Location: Windermere , 34786
Do Not Show Listings
3629 LAKE BUYNAK RD, WINDERMERE, FL 34786
$975,000329 Days on yellowkey MLS ID: G5099846
REDUCED by $225,000 (18.8%) on 06/04/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2618 Built: 1973 Tax: $8,533 (2024)Community: Lake Buynak EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,533
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates presents a rare opportunity to enjoy acreage, privacy and flexibility in one of Central Florida's most desirable locations. Located within the highly sought-after Windermere ZIP code, this 4-bedroom, 3.5-bath residence offers more than 2,600 square feet of living space with a thoughtfully designed split floor plan, two ensuite bedrooms, multiple screened porches and a charming wood-burning fireplace. Whether you're seeking a primary residence, multigenerational living arrangement, investment opportunity or future custom estate, this property provides a versatile foundation for a wide range of possibilities. Some improvements include: energy-efficient double-pane windows and a dual septic system with an expanded drain field which add long-term functionality and value. The expansive 1.3-acre homesite offers abundant room to expand, create outdoor living spaces, accommodate recreational vehicles, add a guest house or accessory dwelling (subject to county approval) or reimagine the property entirely. One of the property's most compelling advantages is its location. Enjoy the prestige and convenience of a Windermere-area address while benefiting from county jurisdiction, providing a level of flexibility that is increasingly difficult to find. Optional HOA membership offers added choice without mandatory fees or oversight. Surrounded by luxury homes near Lake Butler and just minutes from Disney, Universal, premier shopping, dining and major roadways, this property combines convenience with the space and freedom that acreage buyers desire. With large homesites becoming increasingly scarce in the Windermere area, this unique offering presents an exceptional opportunity to create something truly special. Experience the space, flexibility and potential for yourself—call to schedule your private tour today.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tania Matthews (407-497-9660)
7011 NOBLETON DR, WINDERMERE, FL 34786
$580,00018 Days on yellowkey MLS ID: O6412101
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2460 Built: 2003Monthly Fee: $82 Tax: $9,209 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$9,209
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: TOP RATED SCHOOLS!!! Welcome to this beautifully maintained Craftsman-style home in the highly sought-after Lakes of Windermere community. Perfectly positioned on a premium homesite overlooking tranquil conservation views, this 4-bedroom, 2.5-bath residence combines timeless charm with modern upgrades and exceptional indoor-outdoor living. Inside, you’ll find a light-filled floor plan featuring hardwood flooring, elegant transom windows, custom built-ins, and spacious living and dining areas ideal for both everyday living and entertaining. The upgraded kitchen offers granite countertops, solid wood cabinetry, stainless steel appliances, a butler’s pantry, and ample prep and storage space. This is the one you’ve been waiting for—schedule your private showing today.
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Frederico Hexsel (407-745-8841)
8272 BRYCE CANYON AVE, WINDERMERE, FL 34786
$509,000100 Days on yellowkey MLS ID: O6389547
REDUCED by $6,000 (1.2%) on 05/07/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1888 Built: 2016Monthly Fee: $71 Tax: $7,459 (2024)Community: Windermere Trls Ph 3BSingle Family
Taxes:$7,459
Elementary School: Bay Lake Elementary
Remarks: 3BR/2.5BA bungalow-style home in the Windermere Trails community. This well maintained residence offers an open floor plan with high ceilings, and premium tile flooring throughout the main level. The home includes a gourmet kitchen, upgraded cabinetry in the laundry room. Upstairs, a versatile loft provides the perfect space for an office or media room, alongside a spacious master suite and two additional bedrooms. Perfectly located near Publix, dining, and banking, and zoned for A-rated schools with Bay Lake Elementary situated right at the community entrance.
Listing is courtesy of: ON ME REALTY (321-370-1474)
Listing Agent: Eduardo Pavone (407-232-1241)
13161 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$3,200,000297 Days on yellowkey MLS ID: TB8421056
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4500 Built: 2001 Tax: $16,201 (2024)Community: Lake Roper PointeSingle Family
Taxes:$16,201
Remarks: Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion foyer floor design, coffered ceilings, crown molding, and European-style ironwork boasts spectacular views of Lake Roper. The upstairs master bedroom has a beautiful view of Lake Roper. Master bath features an oversized tub and walk-in closet. This Grand Retreat has plenty of outdoor amenities including a basketball court, boat dock and boat lift. Heated family pool and spa. For all your family entertainment, a large open backyard leads to the dock with plenty of land. Stunning cedar and cypress trees surrender the property reminding you of FLORIDA living at its best. The ideal setting for privacy and serenity! Entertainment and fine shopping just minutes away. Close to major highways such as 429, 408 & the Turnpike. Easy access to the airport and Downtown Orlando yet secluded enough to give you a unique home in the heart of Windermere! Close to Windermere Prep school. Convenient to major highways, shops, restaurants, historic sites, major hospitals, and theme parks! Privacy awaits you! Schedule showing!
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Karolina Taylor (813-702-5478)
11051 HAWKSHEAD CT, WINDERMERE, FL 34786
$1,895,00055 Days on yellowkey MLS ID: O6400963
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3728 Built: 2003Monthly Fee: $637 Tax: $16,410 (2025)Community: Reserve At Lake Butler SoundSingle Family
Taxes:$16,410
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a seamless blend of sophistication and comfort. Spanning a thoughtfully designed single-story layout, the residence features five bedrooms, four full baths, and two half baths, all curated with impeccable attention to detail. From the moment you enter, soaring ceilings and an abundance of natural light highlight exquisite porcelain marble flooring that flows seamlessly throughout the main living areas—completely carpet-free for a clean, modern aesthetic. The bedrooms feature rich hardwood flooring, adding warmth and contrast. The open-concept design creates an inviting yet refined atmosphere, ideal for both intimate living and grand entertaining. At the heart of the home, the gourmet chef’s kitchen is a true showpiece, appointed with premium Viking stainless steel appliances, rich granite countertops, and bespoke custom cabinetry. Whether hosting elegant gatherings or enjoying everyday moments, this space is designed to impress. Step outside to your private resort-style sanctuary. The covered lanai, complete with a fully equipped outdoor kitchen and grill, overlooks a beautifully redesigned pool framed by lush, mature landscaping—creating a serene and secluded backdrop for relaxation or entertaining under the Florida sun. This home has been extensively upgraded with no detail overlooked, including a complete pool renovation with new equipment, a new screen enclosure, fresh exterior paint and lighting, two new HVAC systems, updated garage interiors and openers, EV charging capability, a new septic system, and a whole-home reverse osmosis water treatment system. Residents of this distinguished community enjoy 24-hour guard-gated security, private fishing dock on Lake Butler, and impeccably maintained surroundings—all just minutes from world-class attractions, fine dining, upscale shopping, top-rated schools, and major thoroughfares. This is more than a home—it is a statement of refined living in one of Central Florida’s most coveted addresses. Schedule your private tour today and experience it for yourself.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
6110 KEENES POINTE DR, WINDERMERE, FL 34786
$1,900,00077 Days on yellowkey MLS ID: O6393573
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3196 Built: 2002Monthly Fee: $298 Tax: $10,956 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$10,956
Remarks: Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades. This 4-bedroom plus office, 4-bath home features a highly functional, split-floorplan layout with nearly all living space on the main floor, including the primary suite and main living areas, with one bedroom and full bath upstairs. The home has been extensively updated throughout, beginning with all new interior paint and continuing into a fully renovated kitchen with updated finishes and appliances. All four bathrooms have been completely reimagined from floor to ceiling with today’s luxury buyer in mind, creating a cohesive and elevated feel throughout the home. Attention to detail is evident in every space, from the custom built-ins in the office and family room to the all-new lighting and chandeliers installed throughout both the interior and exterior, all integrated with a Lutron system for seamless control. Sonos in-ceiling speakers have been installed throughout the home, creating a whole-home audio experience. What truly sets this home apart is its advanced energy efficiency and independence. Equipped with a Tesla solar system, multiple Powerwalls and electricity backup, the home is designed to operate seamlessly even during outages while significantly reducing long-term energy costs. With the ability to sell excess power back to the grid and the convenience of EV charging at the ready, this is a rare blend of luxury and forward-thinking functionality. The primary suite offers a private retreat with French doors leading to the lanai, ample space for a sitting area, and a spa-inspired bath with dual vanities, soaking tub, walk-in shower, and generous closet space. Secondary bedrooms are well-positioned with direct bath access, providing both comfort and functionality. Outdoor living is equally impressive, featuring a screened pool and an expansive covered lanai designed for both relaxation and entertaining. The rear patio is equipped with an outdoor refrigerator, sink, and TV, creating the perfect setting for year-round enjoyment. The home is also equipped with a Ring security camera system covering the exterior. Ideally located directly across from The Golden Bear Club members' driving range from the front, with golf course views to the rear, this home also provides access to Keene’s Pointe amenities, such as parks and playgrounds, including community boat ramp to Lake Burden, and access to the Butler Chain of Lakes for recreation. Membership at The Golden Bear Club further allows for access to the Jack Nicklaus-designed golf course, tennis courts, fitness center, and restaurant. Residents of Keene's Pointe enjoy a lifestyle that blends privacy, recreation, and convenience, all just minutes from the world's best theme parks and entertainment, Winter Garden Village, Restaurant Row, and top-rated schools. This is a rare opportunity to own a fully updated, energy-efficient custom home in Keene’s Pointe that truly stands apart from the rest. Furniture designed specifically for the home is negotiable, offering a potential turnkey opportunity for the next owner.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Donna Calhoun (407-329-6253)
11333 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,196,000355 Days on yellowkey MLS ID: O6322386
REDUCED by $54,000 (4.3%) on 04/25/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3449 Built: 2004Monthly Fee: $283 Tax: $12,506 (2024)Community: Keenes PointeSingle Family
Taxes:$12,506
Remarks: One or more photo(s) has been virtually staged. "HUGE PRICE REDUCTION" - Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized loft—ideal for a secondary living area, media room, or playroom. The owner’s suite is conveniently located on the first floor, providing privacy and easy access, one bedroom can be used as an office located in the first floor, while the remaining three bedrooms are upstairs, offering ample space for family or guests.Step inside to soaring high ceilings and luxurious travertine tile flooring that flows throughout the main living areas on the first floor, creating a seamless and elegant look. The master bedroom is carpeted for added warmth and comfort.The gourmet kitchen overlooks the open-concept living and dining spaces, making it perfect for entertaining. From the living area, step out onto the covered lanai, ideal for year-round outdoor enjoyment. The fenced backyard provides a secure and private retreat with room for pets, play, or future swimming pool or outdoor enhancements. New roof was just replaced (June 2025), new AC units replaced in 2023. Laundry room with cabinetry and utility sink. Residents of Keenes Pointe enjoy access to world-class amenities including The Golden Bear Club featuring a Jack Nicklaus-designed golf course, clubhouse, dining, fitness center, and lakeside parks. The community is zoned for top-rated schools and is conveniently located near Windermere, Winter Garden Village, major highways, and theme parks.
Listing Agent: Cynthia Noto (407-782-1878)
1118 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,200,00092 Days on yellowkey MLS ID: O6390567
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4230 Built: 2019Monthly Fee: $250 Tax: $23,873 (2025)Community: Estancia/WindermereSpa: NoSingle Family
Taxes:$23,873
Remarks: Nestled within the exclusive enclave of Estancia at Windermere, this exceptional custom pool residence offers the perfect blend of sophisticated design, luxury finishes, and timeless Florida living. Built in 2019 and situated on a professionally landscaped homesite, this stunning two-story estate spans over 4,230 square feet of thoughtfully designed living space with 5 bedrooms and 5 bathrooms. The elegant interior showcases soaring ceilings, expansive living spaces, and a bright open-concept floor plan designed for both everyday comfort and grand-scale entertaining. A gourmet chef's kitchen serves as the heart of the home, featuring an oversized center island, premium built-in appliances, wine refrigerator, custom cabinetry, and generous gathering areas. The luxurious first-floor primary suite offers a private retreat with a spacious bedroom, spa-inspired bath, and oversized walk-in closet. Additional highlights include a dedicated office/den, formal dining room, loft-style secondary living area, media/flex space, oversized laundry room, and abundant storage throughout. High ceilings, designer finishes, custom window treatments, and expansive sliding glass doors enhance the home's sophisticated ambiance. Outdoor living is equally impressive. The resort-style backyard was designed for entertaining and relaxation, featuring a covered lanai, Travertine pool deck, sparkling heated pool, outdoor kitchen, grill station, and a fully fenced private backyard surrounded by mature landscaping. The three-car garage, concrete tile roof, and covered front porch further complement the home's exceptional curb appeal. This property has been upgraded with a $70,000 whole-home solar energy system and automatic backup generator. Whether lowering monthly energy expenses or maintaining power during storms and outages, this home is designed to deliver exceptional reliability, efficiency, and convenience. Located just minutes from charming downtown Windermere, residents enjoy one of Central Florida's most desirable luxury communities known for its tree-lined streets, lakeside setting, upscale estates, highly rated schools, and proximity to world-class golf, dining, shopping, and entertainment. Convenient access to the Butler Chain of Lakes, premier private schools, major highways, and the attractions of the Orlando area make this location as desirable as the home itself. Estancia offers an intimate luxury neighborhood atmosphere with beautifully maintained grounds and estate-sized homesites that provide both privacy and prestige. This extraordinary residence delivers the ultimate Windermere lifestyle—where luxury, comfort, and convenient living come together in one remarkable home.
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Corey Cannon (407-615-0215)
13145 ZORI LN, WINDERMERE, FL 34786
$750,00083 Days on yellowkey MLS ID: O6394437
1 Days Off yellowkey (back on 6/3/2026)
REDUCED by $25,000 (3.2%) on 04/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3597 Built: 2003Monthly Fee: $102 Tax: $10,490 (2025)Community: ProvidenceSingle Family
Taxes:$10,490
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Move-in ready! Situated in the Windermere community of Providence, this home offers spacious living across two floors. Upon entering, you are greeted by the formal living and dining rooms. The family room is open to the kitchen for easy entertaining. The primary suite along with three other bedrooms are on the first floor. On the second floor, there is a large loft with full bathroom and private guest bedroom. The 5 bedroom home scans over 3,500 Sq Ft and sits on 0.21 acres. The private, fenced backyard features a screened patio accessible by the primary suite and family room. Providence features a community pool, playground and sidewalks throughout offering scenic vistas whether you are jogging, walking your dog or strolling to take in the fresh Florida air.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Toni Cafferty (904-449-2184)
5224 LEMON TWIST LN, WINDERMERE, FL 34786
$624,90083 Days on yellowkey MLS ID: O6393299
0 Days Off yellowkey (back on 4/22/2026)
REDUCED by $15,000 (2.3%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2812 Built: 2006Monthly Fee: $130 Tax: $4,660 (2025)Community: SummerportSingle Family
Taxes:$4,660
Remarks: Welcome to one of the lowest-priced single-family home in the highly desirable Summerport community in Windermere. This well-maintained home features 4 bedrooms, 3.5 baths, a formal dining room, a private office, and a versatile loft/bonus space. Recent updates include a new roof (2021), fresh interior paint, and two new HVAC units (2023). The open-concept layout offers a spacious kitchen with 42” maple cabinets, granite countertops, tile backsplash, and stainless-steel appliances with a natural gas range, flowing into the family room with high ceilings. A formal dining room and private office with French doors add flexibility. The first-floor primary suite includes wood flooring, a large walk-in closet, dual sink granite vanities, garden tub, and separate shower. Upstairs features an en-suite bedroom, two additional bedrooms, a full bath, and a loft. Spacious Indoor laundry room with a sink and additional storage for those trips to Costco. Enjoy the screened and covered lanai, perfect for outdoor living. Amenities include a resort-style pool, playgrounds, parks, beach volleyball, tennis and basketball courts, and a scenic pier overlooking the community lake. Conveniently located within 5 minutes of top-rated public schools, this home also offers easy access to everyday essentials and local favorites—just a short bike ride to Foxtail Coffee and Kelly’s Ice Cream, with multiple Publix locations nearby and quick access to the Winter Garden Village, major highways (SR 429, Turnpike, SR 408), and downtown Winter Garden. Lovingly maintained and offered as the sellers relocate to be closer to family.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Carmen Aridas (407-299-6942)
9508 WINDY RIDGE RD, WINDERMERE, FL 34786
$30,000,00016 Days on yellowkey MLS ID: O6411343
Bed: 7 Bath: 13.0 Gar: 12 Liv Area Sq Ft: 51000 Built: 2011 Tax: $162,563 (2024)Community: N/ASpa: YesSingle Family
Taxes:$162,563
Elementary School: Thornebrooke Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provide a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. The vast and open water location offers an ideal space for seaplane arrivals and departures. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
12699 HAWKSTONE DR, WINDERMERE, FL 34786
$2,125,00055 Days on yellowkey MLS ID: O6401293
2 Days Off yellowkey (back on 6/2/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3751 Built: 2006Monthly Fee: $80 Tax: $22,152 (2025)Community: Lakes Windermere Ph 01 49 108Spa: YesSingle Family
Taxes:$22,152
Remarks: Under contract-accepting backup offers. Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and 5 baths, lives large at 3751 sq ft (4936 total), and is ideally situated on pristine shoreline frontage with some of the lake’s most expansive water views. Showcasing fine craftsmanship and opulent elegance in every detail, Chalet du Lac serves up a host of amenities ideal for Florida lakeside living. At the entry, the handcrafted metal and glass doors open to a stunning foyer, capturing sensational pool and lake views from the formal living room. A distinctive formal dining area and generous study greet, then to the large great room overlooking the pool oasis and lake. The kitchen features new appliances, a gas cooktop, a luxurious ogee edged stone island with farmhouse sink plus a huge walk-in pantry. A built-in Miele espresso machine as well as a beverage cooler and even more cabinet space. The primary suite features his and her walk-in custom closets, luxurious spa tub, spacious walk-in shower, oversized double vanities, and an inviting bedroom lounge that opens to the pool area. Poolside, enjoy the elevated patio over the lake, along with Lakeside, the boathouse includes an electric boat lift, with the entire dock made of composite decking, accessed by the walkway dressed with a nautical balustrade. Evenings are enjoyed at the poolside outdoor kitchen and patio, complete with a fireplace to sit by while taking in the moonlight. Verdant, lush landscaping fosters relaxation and inspires reflection and rejuvenation. Lake Sawyer is both a water sports paradise and a prime opportunity for pristine Florida lakefront living. Lake Sawyer features a certified competition water ski slalom course for those who love to ski and is even home to a float plane on the lake. At the north end, Lake Sawyer connects to Little Lake Sawyer, availing more beautiful water to explore. Chalet du Lac is ideally situated with immediate proximity to Windermere Prep and Windermere High School, and only minutes from downtown Windermere, downtown Winter Garden, Walt Disney World and the world-famous attractions of Orlando.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
13936 EDEN ISLE BLVD, WINDERMERE, FL 34786
$655,00017 Days on yellowkey MLS ID: S5150801
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2675 Built: 2004Monthly Fee: $116 Tax: $8,759 (2025)Community: West Point CommonsSingle Family
Taxes:$8,759
Remarks: Welcome to 13936 Eden Isle Blvd, where comfort, space, and modern updates come together in one of Windermere’s desirable and sought after gated communities - Eden Isle. Step into a fresh chapter of elevated living with this beautifully updated 4-bedroom, bonus room, 3.5-bathroom residence offering approximately 2,675 square feet of thoughtfully designed living space. The open and functional floor plan creates the perfect balance for both everyday living and effortless entertaining. The first floor features a seamless flow between the kitchen, dining, and living areas, all enhanced by a blend of vinyl and tile flooring. The sleek kitchen showcases stainless-steel appliances, generous counter space, and brand-new cabinetry with elegant granite countertops, creating a stylish and functional centerpiece of the home. Upstairs, three well-proportioned bedrooms, including a secondary suite, offer comfort, privacy, and a versatile layout ideal for family or guests. The upper level provides a bright and functional living arrangement designed for everyday convenience. The spacious primary suite is located on the main level and features dual vanities, a separate shower, and generous closet space, creating a relaxing private retreat. A versatile bonus room located near the entry adds exceptional flexibility—ideal as a home office, media room, playroom, or additional lounge space. A first-floor laundry room adds everyday convenience, while the attached two-car garage and extended driveway provide ample parking. Recent upgrades include a new roof (2021), downstairs A/C unit replacement (2021), new water heater (2024), new exterior paint (April – May 2026), new carpet fully replaced upstairs and in the downstairs primary suite creating a fresh and cohesive interior feel (April – May 2026), and full kitchen and bathroom cabinetry upgrades with granite countertops (April – May 2026), delivering both style and long-term peace of mind. Outdoor living is just as inviting, with front and back porches perfect for morning coffee or evening relaxation, all set within a well-maintained community environment. Perfectly positioned in Windermere, known for its A-rated schools. The residents from Eden Isle Community enjoy gated security, a private boat dock with canal access to Lake Speer, and a prime location just outside the Summerport shopping plaza and Publix. You’re also minutes from Winter Garden Village, top-rated schools, grocery stores, dining, and major conveniences. This move-in-ready Windermere home delivers the ideal combination of location, upgrades, and lifestyle—an opportunity not to be missed. Schedule your showing today.
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
13019 LANGSTAFF DR, WINDERMERE, FL 34786
$360,00021 Days on yellowkey MLS ID: O6411551
0 Days Off yellowkey (back on 6/2/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1375 Built: 2005Monthly Fee: $200 Tax: $5,303 (2025)Community: Lakes/Windermere-Lk Reams TwnhSpa: NoTownhouse
Taxes:$5,303
Remarks: Under contract-accepting backup offers. Tucked away in the peaceful Lake Reams Townhome community, this charming home offers the perfect balance of excitement and relaxation — just minutes from Disney, shopping, dining, and top-rated schools, yet surrounded by the quiet comfort you’ll love coming home to after a day at the parks. Located at the end of a cul-de-sac with no rear neighbors and serene conservation views, this townhome feels like a private retreat in the heart of it all. Inside, you’ll find a bright eat-in kitchen featuring granite countertops and stainless steel appliances, opening into a spacious living and dining area designed for easy everyday living and entertaining. Outside you’ll find your private courtyard — the ideal spot for morning coffee before heading to Disney or winding down in the evening. The courtyard also leads to the detached 2-car garage for added convenience. Upstairs, the spacious primary suite creates a relaxing escape with double sinks, granite countertops, a garden tub, separate shower, and walk-in closet. The second bedroom includes its own private bathroom as well. The laundry closet is upstairs which makes laundry a breeze and the washer and dryer convey! Additional updates and features include a new AC (2025), newer roof (2022), downstairs half bath, ceiling fans, and generous storage throughout. The HOA takes care of lawn maintenance, exterior pest control, and provides access to the community pool — giving you more time to enjoy everything Central Florida has to offer while still coming home to peace and privacy.
Listing Agent: Tennille Biggers (850-628-4455)
33 MAIN ST, WINDERMERE, FL 34786
$1,575,00038 Days on yellowkey MLS ID: O6406887
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2130 Built: 1961 Tax: $9,485 (2025)Community: Davis ShoresSpa: NoSingle Family
Taxes:$9,485
Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Bruce Higgins (407-883-2728)
12334 SUMMERPORT LN, WINDERMERE, FL 34786
$6,500,00020 Days on yellowkey MLS ID: O6412083
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6182 Built: 1966 Tax: $22,979 (2025)Community: Summerport BeachSpa: YesSingle Family
Taxes:$22,979
Remarks: Under Construction. Welcome to 12334 Summerport Lane, an extraordinary lakefront estate on the prestigious Butler Chain of Lakes in Windermere. Custom built by Davila Homes and featuring the stunning Stanford floor plan, this exceptional residence offers approximately 6,182 square feet of luxurious living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Perfectly positioned on the shores of Lake Butler, this one-of-a-kind waterfront retreat showcases breathtaking panoramic lake views and includes a private covered dock with direct access to the renowned Butler Chain of Lakes, offering the ultimate Florida boating lifestyle. Designed to impress, the home welcomes you through a grand foyer with soaring ceilings and elegant architectural details. The expansive open-concept layout seamlessly connects the formal living areas, family room, and gourmet chef's kitchen, complete with an oversized island, premium appliances, custom cabinetry, and an oversized walk-in pantry. Walls of glass frame spectacular water views and fill the home with natural light. The luxurious first-floor primary suite serves as a private sanctuary overlooking the lake, featuring spa-inspired finishes, dual walk-in closets, and direct access to the outdoor living spaces. Additional guest suites provide comfort and privacy for family and visitors alike. The second level offers spacious en-suite bedrooms, a versatile loft, and a bonus room ideal for a media room, game room, or private retreat. Every detail has been thoughtfully designed to maximize comfort, functionality, and the home's incredible waterfront setting. Outdoor living reaches new heights with expansive covered lanais, resort-style entertaining areas, and endless opportunities to enjoy Windermere's spectacular sunsets over Lake Butler. Whether hosting guests, enjoying water sports, or relaxing by the lake, this property embodies the finest in luxury waterfront living. Located in one of Central Florida's most desirable addresses, 12334 Summerport Lane offers convenient access to top-rated schools, world-class golf, upscale dining, luxury shopping, and all that Windermere has to offer while delivering the exclusivity and prestige of true Butler Chain lakefront ownership.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Fernanda Negromonte (407-592-1744)
WINDERMERE, FL 34786
$369,90056 Days on yellowkey MLS ID: O6400745
INCREASED by $10,900 (3.0%) on 06/02/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $5,436 (2025)Community: Lakes/Windermere-Lk Reams TwhmSpa: NoTownhouse
Taxes:$5,436
Remarks: Welcome to this beautifully maintained 2-bedroom, 2½-bathroom corner lot townhome in the highly desirable Windermere area! Located at 8905 Newmarket Drive, this home offers the perfect blend of comfort, style, and convenience. The spacious open floor plan is filled with natural light and designed for both everyday living and entertaining. The kitchen features clean white appliances, ample cabinetry, and a layout that flows seamlessly into the living and dining areas.The primary suite provides a relaxing retreat with a well-appointed ensuite bathroom. The second bedroom and additional baths offer flexibility for guests, home office use, or hobbies. Enjoy a private backyard and the added benefits of a corner lot, providing extra privacy and space.Situated in a sought-after community, residents enjoy easy access to top-rated schools, shopping, dining, and major roadways, with quick access to Walt Disney World. Nearby golf courses and Windermere’s charm make this location truly exceptional.Don’t miss the opportunity to own this charming corner lot townhome in a prime location—schedule your private showing today!
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
4906 AVIVA GARDEN CT, WINDERMERE, FL 34786
$4,590,00059 Days on yellowkey MLS ID: O6400218
REDUCED by $100,000 (2.1%) on 06/01/2026
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)
12966 VENNETTA WAY, WINDERMERE, FL 34786
$380,00050 Days on yellowkey MLS ID: S5148828
REDUCED by $6,000 (1.6%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $380 Tax: $3,153 (2025)Community: Lake Sawyer South Ph 3Townhouse
Taxes:$3,153
Remarks: PRICE ADJUSTMENT! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 2.5-bath townhouse located in the highly sought-after Lake Sawyer South community in Windermere. Surrounded by picturesque, tree-lined streets, this well-maintained home welcomes you with a bright and open kitchen area featuring granite countertops, stainless steel appliances, and a walk-in pantry. The open living area with elegant French doors lead to a private, paved courtyard that seamlessly connects to the detached 2-car garage—perfect for indoor-outdoor living. The first floor is complete with a spacious laundry room and a half bath. Upstairs, the expansive primary suite offers a peaceful retreat with a dual vanity en suite bath, while two additional bedrooms share a full bathroom—ideal for family, guests, or a home office setup. A conveniently located downstairs laundry room adds everyday ease. Residents enjoy access to exceptional community amenities, including parks, scenic walking trails, playgrounds, tennis and basketball courts, and a resort-style swimming pool. The HOA provides added value by covering lawn care, exterior painting, and the roof—offering low-maintenance living and peace of mind. Located in the charming town of Windermere, known for its top-rated schools and high quality of life, this home is just minutes from Walt Disney World, major highways, upscale dining, and premier shopping destinations. This is one of the best values in the area—schedule your private showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Mae Stigell (631-377-1205)
1924 DOWN HOLLOW LN, WINDERMERE, FL 34786
$1,680,00021 Days on yellowkey MLS ID: O6398100
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1962 Built: 1999 Tax: $8,460 (2025)Community: AcreageSpa: YesSingle Family
Taxes:$8,460
Remarks: Under contract-accepting backup offers. Escape the ordinary! This charming Windermere cottage on the Butler Chain, is set on a beautiful and private wooded lot with a rare opportunity for lake and boat frontage on Lake Down! This inviting residence is nestled on nearly two acres in a serene, Florida-style setting, offering the perfect blend of privacy and convenience. Thoughtfully renovated, this 3-bed, 2.5-bath, 2-car garage home embraces a warm, relaxed style with timeless cottage appeal and inviting indoor-outdoor living. A welcoming front porch entry sets the tone for a spacious great room with a cozy fireplace, an eat-in kitchen with natural light, ample cabinets and counter top space, perfect for everyday living and hosting. The first-floor primary suite includes a walk-in closet and a private bath, featuring a dual vanity and a separate shower. The sunroom sitting areas open to an expansive deck with a recessed spa and TV, creating the perfect setting for entertaining or quiet evenings surrounded by nature. A true retreat, with a private walkway and dock leading directly to Lake Down, offering seamless access to the Butler Chain of Lakes and all the recreation the 13 interconnected lakes have to offer. Conveniently located near Downtown Windermere, top-rated schools, shopping, and dining, with easy access to major roadways and airports, delivers the best of both tranquility and accessibility.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
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