Location: Windermere
Do Not Show Listings
13013 OVERSTREET RD, WINDERMERE, FL 34786
$649,994110 Days on yellowkey MLS ID: O6380917
REDUCED by $15,000 (2.3%) on 05/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 2009Monthly Fee: $82 Tax: $3,146 (2024)Community: Lakes/WindermereSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,146
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for. Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with sleek cabinetry, stainless steel appliances, island, and plenty of storage — perfect for everyday cooking or entertaining friends and family. The primary suite includes a luxurious bathroom with his-and-her sinks and an upgraded California closet with premium built-ins for maximum organization. Enjoy Florida weather year-round in the screened-in patio with a retractable electric screen, extending your living space and providing the perfect spot for morning coffee or evening relaxation. The large, fully fenced backyard features extended brick pavers, offering plenty of room for gatherings, grilling, pets, or future customization. Additional features include a front balcony, a 2-car garage, and an oversized driveway with great curb appeal. This home sits in a prime Windermere location surrounded by some of the best amenities in Central Florida. Just minutes away you’ll find top-rated Windermere schools, scenic lakes, nature trails, Bay Hill, The Butler Chain of Lakes, playgrounds, and community parks. Nearby you’ll enjoy endless shopping, popular restaurants, cafés, breweries, local markets, and everyday conveniences. You’re also close to the Winter Garden Village, Downtown Windermere, major highways, theme parks, and world-class entertainment. The community itself offers resort-style amenities including a sparkling community pool and clubhouse — perfect for relaxing weekends and social gatherings. If you’re looking for a move-in-ready home with modern finishes, incredible outdoor space, and a location that simply can’t be beat, this is the one. Homes like this in Windermere don’t last long — schedule your private showing today! *** A/C and Water Heater replaced in 2024. Roof replaced in 2025. Exterior of home repainted in 2022 ***
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Omar Andreasen (407-883-2989)
11617 CAMDEN PARK DR, WINDERMERE, FL 34786
$1,397,00039 Days on yellowkey MLS ID: O6405409
REDUCED by $53,000 (3.7%) on 06/11/2026
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3463 Built: 2005Monthly Fee: $283 Tax: $7,189 (2025)Community: Keenes PointeSingle Family
Taxes:$7,189
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent walls, adding warmth and architectural elegance. Offering a private tiled patio with electronic screen enclosure, perfect for enjoying Florida's year-round sunshine in comfort and privacy. For buyers seeking a move-in ready luxury home in Orlando's golf course communities, this property checks every box. Major capital improvements are already done: new roof (2023), AC and water heater 2-3 years old — giving buyers the confidence and peace of mind that comes with a truly turnkey luxury purchase. Residents enjoy exclusive access to the Golden Bear Club, a Jack Nicklaus Signature Golf Course, along with clubhouse, tennis, and Lake Tibet-Butler access. The community’s location delivers unmatched convenience with proximity to well-rated schools, along with The Grove, Westside Shoppes, Cornerstone at Summerport, and Downtown Windermere for daily essentials, local dining, and shopping adventures. Entertainment options abound with easy access to Disney, Universal, and the famed Restaurant Row in Dr. Phillips. A rare opportunity.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,149,00081 Days on yellowkey MLS ID: O6393659
REDUCED by $50,000 (4.2%) on 06/02/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2599 Built: 2001Monthly Fee: $283 Tax: $8,252 (2025)Community: Keenes PointeSingle Family
Taxes:$8,252
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: Reduced 50k in price! Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartzite countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026), Driveway replaced 06/2026. This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!
Listing is courtesy of: HAMLIN REALTY (321-299-4279)
Listing Agent: Sharon Brandt (407-310-3623)
7710 FAIRGROVE AVE, WINDERMERE, FL 34786
$390,00048 Days on yellowkey MLS ID: S5148820
1 Days Off yellowkey (back on 6/11/2026)
REDUCED by $6,000 (1.5%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $380 Tax: $3,844 (2025)Community: Lake Sawyer South Ph 03Townhouse
Taxes:$3,844
Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT!! Don’t miss this fantastic opportunity to own a spacious townhouse in the highly desirable Lake Sawyer South community of Windermere, Florida. Nestled among tree-lined streets, this 3-bedroom, 2.5-bath home with a 2-car garage offers comfort, style and tranquility. As you enter, a spacious living room welcomes you - perfect for entertaining. The kitchen boasts granite countertops, stainless steel appliances, and a walk-in pantry, with French doors leading to a large, paved courtyard that connects to the detached 2-car garage. A conveniently located laundry room completes the downstairs layout. Upstairs, the expansive primary suite features an en suite bath with dual vanity, while two additional bedrooms share a full hall bath with a shower/tub combo. Residents of this well-maintained community enjoy multiple parks, trails, playgrounds, tennis and basketball courts, and a refreshing swimming pool. The HOA covers lawn care, exterior painting, and the roof—adding convenience and peace of mind. Known for its top-rated schools and quality of life, Windermere offers proximity to Disney World, theme parks, major roadways, fine dining, and shopping. Start enjoying everything this exceptional home and community have to offer.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Mae Stigell (631-377-1205)
5538 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,195,000139 Days on yellowkey MLS ID: O6376859
REDUCED by $300,000 (8.6%) on 05/15/2026
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6000 Built: 1982Monthly Fee: $67 Tax: $25,546 (2025)Community: Kelso On Lake ButlerSpa: YesSingle Family
Taxes:$25,546
Remarks: Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated access to Kelso's private boat ramp on the prestigious Butler Chain of Lakes. This convergence of private waterfront with chain-of-lakes connectivity creates unparalleled boating and recreational opportunities found in few lakefront estates. The expansive grounds and recent outdoor enhancements create an entertainer's paradise that is second to none! A newly upgraded outdoor bar and grill area, resort-caliber pool and spa, and sweeping lawn frame breathtaking sunset views over the water. Boasting 6 bedrooms, 6 bathrooms, 3 car garage, and more than 6,000 square feet of living space, this custom estate offers privacy, scale, and unforgettable lakefront views from nearly every room. From the moment you arrive, the chic coastal architecture, circular drive, and sprawling presence command attention. Step inside to dramatic 25-foot ceilings in the living room with a two story stacked stone fireplace and walls of glass that dissolve the boundary between interior luxury and lakefront beauty. An adjacent sun-filled flex room provides tranquil views of Lake Davis, while the completely remodeled chef's kitchen, with its oversized island, custom cabinetry, high end appliances, adjacent indoor bar and generous family room, is designed for both intimate moments as well as large scale entertaining. The main level's thoughtfully designed primary suite offers serene seclusion with a private sitting area, spa-inspired bathroom, and expansive walk-in closet, complemented by a convenient main-floor office. Upstairs, five additional oversized bedrooms, a versatile loft, dedicated gym, and stunning rooftop deck provide space for every lifestyle need. Recent upgrades give you the ultimate peace of mind, including upgraded lighting throughout, a new roof with GAF Golden Pledge 20 year workmanship warranty, three newer A/C units, updated water heater, Hayward pool heater, new dock motor, new sprinkler system with a lake-fed pump, and a transferable Massey termite bond. Minutes from Disney's back gates, top-tier schools, and Windermere's celebrated shopping and dining, yet completely private and serene—this is lakefront living without sacrifice. Your Kelso compound awaits!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
9259 TIBET POINTE CIR, WINDERMERE, FL 34786
$6,499,000385 Days on yellowkey MLS ID: O6312645
2 Days Off yellowkey (back on 4/26/2026)
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: Under contract-accepting backup offers. 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.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$3,450,000140 Days on yellowkey MLS ID: O6377244
REDUCED by $25,000 (0.7%) on 05/07/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Monthly Fee: $103 Tax: $28,092 (2025)Community: LakesSpa: YesSingle Family
Taxes:$28,092
Elementary School: Thornebrooke Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
9237 SABAL PALM CIR, WINDERMERE, FL 34786
$749,99573 Days on yellowkey MLS ID: G5110005
REDUCED by $20,000 (2.6%) on 06/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2469 Built: 1985Monthly Fee: $32 Tax: $3,444 (2025)Community: Silver Woods Ph 01Single Family
Taxes:$3,444
Remarks: Nestled in the charming and highly desirable Silverwoods subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwoods is a sought-after neighborhood of just over 250 homes, known for its tree-lined streets, sidewalks, street lighting, and welcoming atmosphere. Residents enjoy access to tennis courts and the ease of walkable surroundings, all while being just minutes from shopping, dining, grocery stores, churches, and everyday conveniences. This inviting residence features three bedrooms and two bathrooms in a thoughtfully designed layout, enhanced by an impressive 650-square-foot addition that includes a spacious sunroom, bar area, and den—creating versatile living spaces ideal for both everyday comfort and entertaining. Originally built in 1985, the home has been extensively updated with a remodeled kitchen featuring new cabinetry, a standalone island, and updated appliances, all complemented by wood and tile flooring throughout. Additional upgrades include high-efficiency windows, a new 4-ton HVAC system with Nest thermostat, new ductwork and attic insulation, and a new 50-gallon water heater—offering both comfort and energy efficiency. Interior improvements such as new doors, refinished ceilings with LED recessed lighting, and a beautifully refinished stone fireplace add to the home’s modern appeal. The expansive Florida room provides a bright and relaxing retreat with year-round enjoyment of the backyard, while exterior enhancements include premium architectural shingles, a new septic field, a 7-zone irrigation system, and a water softener system. Fiber optic internet is also available, supporting today’s connected lifestyle. This is more than a home—it is an opportunity to experience elevated living in one of Windermere’s most desirable and conveniently located communities.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Chelsea Murphy (407-373-8101)
2428 BUTLER BAY DR N, WINDERMERE, FL 34786
$1,150,00018 Days on yellowkey MLS ID: O6410967
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3387 Built: 1990Monthly Fee: $199 Tax: $9,842 (2025)Community: Butler BaySingle Family
Taxes:$9,842
Remarks: This stunning updated 4 bedroom/4 bathroom executive pool home in exclusive Windermere Club has been meticulously maintained and is the perfect place to call home!!! Upon entering the gated community you will be impressed by the oversized lots and sprawling custom homes. When arriving to the residence and turning into the circular paver driveway you will enjoy the homes classic elevation with a tall center gable and a neutral exterior palette with classic French blue shutters. Upon stepping through the double entry doors you will immediately sense this home is special with a fabulous floorpan, open and spacious, perfect for entertaining. Soaring vaulted ceilings, wood moldings, wood flooring, French doors and neutral interior tones all contribute to the allure of a classic and timeless residence. The home offers a study with double doors located off the entry Foyer with custom built-in cabinetry/shelves. The oversized Dining Room overlooks the beautiful swimming pool and patio and is open to the kitchen. The Gourmet Kitchen with 42" cabinets, gorgeous granite counters tops, beautiful glass tile backsplash, a center island, stainless steel appliances is open to the large Breakfast Nook and spacious Family room featuring a gas fireplace with a custom wood mantel making it the perfect space for winding down after a long day or enjoying family gatherings and holidays. The home also benefits from tremendous natural light through its many windows. The oversized Primary Bedroom is fit for a King and Queen with French Doors overlooking the pool, a spa-like 5-piece Travertine bathroom featuring a shower, soaking tub, double vanities and two large walk-in closets with custom built-in shelving systems. The 3 additional bedrooms include 2 with ensuite bathrooms and a 3rd that is served by a hall bathroom. All of the bathrooms have been updated with high-end finishes. The 3 car side-entry garage with spacious car park area offers convenience and significant storage. The Pool area with covered space, an outdoor kitchen/grilling station and nature views is perfect for Florida entertaining! Schedule a showing today and see this amazing home before it's gone!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Randall Gill (407-756-0071)
6288 BLAKEFORD DR, WINDERMERE, FL 34786
$2,550,0006 Days on yellowkey MLS ID: S5151608
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5036 Built: 2003Monthly Fee: $298 Tax: $34,767 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$34,767
Remarks: Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offers five bedrooms, four full bathrooms, and three half bathrooms, combining exceptional golf-front living with breathtaking views of the golf course, pool, and surrounding landscape. A grand foyer welcomes guests with a soaring 22-foot ceiling, while oversized tile flooring extends throughout the first floor. Expansive windows fill the home with natural light while creating a seamless connection to the outdoor living spaces. The well-designed floor plan features a dedicated office with a coffered ceiling, spacious living and dining areas, and a beautifully appointed kitchen with beautiful cabinetry, granite countertops, a professional-grade gas range, center island, and abundant storage. Just off the kitchen and family room is a spectacular custom entertainment bar featuring extensive cabinetry, generous serving space, and four under-counter refrigerators, creating the ultimate setting for entertaining. The first-floor primary suite serves as a private retreat with direct access to the lanai and pool area. The updated spa-inspired bath features designer cabinetry, quartz countertops, a freestanding soaking tub, oversized walk-in shower, premium fixtures, and elegant floor-to-ceiling tilework. Completing the owner's retreat are two spacious walk-in closets, including a large walk-in closet directly off the bedroom and an additional oversized walk-in closet conveniently located off the bathroom, providing exceptional storage and organization. The secondary bedroom layout offers both comfort and privacy for family and guests. Two bedrooms feature en-suite bathrooms, while two additional bedrooms are connected by a Jack-and-Jill bathroom. The expansive second-floor bonus room serves as a versatile gathering space, ideal as a media room, game room, lounge, or secondary family room. A dramatic vaulted tongue-and-groove wood ceiling creates architectural interest and warmth, while large windows and French doors fill the space with natural light and provide direct access to the covered second-floor terrace overlooking the pool and golf course. A conveniently located half bath serves the bonus room and outdoor terrace, making the space perfectly suited for entertaining family and guests. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers an abundance of covered outdoor living space. The resort-style outdoor area features a covered lanai, summer kitchen, pool, spa, dedicated pool bath, and multiple gathering spaces thoughtfully positioned to capture views of the Golden Bear Club's signature finishing hole. An expansive covered second-floor terrace with a tongue-and-groove wood ceiling is accessible from multiple bedrooms as well as the bonus room, providing stunning views of the pool and golf course. A spiral staircase leads to a private third-story observation deck featuring a wet bar and panoramic views across the fairways and surrounding treetops, creating the perfect setting for entertaining, enjoying evening sunsets, or watching play unfold along the Golden Bear Club's signature finishing hole.
Listing is courtesy of: NECTAR REAL ESTATE (407-414-4005)
Listing Agent: Keith Renner (407-361-6371)
4071 ISABELLA CIR, WINDERMERE, FL 34786
$3,290,0006 Days on yellowkey MLS ID: O6413509
Bed: 5 Bath: 7.5 Gar: 4 Liv Area Sq Ft: 7058 Built: 2017Monthly Fee: $480 Tax: $35,637 (2025)Community: CasabellaSpa: YesSingle Family
Taxes:$35,637
Remarks: Embraced on nearly an acre within the gated community of Casabella, The Renaissance at Casabella is an extraordinary Toll Brothers estate offering over 7,000 square feet of refined living space, resort-inspired outdoor amenities, and timeless Mediterranean elegance. A sweeping circular paver drive and stately architectural details create a grand first impression, while inside, soaring ceilings, a dramatic curved staircase, expansive windows, and marble-look porcelain floors set the tone for elevated living. The chef’s kitchen is beautifully appointed with Jenn-Air professional appliances, rich granite countertops, custom cabinetry, and a generous center island, all flowing seamlessly into the impressive two-story family room and sunlit breakfast area. The first-floor owner’s retreat offers a private sitting area, dual walk-in closets, exercise or dressing room space, and a luxurious spa bath. A two-story study with loft library, media room, loft, learning center, guest suite, and spacious secondary bedrooms provide exceptional flexibility for modern living. Outdoor living is elevated with a spectacular screened lanai, decorative infinity-edge spa, custom pool with in-water bar seating, summer kitchen, sunken fire pit lounge, pergola sun deck, fruit trees, and expansive gathering spaces designed for year-round entertaining. Additional upgrades include an oversized 4-car garage, natural gas, tankless water heater, whole-house water treatment, tempered glass windows, and elegant trim and moldings throughout. Ideally located in the heart of Windermere near top-rated schools, golf, dining, and world-class attractions, this exceptional estate offers luxury living at its finest.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Dan Natoli (407-595-8395)
8409 VIVARO ISLE WAY, WINDERMERE, FL 34786
$1,187,00036 Days on yellowkey MLS ID: G5112154
0 Days Off yellowkey (back on 6/10/2026)
REDUCED by $48,000 (3.9%) on 06/03/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4176 Built: 2019Monthly Fee: $299 Tax: $9,493 (2025)Community: Windermere IsleSpa: YesSingle Family
Taxes:$9,493
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Under contract-accepting backup offers. Welcome to 8409 Vivaro Isle Way, an exceptional move-in ready luxury residence located in the highly desirable community of Windermere Isle in Windermere. This impressive home offers 4,176 square feet of living space featuring 6 bedrooms, 4.5 bathrooms, and a dedicated office space. Perfectly positioned approximately 2.5 miles from Magic Kingdom Park at Walt Disney World Resort, this elegant home offers the ideal combination of luxury, comfort, and the sought-after Central Florida lifestyle. Surrounded by conservation areas, residents enjoy privacy, tranquility, and a connection to nature while remaining close to premier golf courses, Hamlin Town Center, Horizon West, upscale dining, shopping, and major roadways. Recently painted inside and out, this energy-efficient smart home was thoughtfully designed with both functionality and sophistication in mind. The expansive open-concept floor plan features elegant 9'4" ceilings on the first floor and 9'0" ceilings on the second level, creating a spacious and airy feel throughout the home. The gourmet kitchen showcases upgraded cabinetry, stainless steel appliances, a walk-in pantry, and generous preparation and gathering space ideal for entertaining. Additional highlights include spacious living and dining areas, beautifully designed finishes throughout, and a private office space ideal for remote work or study. The functional layout includes two bedrooms conveniently located on the first floor, offering flexibility for guests, multigenerational living, or private workspace options. Upstairs, enjoy an ample loft filled with natural daylight, perfect for family gatherings, media space, game room, or flexible living area. The second floor also features a conveniently located laundry room and an additional junior suite with its own private full bathroom. All appliances are included, making this home truly move-in ready. The spacious owner’s suite offers a true private retreat featuring an in-suite bathroom with a generous walk-in closet, relaxing garden tub, and separate shower designed for comfort and relaxation. Step outside into your own private outdoor oasis featuring an extended covered and screened pool, spa, lanai, and travertine deck area designed for entertaining and year-round Florida living. The saltwater, gas-heated pool and spa combined with the spacious outdoor gathering areas create the perfect setting to relax and entertain. The fully fenced backyard and screened enclosure further enhance the outdoor experience. With no rear neighbors and surrounded by conservation, this home offers exceptional privacy and peaceful views. Enjoy breathtaking nightly Disney fireworks and connect with nature from your own backyard. Additional exterior highlights include future outdoor kitchen utility connections already available and newly finished epoxy garage floors that enhance both appearance and functionality. Residents of Windermere Isle enjoy resort-style amenities including a community pool, cabana, playground/tot lot, scenic conservation surroundings, and beautifully maintained streetscapes while remaining close to Disney, golf, shopping, dining, and everyday conveniences. Located within a highly rated school zone, this home presents a rare opportunity to own an exceptional property in one of Windermere’s most desirable communities. Experience the lifestyle, location, elegance, privacy, and convenience that make 8409 Vivaro Isle Way truly exceptional.
Listing is courtesy of: WATSON REALTY CORP., REALTORS (352-243-7374)
Listing Agent: Katherine Figueroa Santiago (407-417-4227)
7612 FAIRGROVE AVE, WINDERMERE, FL 34786
$440,00041 Days on yellowkey MLS ID: S5149402
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1742 Built: 2016Monthly Fee: $347 Tax: $6,515 (2025)Community: Windermere Sound Ph 2Townhouse
Taxes:$6,515
Remarks: Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool, tennis and basketball courts, playgrounds, and scenic ponds, all with lawn care included. Ideally situated just minutes from Disney World, premium shopping, fine dining, and top-rated schools such as Windermere High School, this home perfectly blends comfort, convenience, and luxury living in one of Orlando's most sought-after areas.
Listing is courtesy of: FLORIDA FANTASY REAL ESTATE INC (407-397-9039)
Listing Agent: Maribel Minarro (407-908-3522)
8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$1,150,0008 Days on yellowkey MLS ID: O6413196
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3971 Built: 2016Monthly Fee: $8 Tax: $13,647 (2025)Community: Windermere Trls Ph 3BSpa: YesSingle Family
Taxes:$13,647
Remarks: FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll immediately notice the attention to detail. Inside, exquisite marble floors, crown moulding, upgraded lighting, and a dramatic staircase create a timeless first impression. The recently renovated kitchen is truly the heart of the home. Crisp white cabinetry adorned with traditional millwork, glass display cabinets, brushed gold pendant lighting, and an oversized island blend beauty and function effortlessly. Quartzite, granite, and other fine stone finishes have been thoughtfully incorporated throughout, creating a refined yet comfortable atmosphere. Designed for both entertaining and everyday living, the home features a formal dining room, spacious eat-in kitchen, and multiple gathering spaces overlooking the pool and Lake Reams beyond. Two sets of French doors open to the covered lanai, seamlessly connecting indoor and outdoor living. With five bedrooms, four bathrooms, and a dedicated office on the main level, there is flexibility for growing families, remote work, guests, or multigenerational living. Wake up to water views and enjoy evening sunsets from your private backyard retreat featuring a sparkling pool and covered lanai. The upstairs loft also offers the same beautiful view! Residents of Windermere Trails enjoy miles of walking trails, a community pool, playground, picnic pavilion, and some of the area's most desirable schools. Located just minutes from shopping, dining, and approximately 10 minutes from Disney, this location offers convenience without sacrificing the charm and character that make Windermere so special.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$322,000152 Days on yellowkey MLS ID: TB8465266
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $3,000 (0.9%) on 05/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Taxes:$4,422
Remarks: Under contract-accepting backup offers. Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing Agent: Erin Aaron (727-422-1688)
9317 GLADYS GARDEN CT, WINDERMERE, FL 34786
$7,999,00017 Days on yellowkey MLS ID: O6410843
Bed: 6 Bath: 7.5 Gar: 4 Liv Area Sq Ft: 8038 Built: 2027Monthly Fee: $1,099 Tax: $9,424 (2025)Community: Gardens/IsleworthSpa: YesSingle Family
Taxes:$9,424
Middle School: Chain of Lakes Middle
Remarks: Under Construction. Currently under construction in the renowned golf course community of Isleworth, this exceptional residence by Goehring & Morgan, thoughtfully designed by Ashley Martin, offers 8,038 square feet of refined luxury living. Featuring 6 bedrooms, 6 full bathrooms, 3 half bathrooms, and a 4-car garage, this custom home showcases timeless architecture paired with elevated finishes throughout. The exterior is highlighted by a durable concrete tile roof and resort-inspired outdoor living featuring a stunning pool with sundeck, deck jets, and a fully equipped summer kitchen with a Wolf grill, designed for year round entertaining. Inside, the expansive great room is framed by solid oak wall paneling and anchored by a striking gas Isokern fireplace.The chef’s kitchen is designed for both function and style with dual islands, Sub-Zero appliances, and an adjoining back kitchen for seamless preparation and hosting. Additional gathering spaces include an elegant sitting room with its own fireplace and a dedicated wine room. Thoughtfully designed for everyday convenience, the first-floor laundry room features dual washers, dual dryers, and a dedicated folding station. Sophistication and functionality come together seamlessly throughout this extraordinary Isleworth residence.
Listing Agent: Robert Welker, Iii (321-287-0327)
9119 BALMORAL MEWS SQ, WINDERMERE, FL 34786
$1,450,00047 Days on yellowkey MLS ID: S5146725
REDUCED by $49,000 (3.3%) on 05/27/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4052 Built: 1998Monthly Fee: $267 Tax: $18,350 (2025)Community: BalmoralSingle Family
Taxes:$18,350
Remarks: Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral home to just 32 custom residences—where privacy, elegance, and the coveted Windermere lifestyle come together seamlessly. Situated on over half an acre, this beautifully landscaped property offers a serene retreat with mature greenery and a fully fenced yard designed for both relaxation and entertaining. Step through striking 8-foot wrought iron and glass entry doors into a light-filled interior featuring soaring 12-foot ceilings and thoughtfully designed living spaces. This spacious 4-bedroom, 4-bath home with a dedicated office and large bonus room offers a flexible layout ideal for both everyday living and hosting guests. Formal living and dining areas flow effortlessly into the kitchen and family room, creating a natural gathering space filled with warmth and natural light. The first-floor primary suite serves as a private retreat, complete with direct access to the pool and lanai, along with dual custom closets that provide ample storage. Upstairs, you’ll find generously sized secondary bedrooms, additional bathrooms, and a versatile bonus room perfect for a media room, home gym, or game space. Beyond the home, Windermere offers a lifestyle that’s hard to match. Enjoy charming tree-lined streets, local dining, boutique shopping, and beloved community traditions like farmers markets and seasonal events. Just minutes away, the Butler Chain of Lakes invites you to experience boating, fishing, and waterfront living at its finest, while nearby top-rated schools add to the area’s appeal. Recent updates include new HVAC systems installed in 2021, offering added comfort and peace of mind. Experience refined living in one of Central Florida’s most sought-after communities—this is more than a home, it’s a lifestyle.
Listing is courtesy of: LA ROSA REALTY BEACHES LLC (954-526-7318)
Listing Agent: Seana Abdelmajid (727-278-7862)
7231 SANGALLA DR, WINDERMERE, FL 34786
$1,350,00090 Days on yellowkey MLS ID: O6390817
REDUCED by $48,000 (3.4%) on 06/10/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3835 Built: 2011Monthly Fee: $247 Tax: $11,139 (2025)Community: Casa Del Lago-ReplatSingle Family
Taxes:$11,139
Remarks: Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David Weekley Homes, this nearly 4,000-square-foot residence is thoughtfully designed for both everyday living and entertaining. The home features four bedrooms on the first floor, including two bedrooms positioned on the same side of the home that are connected by a shared playroom or bonus space, while each bedroom maintains its own private en suite bathroom. A formal dining room, dedicated private office, and spacious family room provide multiple areas for gathering and daily living. A convenient pool bath is located just off the main living area with direct access to the pool patio. Upstairs, a large loft-style game room offers flexible living space along with a private fifth bedroom featuring its own full bathroom, making it ideal for guests or multigenerational living. Outdoor living is equally impressive with a luxurious paver patio, screened-in pool, and low-maintenance turf backyard, creating a private retreat perfect for year-round Florida living. The home is also fully wired with a comprehensive CCTV security system featuring 21 cameras for added security and peace of mind. Residents also enjoy the prestigious opportunity to become members of the Golden Bear Club, featuring a full-service golf course and clubhouse located in the neighboring community of Keene’s Pointe. Homes in Casa Del Lago rarely come to market, making this a unique opportunity to own in one of Windermere’s most exclusive gated communities.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Matt Kester (772-494-8550)
11015 HAWKSHEAD CT, WINDERMERE, FL 34786
$1,499,99927 Days on yellowkey MLS ID: O6405977
REDUCED by $30,000 (2.0%) on 06/10/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3868 Built: 2004Monthly Fee: $640 Tax: $18,824 (2025)Community: Reserve At Lake Butler SoundSpa: YesSingle Family
Taxes:$18,824
Remarks: Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort, and functionality. Featuring nearly 3,900 square feet of living space, the home showcases tall ceilings, travertine flooring throughout the main living areas, and thoughtful modern updates completed in recent years. A grand double-door entry opens to formal living and dining spaces highlighted by contemporary accent walls and a striking fireplace. The spacious kitchen is designed for both everyday living and entertaining, featuring upgraded stainless steel appliances, abundant cabinetry, stylish countertops, a beverage refrigerator, and an open flow into the family room. The split-bedroom floor plan includes a private office and a spacious primary suite complete with California closets and a luxurious ensuite bath featuring dual vanities, a walk-in shower, and a freestanding soaking tub. Upstairs, the oversized bonus room with full bath offers flexibility as a guest suite, second primary suite, or media room. Sliding doors lead to an expansive screened pool area ideal for relaxing or entertaining, while the lush backyard garden creates a peaceful setting to enjoy your morning coffee. The home also features a spacious 3-car garage. *Roof and water heater was replaced 5 years ago.* Ideally located near top-rated schools, shopping, dining, and area attractions, this move-in ready Windermere home is one you won’t want to miss.
Listing Agent: Julie Davis, Llc (407-579-7584)
5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$7,250,000153 Days on yellowkey MLS ID: O6373191
REDUCED by $345,000 (4.5%) on 05/21/2026
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 7099 Built: 1988Monthly Fee: $1,224 Tax: $21,279 (2024)Community: IsleworthSingle Family
Taxes:$21,279
Remarks: A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the two-story home features 5 bedrooms, 6.5 bathrooms, and a seamless blend of timeless modern design and resort-style living. A striking 10-foot custom pivot door welcomes you into light-filled interiors, where elegant European porcelain tile and expansive open living spaces create a bright, elevated ambiance. Designed for both entertaining and everyday living, the main living areas flow effortlessly through expansive sliding glass doors to a stunning outdoor retreat, complete with a fully retractable screen enclosure. The chef’s kitchen serves as the centerpiece of the home, appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar enhance both functionality and style. The main-level primary suite offers a private, resort-inspired retreat, featuring a custom walk-in closet, a versatile bonus room ideal for fitness or wellness, and a dedicated in-home spa room. The spa-like primary bath includes a soaking tub, expansive walk-in shower, and a tropical outdoor shower, creating a tranquil escape. Upstairs, the newly constructed addition includes a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room with access to a grand balcony overlooking panoramic golf course views, and a refined home theater. Outdoor living is equally impressive, featuring a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush, manicured landscaping designed for privacy and enjoyment. Additional highlights include a fully integrated Crestron smart home system controlling lighting, audio, climate, and security, as well as a brand-new Generac generator for uninterrupted comfort. Fully remodeled and upgraded throughout, this residence presents a rare opportunity to own a like-new luxury estate in one of Central Florida’s most prominent communities.
Listing is courtesy of: MEM REALTY GROUP (407-/58-3702)
Listing Agent: Armaan Memarpouri (407-583-7028)
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