Location: Windermere
Do Not Show Listings
516 JENNIFER LN, WINDERMERE, FL 34786
$1,295,00022 Days on yellowkey MLS ID: O6419731
0 Days Off yellowkey (back on 6/29/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3021 Built: 1982Monthly Fee: $333 Tax: $6,252 (2025)Community: Windermere OaksSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,252
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2025
Middle School: Chain of Lakes Middle
Remarks: OUTDOOR LIVING, ONE-STORY COMFORT & IN-TOWN WINDERMERE LIFESTYLE COME TOGETHER AT THIS RARE 1.27-ACRE WINDERMERE OAKS PROPERTY. Set within the TOWN OF WINDERMERE, this beautifully maintained one-story pool home offers privacy, space & the lifestyle buyers hope to find, with NATURAL GAS, mature landscaping, a PARTIAL BUTLER CHAIN LAKE VIEW, and exceptional outdoor living that feels like a true extension of the home. The screened pool area is the heart of the property, beautifully finished with brick pavers & designed for everyday enjoyment as well as memorable entertaining. The 35' X 20' IRREGULAR-SHAPED POOL is complemented by multiple water features, a separate step-in spa with bubbler, a custom firepit, and a highly functional summer kitchen with bar seating, grill, ice maker & refrigerator. With approximately 812 SQ FT OF OPEN FINISHED PORCH/LANAI AREA, including a main lanai approximately 62' X 12', there is room to dine, gather, relax, watch the game, host friends, or simply enjoy the peaceful setting in every season. The PRIMARY SUITE is a true highlight of the home, privately positioned and beautifully finished with a spacious bedroom, direct access to the outdoor living area, and a STUNNING PRIMARY BATH that feels calm, elegant & luxurious. Thoughtful details, generous closet space, quality finishes, and a retreat-like feel make this suite stand apart. Inside, the home offers a warm, livable floor plan with NO STAIRS & generous gathering spaces. The main living areas connect comfortably to the outdoor spaces, creating an easy flow for entertaining & everyday life. The kitchen is positioned at the center of the home with generous prep & storage space, natural gas cooking, and a connection to the main living & dining areas that keeps everyone together. Additional bedrooms & flexible rooms provide options for guests, work, hobbies, fitness, or multigenerational living. The ONE-STORY design offers long-term comfort & convenience without sacrificing space or privacy. The setting is what makes this property so special. With 1.27 ACRES inside the Town of Windermere, there is a sense of privacy & breathing room that is increasingly hard to find. Mature trees, established landscaping, and a long residential feel create a peaceful backdrop, while the partial lake view adds a lovely connection to the Butler Chain lifestyle without making the home solely about the view. Life in WINDERMERE OAKS means you are close to the charm of downtown Windermere, weekly farmers markets, community events, local parks, brick streets & the small-town character that makes this area so loved. You are also minutes from top schools, shopping, dining, major roadways & Central Florida attractions, making the location as practical as it is beautiful. This is the kind of Windermere property buyers hope to find but rarely do: 1.27 private acres, ONE-STORY LIVING, NATURAL GAS, exceptional outdoor living, a beautiful PRIMARY SUITE, a PARTIAL BUTLER CHAIN LAKE VIEW, and a setting that makes home feel like the best place to be. It invites you to slow down, gather often, celebrate outside & enjoy the lifestyle that makes the TOWN OF WINDERMERE so special.
Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)
Listing Agent: Cindy Rosenbloom (407-876-9175)
11617 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,375,00070 Days on yellowkey MLS ID: O6405409
REDUCED by $22,000 (1.6%) on 06/18/2026
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3463 Built: 2005Monthly Fee: $283 Tax: $7,189 (2025)Community: Keenes PointeSingle Family
Taxes:$7,189
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent walls, adding warmth and architectural elegance. Offering a private tiled patio with electronic screen enclosure, perfect for enjoying Florida's year-round sunshine in comfort and privacy. For buyers seeking a move-in ready luxury home in Orlando's golf course communities, this property checks every box. Major capital improvements are already done: new roof (2023), AC and water heater 2-3 years old — giving buyers the confidence and peace of mind that comes with a truly turnkey luxury purchase. Equipped with a professionally installed lightning protection system for added peace of mind. Residents enjoy exclusive access to the Golden Bear Club, a Jack Nicklaus Signature Golf Course, along with clubhouse, tennis, and Lake Tibet-Butler access. The community’s location delivers unmatched convenience with proximity to well-rated schools, along with The Grove, Westside Shoppes, Cornerstone at Summerport, and Downtown Windermere for daily essentials, local dining, and shopping adventures. Entertainment options abound with easy access to Disney, Universal, and the famed Restaurant Row in Dr. Phillips. A rare opportunity.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786
$2,650,00025 Days on yellowkey MLS ID: O6418721
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5433 Built: 2003Monthly Fee: $271 Tax: $24,189 (2025)Community: Reserve At Belmere Ph 02 48 144Spa: YesSingle Family
Taxes:$24,189
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Presenting this stunning LAKEFRONT RESIDENCE showcasing spectacular PANORAMIC VIEWS and ideally located within the premier GUARD GATED COMMUNITY of Reserve at Belmere in WINDERMERE. The property is approached by a circular driveway with centerpiece WATER FOUNTAIN set in mature landscaping alongside an adjoining 3 car garage with side entry. Upon arrival, an impressive entryway opens to the foyer and formal living/great room with seamless glass windows framing picture perfect water views. Set over two floors, this CUSTOM-BUILT home (exterior re-painted 2024) perfectly balances grand entertainment spaces with intimate everyday living featuring soaring ceilings alongside rich architectural artistry with its ornate detailing and trim. The sizeable wood paneled EXECUTIVE HOME OFFICE is a masterpiece with its custom cabinetry, wood floor and ceiling treatment. The GOURMET KITCHEN with high-end stainless-steel appliances and granite countertops has an open floor concept flowing effortlessly into a sunlit breakfast nook, countertop seating and spacious family room with focal point fireplace and sliding doors providing direct access to the outdoor area. A formal DINING ROOM, a BILLIARD ROOM with WET BAR also provide further spaces for entertaining both family and guests. The primary bedroom suite is a true RETREAT with sweeping views and sitting area with direct patio access, two large walk-in closets and ensuite bathroom which includes a walk-in shower, tub and dual sinks. A guest bedroom with full ensuite and two further bedrooms with Jack & Jill bathroom suite are also situated on the first floor. Upstairs, the dedicated HOME THEATER with full bar opens up to an adjoining GAMES ROOM with access to a private balcony providing an additional vantage place to avail of the breathtaking sunrises and sunsets. Also on this level is a HOME GYM workout space. [Note: This upstairs area is VERSATILE as could be utilized as a secondary primary suite as there is also a full ensuite bathroom with large walk-in closet]. Nestled on the shores of Lake Whitney and with its own PRIVATE DOCK, enjoy Florida living at its finest in this PRIVATE OASIS with its resort style outdoor area highlighted by a bespoke VANISHING EDGE POOL WITH WATER FOUNTAIN AND INTEGRATED HEATED SPILLOVER SPA (re-surfaced and new pool equipment 2024). There is an expansive covered lanai with plentiful lounge and dining spaces, an outdoor fireplace in addition to a full outdoor kitchen with countertop seating. A GOLF PUTTING GREEN sits to one side of the patio area and a SERENE GARDEN AREA to the other. The residence is in close proximity to the clubhouse and the community’s many amenities which include a fitness center, playground and tennis, basketball and sand volleyball courts. Reserve at Belmere is conveniently located just minutes from historic downtown Windermere, local shops, restaurants, the theme parks, major highways and nearby top-rated schools. THIS ISN’T JUST A HOME, IT’S A LIFESTYLE! Don’t miss out, book your private showing today!
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Alice Anne Jackson (407-520-9957)
13424 HOPKINTON CT, WINDERMERE, FL 34786
$549,99922 Days on yellowkey MLS ID: O6419100
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2190 Built: 2005Monthly Fee: $169 Tax: $7,268 (2025)Community: Lakes Of Windermere-PeachtreeSingle Family
Taxes:$7,268
Elementary School: Bay Lake Elementary
High School: Windermere High School
Middle School: Horizon West Middle School
Remarks: Virtually Staged. Nestled on a quiet cul-de-sac in the highly sought-after Lakes of Windermere – Peachtree community, this spacious 4-bedroom, 3-bath residence offers the perfect blend of comfort, functionality, and location. With over 2,100 square feet of living space, the thoughtfully designed floor plan provides ample room for both everyday living and entertaining. Residents of Lakes of Windermere enjoy access to community amenities, scenic walking paths, parks, and playgrounds while being conveniently located near top-rated schools, shopping, dining, and everyday conveniences. Just minutes from Walt Disney World, Horizon West, Winter Garden Village, and major roadways, this location provides easy access to everything Central Florida has to experience. Whether you're searching for a primary residence or an investment opportunity in one of Windermere's most desirable communities, this home presents an exceptional opportunity to enjoy the best of Florida living . (ONE OR MORE PHOTOS HAVE BEEN VIRTUALLY STAGED)
Listing is courtesy of: LJL REAL ESTATE, INC. (407-355-7889)
Listing Agent: Erik Lynch (407-694-0536)
9316 GLADYS GARDEN CT, WINDERMERE, FL 34786
$6,500,00018 Days on yellowkey MLS ID: O6420326
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5471 Built: 2026Monthly Fee: $2,370 Tax: $9,424 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$9,424
Remarks: Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
9011 CHAPMAN OAK CT, WINDERMERE, FL 34786
$599,00092 Days on yellowkey MLS ID: S5148031
REDUCED by $30,000 (4.8%) on 06/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 1987Monthly Fee: $31 Tax: $8,592 (2025)Community: Silver Woods Ph 05Single Family
Taxes:$8,592
Remarks: Windermere Gem: Fully Updated & Move-In Ready! Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully updated home offers an incredible opportunity for homeowners and investors alike, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities. This property has been meticulously maintained, featuring an extensive list of recent high-value upgrades: Recent Upgrades & Features: Brand New Kitchen (March 2026): Fully updated with modern flooring, custom cabinetry, and premium appliances. Comprehensive Pool Refresh (2026): Newly resurfaced pool and deck (Feb 2026), plus a brand-new pool pump and filter (March 2026). New Roof: Installed August 2024. Septic System: Installed January 2018. AC System: Installed 2017. Full House Re-pipe: Completed August 2016. Additional Features: Pool rescreened (2019) and nearby access to community tennis courts. Whether you're looking for a stylish family residence or a high-performing investment property, this home is truly move-in ready.
Listing is courtesy of: TOWNE CENTER REALTY (407-447-7700)
Listing Agent: Shiran Moyal (407-716-0224)
9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786
$6,000,000196 Days on yellowkey MLS ID: O6370294
REDUCED by $150,000 (2.4%) on 05/01/2026
Bed: 7 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 8000 Built: 1999Monthly Fee: $1,043 Tax: $29,046 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$29,046
Tax Year: 2024
Remarks: Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
1554 LAKE RHEA DR, WINDERMERE, FL 34786
$1,350,00070 Days on yellowkey MLS ID: O6406297
REDUCED by $50,000 (3.6%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3427 Built: 2004Monthly Fee: $241 Tax: $9,102 (2025)Community: Reserve At BelmereSpa: YesSingle Family
Taxes:$9,102
Remarks: Price Improvement! Located behind the gates of the prestigious Reserve at Belmere in sought-after Windermere, this exceptional Mediterranean-inspired estate offers a rare blend of timeless architecture, modern luxury and thoughtful custom enhancements. Built in 2004 by the original owners and expanded during construction, the residence offers more than 3,427 square feet of refined living space and over 4,528 total square feet, creating a larger footprint than many comparable homes within the community. Extensively upgraded with more than $250,000 in recent improvements, this meticulously maintained home showcases true pride of ownership. Significant updates completed within the last three years include three new Trane HVAC systems, replacement windows, premium appliances, pool renovations, designer lighting and numerous interior and exterior enhancements. From the moment you enter, soaring 24-foot ceilings and elegant architectural details set the tone. Crown molding, coffered ceilings, engineered hardwood flooring, custom window treatments and a marble wood-burning fireplace create a sophisticated yet inviting atmosphere. Expansive glass sliding doors frame the outdoor living spaces and provide seamless indoor-outdoor flow ideal for everyday living and entertaining. The chef’s kitchen has been thoughtfully curated with luxurious quartzite countertops, custom pullout cabinetry with rotating shelving systems and an impressive suite of premium German appliances, including a Miele built-in coffee system, convection oven, dishwasher and refrigerator. A professional-grade 48-inch chef gas range with six burners and a griddle, custom lighting and a built-in three-stage water filtration system complete the space. Privately on the main level, the primary suite offers a tranquil retreat with coffered ceilings, newly installed commercial-grade carpeting, serene pool views and direct patio access. The spa-inspired primary bath is appointed with marble and travertine finishes, a soaking tub, a separate shower and custom walk-in closet built-ins. Upstairs, generously sized secondary bedrooms and a spacious loft overlook the formal living and dining areas below. Designed for elevated outdoor living, the resort-style backyard features a resurfaced saltwater pool and spa, an updated pool heater, decorative fountains, remote-controlled pool systems and multiple entertaining areas surrounded by lush European-inspired landscaping, stone pathways and manicured grounds. Canary palms and mature landscaping create a private, luxurious setting. Additional highlights include a new front entry door, an oversized three-car garage, an upgraded security system, a partial roof replacement and designer chandeliers and lighting throughout. Ideally located in one of Windermere’s premier gated communities, residents of Reserve at Belmere enjoy convenient access to top-rated schools, dining, shopping, golf, major roadways and the area’s renowned luxury lifestyle offerings.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Adam Shuler, Ii (407-949-4495)
9110 PALM TREE DR, WINDERMERE, FL 34786
$650,00035 Days on yellowkey MLS ID: O6414631
REDUCED by $25,000 (3.7%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 1985Monthly Fee: $32 Tax: $8,182 (2025)Community: Silver Woods Ph 02Spa: NoSingle Family
Taxes:$8,182
Remarks: Welcome home. This wonderfully kept move-in ready 3 bedroom, 2 bathroom pool home is located in one of SouthWest Orlando's sought after communities, Silver Woods. It features travertine tile flooring throughout most of the home with engineered hardwood flooring in all the bedrooms, an open kitchen with stainless steel appliances and granite countertops overlooking the family room and an inside laundry room for your convenience. After long days, step outside on the patio and enjoy lounging around the open-air sparkling pool. The back yard also has plenty of space for the kids and pets to play. The major components of the home: roof 2022, A/C 2015, water heater 2023, GE electrical panel and CPVC plumbing.
Listing is courtesy of: VICARI REALTY CORP (407-415-4401)
Listing Agent: Tony Vicari (407-415-4401)
6601 DUNCASTER ST, WINDERMERE, FL 34786
$627,90036 Days on yellowkey MLS ID: O6416272
REDUCED by $100 (0.0%) on 06/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3001 Built: 2006Monthly Fee: $82 Tax: $9,473 (2025)Community: Lakes/Windermere Ph 02ASingle Family
Taxes:$9,473
Elementary School: Sunset Park Elem
Remarks: ***NEW ROOF WILL BE INSTALLED BY THE END OF JULY 2026.***Welcome to this spacious 4-bedroom, 3-bath Victorian-style home in the highly desirable Lakes of Windermere community. Boasting over 3,000 square feet of living space, this beautifully designed home offers an exceptional layout ideal for both everyday living and entertaining. A charming covered front porch and elegant curved staircase create a warm and inviting first impression. The open-concept family room flows seamlessly into the upgraded kitchen, featuring granite countertops, stainless steel appliances, a center island, and abundant cabinet space. The oversized primary suite is conveniently located on the first floor, complete with a spacious walk-in closet and a private ensuite bath. Upstairs, you'll find three generously sized bedrooms and additional full bath accommodations, providing flexibility and comfort for family and guests. Situated on a premium corner lot directly across from a community playground, this home also features a rear-entry attached garage and an ideal location within the neighborhood. Residents of Lakes of Windermere enjoy outstanding amenities, including a community pool, fishing dock, playgrounds, tennis courts, scenic lakes, and recreational areas. The home is also zoned for highly rated A+ schools and is conveniently located just minutes from shopping, dining, major roadways, and Central Florida's world-famous attractions. Don't miss this incredible opportunity to own a beautiful home in one of Windermere's most sought-after communities!
Listing is courtesy of: ANTS REALTY LLC (689-800-8851)
Listing Agent: Wenyu Wang (407-505-9864)
12720 JACOB GRACE CT, WINDERMERE, FL 34786
$2,750,000134 Days on yellowkey MLS ID: TB8476930
1 Days Off yellowkey (back on 6/29/2026)
REDUCED by $95,000 (3.3%) on 06/16/2026
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2005Monthly Fee: $300 Tax: $13,298 (2024)Community: Tildens Grove Ph 01 47/65Spa: YesSingle Family
Taxes:$13,298
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central Florida living. A long, winding driveway welcomes you, framed by mature trees and sweeping lawns. Tucked away on a quiet cul-de-sac within a 24-hour guard-gated neighborhood with a manned guard station, the property offers both grandeur and seclusion — a rare combination in today’s luxury market. Thoughtfully designed to maximize natural light and panoramic water views, the home features soaring ceilings, expansive picture windows, and seamless indoor-outdoor flow. The grand foyer opens to a spectacular living room anchored by tranquil lake vistas. The chef’s kitchen is appointed with custom cabinetry, high-end appliances, and an oversized island, effortlessly connecting to spacious dining and living areas — ideal for both intimate evenings and large-scale entertaining. The primary suite, located on the main level, is a private sanctuary with serene lake views and direct access to the outdoor living areas. The spa-inspired bath offers a soaking tub, dual vanities, walk-in shower, and generous closet space. Four additional bedrooms of which two of them include their own en-suite bath, ensuring comfort and privacy for family and guests. A detached in-law suite with private entrance, living area, bedroom, and bath provides exceptional flexibility for multigenerational living, long-term guests, or a private executive office. Step outside to your own outdoor oasis. The resort-style pool overlooks the lake, creating a stunning backdrop for entertaining or quiet relaxation. A charming pool house complete with a Murphy bed offers additional guest accommodations and enhances the estate’s resort-like ambiance. At the water’s edge, a private dock provides access to a private ski lake — perfect for boating, skiing, paddleboarding, or sunset cruises. As evening falls, the magic begins. From your backyard, dock, or expansive windows, enjoy nightly fireworks illuminating the sky above Disney — a spectacular private show reflected across the water. With nearly two acres of lakefront land, six bedrooms, six and a half baths, a detached suite, pool house, long private driveway, and location within one of Windermere’s most prestigious guard-gated communities, 12720 Jacob Grace Ct is more than a home — it is a destination, a sanctuary, and a stage for life’s most extraordinary moments.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Adrian Jacob (832-381-4670)
9620 MAYWOOD DR, WINDERMERE, FL 34786
$2,349,00093 Days on yellowkey MLS ID: O6399315
REDUCED by $51,000 (2.1%) on 06/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3004 Built: 1979 Tax: $20,433 (2025)Community: Lake Down ShoresSpa: NoSingle Family
Taxes:$20,433
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a setting that feels refined and relaxed. From sunrise to sunset, the backdrop is nothing short of extraordinary. Sweeping views stretch across Lake Down, where calm morning waters give way to vibrant evening skies, and a nightly Disney fireworks view adds a subtle sense of wonder to the horizon. The property is thoughtfully oriented to take full advantage of its surroundings, featuring a private beach area, a two-story dock and direct access to the Butler Chain, one of Central Florida’s sought-after and interconnected lake systems, known for its recreational appeal and timeless value. Inside, the home offers a layout designed for everyday living and effortless entertaining. Spacious living and family rooms are complemented by an open kitchen appointed with granite countertops and stainless steel appliances, creating a central gathering space that flows naturally to the outdoors. A dedicated office or den provides flexibility for work or quiet retreat, while an upstairs loft captures elevated, panoramic views of Lake Down, an ideal setting for a secondary lounge, media space or creative studio. The outdoor experience is equally compelling. A resort-style pool anchors the backyard, accompanied by a screened porch and expansive lawn that extends toward the water’s edge. The setting invites relaxed afternoons and large-scale gatherings, with ample room to further enhance or personalize the landscape. A greenhouse and additional storage add charm and functionality, supporting a variety of lifestyle needs. A second-story balcony offers yet another vantage point, where elevated lake views and evening fireworks create a memorable daily backdrop. Whether enjoying a quiet morning coffee or winding down at sunset, this space reinforces the home’s seamless connection to its environment. Positioned in a peaceful and private location, yet just moments from renowned restaurants, shopping and everyday conveniences, the property offers a rare balance of seclusion and accessibility. Its location on one of the desirable stretches of Lake Down further underscores its long-term appeal. This is a compelling opportunity to enjoy the home as it exists today or to reimagine the site as an exceptional custom waterfront estate. In a setting defined by natural beauty, established luxury and enduring demand, properties of this caliber and positioning are increasingly rare.
Listing Agent: Linda O'Grady (407-970-6880)
6965 TETTENHALL LN, WINDERMERE, FL 34786
$699,000289 Days on yellowkey MLS ID: O6340538
REDUCED by $11,000 (1.5%) on 06/28/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3050 Built: 2007Monthly Fee: $75 Tax: $4,946 (2024)Community: Lakes/Windermere Ph 04Single Family
Taxes:$4,946
Remarks: Beautiful updated windermere home featuring 5 bedrooms 3 full bathrooms , with major upgrades already completed for a peace of mind . Enjoy a brand new roof 05/26 , a brand new Ac 2 Units 05/26 and a brand new water heater 05/26 . Marble floor through downstairs and laminate upstairs , along with remodeled Bathrooms . The house is looking over a stunning view of a pond with a water fountain and looking everyday at the Disney fireworks . Perfectly situated minutes from all the attractions Disney , universal , and SeaWorld and also close to all shopping , Dining and major Highways . Walking distance to top rated schools . Fenced backyard with A screened pool .The community offers incredible amenities including a pool,Tennis court , Sand volleyball and Basketball court and two playgrounds . This move-in-ready property combines modern updates comfort , and functionality in one of windermere's most desirable locations .Don't miss this exceptional opportunity. Schedule your showing today . The listing agent is the owner .
Listing is courtesy of: VISION HOME REAL ESTATE, LLC (407-902-6236)
Listing Agent: Nabil Chakrouni (407-963-8548)
9663 GOTHA RD, WINDERMERE, FL 34786
$1,299,90092 Days on yellowkey MLS ID: O6399130
REDUCED by $100,100 (7.2%) on 05/17/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3731 Built: 2000 Tax: $8,425 (2025)Community: Gotha TownSpa: NoSingle Family
Taxes:$8,425
Remarks: Experience refined Florida living in this extensively upgraded estate nestled in the sought-after Windermere–Gotha enclave. Set on a rare and private 0.55-acre homesite with no HOA, this 4-bedroom, 2.5-bath residence offers a seamless blend of luxury, comfort, and versatility. No detail has been overlooked—from the 2023 metal roof and full hurricane-impact windows to brand-new A/C systems, upgraded insulation, and a state-of-the-art water treatment system. Interiors are enhanced with modern finishes, custom window treatments, and fully remodeled spa-inspired bathrooms featuring premium upgrades. Step into your private resort-style retreat, complete with a newly built saltwater pool, expansive paved driveway, and a beautifully designed outdoor living space. The custom gazebo with outdoor kitchen creates the perfect setting for entertaining, while the fully enclosed, air-conditioned patio extends your living space year-round. A standout feature is the detached 1-bedroom, 1-bath guest residence, complete with a full kitchen—ideal for multigenerational living, a private office, or an income-producing opportunity. Located just minutes from Orlando Hospital, Orlando’s premier dining, shopping, and entertainment, including Walt Disney World and Universal Studios Florida, this exceptional property offers the ultimate balance of privacy and convenience.
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)
Listing Agent: Reza Shirzad (407-234-1515)
4303 ISABELLA CIR, WINDERMERE, FL 34786
$2,899,00052 Days on yellowkey MLS ID: O6409406
Bed: 7 Bath: 5.0 Gar: 5 Liv Area Sq Ft: 5122 Built: 2017Monthly Fee: $480 Tax: $22,725 (2025)Community: CasabellaSpa: YesSingle Family
Taxes:$22,725
Remarks: Located in one of Windermere’s most sought-after luxury GATED communities with 24-HOUR SECURITY-SCREENED ENTRY, Casabella, this exceptional custom-enhanced ESTATE showcases ultra-modern design, refined craftsmanship, and elevated INDOOR-OUTDOOR LIVING, offering impressive scale, custom design, and an exceptional lifestyle experience. Designed with both scale and functionality in mind, the home features an OPEN-CONCEPT floor plan with 7 BEDROOMS, including a beautifully appointed MAIN-LEVEL Primary Suite with a spa-inspired bath, freestanding soaking tub, expansive dual custom-designed walk-in closets, oversized glass-enclosed shower, and integrated STEAM SAUNA. The main floor also includes an additional GUEST SUITE and 2 HALF BATHS. Upstairs, 5 additional BEDROOMS, 2 FULL BATHROOMS, and a spacious LOFT create a well-designed secondary living retreat, offering flexibility for gathering, relaxation, and elevated everyday living. The expansive DESIGNER-ENHANCED GOURMET KITCHEN serves as a striking centerpiece of the home, showcasing imported custom cabinetry, architect-inspired detailing, premium JennAir APPLIANCES, and seamless flow into the GREAT ROOM, multiple dining areas, and surrounding living spaces. Additional interior highlights include a custom-designed EXECUTIVE OFFICE, luxury flooring throughout, ELECTRIC blackout shades, DIGITAL CODE LOCK entry systems on all bedroom doors for added privacy and convenience. Across all 4 FULL BATHROOMS and 2 HALF BATHS, the home showcases floor-to-ceiling tilework, integrated bidet systems, and refined finishes throughout, while 1 HALF BATH offers direct OUTDOOR ACCESS, adding convenience for the POOL and surrounding outdoor living spaces. Designed for both relaxation and everyday enjoyment, the outdoor living experience features a HEATED SALTWATER POOL, SPA, SUMMER KITCHEN, FENCED BACKYARD, and mature PRIVACY LANDSCAPING. Set on approximately 0.63 ACRES, the property also includes a 5-CAR GARAGE with EPOXY FLOORING and AIR-CONDITIONED garage space, an estate-style driveway with exceptional space for car enthusiasts and guests, TESLA CHARGER, FULLY PAID SOLAR PANELS, WATER SOFTENER SYSTEM, and a WHOLE-HOUSE GENERATOR. With proximity to premier GOLF COURSES, scenic LAKES including the Butler Chain of Lakes, top-rated public and private schools, shopping, hospitals, and major roadways, plus convenient access to Disney and Orlando’s premier attractions, Casabella offers privacy, security, and elevated luxury living in one of Windermere’s most desirable communities.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Gaby Sadler (865-684-6721)
13339 ROSKIN LN, WINDERMERE, FL 34786
$680,000188 Days on yellowkey MLS ID: S5141148
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2947 Built: 2012Monthly Fee: $82 Tax: $8,674 (2024)Community: Lake Sawyer South Ph 01Single Family
Taxes:$8,674
Remarks: Welcome to a standout opportunity in WINDERMERE , offering closing cost assistance and positioned for a timely sale. This 4 bedroom, 2.5 bath, two-story home with 2,947 sq ft delivers the space, layout, and location today’s buyers are searching for. The thoughtfully designed floor plan includes a first-floor den/office, expansive upstairs loft, and generously sized bedrooms throughout. The oversized primary suite provides a comfortable retreat with ample space to relax. Every room offers flexibility for a variety of living needs. Step outside to a fully fenced backyard featuring an OUTDOOR KITCHEN AND BRICK OVEN, ideal for entertaining and enjoying Florida living year-round. A key highlight of this home is the solar energy system, providing reduced monthly electric costs This translates to significant annual savings and protection against rising utility rates, making it a valuable long-term benefit. Located just 4 minutes from WINDERMERE HIGH School and approximately 15 MINUTES rom Walt DISNEY World and major attractions, the home offers convenient access to dining, shopping, and entertainment. The community features LOWHOA fees and NO CDD. With relocation season underway, homes offering space, efficiency, and location are in high demand. This property is centrally located, well-positioned, and ready for its next owner. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Karla Price (407-761-7764)
1009 DOWN RESERVE CT, WINDERMERE, FL 34786
$3,950,000297 Days on yellowkey MLS ID: O6346638
REDUCED by $700,000 (15.1%) on 06/28/2026
Bed: 5 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 7940 Built: 2026Monthly Fee: $433 Tax: $7,458 (2025)Community: Lake Down ReserveSpa: YesSingle Family
Taxes:$7,458
Remarks: One or more photo(s) has been virtually staged. SELLER MOTIVATED!!! UNMATCHED PRICE AND OPPORTUNITY! Just completed | Never lived in | A rare opportunity to be the very first to call this architectural showpiece home! Positioned in the highly sought after Lake Down Reserve community of Windermere, this custom-built modern Mediterranean estate delivers nearly 8,000 square feet of elevated design, cutting-edge construction, and curated luxury. This home is a true statement of craftsmanship and innovation. From the hollow-core concrete second floor to level five interior walls, hurricane-impact windows and doors, and comprehensive low-voltage wiring, every structural detail reflects next-level quality. Inside, the open-concept floor plan unfolds with dramatic scale and natural light, anchored by a show-stopping LED-lit staircase and seamless indoor-outdoor flow. The chef’s kitchen is outfitted with premium Wolf appliances, custom cabinetry, and refined finishes that balance timeless elegance with modern edge. Designed for both grand entertaining and private retreat, the home features: 5 spacious bedrooms | Dedicated executive office | 6 full baths and 2 half baths (each bath appointed with luxury bidets) | Custom California Closets throughout | Elevator access for effortless convenience | Oversized 4-car garage. A rare “bonus basement” level adds additional flex space – perfect for a media lounge, in-law suite, wine cellar, game room, or collector’s showcase. Outside, enjoy balcony views of Lake Down and a resort-caliber backyard that includes a custom pool and spa, a dramatic sunken outdoor kitchen, fire-pit and expansive entertaining terraces designed for unforgettable evenings under the Florida sky. Lake Down Reserve offers expansive homesites, 24-hour virtual guard security, zoning for top-rated schools, and proximity to fine dining, championship golf, world-class shopping, and Orlando’s renowned attractions – all while still preserving the privacy and tranquility that define Windermere living. This is more than new construction. It is a fully realized modern estate – bold, refined, and built for the most discerning buyer. Welcome to your legacy home!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
3057 PORTO LAGO CT, WINDERMERE, FL 34786
$13,995,00034 Days on yellowkey MLS ID: O6411245
Bed: 6 Bath: 8.5 Gar: 8 Liv Area Sq Ft: 12067 Built: 2026Monthly Fee: $375 Tax: $18,356 (2025)Community: Lake Down Pointe 50 42Spa: YesSingle Family
Taxes:$18,356
Remarks: BRAND NEW ESTATE. A truly exceptional one-of-one on the shores of Lake Down, boasting over 12,000SF, 6BR's, 6/5BA's, and unmatched multigenerational flexibility. Designed by Mark Nasrallah and curated by Sorenson Construction, every inch of this estate was crafted with intention and the finest materials. Two 4-car garages flank either side of the oversized motor court, offering private entry to both the main house and the attached guest house. Off the main foyer, you'll find the formal dining room with Calacatta marble floors, and geometric coffered ceiling. Just beyond the elevator lies a 17x19 laundry room with an expansive island. The east wing is home to the gourmet kitchen, breakfast room, and family room. The chef's kitchen includes a Wolf six-burner gas stove with a built-in range hood, stacked double oven, and Sub-Zero double-wide refrigerator. Two Calacatta Macchia Vecchia marble islands create the ultimate statement. Beyond the main kitchen, behind a hidden door, is the prep/messy kitchen, with a Monogram 4-burner gas stove, Bosch refrigerator, walk-in pantry and butler's pantry. On the opposite side of the kitchen, the spacious breakfast room is bathed in natural light with access to the summer kitchen and pool deck through glass sliding doors. The open-concept layout flows effortlessly to the family room, where a backlit, custom media wall offers endless entertainment options. At the center of the main house is the expansive living room, the heartbeat of the estate. From the backlit coffered ceilings to the handcrafted millwork, and an overwhelming wall of glass, every part of this room feels larger than life. Rich hardwood flooring, built-in bookshelves, and a custom brass fireplace make it feel as charming as it is expansive. For guests, there is a first-floor ensuite bedroom complete with a separate generous lounge room, all overlooking spectacular lake views. Beyond the custom iron staircase on the first floor is the executive office, with built-in library, wood desk, and beautiful herringbone flooring. Adjacent is a stunning powder bath, followed by the interior guesthouse entry, which opens to a generous living room, a full-size kitchen with a Wolf 6-burner gas stove and a beautiful Arpell Azul mosaic backsplash, its own prep/messy kitchen, and full butler's pantry. The guest house's primary suite is its own oasis, with sweeping lake views, an ensuite bathroom, double vanity, clawfoot tub, and a huge walk-in closet. Two additional ensuite bedrooms — one designed for staff — a full-sized laundry room, and a flex room complete the guest house. Upstairs, the primary suite spans the entire east wing, with handcrafted coffered and backlit ceilings that are mesmerizing, plus panoramic views of Lake Down from the balcony. The master ensuite bathroom boasts a freestanding massage bath, his-and-hers vanities, and Walden Onyx designer wall coverings. The immersive primary walk-in closet will simply take your breath away, featuring designated his-and-hers areas, a center island, custom-built-in cabinetry, and an adjacent laundry room for the upper level. Directly next to the primary suite lies a spa retreat with a sauna room. A media room and entertainment den complete with its own kitchenette boast a flex room directly across the hall as well as an oversized ensuite guest suite. Outside, the limestone pool deck & covered summer kitchen, the disappearing-edge pool and spa with retractable screens provide the perfect retreat.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
13330 LONGACRE DR, WINDERMERE, FL 34786
$550,00026 Days on yellowkey MLS ID: O6418405
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2306 Built: 2013Monthly Fee: $115 Tax: $8,281 (2025)Community: Windermere TerraceSingle Family
Taxes:$8,281
Remarks: Welcome to this great maintained residence located in one of Central Florida’s most sought-after communities in Windermere. Offering approximately 2,306 square feet of thoughtfully designed living space, this home features one of the builder’s most popular and highly requested floor plans. The spacious first-floor primary suite provides privacy, comfort, and convenience, making it ideal for today’s lifestyle. Upstairs, you’ll find two generously sized secondary bedrooms along with additional living space perfect for family members or guests. The home includes 2 full bathrooms and 1 half bath, creating a functional layout for both everyday living and entertaining. This property has been meticulously maintained and is truly move-in ready. A major recent upgrade includes a brand-new HVAC system installed last year, providing peace of mind and energy efficiency for years to come. Residents will enjoy the exceptional location, just minutes from world-renowned attractions including Walt Disney World and Central Florida’s premier entertainment destinations. Everyday conveniences are right around the corner, with shopping centers, grocery stores, restaurants, pharmacies, gas stations, banks, and postal services all within close proximity. Commuters will appreciate the easy access to major highways and expressways, allowing seamless travel throughout the Orlando metropolitan area. Orlando International Airport is conveniently located within approximately 30 to 40 minutes. Windermere continues to be one of the most desirable residential markets in Central Florida, known for its beautiful surroundings, outstanding quality of life, strong property values, and excellent accessibility. Opportunities to purchase a well-maintained home with a first-floor primary suite in such a desirable location are increasingly rare. Whether you are searching for a primary residence, vacation home, or long-term investment, this exceptional property offers the perfect combination of location, lifestyle, comfort, and value. Schedule your private tour today and experience everything this remarkable Windermere home has to make.
Listing is courtesy of: SUNSTAR REALTY FL INC (407-350-8266)
Listing Agent: Zhe Wang (407-705-7288)
5128 BUTLER RIDGE DR, WINDERMERE, FL 34786
$1,175,00049 Days on yellowkey MLS ID: O6412016
2 Days Off yellowkey (back on 6/27/2026)
REDUCED by $75,000 (6.0%) on 06/04/2026
Bed: 4 Bath: 3.0 Gar: 7 Liv Area Sq Ft: 2816 Built: 1989 Tax: $9,506 (2025)Community: Butler RidgeSpa: NoSingle Family
Taxes:$9,506
Remarks: Under contract-accepting backup offers. Calling all car enthusiasts or artisans needing a large, detached workshop on your property! This house has it all; including a gorgeous interior, huge pool and lanai equipped with an outdoor kitchen, and a large 30 x 30 detached 5 car garage/workshop in addition to a 2 car attached garage. This house is perfect for work and play! Situated on a rare, 1 acre lot in the coveted town of Windermere, this house is truly 1 of a kind. Surrounded by sweeping oak trees and quiet streets, you’ll feel miles away from the hustle and bustle of the city even though you’re right at its back door. Enjoy entertaining? This is your dream entertaining house with a HUGE kitchen (which was gutted in 2017), high end appliances including a Bosch cook top/built in oven, and all the refrigerating needs you could have, including a wine fridge and a brand-new LG thinQ refrigerator that makes cocktail ice. There is plenty of room for friends and family to sprawl out as this house boasts an eat in kitchen as well as a formal dining area, and dual living room/family room areas that are split by a gorgeous, wood burning fireplace giving this home the coziest, homiest feeling. Love to have fun pool days? There is an oversized 14 x 34 lanai off the rear of the home decked out with an outdoor kitchen from Paradise Grills perfect for grilling out and relaxing. The oversized pool is a perfect place to cool off afterwards. This home has so much charm as a sprawling 1 story on a huge lot with space between houses, which is a rare find in this area. The backyard is fenced in for your furry friends enjoyment, and there is even plenty of land left to build an in-law suite if that is something you desire to do. With a fully renovated kitchen, and newly renovated bathrooms, this home is truly a turnkey experience. The sellers have poured tons of money into this home, please see MLS attachments for full list of recent upgrades. This home is zoned for top ‘A’ rated schools of Orange County including Windermere Elementary, Bridgewater Middle, and Windemere High school making it a great pick for personal enjoyment and resale value. The home has a 2 car garage attached to the home, and a 4 car detached garage in the back. ****Updates the sellers have completed since purchase: New AC unit - main house (Jan 2023) - New water heater (Oct 2021) - New water chlorination filtration system (2025)- Custom trim and molding throughout house (2025) - Custom built in shelving (2025) - Both bathrooms updated w custom cabinetry (2022 and 2025) - aluminum fencing in backyard (2021) - New AC in back garage (Sept 2021) - New refrigerator – LQ ThinQ (2025) - Pool area concrete replaced with pavers and patio extended off the master suite (2022) - New septic drain field and septic pumped (2026)... additionally, the kitchen and master bathroom were gutted and completely renovated in 2017, roof is 2017.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Taylar Colangelo, Llc (781-413-7054)
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