Location: Windermere
Do Not Show Listings
6606 SAWYER SHORES LN, WINDERMERE, FL 34786
$2,500,00049 Days on yellowkey MLS ID: O6386058
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 5516 Built: 2025Community: Sawyer Shores SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees or restrictions, you have the freedom to design and build your dream home exactly as you envision it or use the plans already available and variances approved — saving you time and expense. Offering approximately 5,516 SF of impeccably appointed living space and over 8,316 SF under roof, every detail has been curated to the highest standard of elegance and sophistication. Dramatic sightlines from the grand entry sweep through sun-drenched principal rooms to the resort-caliber outdoor living spaces beyond. The showstopping gourmet kitchen dazzles with extra-thick natural quartzite countertops, an oversized center island, pot filler, a fully integrated refrigerator and dishwasher with bespoke wood-panel cabinetry, and an oversized walk-in pantry — a culinary stage worthy of the most discerning chef. A soaring great room with designer tray ceilings and an elegant formal dining room set the scene for unforgettable entertaining, complemented by a private study and home office. The first-floor primary suite is a true sanctuary — a sumptuous walk-in closet, sculptural freestanding soaking tub, and a spa-inspired shower enclosure deliver five-star hotel indulgence at home. Upstairs, a second master suite, a spectacular lake-view recreation room with oversized balcony, three additional bedrooms, a chic loft with front balcony, and a second laundry suite elevate every aspect of daily life. Outside, a breathtaking covered lanai unfolds into a private lakeside paradise — summer kitchen, outdoor fireplace, alfresco dining, and a heated pool and spa framed by elegant paver decking and the glittering expanse of Lake Sawyer. A 4-car garage with EV charging, dual laundry rooms, impact-rated windows and doors, and bespoke designer finishes complete this extraordinary offering. Minutes from Windermere Prep School, shopping, dining and within minutes of Walt Disney World. *Images have been taken from a similar model home*
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)
Listing Agent: Nick Khela (407-308-9995)
8402 LAKE BURDEN CIR, WINDERMERE, FL 34786
$2,650,000 MLS ID: O6345629
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 6248 Built: 2004Community: Keenes PointeSingle Family
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly added virtually staged images to help with your interior design inspiration! Experience luxury waterfront living in the prestigious guard gated community of Keene's Pointe. This custom estate offers over 6,000 sq ft of elegant living space with 5-bedroom ensuites and a full pool bath with shower and powder room off of the Theater. A chef's kitchen with stainless-steel appliances, gas range with additional built-in oven and microwave. The gourmet kitchen opens to the breakfast nook and family room. Perfect for entertaining, the formal dining room features a Butler’s Pantry with wet bar and two wine refrigerators. Additional features include an office, bonus room with sauna that can be home gym or second floor primary closet. The expansive second floor loft features a full wet bar and separate projection theater with seating for eight. The covered lanai offers motorized screens, summer kitchen and plenty of space for dining and lounging in the shade. The open-air pool features a spa and sun shelf. Rounding out the features of this property is the private boat dock on Lake Burden. Take in sunsets and nightly fireworks as you enjoy all this Florida lakefront has to offer.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Toni Cafferty (904-449-2184)
4029 ISABELLA CIR, WINDERMERE, FL 34786
$3,299,000 MLS ID: O6387864
Bed: 6 Bath: 7.0 Liv Area Sq Ft: 7217 Built: 2018Community: CasabellaSingle Family
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.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Mauro Costa (321-231-6800)
1361 WHITNEY ISLES DR, WINDERMERE, FL 34786
$1,200,000 MLS ID: O6352069
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2787 Built: 2006Community: Whitney Isles/Belmere Ph 02Single Family
Remarks: Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year, the home features new flooring, a kitchen, bathrooms, and both interior and exterior paint, perfectly combining technology, comfort, and sophistication. The integrated sound system extends throughout the house, while the gourmet kitchen impresses with a ceramic range, built-in refrigerator, quartz countertops, and LED lighting. Motorized cabinets, a built-in oven and microwave, a large pantry, and a sink with a glass washer complete this space designed for culinary enthusiasts. Also, a state-of-the-art whole-house water filtration system is installed at the main water line, treating all the water that enters the house. A newly constructed deck is ready for the installation of an oversized jacuzzi, with all plumbing already in place. Additional features such as touch-activated LED stair lighting and vitrified epoxy-coated garage flooring further elevate the living experience. The home offers spacious, bright, and contemporary living areas. The family room, filled with natural light, opens directly to the outdoor area, creating a seamless connection between indoor and garden spaces. The expansive and elegant kitchen serves as the heart of the home, ideal for family gatherings around the central island. The master suite is a true private retreat, offering serene garden views and a luxurious bathroom featuring a soaking tub, the perfect spot to unwind after a long day. The outdoor area provides a tranquil and inviting setting, ideal for family gatherings or moments of peace surrounded by nature. The outdoor kitchen also provides a 6-burner gas stove, gas grill, sink, and a mini refrigerator.
Listing is courtesy of: ALVES AND HOWELL REALTY (407-750-2171)
Listing Agent: Gabriel Mantovani (407-637-9878)
8447 WOBURN CT, WINDERMERE, FL 34786
$1,325,000 MLS ID: O6390148
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2945 Built: 1999Community: Keenes PointeSingle Family
Remarks: Under contract-accepting backup offers. PREMIUM PRESERVE HOMESITE backing directly to Tibet Butler Preserve with NO REAR NEIGHBORS. Located within the 24-HOUR GUARD-GATED COMMUNITY OF KEENE’S POINTE, this beautifully updated 4 bedroom, 3 bath home with Bonus Room and Office, offers nearly 3,000 square feet of spacious living areas ideal for everyday living and entertaining. Extensive FIRST-FLOOR RENOVATION includes a CUSTOM KITCHEN with quartz countertops, custom cabinetry, GAS COOKTOP, and new appliances, along with engineered hardwood flooring and a custom primary bath. Major improvements include NEW ROOF (2022), NEW AC (2024), paver driveway, plantation shutters, and new pool heater and pump. Enjoy a SCREEN-ENCLOSED POOL with water feature overlooking the preserve, creating a private outdoor retreat. Residents of Keene’s Pointe enjoy 24-hour guarded security, parks, walking trails, playgrounds, and PRIVATE BOAT ACCESS to Lake Burden. Optional membership to THE GOLDEN BEAR CLUB offers golf, tennis, pickleball, fitness, dining, and resort-style amenities. Conveniently located near TOP-RATED SCHOOLS, shopping, dining, and major roadways, this home offers the rare combination of a PREMIUM PRESERVE LOT and CUSTOM RENOVATIONS AND QUALITY UPGRADES in one of Windermere’s most desirable communities.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Amy Seelman (407-491-8878)
7208 TATTANT BLVD, WINDERMERE, FL 34786
$599,000 MLS ID: O6389785
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2215 Built: 2012Community: Lake Sawyer South Ph 01Single Family
Remarks: Under contract-accepting backup offers. Welcome to your dream home in the sought-after community of Lake Sawyer in Windermere! Introducing 7208 Tattant Blvd, a beautifully maintained one-story residence featuring 3 bedrooms, 2 bathrooms, and a versatile upstairs bonus/flex space that can easily function as a fourth bedroom or home office, along with a PRIVATE SCREENED POOL AND SPA—perfect for enjoying the best of Florida living. Step inside to an open and airy floor plan with high ceilings and engineered hardwood and tile flooring throughout, creating a warm yet elegant feel. The kitchen is thoughtfully designed for both everyday living and entertaining, offering 42" cabinetry with crown molding, granite countertops, a center island, and a bright eat-in dining space. A window above the sink fills the kitchen with natural light, making it an inviting place to cook, gather, and start the day. The formal living and dining rooms provide a welcoming space for entertaining, while the UPSTAIRS BONUS ROOM offers exceptional flexibility and can easily serve as a fourth bedroom, playroom, media room, home office, gym, or guest retreat. The primary suite is a peaceful escape, featuring a walk-in closet and a spa-inspired bathroom with dual granite vanities, a soaking tub, a separate walk-in shower, and a private water closet. Step outside to your private backyard oasis, where a SCREEN-ENCLOSED SALTWATER POOL AND SPA invite you to relax and entertain. With both heated and chilled settings, the pool can be enjoyed comfortably year-round. The FULLY FENCED BACKYARD with NO REAR NEIGHBORS offers added privacy, and you can watch DISNEY FIREWORKS right from your own backyard—a truly magical way to end the evening. Additional highlights include SOLAR PANELS to help improve energy efficiency and reduce utility costs, a NEW AC (2024), a NEWER WATER HEATER, brick paver driveway, and a charming covered front porch that adds to the home’s curb appeal. Located in the desirable Lake Sawyer community, residents enjoy RESORT-STYLE AMENITIES including a community pool, playground, basketball and tennis courts, and scenic walking trails. The home is ZONED FOR TOP-RATED SCHOOLS including Windermere High School and is just minutes from shopping, dining, and world-class attractions. Experience the best of Windermere living at 7208 Tattant Blvd—where comfort, convenience, and the Florida lifestyle come together.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Ruiz (407-608-0086)
13320 FERNOW ST, WINDERMERE, FL 34786
$730,000 MLS ID: O6388986
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2745 Built: 2007Community: Lake Sawyer South Ph 01Single Family
Remarks: Under contract-accepting backup offers. Welcome to this 4-bedroom, 3.5-bath pool home in Windermere, zoned for top-rated schools including Windermere High School and Horizon West Middle School. With a roof replaced in 2024 and an AC approximately 5 years old, this home offers a great combination of comfort, location, and lifestyle. The open-concept design creates a bright and inviting atmosphere where the kitchen and main living areas naturally connect to the outdoor space. Large sliding doors open to the backyard, creating a seamless indoor-outdoor flow that is perfect for entertaining, whether hosting gatherings by the pool or enjoying relaxed evenings with friends and family. Electric blinds add a sleek and modern touch throughout the home. The first-floor primary suite offers privacy and comfort with a remodeled primary bathroom and a custom closet with built-ins. Upstairs includes the remaining bedrooms, one bedroom with its own en-suite bathroom, and a spacious loft ideal for a media room, home office, or additional living space. The private backyard retreat features a beautiful patio and saltwater pool, creating a resort-style setting perfect for enjoying Florida living year-round. Located near Horizon West shopping, dining, parks, and major roadways, this Windermere pool home combines a desirable location, functional layout, and the indoor-outdoor lifestyle that buyers are searching for in Central Florida.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
6219 TIROCO WAY, WINDERMERE, FL 34786
$2,600,000 MLS ID: O6387454
Bed: 7 Bath: 5.5 Liv Area Sq Ft: 5221 Built: 2014Community: WaterstoneSingle Family
Remarks: Welcome to luxury living in the guarded, gated community of Waterstone in Windermere, Florida. This exceptional residence at 6219 Tiroco Way blends elegance, comfort, and modern efficiency, featuring solar power and an impressive floor plan designed for both everyday living and entertaining. The home offers 7 bedrooms, 5½ bathrooms, a media room, loft, dedicated office, storage room, and separate formal living and dining rooms. Elegant design elements throughout include volume ceilings, designer niches, granite countertops, stainless steel appliances, natural gas cooking, washer and dryer, an under-stairs storage closet, security system, and a spacious three-car garage. A convenient Jack-and-Jill bath with double vanity adds functionality for family or guests. The first-floor primary suite is a private retreat featuring a spacious bedroom with a bay window overlooking the pool and two custom walk-in closets. A sitting area between the bedroom and bath provides space for comfortable chairs or a nursery setup. The luxurious primary bathroom includes dual vanities with abundant counter space, a large soaking tub, and an impressive walk-through shower with dual benches and multiple shower heads. The kitchen is ideal for the home chef, showcasing a large center island with additional storage and two pantries. It opens seamlessly to the family room, dinette, and outdoor living area, creating the perfect layout for gatherings and daily living. Step outside to your private backyard oasis featuring a designer custom pool and spa with waterfall and fountain features, elegant travertine decking, and plenty of space for outdoor entertaining. Two sizeable side yards offer additional room for recreation and privacy. Waterstone is a highly sought-after community located on the shores of Lake Butler, offering 24/7 guarded security, scenic walking trails, beautiful stone accents, and distinctive architecture. Residents also enjoy a private gate to Windermere Preparatory School. Conveniently accessing Walt Disney World, one can even watch the Disney fireworks from the community. Also in proximity are area theme parks, excellent shopping and dining, and major highways including State Road 429 and the Florida Turnpike for easy travel to downtown Orlando, Orlando International Airport, and the region’s booming medical corridor.
Listing is courtesy of: MAXLIFE REALTY LLC (321-373-3536)
Listing Agent: Ryan Solberg (407-748-3436)
2 CHASE RD, WINDERMERE, FL 34786
$3,200,000 MLS ID: O6345197
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3889 Built: 2026Community: WindermereSingle Family
Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Matthew Hughes (407-619-4717)
13542 GORGONA ISLE DR, WINDERMERE, FL 34786
$950,000 MLS ID: O6390582
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2224 Built: 2018Community: Windermere IsleSingle Family
Remarks: One or more photo(s) has been virtually staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From the moment you arrive, the well-maintained landscaping and inviting front porch set a warm and welcoming tone. The home features 4 bedrooms and 3 full bathrooms, with a thoughtfully designed open-concept layout that seamlessly connects the living room, kitchen, and dining area. The gourmet kitchen is a true highlight, equipped with stainless steel appliances, custom cabinetry, quartz countertops, a double oven, and a spacious pantry—perfect for those who love cooking and entertaining. Sliding glass doors open to the outdoor space, where a private pool and summer kitchen are currently being completed and will be ready within one month, creating the perfect setting for relaxing or entertaining guests while enjoying the lake view. The primary suite is spacious and comfortable, featuring vinyl flooring, a generous walk-in closet, and a beautifully designed bathroom with dual vanities. The additional bedrooms also feature vinyl flooring, providing both comfort and easy maintenance throughout the home. The two-car garage offers ample space and convenience. Located in the desirable Windermere Isle community, residents enjoy resort-style amenities including a community pool, cabana, playground, and scenic walking trails. The home is also located near top-rated schools, as well as shopping, restaurants, and all the attractions and magic of Walt Disney World just minutes away. If you are looking for quality of life, a prime location, and a beautiful home for your family, this is the perfect opportunity. Schedule your private showing today and come fall in love with this exceptional home.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
9150 OUTLOOK ROCK TRL, WINDERMERE, FL 34786
$915,000 MLS ID: S5145642
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2988 Built: 2015Community: Windermere Trls Ph 5BSingle Family
Remarks: Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in the grand foyer that immediately sets the tone for the home’s impressive design. The first floor features a versatile bedroom with a full bath, perfect for guests or multi-generational living, along with a formal dining room that can easily serve as a home office. The beautifully remodeled kitchen is a true showpiece, boasting 42” warm white -colored cabinetry, granite countertops. A walk-in pantry, vented built-in microwave, and two full double ovens provide both convenience and functionality. The spacious island is illuminated with elegant pendant lighting, while a butler’s pantry conveniently located between the kitchen and garage adds extra storage and practicality. The home also features brand-new flooring, adding a fresh and modern touch throughout. The main living areas are finished with neutral tile, while the stairwell and entire second floor—including all bedrooms—showcase new Lifeproof wood-look luxury vinyl flooring. The expansive owner’s suite serves as a private retreat, offering two large walk-in closets, a relaxing soaking tub, separate shower, and dual vanities. Each additional bedroom also includes walk-in closets and TV cable feed-throughs for added convenience. Upstairs you’ll also find a spacious bonus/media room pre-wired for A/V components, perfect for movie nights, gaming, or entertaining. Step outside to your private outdoor oasis, featuring a screened lanai and sparkling saltwater pool with a sun shelf, surrounded by elegant glass mosaic tiles in soothing ocean-blue tones. The property has also been recently enclosed with a newly installed vinyl privacy fence, creating the perfect setting for relaxing afternoons or weekend barbecues. This home is not only beautiful but also energy efficient, featuring R-38 insulation, a 15 SEER HVAC system, and a hybrid water heater, helping keep utility costs low while earning an ENERGY STAR rating. Located in the highly desirable Windermere Trails community, surrounded by scenic green spaces and ponds, and just minutes from shopping, dining, and top attractions. Residents enjoy exceptional amenities including a lakeside pool with splash pad, playgrounds, and a running and biking trail. Don’t miss the opportunity to make this stunning home yours. Schedule your private showing today and experience the lifestyle it offers.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Andrea Munoz (407-989-2021)
3013 SEIGNEURY DR, WINDERMERE, FL 34786
$1,890,000 MLS ID: O6377087
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 5130 Built: 2002Community: Harbor IsleSingle Family
Remarks: Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of amenities, right at home. Through the grand entrance, the formal living room is bright and chic, with ceiling niche lighting and picturesque windows to enhance the details of this beautifully-crafted estate. Formal living, wine bar, and fabulous chef’s kitchen with breakfast nook with built-ins, plus generously-sized family room enhance your largest gatherings and everyday living. The chef’s kitchen with island and preparation sink feature gas cooktop with hood, stainless appliances, and double ovens. The vast owner’s retreat spans the entire south wing of the house and includes a lovely sitting area, French doors to the patio, large walk-in closets, and a spa-like bath with double vanities, jetted tub, and large shower. Two additional bedrooms are located on the opposite side of the house on the first floor with a Jack and Jill bath and a secondary bed and bath are upstairs off a large game room. The resort-style pool and spa with mammoth paver patio decking and summer kitchen offers a private outdoor retreat under a large screen enclosure. New carpeting and new Plantation shutters just installed. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
6573 HELMSLEY CIR, WINDERMERE, FL 34786
$639,900 MLS ID: S5145061
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2664 Built: 2008Community: Preston SquareSingle Family
Remarks: Immaculately maintained, MOVE IN READY family home in the highly sought after Preston Square neighborhood located in the heart of 34786 - a well established hidden gem with tree lined streets! Built in 2008 with NEW ROOF IN 2025, this gorgeous, 4 bedroom 3.5 bath home with fully FENCED-IN back yard, has a unique layout with a guest bedroom with ensuite bathroom and french doors leading onto front covered porch, ideal for rocking chair evenings under the shade of the canopy trees. A 2-story ceiling great room adds dramatic appeal and separation to the floor plan, leading back through a dining space to the kitchen and family room all overlooking the private backyard. The kitchen boasts all stainless appliances, new dishwasher in 2023 and new refrigerator in 2024. AC was replaced in 2019 and new coils fitted in 2022. Upstairs is a large loft space overlooking living room - a perfect space for an office desk or gym equipment. The large primary bedroom suite has tray ceiling, walk-in closet, his & her vanities with soaking tub and separate shower. Two additional bedrooms and full bathroom completes the upper floor. Preston square has a charming atmosphere and features its own community pool, park, playground and sport court, all located just minutes from shopping, dining, and theme parks. A short drive to historic Windermere Town with its weekly farmers market, monthly food carts, historic town hall and old school house. Don't miss the opportunity to live the Florida lifestyle in this gorgeous home located within a great school district!
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Sue Webb (407-361-6425)
316 E 5TH AVE, WINDERMERE, FL 34786
$1,100,000 MLS ID: O6383481
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2412 Built: 1962Community: Windermere RepSingle Family
Remarks: Under contract-accepting backup offers. Don’t let the 1962 build date keep you from considering this 4 Bedroom 3 Bath home that received a major renovation to the Electrical, Water Heater & Bath Updates in 2016 * New HVAC 2017 and a New Roof in 2018 made obtaining low cost Tower Hill property insurance easy * in 2025 the luxurious Kitchen was updated with a Thermador Natural Gas Range & top of the line Stainless Appliances with Waterfall Porcelain Tops and all Travertine Stone Backsplash with Marble Inlay Deco Panel – This impressive Craftsman 1 story solid block home offers a very spacious and well laid out floorplan with the Primary Suite overlooking the Pool with a Private Covered Porch – The main house also has a covered porch providing 2 entertaining and BBQ options – The huge 32 x 21 Garage is the perfect setup for family vehicles, golf cart and water toys – The separate 22 x 12 pool cabana provides an inviting space for relaxation and gatherings this ultimate Man Cave or She Shed is limited to your imagination and family’s needs * This very large totally fenced private shaded lot with mature landscaping enjoys the convenience of being within walking distance or just a short golf cart ride to Charming Downtown Windermere, offering Boutique Shopping, Dining, Community Events, Award Winning Schools, Weekly Farmers Market & the Monthly Food Truck Friday Night * No HOA or dues * Oversized windows bring in Natural Light and views to the Landscaped Yard * A Public Dock and Beach on Lake Down are a short walk away, offering opportunities for Fishing, Picnics, Sunset Views, and Water Activities on the Lake Butler Chain of Lakes - a defining feature of Windermere living * With close proximity to Winter Garden Village, Restaurant Row, and all of the Area Attractions you are truly in the Heart of it All.
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
9426 PALM TREE DR, WINDERMERE, FL 34786
$660,000 MLS ID: O6373158
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2063 Built: 1986Community: Silver Woods Ph 03Single Family
Remarks: Under contract-accepting backup offers. This is it! Welcome home to this updated, showstopper in Windermere with an oversized pool. From the moment you walk in the door, you will be impressed with how open and expansive the home feels- the kitchen, dining, family and living areas are included in one great space. The family and living room share a double-sided wood burning fireplace and both overlook the pool area. The kitchen has been upgraded with stainless steel appliances, granite counters, solid wood cabinets and designer fixtures. This split plan has a very private primary suite with access to the pool area. The bathroom has a large walk in closet, tub with separate shower and large dual vanity. The 2nd bath has been updated and also has access to the pool area. No carpet here- Luxury Vinyl has been installed throughout the whole house. Enjoy relaxing nights by the outdoor firepit in the backyard or quiet mornings with coffee in the front porch. NEWER Double Pane Windows and Doors. (ROOF 2021)
Listing is courtesy of: IRON VALLEY REAL ESTATE CENTRAL FLORIDA (407-203-9595)
Listing Agent: Richard Alpizar (386-747-8532)
5186 VARDON DR, WINDERMERE, FL 34786
$4,960,000 MLS ID: O6382040
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4739 Built: 1990Community: IsleworthSingle Family
Remarks: One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate ideally positioned along Isleworth’s renowned championship golf course, showcasing stunning views of the signature 3rd hole. This exceptional residence offers approximately 4739 square feet of refined living space with 4 bedrooms and 4 1/2 bathrooms, soaring ceilings, elegant formal living and dining rooms, a private office, and a spacious owner’s retreat. Designed for elevated living and effortless entertaining, the home features marble and luxury vinyl flooring throughout, as well as a beautifully upgraded chef's kitchen with a casual dining area. Enclosed sunroom provides additional flex space and is not included in the official living square footage. The fully reimagined front and rear grounds create a true estate setting, highlighted by a grand front fountain entrance, a resort-style pool, an expansive lanai, a pavilion, and a summer kitchen. The upper-level balcony offers breathtaking golf course vistas, while the fully fenced private grounds include an extended driveway and an impressive circular motor court. A rare opportunity to own a move-in-ready luxury residence in one of Isleworth’s, golf-front locations.
Listing Agent: Winnie Tam (863-651-4687)
6208 WINTER GARDEN VINELAND RD, WINDERMERE, FL 34786
$3,900,000 MLS ID: O6382642
Bed: 6 Bath: 7.5 Liv Area Sq Ft: 5441 Built: 2025Community: Landings At Lake SawyerSingle Family
Remarks: We present a luxury residence in Windermere, Florida, that combines modern design, spacious areas, and a prime location. Situated at 6208 Winter Garden Vineland Road, this property is strategically positioned in front of Windermere Preparatory School, one of the best private schools in Florida. With 5,441 sqft of climate-controlled living space and a total area of 8,091 sqft, this home impresses with its size and sophistication. It features 6 en-suite bedrooms, all with walk-in closets, plus a half bath and an additional full bathroom dedicated to the pool area, totaling 7.5 bathrooms. The modern architecture, a rare find in Orlando, stands out with its 12-foot ceilings, sliding doors in all bedrooms, and an open-concept social area that provides integration and elegance. The outdoor area is one of the highlights of this property. The swimming pool with a jacuzzi invites relaxation, while the spacious 880 sqft gourmet patio is perfect for entertaining friends and family. The property also features a tennis court. To ensure maximum privacy, the entire 1.29-acre lot will be enclosed with a fence. The house is equipped with modern, energy-efficient appliances, 100% LED lighting, and infrastructure ready for surveillance systems and smart home automation, compatible with the leading platforms on the market. Another great feature is the four-car garage, which includes two electric vehicle chargers, offering convenience and sustainability for its residents. This property offers the perfect balance of luxury, technology, and comfort. Additionally, its location provides easy access to key points in the city, being approximately 30 minutes from Orlando International Airport (MCO), 19 minutes from Magic Kingdom, 18 minutes from Universal Studios, and 20 minutes from downtown Orlando. An added benefit is the absence of HOA fees, allowing total freedom to personalize and use the space as desired. This is a unique opportunity for those seeking an exclusive home in one of Florida's most sought-after areas. Schedule a visit and discover what makes this house truly special!
Listing Agent: Daniel Pavel (407-747-3408)
5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$5,100,000 MLS ID: O6348067
Bed: 4 Bath: 5.5 Liv Area Sq Ft: 6424 Built: 1992Community: IsleworthSingle Family
Remarks: Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
3629 LAKE BUYNAK RD, WINDERMERE, FL 34786
$1,200,000 MLS ID: G5099846
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2618 Built: 1973Community: Lake Buynak EstatesSingle Family
Remarks: Back on market—buyer withdrew for personal reasons, not due to any home-related issues. Set on 1.3 acres in the Lake Buynak Estate community, this 4-bedroom, 3.5-bath home presents an outstanding opportunity for investors, builders, or buyers wanting space and a Windermere-area address with NO HOA. Offering over 2,600 square feet, two ensuite bedrooms, a split layout, multiple screened porches, and a wood-burning fireplace, the home provides a solid framework for renovation, rental use, multigenerational living, or a future custom build. Upgrades include energy-efficient double-paned windows and a dual septic system with an expanded drain field, enhancing functionality and long-term value. The expansive 1.3-acre lot allows for substantial expansion, an ADU, or complete redevelopment in an area surrounded by high-end homes near Lake Butler. With optional HOA membership and no Windermere city restrictions, the property offers freedom that is rarely available in this ZIP code. Located minutes from Disney, Universal, shopping, dining, and major roadways, it combines convenience with the space and privacy acreage buyers crave. Owner financing may be considered. Explore the potential this unique property provides and imagine the possibilities.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tania Matthews (407-497-9660)
2641 HEMPEL AVE, WINDERMERE, FL 34786
$824,900 MLS ID: O6384773
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2404 Built: 1985Community: NoneSingle Family
Remarks: Welcome to this beautifully renovated home in highly desirable Windermere, where modern upgrades meet timeless comfort on a rare one-acre lot with NO HOA. Completely remodeled this home has been thoughtfully updated from top to bottom. Renovations include new flooring throughout, fresh interior paint, a fully redesigned kitchen, updated bathrooms, new windows, new interior doors and custom blinds. Every detail was carefully selected to create a cohesive, move-in-ready space. The kitchen shines with contemporary finishes and flows seamlessly into the main living areas — perfect for both everyday living and entertaining. Bathrooms have been stylishly updated, and custom master and coat closet provide elevated organization and storage. Enjoy true peace of mind with major system upgrades, including: • Whole-house water treatment system (2020), softener equipment updated in (2025) • Septic drain field in (2025) • Trane A/C installed (2026) • Well pump (2024) • Insulation (2021) • Balcony deck and railing (2025) Step outside to your private backyard retreat featuring a saltwater pool with electric heater, ideal for year-round enjoyment. The expansive one-acre property offers space, privacy, and endless possibilities — bring your boat, RV, or build your dream outdoor oasis. This home has been remodeled with tremendous care, offering confidence that the work has been done and done right. A rare opportunity in Windermere combining luxury updates, land, and freedom from HOA restrictions. Move-in ready. Fully upgraded. Peace of mind included.
Listing is courtesy of: KNIGHTS REALTY (407-252-7411)
Listing Agent: Frank Mediavilla (407-252-7411)
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