelain, a freestanding soaking tub, and two custom-designed closets. There are three more en suite bedrooms offering privacy and convenience. This corner-lot haven is framed by mature oak trees and newly installed landscaping and irrigation. A beautiful outdoor deck and built-in fire pit creates a cozy retreat for gatherings. Follow the canal behind the home to access the world-renowned Butler Chain of Lakes. The boathouse features an electric lift, dual Sea-Doo floating docks, and instant access to some of Florida’s most coveted waterways.
Listing Agent: David Warzycha (863-860-3365)
17514 BLACK RAIL ST, WINDERMERE, FL 34786
$725,00088 Days on yellowkey MLS ID: O6376756
0 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2373 Built: 2014Monthly Fee: $167 Tax: $8,578 (2025)Community: EnclaveSingle Family
Taxes:$8,578
Elementary School: None
High School: None
Middle School: None
Remarks: New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and durability. The layout includes 4 bedrooms and 2 bathrooms, plus a large dedicated office, ideal for working from home or for those seeking a quiet, flexible space. Designed for comfortable single-level living, this home is perfect for buyers who appreciate the convenience of no stairs while still enjoying an open and grand feel. Located in the heart of Windermere, the property offers outstanding accessibility, with shopping, dining, and daily amenities just minutes away. AC WAS INSTALLED IN 2022,3.5 TONS. The primary suite is a true retreat, featuring an elegant tray ceiling, serene pond views with screen patio, and direct access to the backyard, allowing you to step outside and enjoy the peaceful water scenery at any time. Both the primary bedroom and the living room overlook the pond, bringing nature and calm into everyday living. This is an ideal home for those seeking privacy, convenience, and refined single-story living in a prime Windermere location.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: He Gao (407-955-0138)
13243 CHARFIELD ST, WINDERMERE, FL 34786
$699,00056 Days on yellowkey MLS ID: O6385405
1 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2794 Built: 2010Monthly Fee: $81 Tax: $6,403 (2024)Community: Lake Sawyer South Ph 02Single Family
Taxes:$6,403
Remarks: Under contract-accepting backup offers. A Windermere pool home under $700K like this is hard to come by, especially on one of the best tree-lined streets in the community. As soon as you walk in, you’re greeted by a two-story entrance and open living area that brings in great natural light and gives the home a larger, more elevated feel. The layout includes a formal dining room and hardwood floors throughout the main living areas, complemented by tile in all the right spaces. This home is set up perfectly for both everyday living and entertaining, with multiple living and dining spaces, a powder bath, and a spacious kitchen featuring wood cabinetry, newer appliances, and direct access to the outdoor area. The primary suite is on the first floor and includes a custom walk-in closet with built-ins, along with a spacious bathroom featuring a double sink vanity, garden tub, and walk-in shower. Upstairs, you’ll find a large loft that works great as an office, game room, or second living space, along with three additional bedrooms. One bedroom has its own en-suite, giving you a second primary-style setup. The backyard is the highlight. A fully screen-enclosed pool with sun deck, waterfalls, brick pavers, multiple seating areas, and a summer kitchen creates a true indoor-outdoor lifestyle. There’s even a large projector screen for movie nights. The yard is fully fenced with plenty of green space left over. Additional features include a 3-car garage, a driveway that fits up to six cars, a welcoming front porch, a large laundry room, and a newer upgraded AC unit. Located in a highly desirable Windermere community with A-rated schools, you’ll also have access to great amenities including a community pool, covered playgrounds, walking trails, a golf putting green, and courts for basketball, tennis, and pickleball, all close to shopping, dining, and everyday convenience. Minutes from Disney and all the fun, you don't want to miss out on this truly incredible home! Schedule your showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$669,99456 Days on yellowkey MLS ID: O6380917
REDUCED by $10,000 (1.5%) on 04/21/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 2009Monthly Fee: $82 Tax: $3,146 (2024)Community: Lakes/WindermereSpa: NoSingle Family
Taxes:$3,146
Remarks: Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for. Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with sleek cabinetry, stainless steel appliances, island, and plenty of storage — perfect for everyday cooking or entertaining friends and family. The primary suite includes a luxurious bathroom with his-and-her sinks and an upgraded California closet with premium built-ins for maximum organization. Enjoy Florida weather year-round in the screened-in patio with a retractable electric screen, extending your living space and providing the perfect spot for morning coffee or evening relaxation. The large, fully fenced backyard features extended brick pavers, offering plenty of room for gatherings, grilling, pets, or future customization. Additional features include a front balcony, a 2-car garage, and an oversized driveway with great curb appeal. This home sits in a prime Windermere location surrounded by some of the best amenities in Central Florida. Just minutes away you’ll find top-rated Windermere schools, scenic lakes, nature trails, Bay Hill, The Butler Chain of Lakes, playgrounds, and community parks. Nearby you’ll enjoy endless shopping, popular restaurants, cafés, breweries, local markets, and everyday conveniences. You’re also close to the Winter Garden Village, Downtown Windermere, major highways, theme parks, and world-class entertainment. The community itself offers resort-style amenities including a sparkling community pool and clubhouse — perfect for relaxing weekends and social gatherings. If you’re looking for a move-in-ready home with modern finishes, incredible outdoor space, and a location that simply can’t be beat, this is the one. Homes like this in Windermere don’t last long — schedule your private showing today! *** A/C and Water Heater replaced in 2024. Roof replaced in 2025. Exterior of home repainted in 2022 ***
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Omar Andreasen (407-883-2989)
9648 WEATHERSTONE CT, WINDERMERE, FL 34786
$2,500,0003 Days on yellowkey MLS ID: O6400680
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4482 Built: 2000Monthly Fee: $227 Tax: $20,450 (2025)Community: Weatherstone On Lake OliviaSpa: NoSingle Family
Taxes:$20,450
Elementary School: Thornebrooke Elem
Remarks: Set within the private gates of Weatherstone on Lake Olivia, this stunning lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views. Boasting 6 bedrooms and 4 full baths, the home blends classic design with thoughtful updates and an inviting, functional layout. A charming wraparound front porch creates a warm first impression, surrounded by mature landscaping and tranquil views, perfect for relaxing mornings or unwinding at the end of the day. Inside, natural light fills the home, highlighting soaring ceilings, rich wood flooring, plantation shutters, crown molding, and carefully curated designer details. The open concept design allows for effortless flow between the main living spaces, many of which capture picturesque lake views. At the center of the home, the updated kitchen serves as a true gathering place, featuring generous prep space, a large island, stainless steel appliances, and a spacious dining area. Two oversized walk in pantries, one with a concealed bar, offer both convenience and a touch of character. The primary suite is located on the first floor, offering serene lake views, a spacious custom closet, and a beautifully redesigned bathroom with dual quartz vanities, a soaking tub, and a walk in shower. The first floor also includes a private office with custom built ins, an additional family room, or optional formal dining space, and a full bath. Upstairs, a well planned layout provides flexibility and privacy with five secondary bedrooms, some connected by updated Jack and Jill baths, plus a dedicated workspace with built in features on the landing area. An additional oversized bonus room with closet can easily function as a media room or play space. The home previously had a large loft area which could quite easily be converted back. Additional highlights include a first floor laundry room, abundant storage throughout, an updated tile roof, refreshed exterior paint, and a three car garage with epoxy flooring and built in storage. Designed for entertaining, the outdoor living space features a covered lanai, summer kitchen, resort style pool, fire pit, artificial turf dog run, and a Trex dock with boat lift, all overlooking the calm waters of Lake Olivia, where you can water ski, have fun on your boat or jet ski's or just enjoy a calm ride on your paddle boards, the fun is endless. With only 13 homes, Weatherstone Ct offers a boutique gated setting just moments from local favorites like The Yellow Dog Eats, parks, top rated schools, and the heart of Windermere. This is lakefront living at its finest, private, spacious, and beautifully appointed. Ideally located with direct access to all the major highways, the home provides seamless connectivity to destinations throughout Central Florida and beyond, while still maintaining a quiet, tucked-away feel.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Andy Neal (407-619-3517)
12761 HOLDENBURY LN, WINDERMERE, FL 34786
$539,90034 Days on yellowkey MLS ID: O6392337
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2380 Built: 2002Monthly Fee: $82 Tax: $3,561 (2025)Community: Lakes/Windermere Ph 01 49 108Single Family
Taxes:$3,561
Remarks: Under contract-accepting backup offers. Come see this wonderful southern style cottage in the beautiful Lakes of Windermere community located in exclusive Windermere. FL. This 4 bedroom 2 bath split bedroom plan with its spacious and open floorpan will impress you. The home offers a charming front porch with dormered windows and a rear screened patio with brick floors. Upon entering the home you will see it's tremendous potential with a large Dining Room with trey ceilings and crown moldings and connected to a Living Room with a view directly into the combined oversized Kitchen, Dining Nook and Family Room. The kitchen offers a large center island, solid surface counter tops, 42" wood cabinets with a pantry and plenty of dining space for casual meals. The oversized Family Room offers wood tile floors that are connected to the tile floors in the dinette and kitchen. The primary bedroom suite offers 2 walk-in closets, trey ceilings with moldings and a 5 piece bathroom with 2 vanities/sinks, tub, shower and water closet. The property is perfect for a growing family with its split bedroom plan or anyone who wants flexibility to have an office and guest rooms. The community offers a fantastic community pool, parks, soccer field and plenty of spaces to enjoy picnics or your favorite sports. Additionally there is a community fishing dock on beautiful Lake Sawyer at the front of the community. In addition to everything the community offers you can't beat the surrounding Windermere area with it's shopping options at Lakeside Village, Westside, Windermere Village and even the Winter Garden Village Town Center and Hamlin Town Center just to the north. You are also close to major roadways including CR 535 and SR 429 with quick access to Florida's Turnpike, SR 408 (to downtown Orlando) and Interstate 4. You will also enjoy fantastic Orange County Schools and best off all the communities proximity to the back entrance to the Walt Disney World complex and the Magic Kingdom. Schedule your showing today!
Listing Agent: Randall Gill (407-756-0071)
11922 ANGLE POND AVE, WINDERMERE, FL 34786
$760,000279 Days on yellowkey MLS ID: O6328443
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3382 Built: 2013Monthly Fee: $81 Tax: $8,155 (2024)Community: Windermere Trls Ph 1BSpa: NoSingle Family
Taxes:$8,155
Elementary School: Bay Lake Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained four-bedroom, three-and-a-half-bath home in the highly sought-after Windermere Trails community, located less than two minutes from Walt Disney World. The front of the home offers multiple flexible living spaces ideal for a home office, sitting room, or hobby area. The open family room flows into a spacious kitchen featuring a large quartz island, brand-new stainless steel appliances, ample cabinetry, and tasteful modern finishes. An additional flex space near the kitchen can serve as formal dining or an additional gathering area. Upstairs, the primary suite provides a peaceful retreat with two walk-in closets and a spa-style bathroom with dual vanities and an oversized walk-in shower. Two bedrooms share a Jack-and-Jill bathroom, while the fourth bedroom has its own private, upgraded bath. A large bonus room with a built-in movie screen adds extra space for entertainment. Step onto the upstairs balcony to enjoy morning coffee or evening breezes. The fully fenced backyard features a screened patio and mature banana, mango, lemon, and orange trees, creating a private tropical setting. Luxury vinyl flooring runs throughout the home, with no carpet. Major updates include a new HVAC system in 2023, whole-home water softener, and fresh interior and exterior paint in 2025. Windermere Trails offers walking trails, lakes, and a resort-style pool. Lakeside Village is less than a mile away with grocery stores, shopping, and restaurants, along with close proximity to downtown Windermere, top-rated A schools, boat ramps, major highways, and Orlando’s best dining and entertainment.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
5186 VARDON DR, WINDERMERE, FL 34786
$6,980,00068 Days on yellowkey MLS ID: O6382040
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4739 Built: 1990Monthly Fee: $985 Tax: $32,002 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$32,002
Remarks: One or more photo(s) has been virtually staged. Fully reimagined golf-front estate in the prestigious Isleworth community with sweeping views of the iconic 3rd hole. Situated on approximately 1 acre, this 4,739 sq ft residence offers 4 bedrooms and 4.5 baths, soaring ceilings, and an upper level Terrace captures stunning golf course views. Fully upgraded front and rear grounds offer a resort-style setting with fountain entry, pool, Terrace, pavilion, and summer kitchen. Gated with automatic luxury gate, extended driveway, and spacious front yard for multiple vehicles. Fully fenced for added privacy. Rare move-in-ready golf-front opportunity in one of Isleworth’s most sought-after locations.
Listing Agent: Winnie Tam (863-651-4687)
9713 ENDICOTT CT, WINDERMERE, FL 34786
$5,250,0006 Days on yellowkey MLS ID: O6393891
Bed: 6 Bath: 7.0 Gar: 6 Liv Area Sq Ft: 7818 Built: 2007Monthly Fee: $313 Tax: $66,793 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$66,793
Remarks: Experience elevated lakefront living in this beautifully updated estate, within the prestigious guard gated golf community of Keene’s Pointe, offering direct access to the Butler Chain of Lakes. With over $850,000 in upgrades, this home is perfectly positioned to capture breathtaking sunset views and nightly Disney fireworks from the primary suite. This home delivers a rare combination of privacy, luxury, and lifestyle. Thoughtfully designed for both everyday living and effortless entertaining, the residence features water views from multiple living spaces, a layout that balances open gathering areas with private retreats, and dedicated spaces for both relaxation and recreation. The primary suite is a true retreat, featuring a private balcony overlooking the tranquil backyard and lake. A dedicated lounge with a beverage bar, updated spa-inspired bathroom, and custom walk-in closet create a refined and relaxing escape. Every bedroom is an ensuite, providing exceptional comfort for family and guests, while two fully remodeled junior suites showcase modern bathrooms and expanded custom closets. On the main level, enjoy formal dining complemented by a wine cellar, while a double-sided gas fireplace connect the family and game rooms which adds warmth and ambiance. The spacious game room and media room ensure there is always something to enjoy indoors. Step outside to your private oasis, where a resort-style pool and spa, fully equipped outdoor kitchen, covered dining area, and outdoor fireplace set the stage for year-round enjoyment. Retractable screens provide shade and comfort during the summer months, while the updated dock and boat lift make lake access effortless. A private canal connects you to Lake Tibet and the greater Butler Chain, offering the best of true lakefront living. For extended stays or multi-generational living, the apartment above the detached garage offers a private, fully functional space complete with a kitchenette, full bath, walk-in closet, and laundry. Positioned on a quiet cul-de-sac, this estate offers enhanced privacy along with an expansive driveway and turnaround for effortless arrivals and guest parking. The impressive five-car garage, along with a dedicated golf cart garage, provides exceptional space for collectors, storage, and embracing the Keene’s Pointe golf lifestyle. This is more than a home—it’s a complete lifestyle experience. From lake days and sunset views to golf, dining, and the best of Central Florida just minutes away, this property delivers the elevated living today’s luxury buyer expects.
Listing Agent: Amy Moline (407-506-7447)
4 CHASE RD, WINDERMERE, FL 34786
$875,00062 Days on yellowkey MLS ID: O6384257
REDUCED by $25,000 (2.8%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2386 Built: 1971 Tax: $7,637 (2024)Community: Windermere TownSingle Family
Taxes:$7,637
Remarks: FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.
Listing Agent: Matthew Hughes (407-619-4717)
6638 BRIDGEWATER VILLAGE RD, WINDERMERE, FL 34786
$664,90094 Days on yellowkey MLS ID: O6374429
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2908 Built: 2013Monthly Fee: $223 Tax: $8,467 (2024)Community: Vineyards/Horizons West Ph 1BSingle Family
Taxes:$8,467
Remarks: Under contract-accepting backup offers. Welcome to Vineyards Horizon West, this stunning 4-bedroom, 2.5-bath home offers about 3,000 square feet of thoughtfully designed living space, all set on a large conservation lot that ensures privacy and tranquility. From the moment you step inside, you will fall in love with the abundance of natural light, highlighting the home's open and airy layout. Downstairs, a versatile flex space awaits perfect for a playroom, additional guest room, or whatever suits your lifestyle best. The gourmet kitchen is a chef's dream, featuring a natural gas cooktop, ample counter space, that make both cooking and entertaining a delight. Upstairs you can find all 4 spacious bedrooms including a primary with window views overlooking the serene conservation. Recent upgrades, including a newer roof and AC, mean worry-free living, while the HOA takes lawn care off your to-do list. Step outside and enjoy the community's resort-style amenities, including two pools, a dog park, and a playground with a tot lot, fun for everyone in the family! This prime location puts you in the heart of Horizon West, just minutes from Disney, Hamlin Town Center, Winter Garden Village, and all the charm and luxury Windermere has to provide. Don't miss your chance to call this exceptional property home!
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Nickolas Amburgey (407-864-7622)
8742 PEACHTREE PARK CT, WINDERMERE, FL 34786
$574,000370 Days on yellowkey MLS ID: O6301023
1 Days Off yellowkey (back on 7/10/2025)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 2016Monthly Fee: $216 Tax: $7,209 (2024)Community: Peachtree ParkSingle Family
Taxes:$7,209
Remarks: Seller Financing Available at below market rates! Welcome to Peachtree Park and this Single-story home boasting an open concept floor plan. Upon entering, you will be greeted with beautiful wood floors that lead to the large living area with a beautiful view of conservation. With no rear neighbors, you will enjoy privacy, especially while relaxing on your large screened-in lanai and your fenced-in backyard. The fully functioning kitchen is complete with granite countertops, an island, Subway tile backsplash and Stainless-Steel appliances and the dining area also features a conservation view. The home offers a split floor plan with 2 bedrooms plus a bathroom in the front of the home and the Master Suite on the back of the home. The Master bedroom has a tray ceiling, ceiling fan and spacious walk-in closet. The en-suite bathroom features a beautifully tiled shower, double vanities and a separate water closet. This home has an attached 2-car garage and a spacious laundry room with built-in cabinets. Ready to go out and play? This home is very close to the Walt Disney World Resort (especially Magic Kingdom), world-class golf courses, fine dining, major theme parks and more. Don’t wait! Call today to schedule your private showing!
Listing is courtesy of: WAYPOINT REAL ESTATE GROUP INC (407-566-8265)
Listing Agent: James Tate (407-566-8265)
4906 AVIVA GARDEN CT, WINDERMERE, FL 34786
$4,690,0003 Days on yellowkey MLS ID: O6400218
Bed: 3 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6236 Built: 2016Monthly Fee: $1,146 Tax: $48,425 (2025)Community: Gardens/Isleworth Un #2Spa: YesSingle Family
Taxes:$48,425
Remarks: Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere. Thoughtfully designed for both everyday comfort and elevated entertaining, the home features a versatile layout including a spacious primary suite, multiple guest bedrooms, an oversized office/playroom, and a dedicated theater room. Expansive living areas flow seamlessly, creating a warm yet Elegant atmosphere throughout—all easily accessible via a private elevator connecting the home’s levels. The home delivers a true turnkey experience with modern finishes and enhancements, including a fully upgraded Crestron smart home system providing whole-home audio and video distribution for effortless control and convenience. A standout feature is the exceptional garage capacity, offering four individual single-car garages two of which are equipped with vehicle lifts. The outdoor living experience is a true highlight, featuring a resort-style pool, generous covered entertaining spaces, and serene water views that create a peaceful and private backdrop. Whether enjoying quiet mornings by the water or hosting guests in the evening, the setting is both inviting and unforgettable. Located within Isleworth—renowned for its championship golf course, world-class amenities, and guard-gated privacy—residents enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes and beautifully manicured grounds. This is a rare opportunity to own a fully updated, move-in ready home that seamlessly combines luxury, technology, and exceptional outdoor living in one of Orlando’s most sought-after communities.
Listing is courtesy of: CAMPBELL CUSTOM HOMES INC (407-947-4392)
Listing Agent: William Campbell (407-947-4392)
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