Windermere Single Family Homes for sale by Neighborhood

Find Windermere Single Family Homes  by clicking on the relevant neighborhood.

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BALMORAL homes for sale BELLARIA homes for sale
BELMERE VILLAGE G2 48 65 homes for sale BUTLER BAY homes for sale
CASA DEL LAGO REP homes for sale CASABELLA homes for sale
CHAINE DE LAC homes for sale CHAINE DU LAC homes for sale
DAVIS SHORES homes for sale ENCLAVE homes for sale
ESTATES AT WINDERMERE homes for sale GLENMUIR 48 39 homes for sale
GOTHA TOWN homes for sale ISLEWORTH homes for sale
ISLEWORTH WEST homes for sale KEENES POINTE homes for sale
KEENES POINTE 46/104 homes for sale KEENES POINTE UNIT 03 46/104 homes for sale
KEENES POINTE UT 04 SEC 31 48 82 homes for sale KELSO ON LAKE BUTLER homes for sale
LAKE BURDEN SOUTH PHASE 1 homes for sale LAKE BUTLER ESTATES homes for sale
LAKE BUTLER PARK PT REP homes for sale LAKE BUYNAK ESTATES homes for sale
LAKE CRESCENT RESERVE homes for sale LAKE DAVIS ESTATES homes for sale
LAKE DOWN CREST homes for sale LAKE DOWN ESTATES homes for sale
LAKE DOWN POINTE 50 42 homes for sale LAKE DOWN RESERVE homes for sale
LAKE DOWN SHORES homes for sale LAKE OLIVIA RESERVE homes for sale
LAKE ROPER POINTE homes for sale LAKE SAWYER SOUTH PH 01 homes for sale
LAKES homes for sale LAKES OF WINDERMERE homes for sale
LAKES WINDERMERE homes for sale LAKES WINDERMERE PH 01 49 108 homes for sale
LAKES/WINDERMERE homes for sale LAKES/WINDERMERE PH 01 49 108 homes for sale
LAKES/WINDERMERE PH 02A homes for sale LAKES/WINDERMERE-PEACHTREE homes for sale
MAGNOLIA PARK WINDERMERE homes for sale MANORS AT BUTLER BAY homes for sale
METCALF PARK REP homes for sale N/A homes for sale
NA homes for sale NONE homes for sale
OXFORD MOOR homes for sale PALMS AT WINDERMERE homes for sale
PEACHTREE PARK homes for sale PRESTON SQUARE homes for sale
PROVIDENCE homes for sale PROVIDENCE PH 01 50 03 homes for sale
RESERVE AT BELMERE homes for sale RESERVE AT BELMERE 48 23 homes for sale
RESERVE AT LAKE BUTLER SOUND homes for sale ROBERTS LANDING homes for sale
SAWYER SOUND homes for sale SILVER WOODS homes for sale
SUMMERPORT homes for sale SUMMERPORT PH 03 homes for sale
TILDENS GROVE homes for sale TILDENS GROVE PH 01 47/65 homes for sale
WATERSTONE homes for sale WESTSIDE VILLAGE homes for sale
WINDERMERE homes for sale WINDERMERE ISLE homes for sale
WINDERMERE LNDGS PH 02 homes for sale WINDERMERE TERRACE homes for sale
WINDERMERE TOWN homes for sale WINDERMERE TRLS PH 1C homes for sale
WINDERMERE TRLS PH 3B homes for sale WINDSOR HILL homes for sale
WINDSTONE homes for sale

Newest Single Family Homes for Sale in Windermere by Neighborhood

View all Windermere Single Family Homes for Sale

  • 7011 NOBLETON DR, WINDERMERE, FL - MLS# O6412101

    LAKES WINDERMERE PH 01 49 108 - O6412101 - 7011 NOBLETON DR, WINDERMERE, FL 34786
    Just Added on 05/31/2026 3:45PM

    $580,000 | Single Family Home | 4 beds | 2.5 baths

    TOP RATED SCHOOLS!!! Welcome to this beautifully maintained Craftsman-style home in the highly sought-after Lakes of Windermere community. Perfectly positioned on a premium homesite overlooking tranquil conservation views, this 4-bedroom, 2.5-bath residence combines timeless charm with modern upgrades and exceptional indoor-outdoor living. Inside, you’ll find a light-filled floor plan featuring hardwood flooring, elegant transom windows, custom built-ins, and spacious living and dining areas ideal for both everyday living and entertaining. The upgraded kitchen offers granite countertops, solid wood cabinetry, stainless steel appliances, a butler’s pantry, and ample prep and storage space. This is the one you’ve been waiting for—schedule your private showing today.

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    Listing is courtesy of: KARDOSH REALTY

  • 6412 GOLDEN DEWDROP TRL, WINDERMERE, FL - MLS# O6412095

    WINDERMERE LNDGS PH 02 - O6412095 - 6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
    1 Day on yellowkey

    $550,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.

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    Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS

  • 1407 HEMPEL AVE, WINDERMERE, FL - MLS# O6410840

    GOTHA TOWN - O6410840 - 1407 HEMPEL AVE, WINDERMERE, FL 34786
    1 Day on yellowkey

    $1,090,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Welcome to this incredible investment opportunity located in one of the most desirable areas in Central Florida. This beautiful property offers the perfect combination of space, privacy, freedom, and location. Featuring 4 spacious bedrooms and 3 full bathrooms, this home sits on more than half an acre of land, giving you and your family the opportunity to truly enjoy comfort and outdoor living. One of the greatest advantages of this property is that it has NO HOA, allowing you the freedom to enjoy your property without restrictive association rules or expensive monthly fees. Whether you are looking for a primary residence, vacation home, or investment property, this home offers endless possibilities. The property features a beautiful swimming pool and stunning water views, creating the perfect atmosphere to relax, entertain guests, and enjoy the Florida lifestyle all year round. The oversized lot provides plenty of space for family gatherings, outdoor activities, parking, or future improvements.

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    Listing is courtesy of: MY REALTY GROUP, LLC.

  • 9317 GLADYS GARDEN CT, WINDERMERE, FL - MLS# O6410843

    GARDENS/ISLEWORTH - O6410843 - 9317 GLADYS GARDEN CT, WINDERMERE, FL 34786
    1 Day on yellowkey

    $7,999,000 | Single Family Home | 6 beds | 7.5 baths | 4 gar

    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.

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    Listing is courtesy of: CORCORAN PREMIER REALTY

  • 5128 BUTLER RIDGE DR, WINDERMERE, FL - MLS# O6412016

    BUTLER RIDGE - O6412016 - 5128 BUTLER RIDGE DR, WINDERMERE, FL 34786
    2 Days on yellowkey

    $1,250,000 | Single Family Home | 4 beds | 3.0 baths | 7 gar

    Calling all car enthusiasts or artisans needing a large, detached workshop on your property! This house has it all; including a gorgeous interior, huge pool and lanai equipped with an outdoor kitchen, and a large 30 x 30 detached garage/workshop. This house is perfect for work and play! Situated on a rare, 1 acre lot in the coveted town of Windermere, this house is truly 1 of a kind. Surrounded by sweeping oak trees and quiet streets, you’ll feel miles away from the hustle and bustle of the city even though you’re right at its back door. Enjoy entertaining? This is your dream entertaining house with a HUGE kitchen (which was gutted in 2017), high end appliances including a Bosch cook top/built in oven, and all the refrigerating needs you could have, including a wine fridge and a brand-new LG thinQ refrigerator that makes cocktail ice. There is plenty of room for friends and family to sprawl out as this house boasts an eat in kitchen as well as a formal dining area, and dual living room/family room areas that are split by a gorgeous, wood burning fireplace giving this home the coziest, homiest feeling. Love to have fun pool days? There is an oversized 14 x 34 lanai off the rear of the home decked out with an outdoor kitchen from Paradise Grills perfect for grilling out and relaxing. The oversized pool is a perfect place to cool off afterwards. This home has so much charm as a sprawling 1 story on a huge lot with space between houses, which is a rare find in this area. The backyard is fenced in for your furry friends enjoyment, and there is even plenty of land left to build an in-law suite if that is something you desire to do. With a fully renovated kitchen, and newly renovated bathrooms, this home is truly a turnkey experience. The sellers have poured tons of money into this home, please see MLS attachments for full list of recent upgrades. This home is zoned for top ‘A’ rated schools of Orange County including Windermere Elementary, Bridgewater Middle, and Windemere High school making it a great pick for personal enjoyment and resale value. The home has a 2 car garage attached to the home, and a 4 car detached garage in the back. ****Updates the sellers have completed since purchase: New AC unit - main house (Jan 2023) - New water heater (Oct 2021) - New water chlorination filtration system (2025)- Custom trim and molding throughout house (2025) - Custom built in shelving (2025) - Both bathrooms updated w custom cabinetry (2022 and 2025) - Black aluminum fencing in backyard (2021) - New AC in back garage (Sept 2021) - New refrigerator – LQ ThinQ (2025) - Pool area concrete replaced with pavers and patio extended off the master suite (2022) - New septic drain field and septic pumped (2026)... additionally, the kitchen and master bathroom were gutted and completely renovated in 2017, roof is 2017.

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    Listing is courtesy of: LOKATION

  • 9960 6TH ST, WINDERMERE, FL - MLS# O6412077

    GOTHA TOWN - O6412077 - 9960 6TH ST, WINDERMERE, FL 34786
    2 Days on yellowkey

    $3,750,000 | Single Family Home | 5 beds | 5.5 baths | 3 gar

    Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and comfortable everyday living, the home features a grand foyer with soaring ceilings, expansive living and family rooms, a private study, and a spectacular gourmet kitchen with an oversized island, walk-in pantry, and premium finishes throughout. The luxurious first-floor owner's retreat serves as a private sanctuary with a spa-inspired bath, oversized walk-in closets, and direct access to the outdoor living areas. Upstairs, you'll find additional en-suite bedrooms surrounding a spacious loft and bonus room, providing the perfect space for family gatherings, a media room, or guest accommodations. Large covered lanais seamlessly blend indoor and outdoor living, creating an ideal setting for entertaining while enjoying Florida's year-round lifestyle. Situated in prestigious Windermere, this exceptional estate combines timeless architecture, thoughtful design, and superior craftsmanship, all within close proximity to top-rated schools, world-class golf, fine dining, shopping, and the Butler Chain of Lakes.

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    Listing is courtesy of: NOVA REAL ESTATE SERVICES INC

  • 2428 BUTLER BAY DR N, WINDERMERE, FL - MLS# O6410967

    BUTLER BAY - O6410967 - 2428 BUTLER BAY DR N, WINDERMERE, FL 34786
    2 Days on yellowkey

    $1,150,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar

    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!

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 13327 LAKE CLARICE DR, WINDERMERE, FL - MLS# O6411453

    THE ESTATES AT LAKE CLARICE - O6411453 - 13327 LAKE CLARICE DR, WINDERMERE, FL 34786
    2 Days on yellowkey

    $2,180,000 | Single Family Home | 5 beds | 4.0 baths | 3 gar

    Nestled on 1.26 pristine lakefront acres within the exclusive Estates at Lake Clarice community and zoned for top-rated public schools, this custom-built estate offers an extraordinary blend of luxury, privacy, and lifestyle in the heart of Windermere. With expansive lake frontage and the opportunity to build your own private dock or gazebo, the property showcases breathtaking water views and even nightly Disney fireworks displays from the comfort of home. Adding to its rare appeal, HOA-owned land and a pond directly across the street ensure no front or rear neighbors, creating a truly serene and private setting. Designed with both elegance and functionality in mind, this impressive 5-bedroom, 4-bath residence features formal living and dining rooms, a private office, and an upstairs bonus/theater room. Complementing the home’s timeless architecture, soaring 12-foot ceilings on the main level and 9-foot ceilings upstairs create a bright and airy atmosphere throughout. From the moment you step through the grand wrought iron and glass entry doors, custom details shine with extensive moldings, intricate ceiling details, and rich hardwood flooring. The private office/study offers a wine cellar, while the luxurious primary suite features a sitting alcove, dual vanities, and a customized walk-in closet. At the heart of the home, the open-concept kitchen is designed for gathering and entertaining, complete with stainless steel appliances, stacked cabinetry with glass accents and lighting, granite countertops, an oversized island, breakfast bar, gas range, and seamless flow into the family room. Framed by expansive windows and French doors, the family room showcases a stunning stone gas fireplace, custom built-ins, and panoramic lake views that beautifully bring the outdoors in. Upstairs, four oversized secondary bedrooms and a spacious bonus/theater room are connected by a second staircase leading directly to the family room below. Outdoor living is equally impressive, with expansive covered porches on both levels — a standout architectural feature admired throughout the neighborhood — offering the perfect spaces to unwind and enjoy the picturesque surroundings. The screened resort-style pool and spa with paver decking, reaching 6 feet deep, provide ample space for recreation and entertaining, while the covered lanai and summer kitchen with grill, refrigeration, and gas outdoor grill connection create the ultimate outdoor retreat. Additional highlights include a spacious laundry room, oversized 3-car garage, Andersen windows newly installed on two-thirds of the home in 2025, and ample room on the expansive lot to build an additional garage, guest house, or mother-in-law suite. This remarkable lakefront estate offers timeless elegance, unmatched privacy,

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    Listing is courtesy of: FLORIDA REALTY INVESTMENTS

  • 9376 WOODBREEZE BLVD, WINDERMERE, FL - MLS# O6411270

    SILVER WOODS PH 03 - O6411270 - 9376 WOODBREEZE BLVD, WINDERMERE, FL 34786
    3 Days on yellowkey

    $675,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Nestled inside the cozy community of Silver Woods, this 4 bedroom/2.5 bathroom residence is ready to welcome you home! Immediately upon pulling up to the house, you'll notice the immaculate landscaping and fresh exterior paint that gives the home a vibrant feel. But the good vibes don't stop at the front door! Once inside, you're immediately greeted with an open concept plan that still offers plenty of privacy. Just to the left you'll find the formal sitting room, perfect for drinks with guests or as a play area for children. Step further into this tranquil retreat and have your jaw dropped by the beautifully renovated chef's kitchen that overlooks the pool and large backyard! The family room is just to the right, providing plenty of comfortable space for unwinding after a long day. Beyond the family room sits 3 bedrooms and a bathroom that connects to the pool deck. Head back into the main living area and towards the opposite end of the house where you'll find the dining room just beyond the kitchen, complete with a stunning wall unit! Step inside your primary suite that is sure to make you feel at peace and ready for a good night's sleep! Then, of course, there's the outdoor living space that will blow you away! Open the pocketing glass doors to a covered seating area that overlooks the screened-in pool with attached spa. Off to the side you'll discover a hidden area perfect for storing pool supplies or grilling equipment OR a bar and couches for entertaining! The park-like backyard will WOW you with the amount of space it provides. Playground and swing included! And if all that isn't enough, this home offers a NEW ROOF, new duct work, new flooring and fresh interior paint! 9376 Woodbreeze Boulevard is sure to please a variety of home buyers, so schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO

  • 11822 SILVERLAKE PARK DR, WINDERMERE, FL - MLS# O6409301

    WINDERMERE TRLS PH 1C - O6409301 - 11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786
    3 Days on yellowkey

    $495,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Meticulously maintained, this 3-bedroom, 2.5-bathroom two-story home sits in an unbeatable location directly across from Bay Lake Elementary. The first level features a welcoming front porch, an open-concept living area with brand-new LVP flooring, an updated half bath, and a beautifully appointed kitchen boasting stone countertops, a walk-in pantry, and a breakfast bar. Upstairs, a versatile spacious loft leads to two guest bedrooms and a primary suite complete with newly installed carpet, updated bathroom with dual vanities, a tile shower, and a walk-in closet. Big-ticket upgrades offer total peace of mind, including a new roof (2022) and a new hybrid water heater (2025). Windemere Trails community offers excellent amenities and is ideally situated just minutes from Lakeside Village Center and Westside Shoppes (Publix, dining, fitness, and more) and a short drive to Orlando's Theme Parks, World Class Dining, Shopping, and Golf. This low-maintenance home offers exceptional accessibility and turnkey living!

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    Listing is courtesy of: REDFIN CORPORATION

  • 1924 DOWN HOLLOW LN, WINDERMERE, FL - MLS# O6398100

    ACREAGE - O6398100 - 1924 DOWN HOLLOW LN, WINDERMERE, FL 34786
    3 Days on yellowkey

    $1,680,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Escape the ordinary! This charming Windermere cottage on the Butler Chain, is set on a beautiful and private wooded lot with a rare opportunity for lake and boat frontage on Lake Down! This inviting residence is nestled on nearly two acres in a serene, Florida-style setting, offering the perfect blend of privacy and convenience. Thoughtfully renovated, this 3-bed, 2.5-bath, 2-car garage home embraces a warm, relaxed style with timeless cottage appeal and inviting indoor-outdoor living. A welcoming front porch entry sets the tone for a spacious great room with a cozy fireplace, an eat-in kitchen with natural light, ample cabinets and counter top space, perfect for everyday living and hosting. The first-floor primary suite includes a walk-in closet and a private bath, featuring a dual vanity and a separate shower. The sunroom sitting areas open to an expansive deck with a recessed spa and TV, creating the perfect setting for entertaining or quiet evenings surrounded by nature. A true retreat, with a private walkway and dock leading directly to Lake Down, offering seamless access to the Butler Chain of Lakes and all the recreation the 13 interconnected lakes have to offer. Conveniently located near Downtown Windermere, top-rated schools, shopping, and dining, with easy access to major roadways and airports, delivers the best of both tranquility and accessibility.

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    Listing is courtesy of: THE REAL ESTATE COLLECTION LLC

  • 12633 HADDON DR, WINDERMERE, FL - MLS# O6411199

    LAKES WINDERMERE - O6411199 - 12633 HADDON DR, WINDERMERE, FL 34786
    3 Days on yellowkey

    $650,000 | Single Family Home | 5 beds | 3.5 baths | 2 gar

    Sitting on a premium corner lot with mature landscaping, this beautiful Kensington model by Ashton Woods is located in the highly sought-after Lakes of Windermere community! Offering nearly 3,000 sq ft, this move-in ready home has been meticulously cared for and features room for a future pool. Recent updates include a new roof (2024), new downstairs A/C (2026), upstairs A/C (2023), upgraded Stainmaster PetProtect carpet (2026), quartz countertops, marble backsplash, cabinet lighting, paver patio, aluminum fencing, and updated landscaping. Inside, you’ll love the open split-bedroom floor plan, crown molding, upgraded flooring, and spacious kitchen with tons of cabinet space and stainless steel appliances overlooking the family room with custom built-in entertainment center wired for home theater. Upstairs 5th bedroom with full bath could also make the perfect theater room, game room, and guest suite. Lakes of Windermere offers a welcoming small-town atmosphere with resort-style amenities including a fishing dock, junior Olympic-size community pool, tennis courts, playgrounds, and organized recreational activities. Ideally located just minutes from Disney, Winter Garden Village, I-4, SR 408, and the Florida Turnpike.

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    Listing is courtesy of: REAL BROKER, LLC

  • 13450 SUNKISS LOOP, WINDERMERE, FL - MLS# O6407409

    SUMMERPORT PH 03 - O6407409 - 13450 SUNKISS LOOP, WINDERMERE, FL 34786
    4 Days on yellowkey

    $574,900 | Single Family Home | 5 beds | 2.5 baths | 2 gar

    This 5-bedroom, 2.5-bathroom two-story home offers a spacious and highly functional layout, perfect for large households or those needing extra space. The main level features a formal front living room and a well-appointed kitchen with all appliances included and in good working order. For added convenience and privacy, the primary suite is located on the first floor, while the four secondary bedrooms and a full bathroom are situated on the second level. Complete with an attached 2-car garage, this home provides a smart separation of space and a move-in-ready interior.

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    Listing is courtesy of: ENTERA REALTY LLC

  • 5199 LATROBE DR, WINDERMERE, FL - MLS# O6409961

    ISLEWORTH - O6409961 - 5199 LATROBE DR, WINDERMERE, FL 34786
    4 Days on yellowkey

    $5,300,000 | Single Family Home | 6 beds | 6.5 baths | 4 gar

    Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.

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    Listing is courtesy of: ISLEWORTH REALTY LLC

  • 2002 WATER KEY DR, WINDERMERE, FL - MLS# O6408915

    RESERVE AT WATERFORD POINTE PH 01 - O6408915 - 2002 WATER KEY DR, WINDERMERE, FL 34786
    4 Days on yellowkey

    $1,299,000 | Single Family Home | 5 beds | 5.0 baths | 3 gar

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Set behind the gates of Reserve at Waterford Pointe, this exceptional 5-bedroom, 5-bathroom estate spans 3,695 square feet on more than half an acre of beautifully manicured grounds, delivering refined everyday living in one of Central Florida's most sought-after lakeside communities. Framed by freshly updated landscaping and mature greenery, the residence commands attention with its stately presence, expansive lot, and genuine sense of privacy. Recent upgrades elevate both comfort and longevity, including a new HVAC system, new water heater, fresh carpet in the main living areas, and tile flooring throughout the primary rooms. A grand entry introduces spectacular formal living and dining spaces designed to elevate both intimate gatherings and large-scale entertaining. At the heart of the home, the chef's kitchen is thoughtfully designed with a large center island, bar seating, stainless steel appliances, abundant cabinetry, and an open-concept layout that flows effortlessly into the main living areas. Overlooking the kitchen, the family room feels both warm and dramatic, anchored by a striking floor-to-ceiling stone feature wall with a gas fireplace that creates an inviting focal point. Privately positioned, the primary suite serves as a luxurious retreat with direct access to the outdoor living spaces. Spacious and serene, it is complemented by a spa-inspired bath with dual vanities, a soaking tub, walk-in shower, and an oversized walk-in closet designed for both comfort and functionality. Upstairs, a generous bonus room doubles as a private movie theatre with a wet bar, offering an ideal space for entertaining, relaxing, or hosting guests in a setting that feels distinctly elevated. Beyond the interiors, the home opens into a private outdoor oasis featuring a sprawling screened lanai, sparkling pool and spa, and a fully equipped summer kitchen with grill and bar seating. The expansive backyard delivers exceptional space and privacy, framed by lush mature landscaping that creates a tranquil, secluded atmosphere. Residents of The Reserve at Waterford Pointe enjoy an exclusive lifestyle with access to private community amenities, including a boat ramp to Lake Roberts, tennis courts, a playground, and beautifully maintained park spaces. Ideally positioned just minutes from Disney, Universal Orlando, SR 429, the Florida Turnpike, and some of Central Florida's finest shopping and dining destinations, this remarkable residence offers a rare combination of luxury, privacy, and convenience.

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    Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC

  • 10520 PARK RIDGE GOTHA RD, WINDERMERE, FL - MLS# O6409659

    NONE - O6409659 - 10520 PARK RIDGE GOTHA RD, WINDERMERE, FL 34786
    4 Days on yellowkey

    $2,400,000 | Single Family Home | 4 beds | 3.5 baths

    This listing presents two distinct 1+ acre residential properties, located at 10532 & 10520 Park Ridge Gotha Rd, offering a unique opportunity: a 2.522-acre residential estate parcel situated in Windermere, Florida. The two adjacent lots, both exceeding one acre, currently feature vacant, yet well-maintained, older single-family homes. Windermere is renowned as one of Central Florida's most desirable, high-end luxury communities. Orange County's A1 zoning permits one single-family home per acre, in addition to horses, agricultural activities, barns, nurseries, sheds, etc. The property offers ample space for various amenities, including a pool, summer kitchen, tennis court, playground, or horses and stables. The neighborhood is predominantly comprised of large, luxury residences. The land is high and dry & flat and level, with only a few mature trees. This premium location provides convenient access to numerous retail developments, hospitals, expressways, restaurants, entertainment venues, golf courses, Publix, Walmart, and other popular shopping areas. Please be advised that these two parcels can only be purchased together as a package; they are not available for individual purchase. Note the attachments for aerial video, surveys, floor plans, and other descriptions.

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    Listing is courtesy of: DAVID WEAVER, REALTOR

  • 8360 VIVARO ISLE WAY, WINDERMERE, FL - MLS# S5150324

    WINDERMERE ISLE - PHASE 2 - S5150324 - 8360 VIVARO ISLE WAY, WINDERMERE, FL 34786
    5 Days on yellowkey

    $690,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Beautiful home located in a quiet and well-maintained community. This property features a functional layout with spacious, light-filled interiors. It offers 4 bedrooms and 2.5 bathrooms. The kitchen is equipped with appliances, and ample storage space—perfect for everyday living and entertaining. Additionally, it includes a private patio, perfect for relaxing or enjoying outdoor time. The community offers great amenities such as a swimming pool and common areas. Prime location close to shopping centers, restaurants, supermarkets, and with easy access to major highways.

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    Listing is courtesy of: MD3 HOMES LLC

  • 12623 PARK AVE, WINDERMERE, FL - MLS# O6410693

    CHAINE DE LAC - O6410693 - 12623 PARK AVE, WINDERMERE, FL 34786
    5 Days on yellowkey

    $3,800,000 | Single Family Home | 5 beds | 6.0 baths | 6 gar

    Experience Unparalleled Luxury in Chaine Du Lac Nestled within the sought- after gated community of Chaine Du Lac, this extraordinary custom estate redefines luxury living. Offering over 7,100 sqft of meticulously crafted living space, this magnificent residence features 5 bedrooms, 5 full bathrooms, and 2 half bathrooms, combining timeless elegance with exceptional craftsmanship in one of Central Florida's most sought-after addresses. A pair of custom wrought-iron front doors welcomes you into a breathtaking foyer highlighted by a dramatic circular dome ceiling and grand architectural details. Porcelain flooring flows throughout the home, while custom barrel ceilings, designer ceiling treatments, extensive tray ceilings, and crown molding showcase the remarkable attention to detail found in every room. Expansive windows fill the residence with natural light, creating a warm and inviting atmosphere throughout. Each of the five bedrooms serves as a private suite, complete with its own luxurious en-suite bathroom and custom walk-in closet. Designer ceilings, elegant trim work, offering comfort, privacy, and sophistication for family and guests alike. Designed for both everyday living and grand-scale entertaining, the chef's kitchen is truly a showpiece. Premium Thermador appliances, a custom hand-hammered copper hood, abundant cabinetry, a spacious walk-in pantry, natural gas, and stunning natural quartzite countertops combine beauty and functionality to create an exceptional culinary experience. The outdoor living spaces are equally impressive, featuring over 7,000 square feet of premium travertine hardscaping, including a grand travertine driveway and expansive rear paver terraces. Covered outdoor living areas on both levels are enhanced by beautiful tongue-and-groove wood ceilings, creating seamless indoor-outdoor living. The expansive upstairs balcony offers the perfect setting to relax, entertain, and enjoy Florida's year-round lifestyle. Car enthusiasts will appreciate the oversized 6-car garage, offering ample space for a prized collection, recreational vehicles, or workshop space. A private executive office has been strategically designed with a direct view into the garage, creating a unique showcase for automotive enthusiasts and allowing your collection to become part of the home's everyday living experience. Entertainment and lifestyle amenities continue throughout the home, including a dedicated theater room, whole-home surround sound system, and a private salon complete with its own half bathroom. A durable and elegant metal roof crowns the residence, while extensive custom millwork and luxury finishes further elevate the home's exceptional quality and craftsmanship. Residents enjoy the prestige and security of a community patrolled by the Windermere Police Department following annexation into the Town of Windermere. Just minutes away, experience the charm of downtown Windermere, where weekly farmers markets, food truck gatherings, boutique shopping, and community events create a lifestyle as inviting as it is exclusive. This extraordinary residence offers a rare combination of architectural excellence, luxury finishes, resort-style outdoor living, and an unmatched location within one of Central Florida's most coveted communities. A true showcase estate designed for those who demand the very best in luxury living. More than a home, it's a masterpiece of luxury living in the coveted Chaine Du Lac.

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    Listing is courtesy of: ELEVATE REAL ESTATE BROKERS

  • 4303 ISABELLA CIR, WINDERMERE, FL - MLS# O6409406

    CASABELLA - O6409406 - 4303 ISABELLA CIR, WINDERMERE, FL 34786
    5 Days on yellowkey

    $2,899,000 | Single Family Home | 7 beds | 5.0 baths | 5 gar

    Located in one of Windermere’s most sought-after luxury GATED communities with 24-HOUR SECURITY-SCREENED ENTRY, Casabella, this exceptional custom-enhanced ESTATE showcases ultra-modern design, refined craftsmanship, and elevated INDOOR-OUTDOOR LIVING, offering impressive scale, custom design, and an exceptional lifestyle experience. Designed with both scale and functionality in mind, the home features an OPEN-CONCEPT floor plan with 7 BEDROOMS, including a beautifully appointed MAIN-LEVEL Primary Suite with a spa-inspired bath, freestanding soaking tub, expansive dual custom-designed walk-in closets, oversized glass-enclosed shower, and integrated STEAM SAUNA. The main floor also includes an additional GUEST SUITE and 2 HALF BATHS. Upstairs, 5 additional BEDROOMS, 2 FULL BATHROOMS, and a spacious LOFT create a well-designed secondary living retreat, offering flexibility for gathering, relaxation, and elevated everyday living. The expansive DESIGNER-ENHANCED GOURMET KITCHEN serves as a striking centerpiece of the home, showcasing imported custom cabinetry, architect-inspired detailing, premium JennAir APPLIANCES, and seamless flow into the GREAT ROOM, multiple dining areas, and surrounding living spaces. Additional interior highlights include a custom-designed EXECUTIVE OFFICE, luxury flooring throughout, ELECTRIC blackout shades, DIGITAL CODE LOCK entry systems on all bedroom doors for added privacy and convenience. Across all 4 FULL BATHROOMS and 2 HALF BATHS, the home showcases floor-to-ceiling tilework, integrated bidet systems, and refined finishes throughout, while 1 HALF BATH offers direct OUTDOOR ACCESS, adding convenience for the POOL and surrounding outdoor living spaces. Designed for both relaxation and everyday enjoyment, the outdoor living experience features a HEATED SALTWATER POOL, SPA, SUMMER KITCHEN, FENCED BACKYARD, and mature PRIVACY LANDSCAPING. Set on approximately 0.63 ACRES, the property also includes a 5-CAR GARAGE with EPOXY FLOORING and AIR-CONDITIONED garage space, an estate-style driveway with exceptional space for car enthusiasts and guests, TESLA CHARGER, FULLY PAID SOLAR PANELS, WATER SOFTENER SYSTEM, and a WHOLE-HOUSE GENERATOR. With proximity to premier GOLF COURSES, scenic LAKES including the Butler Chain of Lakes, top-rated public and private schools, shopping, hospitals, and major roadways, plus convenient access to Disney and Orlando’s premier attractions, Casabella offers privacy, security, and elevated luxury living in one of Windermere’s most desirable communities.

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    Listing is courtesy of: SERHANT

  • 11524 CLAYMONT CIR, WINDERMERE, FL - MLS# O6410754

    KEENES POINTE - O6410754 - 11524 CLAYMONT CIR, WINDERMERE, FL 34786
    5 Days on yellowkey

    $1,288,999 | Single Family Home | 5 beds | 4.0 baths | 3 gar

    *** One of the lowest $/SF in Keene's Pointe *** Welcome to this updated, move-in ready luxury home in Keene’s Pointe, one of Windermere’s premier 24-hour guard-gated golf communities and home to the Golden Bear Club. Offering 5 bedrooms, 4 bathrooms, and 3,358 square feet of living space, this beautifully upgraded residence combines luxury finishes, functional design, and an exceptional Central Florida lifestyle just minutes from Disney, top-rated Windermere schools, shopping, dining, and major highways. Situated on an oversized homesite with a large driveway accommodating up to nine vehicles and a three-car garage, this home makes an immediate impression. Inside, the open-concept floor plan features commercial-grade porcelain tile flooring, crown molding, updated lighting, designer finishes, and spacious living areas designed for both everyday living and entertaining. Just off the entry, a custom wet bar with wine refrigerator and beverage fridge flows seamlessly into the dining area and main living space. The updated chef’s kitchen overlooks the family room and showcases quartz countertops, a large center island with additional 36-inch cabinetry storage, a farmhouse sink, soft-close dovetail cabinetry, stainless steel appliances, a natural gas range with vent hood, and an ideal layout for entertaining guests or hosting family gatherings. The spacious first-floor primary suite serves as a private retreat and features a large custom walk-in closet along with a beautifully updated spa-style bathroom complete with dual vanities, soaking tub, oversized walk-in shower with multiple spray features, and custom tile details. Three additional bedrooms and two updated bathrooms are located on the main level, while all bedrooms include custom closet systems and updated ceiling fans. Upstairs, newly finished stairs lead to a versatile loft with luxury vinyl plank flooring, an additional bedroom, and a full bathroom, creating flexible space ideal for a media room, home office, guest suite, or multigenerational living setup. The outdoor living space is designed for Florida entertaining with an approximately 900-square-foot paver patio, natural gas firepit, spacious backyard, and nightly Disney fireworks views. The rear yard is also prewired with 50-amp power for a future pool installation if desired by the next owner. Additional improvements include a 2021 roof replacement, extensive updates throughout the home, a new natural gas meter installed in 2025, and a meticulously maintained septic system with annual servicing over the past 10 years, a new septic alarm box and meter installed in 2021, and a new septic float installed in early 2025. The property also offers exceptional storage with three overhead garage storage racks rated for 600 pounds each, along with a fully planked, lighted, and walkable attic space above the entire three-car garage. Residents of Keene’s Pointe enjoy access to private boardwalks to Lake Tibet and the Butler Chain of Lakes, two community boat ramps, four playgrounds, and year-round neighborhood events. Optional Golden Bear Club membership offers access to championship Jack Nicklaus-designed golf, tennis courts, resort-style pool, fitness center, dining, and social activities. This updated Windermere luxury home offers a rare opportunity to own in one of Central Florida’s most desirable gated golf communities. Schedule your private showing today.

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    Listing is courtesy of: ALIGN REAL ESTATE LLC

  • 8715 QUIET MEADOWS TRL, WINDERMERE, FL - MLS# O6410762

    WINDERMERE TRLS PH 1C - O6410762 - 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786
    6 Days on yellowkey

    $840,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar

    Experience 8715 Quiet Meadows Trl, a residence recently refreshed with fresh interior paint throughout. The kitchen is equipped with a central island and all stainless steel appliances. The primary bathroom features double sinks and a separate tub and shower, while the primary bedroom contains a walk in closet. Outside, a covered patio overlooks a ground pool and partially fenced. A perfect blend of modern updates and refreshing outdoor comfort. Included 100-Day Home Warranty with buyer activation

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    Listing is courtesy of: OPENDOOR BROKERAGE LLC

  • 13732 SUMMER HARBOR CT, WINDERMERE, FL - MLS# O6410454

    SUMMERPORT TRAIL PH 2 - O6410454 - 13732 SUMMER HARBOR CT, WINDERMERE, FL 34786
    8 Days on yellowkey

    $599,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Wonderful opportunity rental investment . Prepare to be amazed by this beautiful nature friendly corner lot in Summerport. This spacious & immaculate 4-bedroom 2.5 bath features an array of upgrades. Enjoy the tranquil Waterfront pond and Disney fireworks from the comfort of your front porch. This premium lot is sitting on a quiet CUL-DE-SAC, nestled in a corner with no right neighbors and stunning conservation area. The home chef will appreciate the beautiful kitchen that features granite, custom 42" cabinets, stainless appliances and walk-in pantry. The living room boasts of high ceilings all the way to the second story with lots of windows to provide a light and bright area. The second story has four bedrooms including the Master Suite and laundry room for convenience. Community and Recreational Amenities include the following: community recreation/fitness center, tennis courts, junior Olympic pool, playground, basketball court, sand volleyball court, bike/nature trail, 2 lakeside parks with lake access. LOCATION, LOCATION, LOCATION, you’re walking distance from Windermere High School, Publix, shops & restaurants. 5-minute drive from Winter Garden Village center where you can enjoy a list of shops and restaurants. Easy access to major road ways such as the 429, I-4, 408 and Florida Turnpike. Excellent Tenant in place otherwise 60 day-period to move out This gem won't last, schedule your tour today!

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    Listing is courtesy of: SANCHEZ PROPERTIES GROUP LLC

  • 811 MAIN ST, WINDERMERE, FL - MLS# O6409463

    WINDERMERE TOWN - O6409463 - 811 MAIN ST, WINDERMERE, FL 34786
    8 Days on yellowkey

    $649,999 | Single Family Home | 2 beds | 1.5 baths | 1 car

    Exclusive Rare Opportunity to own this expansive 100'x160' double lot in downtown Windermere. Whether you’re looking for a charming home or a prime location to build your dream residence, this property delivers endless potential. The home features arched doorways, luxury vinyl plank (LVP) flooring, and a sunroom filled with natural light. The updated kitchen includes 42” soft-close cabinets, Granite countertops, stainless steel appliances, and a custom island with a breakfast bar. The primary bedroom boasts a spacious walk-in closet with custom built-ins, and the bathroom is finished with marble and subway tile. The nearly half-acre lot offers a fenced backyard, custom pergola, wood deck, fire pit, and a storage shed with electricity, perfect for entertaining or relaxing. Enjoy walking proximity to Windermere’s cafes, parks, and events like the Farmers Market. Deeded access to the Butler Chain of Lakes and Lake Bessie provides excellent opportunities for boating and water sports. With no HOA, A-rated schools, and golf-cart-friendly streets, this property blends convenience and practicality. Schedule your showing today.

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    Listing is courtesy of: CAMERON REALTY GROUP LLC

  • 7867 BERKSHIRE OAK ALY, WINDERMERE, FL - MLS# S5149947

    WESTSIDE VILLAGE - S5149947 - 7867 BERKSHIRE OAK ALY, WINDERMERE, FL 34786
    9 Days on yellowkey

    $539,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    Luxury Living in the Heart of Windermere! Welcome to this beautifully maintained 4 bedrooms and 2.5 bathrooms, single family home, located in the highly desirable community of Windermere. Situated on a charming alley-style streetscape, this elegant property offers the perfect blend of comfort, style, and convenience in one of Central Florida’s most sought-after locations. This spacious home features an open and functional floor plan with abundant natural light, generous living and dining areas, and thoughtfully designed spaces ideal for both everyday living and entertaining. Enjoy a fresh updated feel with NEW interior paint and NEW exterior paint, enhancing both the beauty and curb appeal of the home. The kitchen offers ample cabinetry, modern appliances, and a functional layout overlooking the main living area. The primary suite provides a relaxing private retreat with an en-suite bathroom and spacious closet space, while additional bedrooms flexibility for family, guests, or a home office. Enjoy outdoor Florida living with a private patio/backyard area perfect for relaxing or hosting gatherings. The community features beautifully maintained surroundings and convenient access to nearby parks, walking trails, and recreational areas. Ideally located just minutes from shopping, dining, top-rated schools, major highways, and world-famous attractions, including nearby Walt Disney World Resort. Easy access to Orlando, Winter Garden, and surrounding areas makes this an exceptional opportunity for homeowners seeking both convenience and lifestyle. Don’t miss your opportunity to own this beautiful Windermere home—schedule your private showing today!

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    Listing is courtesy of: MULTI CHOICE REALTY LLC

  • 2230 RIDGEWIND WAY, WINDERMERE, FL - MLS# O6410264

    ESTATES AT WINDERMERE - O6410264 - 2230 RIDGEWIND WAY, WINDERMERE, FL 34786
    9 Days on yellowkey

    $1,349,000 | Single Family Home | 5 beds | 4.0 baths | 3 gar

    One or more photo(s) has been virtually staged. Spacious and beautifully maintained 5-bedroom, 4-bath pool home situated on a 1/2-acre fenced treed lot in desirable Estates at Windermere. This stunning residence offers a great split floorplan with generous living spaces, high ceilings, and abundant natural light throughout. As you enter the home the dining room is to the left and the living room on the right side could also be an office or den. The spacious family room with built-ins creates the perfect gathering space. The kitchen features granite countertops, stainless steel appliances, ample cabinetry and a breakfast area. The primary suite includes a spa-inspired bath, dual vanities, a soaking tub, and a walk-in shower. There are three spacious secondary bedrooms and two full baths offering flexibility for family and guests. There is a bonus room with a closet and full bath that provides endless possibilities like a mother-in-law suite, guest retreat, home office, media room or the 5th bedroom. Step outside to your private backyard oasis complete with a sparkling screened pool, covered lanai, and beautifully landscaped yard that backs to an expansive greenbelt common area that affords privacy. The owners have made many updates over the years and recently including new sliding hurricane doors, new carpet in all four bedrooms, painted the outside of the house and newer appliances. Conveniently located near top-rated schools, shopping, dining, attractions and major roadways. This exceptional home combines comfort, elegance, and the best of Florida living.

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    Listing is courtesy of: COLDWELL BANKER REALTY

  • 11326 LEDGEMENT LN, WINDERMERE, FL - MLS# O6409714

    GLENMUIR 48 39 - O6409714 - 11326 LEDGEMENT LN, WINDERMERE, FL 34786
    10 Days on yellowkey

    $939,000 | Single Family Home | 5 beds | 3.5 baths | 2 gar

    One or more photo(s) has been virtually staged. Experience refined living in this beautifully updated 5-bedroom home, nestled in an exclusive gated community zoned for top-rated schools. The open-concept main level boasts soaring high ceilings, abundant natural light, elegant tile flooring, and a convenient primary suite for ultimate privacy. At the heart of the home is a fully remodeled kitchen (2021) featuring upgraded cabinetry and modern finishes. Upstairs, you'll find premium luxury vinyl plank flooring, newly replaced in 2026. Additional high-value upgrades include a whole-house water filtration system and a private well irrigation system (both installed in 2022). 2 Air Conditioning units installed in October, 2020. Combining security, style, and efficiency, this thoughtfully upgraded home is completely move-in ready!

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    Listing is courtesy of: AAA GLOBAL VENTURES PA





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