Location: Windermere
Do Not Show Listings
8360 VIVARO ISLE WAY, WINDERMERE, FL 34786
$690,00021 Days on yellowkey MLS ID: S5150324
0 Days Off yellowkey (back on 5/28/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2019Monthly Fee: $299 Tax: $9,812 (2025)Community: Windermere Isle - Phase 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,812
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautiful home located in a quiet and well-maintained community. This property features a functional layout with spacious, light-filled interiors. It offers 4 bedrooms and 2.5 bathrooms. The kitchen is equipped with appliances, and ample storage space—perfect for everyday living and entertaining. Additionally, it includes a private patio, perfect for relaxing or enjoying outdoor time. The community offers great amenities such as a swimming pool and common areas. Prime location close to shopping centers, restaurants, supermarkets, and with easy access to major highways.
Listing is courtesy of: MD3 HOMES LLC (407-557-8810)
Listing Agent: Monica Duran (407-702-5796)
13450 SUNKISS LOOP, WINDERMERE, FL 34786
$574,90020 Days on yellowkey MLS ID: O6407409
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2272 Built: 2005Monthly Fee: $131 Tax: $8,219 (2025)Community: Summerport Ph 03Spa: NoSingle Family
Taxes:$8,219
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: This 5-bedroom, 2.5-bathroom two-story home offers a spacious and highly functional layout, perfect for large households or those needing extra space. The main level features a formal front living room and a well-appointed kitchen with all appliances included and in good working order. For added convenience and privacy, the primary suite is located on the first floor, while the four secondary bedrooms and a full bathroom are situated on the second level. Complete with an attached 2-car garage, this home provides a smart separation of space and a move-in-ready interior.
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
6673 DUNCASTER ST, WINDERMERE, FL 34786
$530,000128 Days on yellowkey MLS ID: O6378820
REDUCED by $9,000 (1.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 2005 Tax: $3,351 (2024)Community: Lakes/Windermere Ph 02ASpa: NoSingle Family
Taxes:$3,351
Elementary School: Windermere Elem
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends the living space outdoors. Situated within a well-established community with a low HOA fee of $230 quarterly and no CDD, this property offers long-term cost efficiency compared to many newer developments. The Windermere location provides convenient access to major roadways, shopping, dining, retail centers, and entertainment throughout Central Florida.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Lilyan Machuca (407-738-7463)
14383 CREST PALM AVE, WINDERMERE, FL 34786
$1,166,990143 Days on yellowkey MLS ID: G5107222
16 Days Off yellowkey (back on 5/27/2026)
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3550 Built: 2026Monthly Fee: $245 Tax: $2,489 (2025)Community: Palms At WindermereSingle Family
Taxes:$2,489
Elementary School: Bay Lake Elementary
Remarks: One or more photo(s) has been virtually staged. ELLINGTON II - Our beautiful, huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42" cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. Triple sliding glass doors and an extended covered lanai. 4 Bedrooms upstairs with 2 full baths and loft, overlooking wooded area.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Cindy Sapp (352-516-2843)
11866 CAMDEN PARK DR, WINDERMERE, FL 34786
$959,900103 Days on yellowkey MLS ID: O6381558
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $25,000 (2.5%) on 05/14/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3337 Built: 2006Monthly Fee: $298 Tax: $13,742 (2025)Community: Keenes PointeSingle Family
Taxes:$13,742
Remarks: Welcome. New roof and one new HVAC System in 2026! Residing in the established, guard-gated community of Keene’s Pointe, this delightful five-bedroom, four-bathroom home features a functional two-story layout, with multiple living areas, spacious bedrooms, and modern finishes, creating an environment that is ready for life’s ever-changing needs. At the heart of the home, the gourmet kitchen showcases granite counters, plenty of cabinetry, a breakfast bar, and an island overlooking the family room and backyard, offering a cohesive main living space fit for relaxation and memorable gatherings. If practicality and privacy are aspects at the top of your list, the three-way split-bedroom floor plan allows for incredible flexibility and offers pristine privacy for all. On one side of the home, the large primary suite enjoys a tray ceiling, stylish flooring, a spacious closet, dual vanities, and a separate garden tub there to soothe you each day. On the other side of the home, the remaining bedrooms and bathrooms are designed to maximize privacy, with the ability to easily create en-suites, while the upstairs bonus room, bedroom, and bathroom provide a versatile and private space. High ceilings, crown molding, and ceiling accents throughout the home add a refined finish to the interior spaces. Venture outside to enjoy the sizable, covered lanai, providing a perfect retreat while remaining protected from the elements, or enjoy a journey through the lusciously landscaped community, with multiple parks and a community boat ramp accessing the Butler Chain of Lakes deliver regular delight. If the country club lifestyle is for you, The Golden Bear Club offers social and golf membership for an additional fee, which grants access to the renowned Golden Bear Golf Course and practice facilities, as well as the resort-style pool, tennis courts, state-of-the-art fitness center, and dining. 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. Schedule your private showing today to experience the full charm of this practical home.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
13118 SUNKISS LOOP, WINDERMERE, FL 34786
$570,000106 Days on yellowkey MLS ID: O6385211
REDUCED by $9,000 (1.6%) on 05/21/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2547 Built: 2005Monthly Fee: $130 Tax: $7,821 (2024)Community: Summerport Ph 03Spa: NoSingle Family
Taxes:$7,821
Remarks: One or more photo(s) has been virtually staged. 13118 Sunkiss Loop | Summerport, Windermere Located in the heart of Summerport, one of Windermere's most sought-after communities, this spacious two-story home offers over 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 bathrooms. Recent updates make this home truly move-in ready. A new roof was installed in February 2025, along with fresh interior and exterior paint, new ceiling fans, new toilets, and brand new appliances throughout (washer and dryer excluded). All appliances convey with the sale. The layout is both functional and welcoming, featuring a formal living room and separate dining area well suited for entertaining. The first floor is finished with tile and laminate flooring, and the second floor carries laminate throughout for a clean, consistent feel from top to bottom. Out back, a screened porch with a paved patio and approximately 100 square feet of covered space provides the perfect setting for outdoor dining and relaxing Florida evenings. A two-car garage adds everyday convenience. Positioned close to major shopping, grocery stores, and retail, and zoned for highly rated schools, this home delivers the space, updates, and location that Windermere buyers are looking for.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Desmond Garcia Llc (407-202-5104)
6130 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$3,150,000206 Days on yellowkey MLS ID: O6361099
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4676 Built: 2010Monthly Fee: $283 Tax: $24,892 (2024)Community: Keenes PointeSingle Family
Taxes:$24,892
Remarks: Exceptional Waterview Estate in Keenes Pointe / Resort-Style Outdoor Living. Located on a quiet cul-de-sac in the exclusive guard-gated community of Keenes Pointe, this custom Goehring & Morgan residence offers luxurious main-floor living paired with spectacular outdoor entertaining spaces and tranquil water views. Designed for both comfort and entertaining, the home features a heated saltwater pool with travertine decking, expansive covered lanai with automatic screens, summer kitchen, fire pit, fenced yard, and breathtaking sunset views. Inside, enjoy soaring ceilings, travertine flooring, custom millwork, 10-ft sliding doors, a wine cellar, hidden walk-in pantry, and a chef’s kitchen with Wolf 48” gas cooktop and custom cabinetry. The main-floor primary suite offers lanai access and a spa-inspired bath, while three additional bedroom suites are also conveniently located on the first floor. A spacious upstairs bonus/game room with full bar creates the perfect media, entertainment, or multigenerational flex space. Additional highlights include: • Oversized 3-car garage • 4 HVAC units + dehumidifier system • Updated pool equipment (2022) • Elevated garden shed + premium Vego garden beds • Office with custom built-ins Residents enjoy access to the Golden Bear Club lifestyle with golf, tennis, fitness, dining, Butler Chain lake access, and proximity to Windermere Prep, Disney, and Universal. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
7330 BRIGHTLAND ST, WINDERMERE, FL 34786
$465,00070 Days on yellowkey MLS ID: O6397124
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1881 Built: 2010Monthly Fee: $246 Tax: $6,905 (2025)Community: Lake Burden South Ph ITownhouse
Taxes:$6,905
Elementary School: Sunset Park Elem
Remarks: One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Lake Burden South, where this immaculately maintained 3-bedroom, 2.5-bath END UNIT townhome delivers the space, style and location you have been searching for in the perfect Windermere location! Formerly the MODEL HOME for the community, this residence showcases UPGRADED FINISHES, TIMELESS DESIGN elements and a thoughtful layout that feels both functional and elevated from the moment you step inside. Crown molding, abundant natural light and move-in ready condition create a polished feel throughout, while the walkable community setting puts shopping, dining and everyday conveniences just moments away. The main floor offers defined yet connected living and dining spaces, creating a natural flow for both entertaining and daily living. The UPGRADED KITCHEN feels classic and refined with sleek granite countertops, 42” cabinetry topped with crown molding, STAINLESS STEEL APPLIANCES, pantry storage and a large ISLAND with bar seating. A wall of windows keeps the entire space light and bright, while the adjacent breakfast nook and direct access to the PRIVACY FENCED PAVER PATIO make indoor/outdoor living effortless. A convenient half bath for guests, plus a rear-facing 2-car garage, add even more functionality. Upstairs, the spacious PRIMARY SUITE is privately positioned on one side of the home and features a WALK-IN CLOSET along with a beautifully upgraded en-suite bath complete with dual sinks, a SOAKING TUB and a WALK-IN SHOWER with CUSTOM TILE SURROUND. Two additional bedrooms are situated on the opposite side of the second floor and share a full bath, while the LOFT area includes a built-in desk for added flexibility and storage. Residents of Lake Burden South enjoy access to a COMMUNITY POOL and an unbeatable Windermere location with easy access to Winter Garden Vineland Road, nearby lakes, shopping, dining, entertainment and area attractions including Disney parks. Whether you are searching for a beautiful primary residence, a vacation home near Central Florida’s top destinations or a strong investment opportunity, this townhome checks every box. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
11524 CLAYMONT CIR, WINDERMERE, FL 34786
$1,288,99921 Days on yellowkey MLS ID: O6410754
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3358 Built: 2003Monthly Fee: $298Community: Keenes PointeSingle Family
Taxes:$0
Remarks: *** One of the lowest $/SF in Keene's Pointe *** Welcome to this updated, move-in ready luxury home in Keene’s Pointe, one of Windermere’s premier 24-hour guard-gated golf communities and home to the Golden Bear Club. Offering 5 bedrooms, 4 bathrooms, and 3,358 square feet of living space, this beautifully upgraded residence combines luxury finishes, functional design, and an exceptional Central Florida lifestyle just minutes from Disney, top-rated Windermere schools, shopping, dining, and major highways. Situated on an oversized homesite with a large driveway accommodating up to nine vehicles and a three-car garage, this home makes an immediate impression. Inside, the open-concept floor plan features commercial-grade porcelain tile flooring, crown molding, updated lighting, designer finishes, and spacious living areas designed for both everyday living and entertaining. Just off the entry, a custom wet bar with wine refrigerator and beverage fridge flows seamlessly into the dining area and main living space. The updated chef’s kitchen overlooks the family room and showcases quartz countertops, a large center island with additional 36-inch cabinetry storage, a farmhouse sink, soft-close dovetail cabinetry, stainless steel appliances, a natural gas range with vent hood, and an ideal layout for entertaining guests or hosting family gatherings. The spacious first-floor primary suite serves as a private retreat and features a large custom walk-in closet along with a beautifully updated spa-style bathroom complete with dual vanities, soaking tub, oversized walk-in shower with multiple spray features, and custom tile details. Three additional bedrooms and two updated bathrooms are located on the main level, while all bedrooms include custom closet systems and updated ceiling fans. Upstairs, newly finished stairs lead to a versatile loft with luxury vinyl plank flooring, an additional bedroom, and a full bathroom, creating flexible space ideal for a media room, home office, guest suite, or multigenerational living setup. The outdoor living space is designed for Florida entertaining with an approximately 900-square-foot paver patio, natural gas firepit, spacious backyard, and nightly Disney fireworks views. The rear yard is also prewired with 50-amp power for a future pool installation if desired by the next owner. Additional improvements include a 2021 roof replacement, extensive updates throughout the home, a new natural gas meter installed in 2025, and a meticulously maintained septic system with annual servicing over the past 10 years, a new septic alarm box and meter installed in 2021, and a new septic float installed in early 2025. The property also offers exceptional storage with three overhead garage storage racks rated for 600 pounds each, along with a fully planked, lighted, and walkable attic space above the entire three-car garage. Residents of Keene’s Pointe enjoy access to private boardwalks to Lake Tibet and the Butler Chain of Lakes, two community boat ramps, four playgrounds, and year-round neighborhood events. Optional Golden Bear Club membership offers access to championship Jack Nicklaus-designed golf, tennis courts, resort-style pool, fitness center, dining, and social activities. This updated Windermere luxury home offers a rare opportunity to own in one of Central Florida’s most desirable gated golf communities. Schedule your private showing today.
Listing is courtesy of: ALIGN REAL ESTATE LLC (305-389-2922)
Listing Agent: Immu Korvenmaa (407-242-2952)
7180 BEEK ST, WINDERMERE, FL 34786
$780,00084 Days on yellowkey MLS ID: O6393213
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3648 Built: 2013Monthly Fee: $124 Tax: $11,023 (2025)Community: Windermere TerraceSingle Family
Taxes:$11,023
Remarks: Spacious 6-Bedroom Home Just Minutes from Disney! Discover the perfect blend of space, comfort, and convenience in this stunning Hayden floorplan by Pulte Homes, located in the highly sought-after Windermere Terrace community. This beautifully maintained home offers 6 bedrooms + a bonus room, 4 full bathrooms, and a 3-car garage — ideal for growing families or hosting guests. A private guest suite with full bath – perfect for visitors or multi-generational living. Formal dining room for special occasions. Open-concept kitchen, breakfast nook, and family room — great for everyday living and entertaining. Spacious master suite on the first floor with a luxurious bathroom featuring dual sinks, soaking tub, and separate shower. Convenient laundry room with built-in cabinets and sink. "Drop-zone" near the garage entry for shoes, bags, and daily essentials. The kitchen is a chef’s dream with 42” cabinets, granite countertops, and all major appliances included. Upstairs, you'll find 4 additional bedrooms, 2 full baths, and a versatile loft/game room — an ideal space for movie nights, play area, or home office. Step outside and enjoy a private backyard perfect for entertaining family and friends. Community Pool. Close to top-rated schools, shopping, dining, and entertainment (including Winter Garden Village & Hamlin Town Center at Horizon West). Easy access to major highways: I-4, Florida Turnpike, SR 429 & 408. Just minutes from Magic Kingdom and other Orlando attractions. This is more than a home — it's a lifestyle upgrade. Schedule your showing today and see why Windermere Terrace is one of the area's most desirable places to live!
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Maria Ubillus (954-242-7900)
6462 DEACON CIR, WINDERMERE, FL 34786
$6,950,00034 Days on yellowkey MLS ID: O6407107
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 7178 Built: 1997Monthly Fee: $1,224 Tax: $108,011 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$108,011
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Ideally positioned near the driving range and just moments from Isleworth’s racquet center, clubhouse, fitness facilities, dining, and pool, the residence combines privacy with convenience.Designed by renowned architect Mark Nasrallah, the home spans more than 7,100 square feet and showcases sophisticated detailing and elevated finishes throughout. A grand foyer introduces the residence with a sweeping floating staircase and dramatic tiered crystal chandelier, leading into the formal living room where soaring ceilings, dual chandeliers, a fireplace, and expansive lake views create an impressive yet inviting setting.Marble flooring transitions seamlessly into the home’s primary living spaces, where rich hardwood floors enhance the warmth of the open-concept kitchen, casual dining area, and family room. The kitchen is both functional and elegant, featuring an oversized island, custom cabinetry, quarried quartz countertops, and professional-grade appliances by Wolf, Sub-Zero, and Bosch. A contemporary, temperature-controlled wine room accommodating over 100 bottles adds a distinctive touch. Architectural millwork in a diamond pattern defines the dining space, while custom media built-ins in the family room enhance the home’s cohesive design. Both areas open effortlessly to the lanai and pool deck.The primary suite serves as a private retreat, complete with a sitting area, designer lighting, and a spa-inspired bath featuring a soaking tub, expansive dual vanities, and a large walk-in shower. Additional interior highlights include a modern office with custom built-ins and private pool access, as well as a spacious game room with a full bar and captivating water views. Outdoors, the covered lanai extends to a resort-style pool and spa, surrounded by generous lounging areas and complemented by the private boat dock - creating an unparalleled setting for boating, entertaining, and year-round enjoyment in Florida's tropical climate.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
9323 GLADYS GARDEN CT, WINDERMERE, FL 34786
$11,900,000123 Days on yellowkey MLS ID: O6381880
REDUCED by $600,000 (4.8%) on 05/26/2026
Bed: 6 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 9770 Built: 2026Monthly Fee: $1,099 Tax: $21,279 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$21,279
Remarks: Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage plus golf cart garage, and a friends-and-family entry with covered parking. Inside, discover Sierra Pacific casement windows with stained interior mullions flood the home with natural light, highlighting warm beams, wide-plank floors, and curated details. Lutron lighting, Sonos audio, and powered draperies enhance modern comfort without compromising design. The formal dining room features a stained white oak arched opening, classic dentil molding, and built-in wine display. The living room is anchored by a gas Isokern fireplace with precast surround, custom built-ins, stained beams, and sculptural custom one off lighting, while an interior glass breezeway subtly defines the transition to the private primary wing. The primary suite offers a serene retreat with custom arch detailing, a nickel joint ceiling, and stained beams. The spa-inspired bath includes a marble soaking tub and a dramatic solid limestone staircase leading to a hidden upper-level flex space, ideal for an office or gym, complete with beverage refrigeration and powered Roman shade. The boutique-style closet features dual islands and an integrated wash tower. At the heart of the home, the chef’s kitchen stuns with soaring 18-foot ceilings, exposed beams, a curved reeded island, and custom Urban Electric pendants designed specifically for the residence. Sub-Zero refrigeration, freezer, and wine column, a 60-inch Wolf range, dual integrated dishwashers, and a fully equipped back kitchen ensure effortless entertaining. Indoor and outdoor living connect seamlessly to a private courtyard-style retreat featuring a resort-inspired pool with copper scupper water features, a summer kitchen with Wolf grill, powered screens, and multiple lounging areas designed for year-round enjoyment. Additional highlights include four upstairs en-suite bedrooms, including a secondary primary suite, an upstairs laundry with linen towers and folding station, a third-level bonus floor with theater, bar, powder bath, and storage, elevator-ready construction, and an advanced security system with AI-enabled cameras and window vibration sensors. Designed with architectural intention, this home pairs refined craftsmanship with warmth, creating spaces that feel both elevated and deeply livable.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
111 MAIN ST, WINDERMERE, FL 34786
$889,00035 Days on yellowkey MLS ID: O6407060
2 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2272 Built: 1984 Tax: $9,734 (2025)Community: Windermere TownSingle Family
Taxes:$9,734
Remarks: Prime Windermere Location! Fully Renovated and Move-In Ready! Don't miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms perfect for comfortable family living and entertaining. Recent Upgrades Include: Fresh interior and exterior paint. Brand-new luxury vinyl flooring Stunning 2x4 porcelain tile in the kitchen, foyer, and dining room. Sleek European-style kitchen cabinets with quartz countertops. Modern interior doors throughout. Stylishly renovated bathrooms. Energy-efficient LED recessed lighting throughout the home. As a Windermere resident, you'll also enjoy exclusive access to the community lakes perfect for boating, fishing, and relaxing outdoors.
Listing is courtesy of: CENTURY 21 CARIOTI (407-770-0322)
Listing Agent: Sammy Nakhleh (407-360-4435)
6120 GREATWATER DR, WINDERMERE, FL 34786
$4,399,00043 Days on yellowkey MLS ID: O6404574
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5580 Built: 1999Monthly Fee: $298 Tax: $32,016 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$32,016
Remarks: Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
7560 BENTONSHIRE AVE, WINDERMERE, FL 34786
$445,00041 Days on yellowkey MLS ID: O6405384
1 Days Off yellowkey (back on 5/26/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1905 Built: 2009Monthly Fee: $185 Tax: $6,652 (2025)Community: Wickham Park 04 05 06 09 10 11 12 01Townhouse
Taxes:$6,652
Remarks: Under contract-accepting backup offers. Welcome Home! Do not miss out on this Turnkey Corner Lot Townhome with 2 PRIMARY BEDROOMS. This desirable unit features 4 bedrooms, 3.5 bathrooms a rear-entry 2-car garage. The oversized kitchen is equipped with stainless steel appliances that are 5 years of age, Silestone countertops, 42-inch soft-close cabinets with under cabinet lighting and a double size pantry providing plenty of storage. Downstairs offers wood flooring and tile throughout. A convenient first-floor Primary Bedroom makes the perfect In Law Suite. Upstairs features Brand New Berber Carpet, Second Primary Bedroom, Bedrooms 3 and 4 with a Jack and Jill Bathroom. Washer and dryer are included for added convenience, 5 years of age. Enjoy fresh exterior paint and new roof 2024. Front Door replaced and upgraded to Vinyl. Interior offers new paint and upgraded baseboards downstairs. AC unit is 7 years old. Community Amenities include a sparkling pool and a Clubhouse ideal for parties and events. The community also features a Dog Park, Playground, Walking/Biking Trails throughout and 2 ponds. Located close to top-rated area schools, excellent shopping and dining destinations, and just minutes from Disney Parks — this home offers both comfort and a highly desirable location!
Listing is courtesy of: SOLD BY SIX REALTY, LLC (407-375-2330)
Listing Agent: Sharon Six (407-375-2330)
9011 CHAPMAN OAK CT, WINDERMERE, FL 34786
$629,00061 Days on yellowkey MLS ID: S5148031
REDUCED by $20,000 (3.1%) on 05/26/2026
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)
1361 WHITNEY ISLES DR, WINDERMERE, FL 34786
$1,200,000243 Days on yellowkey MLS ID: O6352069
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2787 Built: 2006Monthly Fee: $136 Tax: $6,975 (2024)Community: Whitney Isles/Belmere Ph 02Single Family
Taxes:$6,975
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
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)
1849 WATERMERE LN, WINDERMERE, FL 34786
$1,299,00094 Days on yellowkey MLS ID: O6389840
0 Days Off yellowkey (back on 5/25/2026)
REDUCED by $26,000 (2.0%) on 05/04/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3934 Built: 2005Monthly Fee: $267 Tax: $8,439 (2024)Community: Windermere GrandeSpa: YesSingle Family
Taxes:$8,439
Remarks: Under contract-accepting backup offers. 1849 Watermere Ln. offers a traditional-styled, versatile nearly 4000 ft.² floor plan with 4 to 5 bedrooms and 3 1/2 baths. It features a three-car side-entry garage situated on three-quarter acres with no rear neighbors overlooking a 3-acre common area. To the back of the house, there’s a 1000 ft.² lanai undercover and a 1500 ft.² under screen. The 30-foot-long LED changing color lighted pool is equipped with an underground salt water filtration system and lighted bubbler. The back wall of the pool is lined with a blue, purple, and green iridescent tile. The pool has a pebble tech finish with a maximum depth of 6 1/2 feet. There’s also a separate six-person heated therapeutic spa with 72 powerful jets and changing light colors. The house has undergone upgrades to enhance energy efficiency and reduce utility costs. It boasts 74 Tesla solar panels on the roof that collect energy from dawn until sunset. Two Tesla storage batteries power the house when the sun sets. This system is designed to be off-grid, and Duke Energy purchases electricity from our system. We have an instant hot water system that allows simultaneous showers, baths, and appliance use. A well is used to irrigate the three-quarter acres of grass and planting. Household water usage is less than $25 month. There’s ample parking in a brick paver driveway with a long walkway leading to the front door. Double doors open to a spacious foyer, dining room, and formal living room. The ceilings are 14 feet high with crown molding and two large crystal contemporary chandeliers. The floors are Daltile continental slate in Egyptian beige, set diagonally throughout the house except for the bedrooms. Through a 12-foot sliding glass door in the living room, you can see the lanai, the pool, and the water features. To the right of the foyer and living room lies the master bedroom, featuring Brazilian teakwood hardwood floors, a tray ceiling, and a sliding glass door leading to the lanai. The master bedroom hallway connects to a spacious closet, the master bathroom equipped with a jetted tub, and a door that leads to the study, nursery, and sitting area. To the left of the living room, an archway entrance opens up to the U-shaped kitchen. This kitchen boasts real wood cabinets with granite countertops and a five-burner stove top. A large island and a two-door pantry complete the kitchen’s features. The kitchen overlooks the family room and TV room, which have two sliding glass doors that open up to the lanai and pool area. Adjacent to the family room is an in-law suite. This suite features cathedral ceilings with its own bedroom and bathroom, a kitchenette, and a sliding glass door that leads to the lanai. There’s also a separate entrance with a brick paver walkway that leads to the driveway. To the far left of the house, there are two additional bedrooms, a large bathroom, a stairway that leads to the bonus room above the three-car garage, and a laundry room lined with upper wood cabinets. The house also has a three-car garage, each with its own garage door. In 2017, the air conditioning system was replaced with a Trane system, and the house now has five air-conditioning zones throughout.
Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)
Listing Agent: Susana Stutsman (321-278-0334)
13730 CALERA ALY, WINDERMERE, FL 34786
$465,00023 Days on yellowkey MLS ID: O6410129
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2091 Built: 2017Monthly Fee: $439 Tax: $7,593 (2025)Community: Vineyards/Horizons West Ph 2BTownhouse
Taxes:$7,593
Elementary School: Independence Elementary
Remarks: Welcome to 13730 Calera Alley, a rare 4-bedroom fully furnished end-unit townhome that offers a combination that’s incredibly difficult to find in the community, providing additional privacy, extra natural light, and a more spacious feel compared to interior units. With additional windows and only one shared wall, this home lives much more like a single-family residence while still offering the convenience of townhome living. Adding to the appeal is a private covered patio — the perfect space to enjoy your morning coffee, unwind in the evenings, or create an outdoor living area with added privacy that’s hard to come by in townhome communities. Inside, the home has been thoughtfully upgraded with custom closet systems installed throughout the bedrooms. The primary suite features a massive walk-in closet complete with a fully customized organization system designed to maximize storage. Located just off Winter Garden Vineland Road, The Vineyards is loved for its charming streetscapes, resort-style pool and cabana, playground, and HOA-maintained landscaping, allowing residents to enjoy the lifestyle without the constant exterior upkeep. The neighborhood also stands out for having no CDD fees, which is increasingly rare for newer communities in the area. The home's location places you right in the middle of everything buyers are looking for in Horizon West. Just minutes away, you’ll find the rapidly growing Hamlin and Windermere corridor filled with shopping, dining, fitness studios, coffee shops, grocery stores, and everyday conveniences. Nearby favorites include Publix, Lakeside Village, Windermere Village, and an endless variety of restaurants and retail throughout Horizon West. It also offers quick connectivity to SR-429, Walt Disney World property, Winter Garden Village and major employment hubs throughout Central Florida. Outdoor enthusiasts will also appreciate being close to the Butler Chain of Lakes area, walking trails, parks, and nearby preserves. The Vineyards offers a balance that’s difficult to find — a true neighborhood feel with newer construction, maintained community spaces, and proximity to top-rated Windermere-area schools, all while being tucked away from the congestion of larger master-planned communities. Whether buyers are looking for extra space, a lock-and-leave lifestyle, or simply a rare end-unit opportunity in one of Windermere’s most convenient locations, this home delivers.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nick Nelson (262-914-9427)
9527 QUEENSBURY CT, WINDERMERE, FL 34786
$1,499,90027 Days on yellowkey MLS ID: O6408997
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5378 Built: 1998Monthly Fee: $101 Tax: $20,104 (2025)Community: Windsor HillSpa: YesSingle Family
Taxes:$20,104
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Rare opportunity to purchase in the Windermere's Windsor Hill community on a quiet cul-de-sac. This spacious 5-bedroom home offers over 5,300 square feet of flexible living space designed for both everyday living and entertaining. Situated on nearly half an acre, the property features a functional layout with large gathering spaces, high ceilings, and plenty of natural light throughout. The kitchen includes stainless steel appliances, ample cabinet space, a center island, and connects directly to the main living areas, making it ideal for hosting or family life. The first-floor primary suite offers dual walk-in closets and a large ensuite bath, while the additional bedrooms and living spaces provide room for guests, work-from-home setups, or multigenerational living. One of the standout features of the home is the custom Indiana Jones-themed movie room, creating a unique and immersive entertainment space. The home also includes a bonus enclosed patio area that can function as a home gym or creative workspace. Outside, enjoy a large backyard, covered outdoor areas, and a private pool setting perfect for Florida living. Conveniently located near top-rated schools, shopping, dining, and major roadways, this Windermere home combines size, character, and functionality in a desirable location.
Listing is courtesy of: THE PROPERTY PROS REAL ESTATE, INC (407-879-7591)
Listing Agent: Tamar Hill (818-445-8263)
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