Location: Windermere
Do Not Show Listings
17514 BLACK RAIL ST, WINDERMERE, FL 34786
$725,00087 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,578
Elementary School: None
High School: None
Tax Year: 2025
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
$699,00055 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
Tax Year: 2024
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
$669,99455 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
Elementary School: Sunset Park Elem
High School: Windermere High School
Middle School: Horizon West Middle School
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
$2,500,0002 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
High School: Olympia High
Middle School: Gotha Middle
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)
13312 LONGACRE DR, WINDERMERE, FL 34786
$534,900106 Days on yellowkey MLS ID: S5141031
REDUCED by $9,000 (1.7%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2058 Built: 2013Monthly Fee: $120 Tax: $7,533 (2024)Community: Windermere TerraceSingle Family
Taxes:$7,533
Remarks: Move in ready and recently refreshed! This inviting 3-bedroom, 2-bathroom home features a versatile flex room, a screened patio, and a private backyard, offering comfortable and functional living spaces. Located in a quiet, well-established neighborhood, the home is just 12 minutes from Walt Disney World and close to top rated schools, parks, shopping centers, restaurants, and supermarkets, with easy access to major roadways for convenient commuting. The property also includes an attached two car garage with rear entry and automatic door opener, plus a driveway with space for two additional vehicles.
Listing is courtesy of: LA ROSA REALTY INTERNACIONAL L (407-600-7542)
Listing Agent: Mariesy Davila (407-548-4718)
12761 HOLDENBURY LN, WINDERMERE, FL 34786
$539,90033 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 is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Randall Gill (407-756-0071)
11922 ANGLE POND AVE, WINDERMERE, FL 34786
$760,000278 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
$6,980,00067 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
Elementary School: Windermere Elem
Middle School: Chain of Lakes Middle
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 is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Winnie Tam (863-651-4687)
9713 ENDICOTT CT, WINDERMERE, FL 34786
$5,250,0005 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
Middle School: Bridgewater Middle
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
$875,00061 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
$664,90093 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
$574,000369 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
$4,690,0002 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)
9621 WINDY RIDGE RD, WINDERMERE, FL 34786
$13,550,0002 Days on yellowkey MLS ID: O6400740
Bed: 9 Bath: 13.0 Gar: 8 Liv Area Sq Ft: 20445 Built: 2025 Tax: $13,931 (2025)Community: Windsor HillSingle Family
Taxes:$13,931
Remarks: Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool with a spa and massage room ! Highlights: • Custom-built mansion in progress — secure it now to choose your colors, flooring, cabinetry, countertops, lighting, and finishes • Private helicopter pad for seamless arrival and departure • Luxury bowling alley in development — your private entertainment retreat of turn into extra car show storage garage area ! • Grand open floor plan, soaring ceilings, and estate-level architecture • Massive gourmet kitchen + walk-in pantry, ideal for chef-level entertaining • Space for home theater, gym, wine cellar, or guest quarters • Oversized garages and motor court • For our equestrian lovers, you are permitted one horse for each acre. Location Perks: • Situated in one of Windermere’s most coveted neighborhoods • Minutes to Lake Butler Chain, championship golf, and elite private schools • Close to Winter Garden Village and exclusive dining/shopping This is a rare opportunity to own a truly bespoke estate before completion — where every detail is yours to design, and your view is forever protected. Inquire now for private plans, customization walkthrough, and completion timeline. Step into your own private paradise with this one-of-a-kind resort-style property featuring every amenity for ultimate relaxation and recreation. Highlights include: • Lagoon-style pool with a swim-up bar, perfect for hosting or unwinding in luxury • Private spa sanctuary with a designated massage room and indoor heated pool, offering year-round wellness experiences • Full-size tennis court for active days and fun with friends or family • Charming barn – ideal for equestrian use, storage, or a stunning rustic event space Whether you’re dreaming of daily spa treatments, evening swims under the stars, or tennis matches followed by cocktails poolside, this property delivers the ultimate blend of luxury and leisure.
Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)
Listing Agent: Natalie Citarelli (321-607-3586)
6036 GREATWATER DR, WINDERMERE, FL 34786
$1,999,9992 Days on yellowkey MLS ID: O6400277
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4013 Built: 2001Monthly Fee: $298 Tax: $15,493 (2024)Community: Keenes PointeSpa: YesSingle Family
Taxes:$15,493
Remarks: Classic elegance defined in this stately Keene’s Pointe residence, set along the 17th Fairway of the renowned Jack Nicklaus Signature Golf Course. An impressive grand foyer with warm hardwood flooring greets guests to a traditional-style home with office and formal plus family living spaces on the first floor, along with a guest suite. The primary bedroom and two other secondary bedrooms are upstairs, offering an elevated view of the golf course. A balcony spans the second floor of the home. All bedrooms feature new carpet and fresh interior paint and LED lighting. The updated kitchen features striking white cabinetry, stainless WOLF double ovens and gas cooktop with hood, Sub Zero built-in refrigerator, dishwasher, and two fridge drawers. A butler’s pantry off the dining room is perfectly suited with a beverage fridge and Miele espresso coffee bar. A covered back patio and summer kitchen is the ideal complement to the refreshing pool and paver patio, for outdoor entertaining. Roof replaced in 2023. New HVAC for the upstairs in 2024. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
6799 HELMSLEY CIR, WINDERMERE, FL 34786
$658,000156 Days on yellowkey MLS ID: O6361417
3 Days Off yellowkey (back on 4/20/2026)
REDUCED by $12,000 (1.8%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2615 Built: 2011Monthly Fee: $129 Tax: $9,339 (2024)Community: Preston SquareSingle Family
Taxes:$9,339
Remarks: Windermere Lake View Home with Disney Fireworks - Best Value in the Area! Recent price improvement - now one of the best opportunities in Windermere. Welcome to your dream home! This beautiful 4-bedroom, 3.5-bathroom residence offers the perfect blend of elegance, comfort, and convenience — ideally located in one of Windermere’s most sought-after communities with top-rated “A” schools. Enjoy breathtaking views of the lake and conservation area right from your spacious covered screened lanai, with a large backyard ready for your future pool. The open-concept kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and entertainment. On the first floor, you’ll find a guest suite with a full bath, a private office, and a welcoming foyer. Upstairs features a massive loft — perfect as a media room, playroom, or second family room — along with the master suite and two additional bedrooms. The home also features a newer air conditioning system replaced just two years ago, offering added comfort and peace of mind. Enjoy the exclusive community amenities, including a clubhouse, pool, playground, and sports court. From your backyard, you can even watch the Disney fireworks at night! Conveniently located near shopping centers, dining, and entertainment, this home truly combines luxury, location, and lifestyle — the perfect place for your family in Windermere! Seller willing to consider offers.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Maqueli Gewehr (863-258-5656)
6443 CARTMEL LN, WINDERMERE, FL 34786
$1,475,000788 Days on yellowkey MLS ID: O6179128
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4257 Built: 2004Monthly Fee: $520 Tax: $14,632 (2023)Community: Reserve At Lake Butler Sound Unit 2Spa: YesSingle Family
Taxes:$14,632
Tax Year: 2023
Remarks: Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted Reserve at Lake Butler Sound community, this meticulously crafted residence epitomizes luxury living. Boasting classical architecture and spanning 4,257 square feet, this property offers a sophisticated retreat with unparalleled amenities. Upon entry, a raised travertine and marble foyer sets the tone for the residence, leading to the grand salon and dining room adorned with sculptured ceilings and columns. Beyond French doors, a private study offers a serene escape. The family room features a coffered ceiling and French doors opening to the covered veranda, seamlessly blending indoor and outdoor living. Elegant travertine, marble, and wood flooring flow seamlessly throughout, enhancing the ambiance of every space. A sprawling 30x12 ft. pool and spa are the focal point of outdoor entertainment and relaxation. The heart of the home lies in its gourmet kitchen, where a center island, built-in double ovens, walk-in pantry and granite countertops provide the perfect backdrop for culinary endeavors. The master suite is a sanctuary unto itself, boasting a morning kitchen, French doors to the veranda, dual walk-in closets, and a luxurious spa-style master bath with a dual-head shower and separate whirlpool tub. Ascending to the second floor, a versatile bonus room/fifth bedroom suite awaits, complete with a full bath, and walk-in closet. This space offers endless possibilities, whether as a home theater, game room, or private retreat. Luxury appointments abound, including travertine and exotic Kenpass hardwood flooring, an additional bonus space off the master, currently used as an exercise room, and an oversized three-car garage. Lavish landscaping completes the allure of this exceptional residence, offering a tranquil oasis in a prestigious community.
Listing Agent: Julie Bettosini, Pa (321-689-9594)
13430 HOPKINTON CT, WINDERMERE, FL 34786
$585,000208 Days on yellowkey MLS ID: O6346406
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1732 Built: 2005Monthly Fee: $167 Tax: $7,277 (2024)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$7,277
Remarks: ***Charming Windermere Home in Lakes of Windermere – Peachtree! *** Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations. Step inside to find a bright and open floor plan with a spacious great room, dining area, and a well-appointed kitchen featuring ample cabinetry and counter space and kitchen eat in nook. The primary suite includes a walk-in closet and an en-suite bath, while two additional bedrooms and a full bath provide plenty of room for family or guests. Outside, enjoy a large screened in patio perfect for relaxing or entertaining. The home also features a finished garage, new roof, recent exterior painting, storage racks in the garage, central heating & cooling, and fresh curb appeal. Located just minutes from Disney, shopping, dining, top-rated schools, and major highways, this property offers the ideal balance of convenience and community living. The HOA includes access to neighborhood amenities and ensures a well-kept environment. Don’t miss the opportunity to make this charming Windermere home yours!
Listing Agent: Lynn London (410-206-0952)
12411 MONTALCINO CIR, WINDERMERE, FL 34786
$1,550,0005 Days on yellowkey MLS ID: O6400067
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3399 Built: 2011Monthly Fee: $150 Tax: $11,027 (2025)Community: Casa Del LagoSpa: YesSingle Family
Taxes:$11,027
High School: West Orange High
Remarks: A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a full Carrera marble master bath with floating vanities, organize closet system in every bedroom, all bedrooms have their own private bath, $15,000 worth of plantation shutters, $5,000 security system with cameras with access from your smart phone, all of the wood in the home is African Sapele, 7.25" crown molding and base boards in every room, pre-wired surround sound, casement double pane windows as well as spray foam insulation. Too many extras to list. This home is a MUST SEE!!
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Mauro Costa (321-231-6800)
4029 ISABELLA CIR, WINDERMERE, FL 34786
$3,299,0006 Days on yellowkey MLS ID: O6400064
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 7217 Built: 2018Monthly Fee: $480 Tax: $30,300 (2025)Community: CasabellaSpa: YesSingle Family
Taxes:$30,300
Remarks: Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak finish with bathrooms featuring porcelain floors and walls. Tech enthusiasts will marvel at the Lutron smart home system's ability to control power shades and lighting throughout the home. enterprise-grade 10Gbps networking backbone. Cinema lovers will find no equal in the custom movie theater, boasting a 133” anti-reflection screen, Sony 4K 3D projection, and a commercial-grade Dolby Atmos 11.2 3D sound system within a fully soundproofed environment. The backyard is a tropical paradise featuring imported African white marble flooring, a custom smart pool, and a professional Alfresco summer kitchen. The centerpiece is a magnificent 20,000-gallon Obsidian & Natural Stone Koi garden, fully equipped with UV/scrub filters and gas heating to protect its world-class inhabitants. Located minutes from top-rated Windermere schools, Orlando Health Central, and Dr. P. Phillips Hospital, with easy access to Downtown Orlando. This is not just a home; it is a high-tech fortress and a private resort
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