Location: Windermere
Do Not Show Listings
13712 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786
$444,90065 Days on yellowkey MLS ID: S5143431
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1997 Built: 2019Monthly Fee: $171 Tax: $5,448 (2025)Community: Vineyards/Horizons West Ph 4Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,448
Elementary School: Independence Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Location!!! Great price!!! Top-rated school district!!! and a Renovated!!! Property ready for you to move in or invest. High rental demand and low inventory, ideal for investors or families. Fresh paint inside and out, new carpets, new indoor A/C with warranty, rear entry 2-car garage with epoxy flooring, and a spacious driveway. Kitchen island, granite counters, breakfast bar, stainless appliances large porch with relaxing views, a patio ideal for barbecues or outdoor breakfasts, surrounded by beautiful landscaping. Upstairs: 3 spacious bedrooms, plus a flexible loft. Primary Suite with walk-in closet and bath with dual sinks, second bedroom with walk -in closet, third bedroom with a reach-in closet, shared bathroom with dual sinks. Vineyard at Horizon West community amenities include: 2 clubhouses, swimming pools, park, community mailbox, sidewalks and recreational areas. Windermere High School (0.6 mi) Independence Elementary (1,3 mi) Bridgewater Middle School (1,7 mi). Just minutes from Winter Garden Village, hospitals, Disney Springs, Walt Disney World, Universal Studios, and Orange County National Golf Center and lodge. Approx 3,5 miles to FL-429 exit 19. With our preferred lender, you'll receive an additional benefit. Contact me today and don't let this opportunity pass you by! For security purposes, property is equipped with Ring exterior security cameras located at the front entrance and garage.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Carines Hernandez Bustillo (786-727-7434)
13858 CAYWOOD POND DR, WINDERMERE, FL 34786
$963,00050 Days on yellowkey MLS ID: O6382987
2 Days Off yellowkey (back on 4/5/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3070 Built: 2004Monthly Fee: $130 Tax: $12,050 (2025)Community: Summerport Ph 1Single Family
Taxes:$12,050
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is more than a home-it's a lifestyle. From the moment you arrive, the home’s curb appeal impresses with a beautiful stone façade, charming arbor detail, spacious covered front porch, and a 3-car split garage. Inside, you are welcomed by a dramatic 20-foot ceiling in the formal living room, highlighted by elegant arched openings, a sweeping staircase, and a curved balcony overlooking the space below. Fresh updates throughout create a bright, modern feel, making this home truly move-in ready. Major improvements include a recently updated roof in last 6 years, brand-new AC system, and new water heater, new pool pump, new spa gas heater — offering comfort and peace of mind for years to come. Step outside to your private screened-in pool oasis. Cool off in the sparkling pool while enjoying serene lake views, mature landscaping, and added privacy from lush greenery — the perfect setting for relaxing or entertaining. Residents of Summerport enjoy resort-style amenities including a community pool, fitness center, basketball and tennis courts — all just minutes from shopping, dining, and entertainment at Winter Garden Village, and zoned for top-rated Windermere schools. Experience luxury lakefront living with privacy, elegance, and timeless charm — all in one of Central Florida’s most sought-after communities. Information deemed reliable but not guaranteed.
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
12132 MONTALCINO CIR, WINDERMERE, FL 34786
$3,950,000161 Days on yellowkey MLS ID: O6319854
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
Elementary School: Sunset Park Elem
Tax Year: 2024
Middle School: Horizon West Middle School
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)
11455 CLAYMONT CIR, WINDERMERE, FL 34786
$1,249,00011 Days on yellowkey MLS ID: O6396381
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2262 Built: 2003Monthly Fee: $298 Tax: $7,673 (2025)Community: Keenes PointeSingle Family
Taxes:$7,673
Elementary School: Windermere Elem
Remarks: Better-Than-New Fully Renovated Pool Home in 24-hour gated/attended Keene's Pointe. Home to The Golden Bear Club an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming. Welcome to your dream home—completely renovated and truly move-in ready! This stunning residence offers the perfect blend of modern upgrades, thoughtful design, and luxurious indoor-outdoor living. Step inside to discover a spacious, light-filled layout featuring three bedrooms, three full bathrooms, formal dining room, and a dedicated office, ideal for working from home or creating a private retreat. A formal dining room with arched window greets you at the entrance, while the heart of the home opens into an expansive great room with an open-concept floor plan, seamlessly connecting the living, dining, and kitchen areas—perfect for entertaining. The low maintenance wood-look tile carries throughout the home.The beautifully updated kitchen boasts a large island that seats 6 comfortably and provides additional storage. White and oak shaker cabinets, Verona quartz on the counters and backsplash, and new stainless steel appliances, create a warm and inviting atmosphere for gatherings both large and small.The primary suite offers two custom closets and bathroom with dual vanities, free-standing tub and zero entry shower. On each side of the kitchen are the two additional bedrooms with full baths to service each offering custom tile detailing and decorative free-standing vanities. From the great room through the triple-panel sliding door you enter the patio overlooking your own private oasis with an oversized pool and spa, recently resurfaced and enhanced with a new pool motor and heater—perfect for year-round relaxation and entertaining. Throughout this home you will find quality features such as designer lighting, crown moldings, and coffered and tray ceilings. Additional highlights include: 3-car garage with ample storage space, tankless gas water heater for energy efficiency and endless hot water, new roof (2022), professionally designed landscaping and much more. Every detail has been thoughtfully updated, offering the feel of new construction without the wait. Located in close proximity to shopping, dining, major tourist attractions, expressways and top-rated public and private schools - space, style and upgrades in every corner, this home truly has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
9237 SABAL PALM CIR, WINDERMERE, FL 34786
$789,99511 Days on yellowkey MLS ID: G5110005
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
Elementary School: None
High School: None
Middle School: None
Remarks: Nestled in the charming and highly desirable Silverwood subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwood 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 provides three bedrooms and two bathrooms in a thoughtfully designed layout. Originally built in 1985, the home has been tastefully updated, including a modernized kitchen that serves as the heart of the home. A standout feature is the expansive Florida room, added by the current owners, creating a bright and versatile living space perfect for entertaining, relaxing, or enjoying views of the backyard year-round.Whether you’re drawn to the peaceful neighborhood setting or the unbeatable location close to everything Windermere has to share, this home presents a wonderful opportunity to enjoy both charm and convenience in one of the area’s most appealing communities.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Chelsea Murphy (407-373-8101)
1002 DOWN RESERVE CT, WINDERMERE, FL 34786
$6,490,00053 Days on yellowkey MLS ID: O6383597
0 Days Off yellowkey (back on 4/4/2026)
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6706 Built: 2021Monthly Fee: $433 Tax: $61,838 (2024)Community: Rosser Reserve RepSingle Family
Taxes:$61,838
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: UNDER CONTRACT ACCEPTING BACKUP OFFERS! Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment you arrive, the home captivates with its contemporary architecture, expansive paver driveway, and striking façade. Clean lines, refined finishes, and manicured landscaping create an unforgettable first impression. Inside, soaring ceilings, exposed wood beams, and designer lighting enhance the open-concept layout. Oversized sliding glass doors frame breathtaking panoramic lake views while creating a seamless indoor-outdoor flow filled with natural light. The gourmet kitchen serves as the heart of the home, featuring an oversized quartz island, custom cabinetry, and premium stainless steel appliances — perfectly designed for both intimate gatherings and grand-scale entertaining. With 6 spacious bedrooms, 5 full bathrooms, and 1 powder room, the residence offers comfort and privacy for family and guests. Beyond the main living areas, this home delivers an exceptional lifestyle experience with a private gym, dedicated cinema room, game room, and playroom — thoughtfully designed for wellness, entertainment, and family enjoyment. Step outside into your private lakeside retreat. The resort-style pool with integrated spa is complemented by sleek glass railings that preserve unobstructed water views. The covered outdoor living area is a masterpiece, featuring a wood-paneled ceiling, oversized ceiling fan, stone fireplace, mounted TV, and a fully equipped summer kitchen with professional-grade stainless steel grill and hood — ideal for year-round entertaining. The private covered dock accommodates boats and jet skis and provides direct access to all 12 lakes of the Butler Chain, making this property a true paradise for boating enthusiasts. Additional features include: Whole-house water filtration system High-capacity generator capable of powering the entire residence Located within an exclusive gated community with meticulously maintained infrastructure Offering privacy, security, expansive outdoor space, and one of Windermere’s most coveted lakefront settings, this is more than a residence — it is a lifestyle defined by elegance, recreation, and exclusivity. Schedule your private showing and experience lakefront living at its finest.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786
$1,990,00032 Days on yellowkey MLS ID: O6390656
Bed: 6 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5430 Built: 1997Monthly Fee: $267 Tax: $12,735 (2025)Community: BalmoralSingle Family
Taxes:$12,735
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive ¾-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water fountain, creating a grand sense of arrival. The residence also features a spacious four-car garage equipped with two EV charging stations, offering modern convenience for today’s lifestyle. Custom front entry doors open to an impressive grand foyer with elegant marble tile flooring, introducing the refined finishes that define the home. Inside, the residence has been beautifully transformed with brand-new flooring throughout, custom recessed lighting, upgraded designer fixtures, and crown molding across the main level. At the heart of the home is a stunning designer gourmet kitchen featuring custom white cabinetry, granite countertops, a striking tile mosaic accent wall, and premium KitchenAid stainless steel appliances, including a built-in oven, microwave, and cooktop. Perfect for entertaining or multi-generational living, the home also features a fully rebuilt second kitchen with granite countertops, custom cabinetry, and stainless steel appliances with direct access to the outdoor entertaining area. The home offers two luxurious primary suites, each thoughtfully designed as a private retreat. The upstairs primary suite features a spa-inspired bathroom with dual vanities, custom cabinetry, a dedicated makeup vanity, an oversized jacuzzi soaking tub, and a beautifully tiled walk-in shower. Outdoor living is equally impressive with a custom outdoor kitchen complete with built-in grill, professional venting, and built-in speakers, creating the perfect setting for entertaining and relaxation. Three brand-new sliding glass doors upstairs open to a private balcony, enhancing the home’s seamless indoor-outdoor lifestyle. Recent upgrades provide comfort and peace of mind, including a new Carrier 5-ton air conditioning system, new 50-gallon water heater, whole-home water purification system, and a new pool pump installed within the last six months. With extensive renovations, luxurious finishes, and exceptional indoor-outdoor living, this remarkable residence offers the sophistication, comfort, and lifestyle expected of a premier luxury estate.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ryan Rogers (407-492-0674)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$679,99448 Days on yellowkey MLS ID: O6380917
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 2009Monthly Fee: $82 Tax: $3,146 (2024)Community: Lakes/WindermereSingle Family
Taxes:$3,146
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)
4 CHASE RD, WINDERMERE, FL 34786
$900,00054 Days on yellowkey MLS ID: O6384257
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2386 Built: 1971 Tax: $7,637 (2024)Community: Windermere TownSingle Family
Taxes:$7,637
Remarks: FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.
Listing Agent: Matthew Hughes (407-619-4717)
11835 GOLD CREEK TRL, WINDERMERE, FL 34786
$900,00062 Days on yellowkey MLS ID: O6382068
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3119 Built: 2012Monthly Fee: $75 Tax: $9,395 (2024)Community: Windermere Trls Ph 1ASingle Family
Taxes:$9,395
Remarks: Windermere Trails Award Winning Model - Voted #1 Model by HBA 2013 It's surrounded by The Butler Chain of Lakes, with fabulous shopping and dining just minutes away. These are just a few of the celebrated qualities you'll love about Windermere Trails. Located in Windermere, FL, Windermere Trails is a community of new, incredibly energy-efficient homes, ranging 2,260 - 4,400 sq. ft. just south-east of downtown Orlando and is only a short drive to the SR 429 giving you access to the Florida Turnpike, SR 408 and I4; so you're close to all of Orlando's most popular area attractions. If golfing, boating, shopping and great schools are on your list of must-haves, you'll absolutely cherish living at Windermere Trails with Butler Chain of Lakes, several area golf courses and excellent schools, such as Windermere Prep nearby. Every home we build showcases our commitment to providing incredibly energy-efficient homes that let you spend your money on better things than utility bills. After all, we believe in building new homes and communities the way they can, and should be, built. That's why every Meritage home at Windermere Trails is built standard with the following energy- and money-saving features: - Spray-Foam Insulation - ENERGY STAR Appliances - ENERGY STAR Programmable Thermostat - Low-E2 Double pane/tinted Vinyl Windows - Variable SEER 15 HVAC - CFL Lighting and Fixtures - Weather-Sensing Irrigation - Water-Efficient Fixtures - Dual-Flush Toilets - Low VOC Carpets, Paints and Finishes
Listing is courtesy of: BB GROUP REALTY CORP (407-624-7625)
Listing Agent: Flavio Vieira De Melo (407-470-5008)
11401 EVESHAM DR, WINDERMERE, FL 34786
$455,00042 Days on yellowkey MLS ID: O6386678
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1847 Built: 2008Monthly Fee: $315 Tax: $3,077 (2024)Community: Preston SquareTownhouse
Taxes:$3,077
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome home to this beautifully appointed 3-bedroom, 2.5-bath corner townhome in the highly desirable Preston Square community of Windermere. Ideally positioned, this townhome conveniently faces the community amenities, offering easy access while maintaining a welcoming neighborhood feel. From the moment you step onto the charming front porch, you'll appreciate the warmth and character this home provides. Inside, natural light fills the space through wrap-around windows, highlighting the 10-foot ceilings and rich hardwood flooring. The thoughtfully designed floor plan blends comfort and functionality, making it ideal for both everyday living and entertaining. A standout feature of this home is the private courtyard, creating a peaceful outdoor retreat perfect for gatherings, grilling, or simply relaxing. The kitchen is well-equipped with 42" solid wood cabinetry, granite countertops, and stainless steel appliances, a space any home chef will appreciate. The main level features a spacious primary suite with a tray ceiling and a luxurious en-suite bath, complete with dual vanities, a garden tub, and a walk-in shower with dual shower heads. Upstairs, you’ll find a spacious, open-concept loft with two additional bedrooms, providing comfortable accommodations and privacy for family members or visitors. The laundry room includes a utility sink, and a window for added natural light. The rear-entry two-car garage features overhead storage racks and a long driveway for additional parking. Residents of Preston Square enjoy resort-style amenities, including a stunning swimming pool, lush landscaping, basketball court, playground, fitness stations, and a large park that hosts movie nights and food trucks. Conveniently located near top-rated schools, shopping, dining, golf courses, hospitals, and major roadways, with easy access to Orlando, Windermere, Winter Garden, and the area’s world-renowned theme parks. A fantastic opportunity to own a home in one of Windermere’s most desirable communities.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nora Arenivas Llc (407-230-5487)
13421 BONICA WAY, WINDERMERE, FL 34786
$1,369,99926 Days on yellowkey MLS ID: O6392381
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4869 Built: 2005Monthly Fee: $317 Tax: $19,939 (2025)Community: Tildens Grove Ph 02Single Family
Taxes:$19,939
Remarks: Gorgeous East facing custom estate on a .63-acre lot in the highly sought-after 24-hour guard-gated community of Tildens Grove in Windermere. This elegant home offers 6 bedrooms, 4.5 baths, and an open layout perfect for entertaining, all located near top-rated schools, the Butler Chain of Lakes, Winter Garden Village, major highways, and Walt Disney World. Kitchen has two-tone cabinetry, granite countertops, an oversized island, gas cooktop, double ovens, walk-in pantry, and brick wine cellar with cast iron doors. The kitchen opens to a spacious family room with custom built-ins, gas fireplace, and French doors leading to the lanai. Formal living and dining rooms showcase tray and coffered ceilings, with travertine flooring and crown molding throughout the main areas. Fenced yard. The primary suite features a sitting area, bay windows, French doors to the pool, dual walk-in closets, and a bath with soaking tub, dual vanities, and walk-in shower. A connected flex room can serve as an office, nursery, or additional bedroom. The split floor plan offers privacy, while upstairs includes a bonus room, bedroom, full bath. Additional highlights include a dedicated office, oversized 3-car garage, and numerous updates such as new A/C, water softener, gas stove, washer/dryer, electrical upgrades, and fresh exterior paint. Tildens Grove is an exclusive community of 140 homes offering tennis courts, playground, basketball court, and soccer field, with a neighborhood park just steps away.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Aparajita Leekha (352-562-3731)
8375 BOWDEN WAY, WINDERMERE, FL 34786
$1,369,000170 Days on yellowkey MLS ID: S5137385
1 Days Off yellowkey (back on 4/4/2026)
REDUCED by $1,000 (0.1%) on 03/31/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3809 Built: 1999Monthly Fee: $283 Tax: $9,709 (2025)Community: Keenes Pointe Unit 1Single Family
Taxes:$9,709
Remarks: The kitchen has been recently upgraded with brand-new white quartz (Calacatta Belardo) countertops and backsplash, creating a bright, modern, and spacious feel. This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated. The highlight of this home is its backyard oasis — a peaceful retreat overlooking the sparkling pool and tranquil pond views, creating the perfect setting for relaxation and entertainment. A nice added air-conditioned covered patio area allows you to enjoy the outdoors year-round, even on the warmest Florida days. Inside, you’ll find beautifully appointed living spaces, elegant finishes, and a floor plan designed for both comfort and functionality — ideal for families or those who love to host. Recent Updates Include: A/C Unit: 2025,A/C Unit: 2016,Roof: 2018,Pool Heater: 2020, Irrigation Well: 2022 Water Heater: 1999 Life in Keene’s Pointe is truly exceptional. Residents enjoy a gated, golf-course lifestyle surrounded by nature, scenic lakes, and the renowned Golden Bear Club, designed by Jack Nicklaus. This exclusive Windermere community offers an active, social, and family-friendly atmosphere unlike anywhere else. Don’t miss the opportunity to make this stunning French-style home your own — a perfect blend of elegance, comfort, and Florida charm.
Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE (407-217-7573)
Listing Agent: Oscar Rodriguez (321-297-7264)
3138 SEIGNEURY DR, WINDERMERE, FL 34786
$1,350,00036 Days on yellowkey MLS ID: O6387397
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3831 Built: 1997Monthly Fee: $250 Tax: $11,794 (2024)Community: Harbor IsleSingle Family
Taxes:$11,794
Remarks: Under contract-accepting backup offers. Timeless style and classic design unfold behind the gates of Harbor Isle, one of Windermere’s most sought-after communities. This custom-built estate residence offers captivating views of Lake Down on the pristine Butler Chain of Lakes. Featuring all living areas on the first floor except for a bonus room upstairs, this thoughtfully crafted home offers separate formal and living spaces and a private den. The generously-sized primary retreat has a gas fireplace and large bath including oversized shower. Clerestory windows bathe the home in an abundance of natural sunlight. Three secondary bedrooms on the first floor include a guest room with pool bath and a pocket door feature to create a private suite. The additional bedrooms on the first floor are joined by a jack-and-jill-style bathroom. A multi-use space on the second floor is mammoth in size and is a perfect retreat for working from home, game room, or playroom. With an adjacent full bath, the space is large enough to be converted into two additional bedrooms. The screen enclosed pool and spa with patio offers a tranquil escape with lake views in the distance. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
14217 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786
$600,00012 Days on yellowkey MLS ID: O6396155
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2419 Built: 2006Monthly Fee: $131 Tax: $8,205 (2026)Community: SummerportSingle Family
Taxes:$8,205
Tax Year: 2026
Remarks: Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing Elementary, Bridgewater Middle and Windermere high
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Azim Manji (407-342-3548)
8533 GREENBANK BLVD, WINDERMERE, FL 34786
$550,000175 Days on yellowkey MLS ID: O6354672
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2551 Built: 2004Monthly Fee: $176 Tax: $3,300 (2024)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$3,300
Remarks: Roof is 2022, A beautiful Home in a wonderful Gated Community in Windermere. Home sits on a big lot that extends all the way to the high tree, and it has fruit trees, avocado, and mango. Home is very spacious with Master downstairs, one owner, the upper floor was not even being used by seller. Come see this beauty, priced to sell. Motivated Seller, please bring your offers.
Listing is courtesy of: CENTURY 21 CARIOTI (407-354-0074)
Listing Agent: Faneeza Mohamed (321-438-7843)
9323 GLADYS GARDEN CT, WINDERMERE, FL 34786
$12,500,00061 Days on yellowkey MLS ID: O6381880
REDUCED by $1,495,000 (10.7%) on 04/03/2026
Bed: 6 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 9770 Built: 2026Monthly Fee: $1,099 Tax: $21,279 (2025)Community: IsleworthSingle Family
Taxes:$21,279
Remarks: Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage plus golf cart garage, and a friends-and-family entry with covered parking. Inside, discover Sierra Pacific casement windows with stained interior mullions flood the home with natural light, highlighting warm beams, wide-plank floors, and curated details. Lutron lighting, Sonos audio, and powered draperies enhance modern comfort without compromising design. The formal dining room features a stained white oak arched opening, classic dentil molding, and built-in wine display. The living room is anchored by a gas Isokern fireplace with precast surround, custom built-ins, stained beams, and sculptural custom one off lighting, while an interior glass breezeway subtly defines the transition to the private primary wing. The primary suite offers a serene retreat with custom arch detailing, a nickel joint ceiling, and stained beams. The spa-inspired bath includes a marble soaking tub and a dramatic solid limestone staircase leading to a hidden upper-level flex space, ideal for an office or gym, complete with beverage refrigeration and powered Roman shade. The boutique-style closet features dual islands and an integrated wash tower. At the heart of the home, the chef’s kitchen stuns with soaring 18-foot ceilings, exposed beams, a curved reeded island, and custom Urban Electric pendants designed specifically for the residence. Sub-Zero refrigeration, freezer, and wine column, a 60-inch Wolf range, dual integrated dishwashers, and a fully equipped back kitchen ensure effortless entertaining. Indoor and outdoor living connect seamlessly to a private courtyard-style retreat featuring a resort-inspired pool with copper scupper water features, a summer kitchen with Wolf grill, powered screens, and multiple lounging areas designed for year-round enjoyment. Additional highlights include four upstairs en-suite bedrooms, including a secondary primary suite, an upstairs laundry with linen towers and folding station, a third-level bonus floor with theater, bar, powder bath, and storage, elevator-ready construction, and an advanced security system with AI-enabled cameras and window vibration sensors. Designed with architectural intention, this home pairs refined craftsmanship with warmth, creating spaces that feel both elevated and deeply livable.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
1625 DOWN LAKE DR, WINDERMERE, FL 34786
$1,400,00048 Days on yellowkey MLS ID: O6385420
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3383 Built: 1984Monthly Fee: $89 Tax: $11,274 (2025)Community: The LakesSingle Family
Taxes:$11,274
Remarks: One or more photo(s) has been virtually staged. A RARE OFFERING in Windermere’s established Lakes / Lake Down neighborhood — this exceptional builder’s home combines ONE ACRE, FIVE EN-SUITE BEDROOMS, and BOAT ACCESS TO THE BUTLER CHAIN OF LAKES with the quality, craftsmanship, and timeless finishes typically found at much higher price points. Tucked within an intimate enclave of just 60 homes, this is a rare chance to own a property that delivers the space, privacy, and lifestyle buyers want — yet seldom find this close to downtown Windermere. From the moment you arrive, the sweeping paver drive and circular approach create a true estate presence. Inside, timeless architectural details and thoughtful finishes define the home. SOLID BIRCH HARDWOOD FLOORS, CROWN MOLDING, DESIGNER LIGHTING, RECESSED LIGHTING, and PLANTATION SHUTTERS throughout create a warm, polished backdrop that feels both elevated and comfortable. The floor plan lives beautifully for everyday life while offering the scale and flow needed for entertaining. At the heart of the home, the open kitchen and family room are light-filled, inviting, and designed to gather people naturally. The kitchen is a standout space featuring QUARTZITE COUNTERTOPS, a substantial wood island, FARMHOUSE SINK, polished gooseneck faucet with side sprayer, classic SUBWAY TILE BACKSPLASH, WALL-MOUNTED POT FILLER, DOUBLE OVENS, and an extra-wide side-by-side refrigerator. The spacious family room offers a built-in media wall and FRENCH DOORS opening directly to the lanai and pool for seamless indoor-outdoor living. The PRIMARY SUITE ON THE MAIN LEVEL feels like a private retreat — spacious, serene, and beautifully finished with plantation shutters, elegant lighting, and room for a sitting area. The spa-inspired bath features dual vanities with vessel sinks, abundant storage, a soaking tub, and a large walk-in shower with designer tile accents. A standout feature is the rare bedroom configuration: FIVE EN-SUITE BEDROOMS, offering exceptional comfort and privacy for family and guests. Upstairs, a generous loft/family room with impressive gray built-in bookcases provides the perfect flex space for movies, game nights, a homework hub, second lounge, or media retreat. Step outside and the lifestyle only gets better. A FULL SCREENED ENCLOSURE and expansive 60' x 12' COVERED LANAI create a dramatic extension of the living space. The RESORT-STYLE POOL AND RAISED SPA are framed by travertine decking with a custom grid pattern and turf inlays, offering generous room for lounging, dining, and entertaining, with space to add an outdoor kitchen. And then there is the unforgettable feature that truly sets this property apart — a CUSTOM ELEVATED TREE HOUSE tucked among the trees. Designed with multiple windows, a charming wood door, circular staircase, and tubular slide, this remarkable space can serve as an art studio, workout room, creative office, homeschool room, reading nook, or unforgettable teen retreat. Neighborhood amenities include a TENNIS/PICKLEBALL COURT and PRIVATE BOAT RAMP to Lake Down, connecting to the BUTLER CHAIN OF LAKES. Major updates include ROOF (2021), WATER HEATER (2026), A/C 2-TON (2018), and A/C 4-TON (2016). Zoned for THORNEBROOKE ELEMENTARY within walking distance, plus GOTHA MIDDLE and OLYMPIA HIGH. Convenient access to 429, Turnpike, 408, and downtown Windermere completes the package.
Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)
Listing Agent: Cindy Rosenbloom (407-876-9175)
8256 MARITIME FLAG ST #103| 1710, WINDERMERE, FL 34786
$338,49022 Days on yellowkey MLS ID: O6393278
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2009 Tax: $1,540 (2024)Community: Lakeside/Lks/Windermere Ph 17Condo
Taxes:$1,540
Remarks: Under contract-accepting backup offers. Rare opportunity to own a first-floor 3-bedroom, 2-bath condo in the only condo community located in highly sought-after Windermere. This corner-unit offers added privacy and a unique “home-like” feel, featuring a spacious screened terrace with an open and peaceful setting — no direct rear neighbors, allowing you to enjoy a more private outdoor space. The interior showcases ceramic tile flooring throughout, a modern kitchen with granite countertops, and a well-maintained condition with no pending repairs. Recent upgrades include a new water heater and an updated interior A/C unit for added efficiency and comfort. The unit has plenty of storage, multiple linen closets, and a spacious pantry The community offers resort-style amenities, including a clubhouse, fitness center, swimming pool, and beach volleyball court, creating a lifestyle that blends convenience and leisure. Additional features include two assigned parking spaces, an electronic door lock, pre-wired alarm system, ceiling fans throughout, and window treatments in all areas. Ideally located near top-rated schools, shopping, dining, and major roadways, this property is perfect for both homeowners and investors seeking value in one of Central Florida’s most desirable areas.
Listing is courtesy of: METROPOLITAN R.E SOLUTIONS INC (407-953-6501)
Listing Agent: Alejandra Silva (407-929-7308)
5130 SUN PALM DR, WINDERMERE, FL 34786
$525,00013 Days on yellowkey MLS ID: O6390875
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1723 Built: 1987Monthly Fee: $30 Tax: $8,032 (2025)Community: Silver Woods Ph 04Single Family
Taxes:$8,032
Remarks: Welcome to 5130 Sun Palm Drive, located in the heart of WINDERMERE! This beautifully maintained 3-bedroom, 2-bath home offers 1,723 sqft of living space on a spacious ¼-acre FULLY FENCED lot — perfect for outdoor enjoyment and privacy. Recent upgrades include a new ROOF (2022) and a new AC SYSTEM (2020). ALL FLOORING HAS BEEN UPDATED. The carpet was removed and replaced with Mohawk Pergo luxury vinyl plank. The original tile was replaced with fresh ceramic tile throughout the rest of the house—NO MORE POPCORN CEILING, all was removed, and now it has a beautiful finished ceiling. A brand NEW SLIDING GLASS DOOR opens to the NEW PATIO DECK recently installed. Ideal for indoor-outdoor living. Just minutes from the famous Sand Lake Restaurant Row, conveniently located near the distinguished Bay Hill Golf Community, and backing up to the exclusive Isleworth Court private community. Zoned for top-rated schools, and ideally situated just 20 MINUTES from Walt Disney World and 10 minutes from Universal Studios — this location truly offers the best of Central Florida living!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Elle Walters (407-431-4600)
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