Location: Windermere , 34786
Do Not Show Listings
6152 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$1,130,00014 Days on yellowkey MLS ID: O6396835
Bed: 8 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4830 Built: 2012Monthly Fee: $133 Tax: $14,684 (2025)Community: Windermere Lndgs Fd-1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,684
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: More pictures coming soon. Beautiful and spacious 8-bedroom, 5-bathroom corner home offering 4,830 sqft of living space. This well-designed property features a generous layout with plenty of room for comfortable living and entertaining. The fenced backyard provides a great outdoor space, perfect for relaxing or enjoying time outside. Located on a desirable corner lot, offering added space and privacy.
Listing is courtesy of: VESTI LLC (407-749-5489)
Listing Agent: Vitor Silva (407-506-3712)
1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,380,00023 Days on yellowkey MLS ID: S5146178
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5108 Built: 2019Monthly Fee: $250 Tax: $1,982 (2025)Community: Estancia/WindermereSingle Family
Taxes:$1,982
Elementary School: Windermere Elem
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. This home is being offered fully furnished, providing a truly turnkey, move in ready experience. Built in 2019 on an oversized homesite, this beautifully appointed residence showcases modern architecture, generous living areas filled with natural light, and high end finishes throughout. The open concept layout is ideal for both everyday living and entertaining, with a gourmet style kitchen, elegant dining spaces, and seamless flow to the outdoor living area. Enjoy Windermere’s signature lifestyle just minutes from top rated schools, charming downtown Windermere, and world class Orlando attractions, including Walt Disney World and Universal Studios. Estancia is a boutique community of luxury homes featuring a private, serene atmosphere with conservation surroundings, while still offering quick access to major highways, shopping, dining, parks, and the Butler Chain of Lakes. This is an outstanding opportunity to own a stylish, fully furnished, move in ready home in one of Windermere’s most desirable neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Catalina Gomez (407-289-9029)
5145 LATROBE DR, WINDERMERE, FL 34786
$3,449,00066 Days on yellowkey MLS ID: O6382287
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4512 Built: 1991Monthly Fee: $1,224 Tax: $27,776 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$27,776
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
8350 BOWDEN WAY, WINDERMERE, FL 34786
$1,199,00019 Days on yellowkey MLS ID: O6395966
0 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3368 Built: 2001Monthly Fee: $298 Tax: $8,638 (2025)Community: Keenes PointeSpa: NoSingle Family
Taxes:$8,638
Remarks: Under contract-accepting backup offers. Gated/24-hour attended Keene's Pointe. Home of The Golden Bear Club, a private membership club offering golf, tennis, fitness, dining and swimming. This thoughtfully designed home offers both space and functionality for modern living. Upon entry, you’re welcomed by a spacious formal dining room, formal living room, and a private office featuring classic French doors—perfect for working from home. Wood-look tile flooring flows seamlessly throughout the entire first floor, adding warmth and durability.The private primary suite is a true retreat, complete with a large walk-in closet featuring custom shelving and an en suite bathroom. The updated kitchen boasts white shaker cabinets, stainless appliances, ample storage, and a cozy breakfast nook that opens to the inviting family room—ideal for everyday living and entertaining.The first floor also includes two additional bedrooms, a fully renovated bathroom, and bonus space for work or play, offering flexibility for family or guests. Upstairs, you’ll find a spacious bonus room that can easily serve as a fourth bedroom along with a full bathroom—perfect for a guest suite or multi-purpose space.The back yard provides plenty of space for a future pool or entertaining area. There is also a garage with 2 spaces for cars and a tandem third space for golf cart or storage.Tankless gas water heater, water softner system, NEW ROOF in 2022, updated HVAC units (2026 and 2021), new paver driveway in 2026, designer touches throughout, and much more! This home combines comfort, style, and versatility—ready for you to move in and make it your own.
14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786
$360,00016 Days on yellowkey MLS ID: O6396784
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 2013Monthly Fee: $541 Tax: $3,885 (2025)Community: Oasis Cove Ii/Lakeside Village #XiSpa: NoCondo
Taxes:$3,885
Remarks: Don't miss 14368 Desert Haven St, recently enhanced with a partial flooring replacement, providing an updated surface throughout. The kitchen is equipped with stainless steel appliances for functional meal preparation. This residence includes a primary bedroom with a spacious walk-in closet, and its connecting bathroom provides double sinks and a separate tub and shower, contributing to its practical design. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1849 WATERMERE LN, WINDERMERE, FL 34786
$1,325,00039 Days on yellowkey MLS ID: O6389840
REDUCED by $70,000 (5.0%) on 04/03/2026
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
Elementary School: Lake Whitney Elem
High School: West Orange High
Tax Year: 2024
Middle School: SunRidge Middle
Remarks: Nestled at the heart of Windermere Grande, a 28-home gated community situated on a north-facing 3/4-acre lot, stands an executive 4000 sq ft home with 4 to 5-bedrooms. There is a three-car side-entry garage. The house features a flat tile roof, and an impressive 74 Tesla solar panels. In-law au pair suite with an en-suite bathroom with walk in shower. Under a cathedral ceiling is an appliance -ready kitchenette and great room with shutter window treatment and its own sliding glass door to the lanai. This in-law suite has its own entrance with a paver sidewalk leading to the driveway. Soaring 14-foot ceilings adorned with crown molding create an awe-inspiring atmosphere. Modern crystal chandeliers illuminate the foyer and dining room, while walls of sliding glass doors seamlessly connect the living room, family room, Florida room, and master bedroom, offering breathtaking views of a 3-acre community green space. This green space features a playground, a 1-Mile coquina walking path, and a retention pond with a tall spout-lit fountain. The five sets of sliding glass doors open to a spacious 1000 ft² covered lanai that transitions into a 1500 ft² open area under a screened cage that was re-screened in 2025. This open space is adorned with pavers and features a 30-foot-long pool with end-to-end blue, green, and purple iridescent tiles that shimmer in the water’s reflection. The pool includes an 8 x 8 sun shelf with a lighted bubbler for entertainment and accommodates an umbrella pole, positioned directly across from a bench seat with a waterfall feature from the top tier and three LED underwater changing color lights. Additionally, the pool is equipped with an underground pop-up water-jet self-cleaning system for effortless maintenance. The pool filter is new as of February 2026. Adjacent to the pool, on a pre-poured concrete slab, lies a six-seater heated above-ground Bahama spa with 75 therapeutic jets designed to relax and rejuvenate muscles. The expansive under-cover freshly painted lanai has been utilized for many celebrations. The house has a Bose speaker system installed in every major room. This gourmet U-shaped kitchen features 42-inch mocha upper cabinets, glass cabinet doors, Santa Cecilia granite countertops, and an island with onyx granite and gold accents. It includes a five-burner 36-inch GE Profile cooktop and a microwave/convection oven combination. The laundry room is equipped with 42-inch upper cabinets for ample indoor storage, complemented by a 48-inch granite countertop. The oversize master bedroom has a sliding glass door with access to the lanai. There is a tray ceiling with fan and recessed lights over the bed headboard. The master bathroom has a jetted tub/Jacuzzi, dual sink stations, separate shower stall, and water closet. A powerful Central VAC system with two outlets. Each outlet is equipped with a 60-foot hose. The 5-zone air conditioning damper system ensures individual climate control for each room. In 2018, the system was upgraded with a 5-ton and 3-ton new air conditioning units. Tankless water heater. This house offers the opportunity for personalized customization and renovation, transforming it into a cherished asset within the community.
Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)
Listing Agent: Susana Stutsman (321-278-0334)
8259 MARITIME FLAG ST #4, WINDERMERE, FL 34786
$320,000272 Days on yellowkey MLS ID: O6329585
1 Days Off yellowkey (back on 3/24/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1460 Built: 2011Monthly Fee: $459 Tax: $4,052 (2024)Community: Lakeside VillasCondo
Taxes:$4,052
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the best of Windermere living! This freshly updated two-story townhome offers resort-style amenities and unbeatable convenience, all just 10 minutes from Disney! Step inside to discover fresh paint throughout, brand new carpet, and an open-concept first floor with a kitchen/living room combo and a half bath. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a laundry closet with washer and dryer included. Located in the resort-style community of Lakeside Villas, enjoy access to a beautiful pool, well-equipped fitness center, playgrounds, sand volleyball and tennis courts, clubhouse, dog park, and more just steps from your front door. Walk across the street to Lakeside Village’s Publix grocery store and local restaurants, or unwind at the nearby Tibet-Butler Preserve, home to 3.6 miles of peaceful walking trails. Plus, you'll enjoy quick access to Orlando’s top amusement parks, Evermore Resort and downtown Orlando, making this home the perfect full-time residence or investment opportunity. Call today for your private showing!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lindsey Hudson (865-712-8452)
5151 LATROBE DR, WINDERMERE, FL 34786
$4,100,00033 Days on yellowkey MLS ID: O6392380
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5301 Built: 2000Monthly Fee: $1,224 Tax: $23,020 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$23,020
Remarks: Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
6631 CRESTMONT GLEN LN, WINDERMERE, FL 34786
$834,000287 Days on yellowkey MLS ID: O6323076
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3068 Built: 2002Monthly Fee: $170 Tax: $9,573 (2024)Community: GlenmuirSpa: NoSingle Family
Taxes:$9,573
Remarks: Welcome to 6631 Crestmont Glen Lane, a beautifully maintained executive home in the gated community of Glenmuir. Set on a large and spacious, landscaped lot, this 4-bedroom, 3.5-bath residence offers an ideal blend of space, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open-concept layout designed for both entertaining and relaxed living. The gourmet kitchen features granite countertops, ample cabinetry, and a breakfast nook that flows seamlessly into the inviting family room. Enjoy year-round Florida living in your private screened lanai—perfect for quiet mornings or hosting guests. The primary suite offers a true retreat with a spa-like bath, walk-in closets, and direct access to the outdoor living space. Residents of Glenmuir enjoy a peaceful, tree-lined setting with a private park, playground, and walking paths—just minutes from top-rated schools, golf, dining, shopping, and world-renowned attractions including Walt Disney World.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
6117 LOUISE COVE DR, WINDERMERE, FL 34786
$5,250,000103 Days on yellowkey MLS ID: O6372197
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5752 Built: 2002Monthly Fee: $1,224 Tax: $50,728 (2025)Community: Isleworth WestSingle Family
Taxes:$50,728
Remarks: Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story estate represents the finest in lakefront living. Offering four bedrooms, four-and-a-half baths, and more than 5,700 square feet of living space, the residence has been fully reimagined with sophisticated, modern finishes throughout. Recent enhancements include a new roof, windows, and doors; an all-new boat dock including a new roof; a new summer kitchen; exquisite white marble flooring, a dramatic glass-and-iron double-door entry, sleek modern air vents, and a host of elevated appointments that create a seamless blend of style and comfort. Grand living spaces—including the living room, kitchen, and family room—all feature soaring ceilings and an abundance of natural light, providing an ideal backdrop for both elegant entertaining and everyday living. The first-floor primary retreat is a true sanctuary, featuring a spacious bedroom and private sitting room divided by a stunning double-sided fireplace. A secondary primary suite, also located on the first floor, offers exceptional privacy and flexibility for guests or multigenerational living. Outdoors, the estate embraces its idyllic lakefront setting with a resort-style pool, summer kitchen, and private boat dock offering direct access to Lake Louise—perfect for boating, sunset cruises, and lakeside leisure. This is a rare opportunity to experience lakefront living at its finest in one of the community’s most coveted settings.
Listing Agent: Sarah Longwell (407-920-8451)
4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,200,000272 Days on yellowkey MLS ID: O6330108
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3745 Built: 2006Monthly Fee: $1,146 Tax: $33,607 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,607
Remarks: Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.
Listing Agent: Michelle Corbin (407-491-2690)
9648 MCCORMICK PL, WINDERMERE, FL 34786
$3,800,000208 Days on yellowkey MLS ID: O6346918
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4751 Built: 1988Monthly Fee: $1,224 Tax: $33,873 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,873
Remarks: Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level. Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. A striking glass wall encases the pool area, maximizing panoramic views of both the golf course and the lake. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brand-new heater, or unwind in the extended backyard, which offers an additional 15 feet added to one side of the property. Every detail of this outdoor transformation has been designed to enhance both beauty and livability, making this property the perfect retreat for year-round enjoyment.
9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786
$3,400,000249 Days on yellowkey MLS ID: O6336655
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4877 Built: 1986Monthly Fee: $1,224 Tax: $19,867 (2024)Community: IsleworthSingle Family
Taxes:$19,867
Remarks: Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.
4226 DOWNEAST LN, WINDERMERE, FL 34786
$10,500,000180 Days on yellowkey MLS ID: O6355233
REDUCED by $1,300,000 (11.0%) on 04/08/2026
Bed: 5 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 5316 Built: 1980 Tax: $10,926 (2024)Community: NaSingle Family
Taxes:$10,926
Remarks: DRAMATIC PRICE IMPROVEMENT. Exceptional DEVELOPMENT OPPORTUNITY, currently R-CE zoning should allow for 3 Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, part of the coveted BUTLER CHAIN of Lakes. This is a rare chance to create a premier LAKEFRONT ESTATE or subdivide to create three ideally sized lots with water frontage. At present, the property includes an older 5,000 sq ft home (5 bedrooms, 3.1 baths) and an oversized four car garage, which can serve as a temporary residence or teardown to make way for your vision. Why this property stands out, Unmatched location: Situated on the east side of Windermere, with convenient access from Conroy Windermere Road and Apopka Vineland. Windermere prestige, Offers the cachet of a WINDERMERE ADDRESS and proximity to luxury amenities. Prime access: Minutes to Isleworth Country Club, Bay Hill, and downtown Windermere. Development upside: Ready canvas for luxury estates in one of Central Florida’s most desirable waterfront corridors. Whether you’re a developer, custom builder, or investor, this is your opportunity explore and deliver truly exceptional homes in a highly sought-after market. Property is also listed as vacant land on MLS #O6367852.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thad Czapka (407-257-4253)
9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786
$750,00053 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
Taxes:$11,111
Elementary School: Thornebrooke Elem
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)
9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786
$6,395,000226 Days on yellowkey MLS ID: O6341883
Bed: 5 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 11861 Built: 2017 Tax: $50,738 (2024)Community: Gotha TownSpa: YesSingle Family
Taxes:$50,738
Remarks: Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking. From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired façade that opens to interiors of soaring scale and meticulous marble craftsmanship. Light cascades through walls of glass, illuminating a series of living spaces designed for entertaining at the highest level. Every detail speaks of refinement: bespoke millwork, hand-selected stone, intricate ceiling treatments, and custom finishes curated with an uncompromising standard. The expansive chef’s kitchen blends culinary excellence with artful design, while the bar, wine room, and multiple gathering spaces ensure that every occasion, from intimate family dinners to grand celebrations, is unforgettable. The state-of-the-art theater begs you to slow down and enjoy the latest movie release. Conveniently adjacent to the theater is a home gym and lakefront cardio room that rivals most commercial gyms! Once the day winds down, the private retreats within the home offers warmth and convenience so you never have to leave. The first floor conveniently offers a full guest suite, and the second floor boasts an additional four bedrooms all with en-suite bathrooms. Additionally located on the second floor is a kid’s study, playroom, guest apartment and handsome cigar room. Outdoors, the estate transforms into a private resort. A sweeping terrace frames an oversized resort style pool and spa, surrounded by gardens, fountains, and tranquil seating venues. Enjoy the piece of your surroundings, from al fresco dining beneath the pergola to evenings spent overlooking Lake Olivia, one of Central Florida’s most sought-after ski lakes. Beyond the main residence, a detached guest retreat and showcase garages offering space for up to 14 cars will satisfy the most serious car collector. Set on a significant 4.43 acre parcel of land, the estate is both sanctuary and statement, offering numerous spaces to live, create, and entertain. Enjoy living in the heart of it all without compromising your privacy. Plus, with easy access to major highways, theme parks, downtown Windermere, and less than 10 minutes from Whole Foods, Restaurant Row, and championship golf courses, you’re never far from the very best of what Central Florida has to offer. Perfectly positioned with easy access to Windermere Prep, Lake Highland, and Montverde Academy...this location does not get any better! Rarely does a property of this magnitude become available. This is not simply a home — it is an heirloom, a landmark, and an invitation to experience luxury on a level few will ever know. Call today for an exclusive private showing.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
17521 BLACK RAIL ST, WINDERMERE, FL 34786
$1,495,000111 Days on yellowkey MLS ID: O6370115
0 Days Off yellowkey (back on 4/7/2026)
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5316 Built: 2015Monthly Fee: $167 Tax: $16,243 (2025)Community: EnclaveSpa: YesSingle Family
Taxes:$16,243
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. *** Now priced under $1.5M offering strong value at approximately $281/SF compared to similar Windermere homes*** PRIME opportunity for a LIKE NEW spacious MOVE-IN READY Windermere pool home just 1.5 miles from Windermere Preparatory School, and conveniently located near other top-rated public and private schools. Offering over 5,300 sq ft of thoughtfully designed living space, this 6 bedroom/4.5 bath home combines privacy, flexibility, and modern comfort, ideal for today’s lifestyles, including multi-generational living. The main level features wood-floored living areas and an open, airy layout anchored by a chef’s kitchen with oversized center island, stone countertops, stainless appliances, walk-in pantry, and pass-through butler’s pantry, perfect for everyday living and entertaining. Expansive glass doors open to the newly renovated screened, heated pool and spa (2024) with covered patio and summer kitchen, creating seamless indoor-outdoor living. A downstairs ensuite bedroom provides excellent flexibility for guests, extended family, or home office needs. Upstairs, the spacious primary suite is joined by a large bonus loft with wet bar and built-in desk area, and four additional bedrooms, two of which share a Jack-and-Jill bathroom. All bedrooms feature walk-in closets with built-in shelving, offering exceptional storage throughout. A well-appointed laundry room includes a sink and 2023 LG washer and dryer. Notable upgrades include variable-speed HVAC systems (2021 & 2023), fresh interior and exterior paint (2021), smart-controlled motorized window shades on the main level, a fully renovated pool and patio (2024) with 2025 Hayward pump, heater, lighting, and rescreening, 2023 vinyl fencing, and two finished garages (1-car + 2-car) with durable interlocking rubber flooring. Enjoy added privacy with neighborhood green space directly next door, all in a prime Windermere location near top schools, the Butler Chain of Lakes, Keene's Pointe, Downtown Windermere and Winter Garden, Winter Garden Village, major roadways, Disney and area attractions. A pre-listing home inspection report is available after the first showing, offering added transparency and peace of mind. Home is IMMACULATE. Schedule your private showing today.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rebecca Puig (407-970-1149)
9259 TIBET POINTE CIR, WINDERMERE, FL 34786
$6,499,000330 Days on yellowkey MLS ID: O6312645
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6257 Built: 2007Monthly Fee: $298 Tax: $35,727 (2024)Community: Keenes PointeSpa: NoSingle Family
Taxes:$35,727
Remarks: Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet. This meticulously updated estate showcases high-end finishes throughout, with no detail overlooked. Enjoy a brand-new gourmet kitchen equipped with top-of-the-line appliances, custom cabinetry, and designer fixtures. The open-concept layout flows seamlessly into spacious living and dining areas, perfect for entertaining or relaxing while taking in panoramic lake views. The home’s thoughtfully reimagined floor plan features luxurious bedrooms, spa-inspired bathrooms, and refined touches such as wide-plank hardwood flooring, quartz countertops, and designer lighting. Expansive windows and glass doors fill the home with natural light and lead to a private outdoor retreat with fireplace and summer kitchen - ideal for enjoying Central Florida sunrises over the water. Additional improvements include hardwood and porcelain flooring, tankless gas water heater, updated AC units (2), water softener, new pool heater, and much more. A 4-car garage completes this amazing property. Located in the heart of Windermere, Keene’s Pointe offers world-class amenities including the renowned Golden Bear Club with golf, tennis, fitness, swimming and dining. Don’t miss this rare opportunity to own a move-in ready, lakefront masterpiece on the Butler Chain of Lakes. Schedule your private tour today and experience luxury lakefront living at its finest.
12405 CRUXBURY DR, WINDERMERE, FL 34786
$415,00022 Days on yellowkey MLS ID: O6394966
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $5,463 (2025)Community: Lakes/Windermere-Lk Reams TwhmSpa: NoTownhouse
Taxes:$5,463
Elementary School: Bay Lake Elementary
Remarks: Discover this spotless corner-unit townhome in Windermere Lakes, offering some privacy with a serene conservation area behind the home and no neighbors on one side. The open-concept layout seamlessly connects the kitchen to the living area, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel appliances, 42” cabinets, added custom cabinetry, and tile flooring throughout the main areas. An extra half bath downstairs adds convenience for guests. Upstairs, the master bedroom and shower are sure to impress. Enjoy beautiful tree-lined streets, mature landscaping, and a detached two-car garage with a charming, paved courtyard perfect for grilling and relaxing outdoors. The community offers a pool and clubhouse, ideal for soaking up the Florida sunshine. The low HOA includes exterior maintenance, roof maintenance, landscaping, and access to community amenities. Located just minutes from Disney World and all the Disney parks, with shopping, dining, major highways, and top attractions close by, as well as minutes from the Tibet Butler Preserve, where you can enjoy the natural beauty of Florida. Make your appointment today to view this beautiful home.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Steve Lang (407-435-0290)
14371 CREST PALM AVE, WINDERMERE, FL 34786
$1,114,98916 Days on yellowkey MLS ID: G5110664
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 2025Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Remarks: One or more photo(s) has been virtually staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, large center island, upgraded cabinetry, quartz countertops, walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living.2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden,—ideal for entertaining or relaxing outdoors.Move-In Ready: No waiting required.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
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