Location: Windermere
Do Not Show Listings
9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786
$750,000112 Days on yellowkey MLS ID: O6386605
REDUCED by $100,000 (11.8%) on 04/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3435 Built: 2001Monthly Fee: $115 Tax: $11,111 (2024)Community: Westover Club Ph 01 44/139Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,111
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: PRICED TO SELLLL!!! Behind the gates of Westover Club, 9669 Westover Club Circle offers a timeless Windermere setting with privacy, mature landscaping, and seamless indoor-outdoor living on nearly half an acre. Designed for both entertaining and everyday comfort, the home blends classic style with a functional layout in one of the area’s most desirable gated communities. Featuring 4 bedrooms, 4 bathrooms, and over 3,400 square feet, the home includes formal living and dining spaces and a flexible floor plan with distinct yet connected living areas. A newer AC system and roof (approx. 5 years old) provide valuable updates and peace of mind. Enjoy a screened lanai, open porch, and private pool overlooking a spacious, hedge-lined backyard. While the home would benefit from cosmetic updates, it presents an excellent opportunity to personalize, with a seller who is flexible. A Generac generator adds comfort and year-round security.
Listing is courtesy of: FIRST WORLD REALTY GROUP (954-457-0114)
Listing Agent: Regina Ferdinand (954-665-9885)
13448 BELLARIA CIR, WINDERMERE, FL 34786
$3,200,000271 Days on yellowkey MLS ID: O6346484
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6308 Built: 2014Monthly Fee: $483 Tax: $29,164 (2024)Community: BellariaSingle Family
Taxes:$29,164
Elementary School: Windermere Elem
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting the elegant handcrafted staircase in the foyer. The formal living and dining areas set the tone for refined entertaining, enhanced by a gas fireplace, a well-appointed wet bar, and expansive views of the sparkling pool and two-story covered porch. Just off the entry, the study provides an intimate retreat with porcelain flooring and clerestory windows, filling the space with natural light and framing serene outdoor vistas. The open-concept family room and kitchen create the heart of the home, where a wall of glass doors seamlessly blends indoor and outdoor living. The gourmet kitchen is a chef’s delight, featuring stainless steel appliances, exotic granite, custom cabinetry, tile flooring, and a spacious walk-in pantry. The first-floor master suite, thoughtfully tucked away for privacy, serves as a true sanctuary. Its spa-inspired bath is adorned with paneled cabinetry, exotic granite, a rainforest shower, soaking tub, and expansive closet areas—both beautiful and functional. Two additional en suite guest bedrooms, a versatile bonus room, and generous living and dining spaces make the main level ideal for everyday living or hosting. Upstairs, the thoughtful layout continues with three bedrooms, a loft, a sitting area, a bonus room, and even a second laundry room for added convenience. These flexible spaces adapt easily to the needs of a growing family or guests, offering opportunities for work, play, or relaxation. Blending elegance with livability, this home captures the essence of Florida living—where interiors open gracefully to resort-style outdoor spaces, making it perfect for both intimate family life and grand entertaining.
Listing is courtesy of: KENNEDY REALTY GROUP LLC (407-590-6192)
Listing Agent: Shawn Kennedy (407-590-6192)
9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786
$4,450,00072 Days on yellowkey MLS ID: O6397842
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5004 Built: 2019Monthly Fee: $1,146 Tax: $35,432 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$35,432
Tax Year: 2025
Middle School: Chain of Lakes Middle
Remarks: Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.
Listing is courtesy of: MEGAN DOWDY REALTY, LLC (407-509-9279)
Listing Agent: Megan Dowdy (407-509-9279)
6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$550,00021 Days on yellowkey MLS ID: O6412095
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1984 Built: 2012Monthly Fee: $130 Tax: $6,210 (2025)Community: Windermere Lndgs Ph 02Single Family
Taxes:$6,210
Elementary School: None
High School: None
Middle School: None
Remarks: RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Jose Rojo (786-502-6162)
1407 HEMPEL AVE, WINDERMERE, FL 34786
$1,090,00021 Days on yellowkey MLS ID: O6410840
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2842 Built: 1989 Tax: $10,727 (2025)Community: Gotha TownSingle Family
Taxes:$10,727
Remarks: Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor living. One of the greatest advantages of this property is that it has NO HOA, allowing you the freedom to enjoy your property without restrictive association rules or expensive monthly fees. Whether you are looking for a primary residence, vacation home, or investment property, this home offers endless possibilities. The property features a beautiful swimming pool and stunning water views, creating the perfect atmosphere to relax, entertain guests, and enjoy the Florida lifestyle all year round. The oversized lot provides plenty of space for family gatherings, outdoor activities, parking, or future improvements.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Lina Abi Hanna De El Bonney (407-227-1740)
2002 WATER KEY DR, WINDERMERE, FL 34786
$1,299,00024 Days on yellowkey MLS ID: O6408915
0 Days Off yellowkey (back on 5/30/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3695 Built: 2002Monthly Fee: $335 Tax: $16,085 (2025)Community: Reserve At Waterford Pointe Ph 01Spa: YesSingle Family
Taxes:$16,085
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Set behind the gates of Reserve at Waterford Pointe, this exceptional 5-bedroom, 5-bathroom estate spans 3,695 square feet on more than half an acre of beautifully manicured grounds, delivering refined everyday living in one of Central Florida's most sought-after lakeside communities. Framed by freshly updated landscaping and mature greenery, the residence commands attention with its stately presence, expansive lot, and genuine sense of privacy. Recent upgrades elevate both comfort and longevity, including a new HVAC system, new water heater, fresh carpet in the main living areas, and tile flooring throughout the primary rooms. A grand entry introduces spectacular formal living and dining spaces designed to elevate both intimate gatherings and large-scale entertaining. At the heart of the home, the chef's kitchen is thoughtfully designed with a large center island, bar seating, stainless steel appliances, abundant cabinetry, and an open-concept layout that flows effortlessly into the main living areas. Overlooking the kitchen, the family room feels both warm and dramatic, anchored by a striking floor-to-ceiling stone feature wall with a gas fireplace that creates an inviting focal point. Privately positioned, the primary suite serves as a luxurious retreat with direct access to the outdoor living spaces. Spacious and serene, it is complemented by a spa-inspired bath with dual vanities, a soaking tub, walk-in shower, and an oversized walk-in closet designed for both comfort and functionality. Upstairs, a generous bonus room doubles as a private movie theatre with a wet bar, offering an ideal space for entertaining, relaxing, or hosting guests in a setting that feels distinctly elevated. Beyond the interiors, the home opens into a private outdoor oasis featuring a sprawling screened lanai, sparkling pool and spa, and a fully equipped summer kitchen with grill and bar seating. The expansive backyard delivers exceptional space and privacy, framed by lush mature landscaping that creates a tranquil, secluded atmosphere. Residents of The Reserve at Waterford Pointe enjoy an exclusive lifestyle with access to private community amenities, including a boat ramp to Lake Roberts, tennis courts, a playground, and beautifully maintained park spaces. Ideally positioned just minutes from Disney, Universal Orlando, SR 429, the Florida Turnpike, and some of Central Florida's finest shopping and dining destinations, this remarkable residence offers a rare combination of luxury, privacy, and convenience.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
11434 JASPER KAY TER #106, WINDERMERE, FL 34786
$320,00022 Days on yellowkey MLS ID: S5150874
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1455 Built: 2007Monthly Fee: $485 Tax: $4,640 (2025)Community: Lakeside/Lks/WindermereCondo
Taxes:$4,640
Remarks: investment property with a very high rental demand for its location and comfort or a vacation retreat, this condo is perfect for you. Beautiful condo located in Lakeside at Lakes of Windermere, corner unit on the first floor (ground floor) with covered lanai Welcome to this stunning condo located in one of the best and most exclusive areas of Orlando Fl such as Windermere, with 3 bedrooms and 2 bathrooms, this condo which is in perfect condition of care and maintenance, offers a spacious and open layout that perfectly combines the kitchen, dining and living areas, ideal for both everyday life and entertaining. The master suite, located to one side for privacy, has a generous bathroom with a garden-style tub/shower and a large walk-in closet. The kitchen is beautifully equipped with wood cabinets. On the opposite side, you will find the secondary bedrooms along with the second bathroom, a convenient laundry closet and ample storage space throughout. The gated resort-style community includes a clubhouse, pool, fitness room, walkways, green areas, parks, sports areas, on-site management and valet trash service, ensuring convenience and comfort. Located in the heart of Windermere in a strategic location just minutes from Walt Disney World and Downtown Winter Garden, easy access to major streets and highways that bring you closer to other important areas of the city and other local attractions such as Universal Studios, it is close to Publix, shops, restaurants and stores.
Listing is courtesy of: NUMBER 1 BROKER, LLC (407-566-3400)
Listing Agent: Eric Jia (407-401-1431)
13048 LAKE ROPER CT., WINDERMERE, FL 34786
$1,890,000281 Days on yellowkey MLS ID: O6342354
5 Days Off yellowkey (back on 5/30/2026)
REDUCED by $60,000 (3.1%) on 04/22/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4130 Built: 2002Monthly Fee: $333 Tax: $14,738 (2025)Community: Windermere PointeSingle Family
Taxes:$14,738
Remarks: Under contract-accepting backup offers. Back on the market. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage. Lake Roper is renowned for its water sports, water skiing, jet skiing and fishing only acceded by the surrounding houses (No Public Ramps). This is one of the largest lots in the community. Location: Only minutes from Winter Garden Village and Downtown Windermere, minutes from main roads like 429 and 408 and a short distance from Theme Parks and Shopping Areas. Great School District. Kitchen: Totally renewed, custom-built cabinetry, high-end stainless still appliances, built in induction cook top, built in microwave and oven, huge island built with one piece of quartz, no sims. Pop-out outlets, touchless faucet and built in hood. Bathrooms: Contemporary look with porcelain tiles, quartz tops, custom made cabinetry and modern metals. Pool area: The pool was resurfaced, surrounded by new pavers overviewing the lake and a brand-new equipped summer kitchen just built. Dock: Wood dock and fishing pier with Electric Boat lift. The house was completely renovated from top to bottom including new engineering hardwood floors, 3 new A/Cs, new water heater, new irrigation system, fresh painted and new roof installed in 2020. Important Notice: "Seller is willing to accept a smaller house as part of the payment".
Listing is courtesy of: WOODSTONE INVESTMENTS LLC (407-300-4727)
Listing Agent: Fernando Teixeira (407-300-4727)
13106 ORANGE ISLE DR, WINDERMERE, FL 34786
$870,000194 Days on yellowkey MLS ID: O6361057
INCREASED by $20,000 (2.4%) on 05/30/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3312 Built: 2022Monthly Fee: $95 Tax: $11,893 (2025)Community: Sanctuary/Lks/WindermereSpa: NoSingle Family
Taxes:$11,893
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration. Current under one year lease.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Victor De Oliveira (321-393-2772)
13124 FILLY CT, WINDERMERE, FL 34786
$1,575,000421 Days on yellowkey MLS ID: O6303140
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3300 Built: 1989Monthly Fee: $46 Tax: $15,459 (2024)Community: FarmsSpa: NoSingle Family
Taxes:$15,459
Remarks: Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As you step up to the front entrance, you are greeted by beautiful water fountain. Once inside your living room with a wood burning fireplace welcomes you to your living room on the right. Continuing your way into the house, your inviting family room awaits with an eat in kitchen island completing the scene. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances and plentiful cabinetry. Retreat to the oversized owner’s suite with double walk-in closets, a luxurious master bathroom and a private sitting area overlooking the pool area. Enjoy an enclosed pool area and expansive backyard. There is also a second master suite with private bathroom and walk-in closet. At the opposite end of the family room there is a hallway leading to another full bathroom and three additional bedrooms. Located just minutes from championship golf courses, downtown Windermere, Winter Garden Village, and top-rated schools, this home offers the perfect blend of tranquility and convenience. Don’t wait, schedule your showing today!
Listing is courtesy of: HOME N OFFICES INTERNATIONAL (407-864-4590)
Listing Agent: Marcelo Brandao (407-864-4590)
9960 6TH ST, WINDERMERE, FL 34786
$3,750,00022 Days on yellowkey MLS ID: O6412077
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6182 Built: 2027 Tax: $5,791 (2025)Community: Gotha TownSingle Family
Taxes:$5,791
Remarks: Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and comfortable everyday living, the home features a grand foyer with soaring ceilings, expansive living and family rooms, a private study, and a spectacular gourmet kitchen with an oversized island, walk-in pantry, and premium finishes throughout. The luxurious first-floor owner's retreat serves as a private sanctuary with a spa-inspired bath, oversized walk-in closets, and direct access to the outdoor living areas. Upstairs, you'll find additional en-suite bedrooms surrounding a spacious loft and bonus room, providing the perfect space for family gatherings, a media room, or guest accommodations. Large covered lanais seamlessly blend indoor and outdoor living, creating an ideal setting for entertaining while enjoying Florida's year-round lifestyle. Situated in prestigious Windermere, this exceptional estate combines timeless architecture, thoughtful design, and superior craftsmanship, all within close proximity to top-rated schools, world-class golf, fine dining, shopping, and the Butler Chain of Lakes.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Fernanda Negromonte (407-592-1744)
12132 MONTALCINO CIR, WINDERMERE, FL 34786
$3,790,000227 Days on yellowkey MLS ID: O6319854
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $160,000 (4.1%) on 05/13/2026
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 5709 Built: 2016Monthly Fee: $242 Tax: $38,798 (2024)Community: Casa Del Lago RepSingle Family
Taxes:$38,798
Remarks: Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout. The gourmet kitchen features custom dark cabinetry, quartz countertops, a designer mosaic backsplash, pendant lighting, and top-of-the-line stainless-steel appliances. The primary suite is a serene retreat showcasing peaceful lake views, a spa-inspired bathroom with a freestanding soaking tub, dual vanities, and a custom-designed walk-in closet. This remarkable home also includes a fully equipped theater room, a complete gym setup, multiple TVs, and select designer furniture pieces in the dining room, living room, and office, along with all chandeliers and lighting fixtures. Outdoors, enjoy a resort-style pool, spacious travertine patio, and a private dock with lifts for both a Yamaha boat and Jet Ski, which are included in the sale for your convenience. With its three-car garage, lush landscaping, and proximity to fine dining, golf, and top-rated schools, this residence exemplifies modern sophistication and lakefront elegance in Windermere.
Listing is courtesy of: BELLA VIEW REALTY LLC (407-616-7653)
Listing Agent: Caroline Perotti (407-460-9019)
11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$495,00023 Days on yellowkey MLS ID: O6409301
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1829 Built: 2014Monthly Fee: $85 Tax: $6,641 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,641
Elementary School: Bay Lake Elementary
Remarks: Meticulously maintained, this 3-bedroom, 2.5-bathroom two-story home sits in an unbeatable location directly across from Bay Lake Elementary. The first level features a welcoming front porch, an open-concept living area with brand-new LVP flooring, an updated half bath, and a beautifully appointed kitchen boasting stone countertops, a walk-in pantry, and a breakfast bar. Upstairs, a versatile spacious loft leads to two guest bedrooms and a primary suite complete with newly installed carpet, updated bathroom with dual vanities, a tile shower, and a walk-in closet. Big-ticket upgrades offer total peace of mind, including a new roof (2022) and a new hybrid water heater (2025). Windemere Trails community offers excellent amenities and is ideally situated just minutes from Lakeside Village Center and Westside Shoppes (Publix, dining, fitness, and more) and a short drive to Orlando's Theme Parks, World Class Dining, Shopping, and Golf. This low-maintenance home offers exceptional accessibility and turnkey living!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: John Callahan (407-716-3541)
5001 LATROBE DR, WINDERMERE, FL 34786
$3,299,99995 Days on yellowkey MLS ID: O6389183
REDUCED by $200,000 (5.7%) on 05/28/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4417 Built: 1990Monthly Fee: $1,043 Tax: $30,452 (2024)Community: IsleworthSpa: NoSingle Family
Taxes:$30,452
Remarks: One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private en-suites and large walk-in closets, and three bedrooms upstairs, with one of the upstairs bedrooms having a private ensuite. This home underwent a $400,000 update in 2019. Looking for an open layout with the kitchen overlooking the family room? Look no further! Updated ivory cabinetry, a Viking gas range with a French hood, double islands, and three ovens are ideal for daily meal prep and for hosting get-togethers with friends and family. There is ample seating, perfect for accommodating family and guests, with a formal dining room that flows into a family room with panoramic views overlooking the 6th tee. The family room shares a double-sided fireplace with the living room, which is open to the kitchen and has French doors to the covered, screened-in patio. Enjoy the Florida lifestyle with a large covered travertine patio, summer kitchen, heated pool, and an open-air travertine courtyard overlooking Lake Bessie at sunset. A three-car garage and expansive paver driveway provide ample parking. This is an ideal first home in Isleworth or as a vacation home. This is the perfect size and layout for real, everyday livable luxury in Isleworth. All offers will be considered. Schedule your private showing today.
Listing is courtesy of: Q BOUTIQUE SPECIALTY REALTY INC (407-863-7965)
Listing Agent: Laura Diss (407-388-4103)
6219 TIROCO WAY, WINDERMERE, FL 34786
$2,600,000104 Days on yellowkey MLS ID: O6387454
Bed: 7 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5221 Built: 2014Monthly Fee: $310 Tax: $27,796 (2025)Community: WaterstoneSpa: YesSingle Family
Taxes:$27,796
Remarks: One or more photo(s) has been virtually staged. Welcome to luxury living in the guarded, gated community of Waterstone in Windermere, Florida. This exceptional residence at 6219 Tiroco Way blends elegance, comfort, and modern efficiency, featuring solar power and an impressive floor plan designed for both everyday living and entertaining. The home offers 7 bedrooms, 5½ bathrooms, a media room, loft, dedicated office, storage room, and separate formal living and dining rooms. Elegant design elements throughout include volume ceilings, designer niches, granite countertops, stainless steel appliances, natural gas cooking, washer and dryer, an under-stairs storage closet, security system, and a spacious three-car garage. A convenient Jack-and-Jill bath with double vanity adds functionality for family or guests. The first-floor primary suite is a private retreat featuring a spacious bedroom with a bay window overlooking the pool and two custom walk-in closets. A sitting area between the bedroom and bath provides space for comfortable chairs or a nursery setup. The luxurious primary bathroom includes dual vanities with abundant counter space, a large soaking tub, and an impressive walk-through shower with dual benches and multiple shower heads. The kitchen is ideal for the home chef, showcasing a large center island with additional storage and two pantries. It opens seamlessly to the family room, dinette, and outdoor living area, creating the perfect layout for gatherings and daily living. Step outside to your private backyard oasis featuring a designer custom pool and spa with waterfall and fountain features, elegant travertine decking, and plenty of space for outdoor entertaining. Two sizeable side yards offer additional room for recreation and privacy. Waterstone is a highly sought-after community located on the shores of Lake Butler, offering 24/7 guarded security, scenic walking trails, beautiful stone accents, and distinctive architecture. Residents also enjoy a private gate to Windermere Preparatory School. Conveniently accessing Walt Disney World, one can even watch the Disney fireworks from the community. Also in proximity are area theme parks, excellent shopping and dining, and major highways including State Road 429 and the Florida Turnpike for easy travel to downtown Orlando, Orlando International Airport, and the region’s booming medical corridor.
Listing is courtesy of: MAXLIFE REALTY LLC (321-373-3536)
Listing Agent: Ryan Solberg (407-748-3436)
5199 LATROBE DR, WINDERMERE, FL 34786
$5,300,00024 Days on yellowkey MLS ID: O6409961
Bed: 6 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 4665 Built: 1993Monthly Fee: $1,224 Tax: $37,241 (2025)Community: IsleworthSingle Family
Taxes:$37,241
Remarks: Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
10624 REAMS RD, WINDERMERE, FL 34786
$475,000303 Days on yellowkey MLS ID: O6338130
REDUCED by $12,000 (2.5%) on 05/28/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2092 Built: 2014Monthly Fee: $81 Tax: $5,459 (2024)Community: Windermere Trls Ph 1CSingle Family
Taxes:$5,459
Remarks: Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design connects the spacious living and with the kitchen, perfect for entertaining. The primary suite offers a walk-in closet, dual sink vanity, and walk-in shower, while the upstairs loft provides a versatile space for a playroom, office, or media area. Recent updates include a new A/C (2022) and water heater (2023). Windermere Trails offers fantastic community amenities, including a resort-style pool, playground, picnic areas, and scenic walking trails. Located near top-rated (A+) schools, beautiful parks, and a variety of dining and entertainment options, this home combines comfort, convenience, and lifestyle. Don’t miss this opportunity—schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jeff Taulbee (407-622-2122)
12623 PARK AVE, WINDERMERE, FL 34786
$3,800,00025 Days on yellowkey MLS ID: O6410693
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 7120 Built: 2023Monthly Fee: $687 Tax: $23,243 (2025)Community: Chaine De LacSingle Family
Taxes:$23,243
Remarks: Experience Unparalleled Luxury in Chaine Du Lac Nestled within the sought- after gated community of Chaine Du Lac, this extraordinary custom estate redefines luxury living. Offering over 7,100 sqft of meticulously crafted living space, this magnificent residence features 5 bedrooms, 5 full bathrooms, and 2 half bathrooms, combining timeless elegance with exceptional craftsmanship in one of Central Florida's most sought-after addresses. A pair of custom wrought-iron front doors welcomes you into a breathtaking foyer highlighted by a dramatic circular dome ceiling and grand architectural details. Porcelain flooring flows throughout the home, while custom barrel ceilings, designer ceiling treatments, extensive tray ceilings, and crown molding showcase the remarkable attention to detail found in every room. Expansive windows fill the residence with natural light, creating a warm and inviting atmosphere throughout. Each of the five bedrooms serves as a private suite, complete with its own luxurious en-suite bathroom and custom walk-in closet. Designer ceilings, elegant trim work, offering comfort, privacy, and sophistication for family and guests alike. Designed for both everyday living and grand-scale entertaining, the chef's kitchen is truly a showpiece. Premium Thermador appliances, a custom hand-hammered copper hood, abundant cabinetry, a spacious walk-in pantry, natural gas, and stunning natural quartzite countertops combine beauty and functionality to create an exceptional culinary experience. The outdoor living spaces are equally impressive, featuring over 7,000 square feet of premium travertine hardscaping, including a grand travertine driveway and expansive rear paver terraces. Covered outdoor living areas on both levels are enhanced by beautiful tongue-and-groove wood ceilings, creating seamless indoor-outdoor living. The expansive upstairs balcony offers the perfect setting to relax, entertain, and enjoy Florida's year-round lifestyle. Car enthusiasts will appreciate the oversized 6-car garage, offering ample space for a prized collection, recreational vehicles, or workshop space. A private executive office has been strategically designed with a direct view into the garage, creating a unique showcase for automotive enthusiasts and allowing your collection to become part of the home's everyday living experience. Entertainment and lifestyle amenities continue throughout the home, including a dedicated theater room, whole-home surround sound system, and a private salon complete with its own half bathroom. A durable and elegant metal roof crowns the residence, while extensive custom millwork and luxury finishes further elevate the home's exceptional quality and craftsmanship. Residents enjoy the prestige and security of a community patrolled by the Windermere Police Department following annexation into the Town of Windermere. Just minutes away, experience the charm of downtown Windermere, where weekly farmers markets, food truck gatherings, boutique shopping, and community events create a lifestyle as inviting as it is exclusive. This extraordinary residence offers a rare combination of architectural excellence, luxury finishes, resort-style outdoor living, and an unmatched location within one of Central Florida's most coveted communities. A true showcase estate designed for those who demand the very best in luxury living. More than a home, it's a masterpiece of luxury living in the coveted Chaine Du Lac.
Listing is courtesy of: ELEVATE REAL ESTATE BROKERS (954-772-3870)
Listing Agent: Mohamed Inshan (321-438-5211)
14422 DESERT HAVEN ST #4206, WINDERMERE, FL 34786
$385,00053 Days on yellowkey MLS ID: S5148708
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 2013Monthly Fee: $541 Tax: $4,948 (2025)Community: Oasis Cove Ii/Lakeside VillageTownhouse
Taxes:$4,948
Remarks: Beautiful townhome located in a quiet and well-maintained community. This property features a functional layout with spacious, light-filled interiors. It offers 3 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 home features a garage and additional parking spaces. 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. An excellent opportunity for homeowners or investors!
Listing is courtesy of: MD3 HOMES LLC (407-557-8810)
Listing Agent: Monica Duran (407-702-5796)
8360 VIVARO ISLE WAY, WINDERMERE, FL 34786
$690,00025 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
Taxes:$9,812
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.
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