Windermere Real Estate for Sale by Neighborhood

Find Windermere Real Estate for Sale by clicking on the relevant neighborhood.

View all Windermere Real Estate for Sale

BALMORAL real estate for sale BELLARIA real estate for sale
BELMERE VILLAGE G2 48 65 real estate for sale BUTLER BAY real estate for sale
CARRINGTON real estate for sale CASABELLA real estate for sale
DAVIS SHORES real estate for sale EDEN ISLE real estate for sale
ENCLAVE real estate for sale ESTANCIA/WINDERMERE real estate for sale
ESTATES AT LAKE CLARICE real estate for sale GOTHA TOWN real estate for sale
ISLEWORTH real estate for sale KEENES POINTE real estate for sale
KEENES POINTE UT 04 SEC 31 48 82 real estate for sale KELSO ON LAKE BUTLER real estate for sale
LAKE BURDEN SOUTH PH 2 real estate for sale LAKE BURDEN SOUTH PH I real estate for sale
LAKE BUTLER ESTATES real estate for sale LAKE CAWOOD COVE real estate for sale
LAKE DOWN SHORES real estate for sale LAKE DOWN WOODS real estate for sale
LAKE ROPER POINTE real estate for sale LAKE SAWYER real estate for sale
LAKE SAWYER SOUTH real estate for sale LAKE SAWYER SOUTH PH 01 real estate for sale
LAKE SAWYER SOUTH PH 03 real estate for sale LAKE SAWYER SOUTH PH 2 real estate for sale
LAKE SAWYER SOUTH PH 3 real estate for sale LAKE SAWYER SOUTH PH 5 real estate for sale
LAKE SAWYER SOUTH PHASE 5 real estate for sale LAKES real estate for sale
LAKES OF WINDERMERE - LAKE REAMS TOWNHOMES real estate for sale LAKES OF WINDERMERE-PEACHTREE real estate for sale
LAKES WINDERMERE real estate for sale LAKES WINDERMERE PH 01 49 108 real estate for sale
LAKES/WINDERMERE real estate for sale LAKES/WINDERMERE PH 02A real estate for sale
LAKES/WINDERMERE-LK REAMS TWHM real estate for sale LAKES/WINDERMERE-LK REAMS TWNH real estate for sale
LAKES/WINDERMERE-PEACHTREE real estate for sale LAKESIDE/LKS/WINDERMERE real estate for sale
MAGNOLIA PARK WINDERMERE real estate for sale METCALF PARK REP real estate for sale
N/A real estate for sale NA real estate for sale
PALMS AT WINDERMERE real estate for sale PRESTON SQUARE real estate for sale
RESERVE AT BELMERE real estate for sale RESERVE AT BELMERE PH 02 48 144 real estate for sale
RESERVE AT LAKE BUTLER SOUND real estate for sale SAWYER SOUND real estate for sale
SILVER WOODS real estate for sale SUMMERPORT real estate for sale
SUMMERPORT PH 03 real estate for sale SUMMERPORT PH 05 real estate for sale
TILDENS GROVE real estate for sale VINEYARDS/HORIZONS WEST PH 2B real estate for sale
VINEYARDS/HORIZONS WEST PH 4 real estate for sale WATERSTONE real estate for sale
WEATHERSTONE ON LAKE OLIVIA real estate for sale WESTSIDE VILLAGE real estate for sale
WILLOWS AT LAKE RHEA PH 02 real estate for sale WINDERMERE real estate for sale
WINDERMERE CLUB real estate for sale WINDERMERE DOWNS real estate for sale
WINDERMERE ISLE real estate for sale WINDERMERE SOUND real estate for sale
WINDERMERE TERRACE real estate for sale WINDERMERE TOWN real estate for sale
WINDERMERE TRLS PH 1C real estate for sale WINDERMERE TRLS PH 3B real estate for sale
WINDERMERE TRLS PRCL 3 real estate for sale WINDSOR HILL real estate for sale
WINDSTONE real estate for sale

Newest Real Estate in Windermere by Neighborhood

View all Windermere Real Estate for Sale

  • 4482 BEGONIA CT, WINDERMERE, FL - MLS# O6424551

    MAGNOLIA PARK WINDERMERE - O6424551 - 4482 BEGONIA CT, WINDERMERE, FL 34786
    Just Added on 07/16/2026 10:51AM

    $950,000 | Single Family Home | 5 beds | 4.5 baths | 3 gar

    Under contract-accepting backup offers. Rarely does an opportunity like this become available in one of Windermere's most exclusive gated communities. Set behind the gates of Magnolia Park, an intimate enclave of just 32 custom-designed homes, this pool estate offers 4,544 heated square feet with 5 bedrooms, 4 full bathrooms, 1 half bath, a 3-car garage, and a circular driveway, all on an impressive 0.85-acre homesite. Whether you're looking to create your forever home or invest in one of Windermere's premier communities, this is a rare opportunity to customize a luxury estate to your exact vision. Situated on a quiet cul-de-sac, this impressive residence welcomes you with soaring ceilings exceeding 20 feet in the family room, creating an impressive sense of space and natural light. Formal living and dining rooms provide elegant spaces for entertaining, while the thoughtfully designed floor plan offers exceptional flexibility for today's lifestyle. The private first-floor primary suite features an oversized ensuite bathroom ready for your custom design and personal finishes. Toward the rear of the home, you'll find a private office, a flexible bonus room that could easily serve as a sixth bedroom, and a full pool bath with direct access to the lanai—ideal for working from home, accommodating guests, or creating a private retreat. The spacious kitchen offers exceptional storage with two walk-in pantries, a breakfast nook overlooking the backyard, and an open layout ready to become the heart of the home. A generously sized laundry room with a utility sink is conveniently located near the garage. Upstairs features four generously sized bedrooms, two full bathrooms, and a versatile loft that can easily function as a media room, game room, second living area, or homework space. Step outside to enjoy the Florida lifestyle with a covered lanai, expansive paver patio, sparkling pool and spa, and an oversized backyard offering privacy and endless possibilities for outdoor entertaining, recreation, or future enhancements. The transformation has already begun, allowing the next owner to bring their own vision to life. Whether your style is modern, transitional, or timeless, this home provides an exceptional opportunity to personalize a luxury estate while building equity in one of Windermere's premier gated communities. Magnolia Park offers a peaceful setting while remaining just minutes from Downtown Windermere, Winter Garden Village, and the renowned shopping, dining, and entertainment of Dr. Phillips. Enjoy convenient access to SR 429, Florida's Turnpike, SR 408, and I-4, making travel throughout Central Florida effortless. Disney, championship golf courses, world-famous attractions, Orlando International Airport, and many of the area's top-rated public and private schools are all within easy reach. With its exclusive location, generous floor plan, expansive homesite, outstanding potential, and the opportunity to create a truly one-of-a-kind residence, this is one of the most compelling opportunities to come to market in Windermere. Opportunities like this in Magnolia Park are few and far between.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY

  • 13736 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL - MLS# O6425332

    VINEYARDS/HORIZONS WEST PH 4 - O6425332 - 13736 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786
    Just Added on 07/16/2026 9:37AM

    $440,000 | Townhouse | 3 beds | 2.5 baths | 2 gar

    A Windermere address is more than a location—it is a lifestyle. Welcome to 13736 Summerport Village Parkway, an opportunity to own in one of Central Florida's most desirable and enduring communities. Nestled within The Vineyards of Windermere, this elegant three-bedroom townhome offers the perfect blend of refined living, everyday convenience, and the prestige that continues to make the Windermere ZIP code one of the area's most sought-after destinations. Designed for effortless living, the home welcomes you with an open-concept layout featuring laminate flooring throughout the main level, a beautifully appointed kitchen with PREMIUM GRANITE COUNTERTOPS, an elegant designer tile backsplash, UPGRADED STAINLESS STEEL APPLIANCES, and bright, inviting living spaces that transition seamlessly from everyday comfort to entertaining. Just beyond the kitchen, sliding glass doors open to a PRIVATE FENCED PATIO—the perfect setting to enjoy your morning coffee, an al fresco breakfast, or unwind at the end of the day while filling the home with an abundance of natural light. Adding even greater peace of mind, the ROOF WAS REPLACED IN 2025, offering lasting value for years to come. Life here extends well beyond your front door. Residents enjoy beautifully maintained amenities including TWO RESORT-STYLE POOLS, A PLAYGROUND, AND A DOG PARK, all within a community known for its walkability and welcoming atmosphere. Everyday essentials are just a short stroll away, allowing you to enjoy the rare convenience of shopping, dining, and neighborhood services without leaving your community. One of the greatest advantages of this home is its exceptional location. Situated in the coveted Windermere area, you'll enjoy close proximity to TOP-RATED ORANGE COUNTY PUBLIC SCHOOLS, the vibrant Hamlin Town Center, Winter Garden Village, world-renowned theme parks, championship golf courses, and an impressive collection of restaurants, cafés, fitness studios, and outdoor recreation. Easy access to major highways places Downtown Orlando, Orlando International Airport, and Central Florida's premier destinations within comfortable reach. Whether you're looking for a primary residence or a long-term investment in one of the region's strongest real estate markets, this home represents an opportunity to secure both lifestyle and lasting value in a location where demand continues to remain exceptionally strong. Experience the charm, convenience, and timeless appeal that have made Windermere one of Central Florida's most coveted places to call home.

    Contact Yellowkey Agent

    Listing is courtesy of: LUXE HUNTER REAL ESTATE

  • 14250 SONCO, WINDERMERE, FL - MLS# O6425518

    SUMMERPORT - O6425518 - 14250 SONCO, WINDERMERE, FL 34786
    Just Added on 07/16/2026 6:36AM

    $360,000 | Townhouse | 2 beds | 2.0 baths | 2 gar

    Location, Location, Location! Welcome to this charming one-story end-unit townhome in the highly desirable Summerport community of Windermere! Ideally situated to Keene's Crossing Elementary School and the community's exceptional amenities. The open-concept floor plan creates a bright, spacious atmosphere, seamlessly connecting the living room, dining area, and kitchen—perfect for everyday living and entertaining. The generously sized eat-in kitchen features a breakfast bar, LG appliances, 42-inch cabinetry, granite countertops, tile flooring, an attractive art niche, and French doors that open to a covered, screened porch. The primary suite boasts a double tray ceiling, walk-in closet, dual vanities, a relaxing soaking tub, and a linen closet. The secondary bedroom is conveniently located adjacent to the guest bathroom. Additional highlights include an inside laundry room with Maytag washer and dryer included, a spacious rear-entry two-car garage, and all ceiling fans, light fixtures, and window treatments conveying with the sale. Summerport residents enjoy an impressive array of amenities, including a clubhouse, resort-style pool, fitness center, tennis courts, basketball and volleyball courts, scenic walking trails, fishing docks, playgrounds, and more. Conveniently located near SR 429, Hamlin Town Center shopping, dining, world-famous theme parks, and countless Central Florida attractions, this home truly offers the perfect combination of location, lifestyle, and value!

    Contact Yellowkey Agent

    Listing is courtesy of: WATSON REALTY CORP

  • 6533 CARTMEL LN, WINDERMERE, FL - MLS# O6425396

    RESERVE AT LAKE BUTLER SOUND - O6425396 - 6533 CARTMEL LN, WINDERMERE, FL 34786
    1 Day on yellowkey

    $1,595,000 | Single Family Home | 5 beds | 3.5 baths | 3 gar

    Welcome to The Reserve at Lake Butler Sound, one of Windermere's most prestigious 24-hour guard-gated luxury communities, where estate homes, tree-lined streets, and access to the renowned Butler Chain of Lakes create an unmatched lifestyle. Perfectly positioned on over half an acre at the end of a quiet cul-de-sac, this impeccably maintained 5-bedroom, 3.5-bath residence offers more than 3,750 square feet of thoughtfully designed single-story living with timeless architecture and sophisticated modern finishes. A paver driveway, mature tropical landscaping, and stately columns create an unforgettable first impression. Inside, grand beveled-glass French doors open to soaring ceilings, elegant architectural details, and expansive sightlines that lead directly to the screened pool and spa with a beautiful ceramic tiled deck, creating a seamless connection between indoor and outdoor living. Designed for both everyday comfort and elegant entertaining, the executive open-concept floor plan features formal living and dining spaces accented by tray ceilings, custom lighting, and graceful archways. Rich wood flooring, abundant natural light, and refined finishes elevate every room. At the heart of the home, the chef's kitchen is as functional as it is beautiful, featuring granite countertops, generous prep space, a large breakfast bar, natural gas counter top and a bright breakfast nook overlooking the outdoor pool and living area. The kitchen flows seamlessly into the spacious family room, where a cozy natural gas fireplace creates the perfect gathering space for family and guests. Privately tucked away, the owner's suite serves as a luxurious retreat with travertine flooring, dual custom walk-in closets, and a spa-inspired bath complete with dual vanities, an oversized walk-in shower with dual shower heads, and a convenient wet bar. An adjoining flex space offers endless possibilities as a private office, fitness room, reading lounge, or nursery. The secondary bedrooms are thoughtfully positioned for privacy and functionality, featuring a Jack-and-Jill bathroom, an additional full bath, and spacious accommodations for family or guests. A dedicated office at the front of the home functions as a fifth bedroom, providing exceptional flexibility for today's lifestyle. Step outside to your private backyard oasis, where the screened pool and spa are surrounded by lush landscaping, ambient lighting, and an expansive covered lanai—perfect for entertaining year-round or enjoying peaceful Florida evenings. Living in Lake Butler Sound means more than owning an exceptional home—it's embracing one of Central Florida's most coveted luxury lifestyles. Residents enjoy 24-hour guarded security, a private community fishing pier on Lake Butler, beautifully maintained parks and green spaces, and proximity to the Butler Chain of Lakes, one of Florida's most desirable chains for boating, skiing, paddleboarding, and waterfront recreation. The community is also zoned for top-rated schools and is just minutes from downtown Windermere, Restaurant Row, world-class golf, major highways, Orlando's premier attractions, and an exceptional collection of luxury shopping and dining. This is a rare opportunity to own an elegant estate in one of Windermere's most sought-after luxury communities, where privacy, location, and lifestyle come together in perfect harmony.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 11468 MISTY OAK ALY, WINDERMERE, FL - MLS# O6425336

    ASHLIN PARK PH 1 - O6425336 - 11468 MISTY OAK ALY, WINDERMERE, FL 34786
    1 Day on yellowkey

    $558,900 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Ashlin Park - One of Windermere's most desirable communities. This very private cornet lot offers an oversized homesite with breathtaking water views. Featuring 3 bedrooms, 2.5 baths, 2 car garage, and contemporary upgrades throughout. The first floor showcases title and beautiful upscale wood flooring, an upgraded kitchen ideal for everyday living and entertaining, PLUS A VERSATILE SMALL OFFICE OR FLEX SPACE. All bedrooms are upstairs, including serene primary suite with a relaxing bathtub and a laundry room with upscale washer and dryer include. Notably, the home is equipped with a surround sound system in the family room and in the primer bathroom. Step outside to a tranquil backyard with peaceful water view and community walking paths. Residents enjoy a resort -style pool, clubhouse, and playground, all just10 minutes from Disney with easy access to shopping, dining, and major highways. Easy to show. Schedule your PRIVATE TOUT TODAY!!

    Contact Yellowkey Agent

    Listing is courtesy of: REAL ESTATE FIRM OF ORLANDO

  • 6119 GROSVENOR SHORE DR, WINDERMERE, FL - MLS# O6421205

    KEENE'S POINT - O6421205 - 6119 GROSVENOR SHORE DR, WINDERMERE, FL 34786
    1 Day on yellowkey

    $15,900,000 | Single Family Home | 7 beds | 8.5 baths | 6 gar

    Experience luxury lakefront living on a grand scale in this exquisite estate on Lake Tibet, part of the pristine Butler Chain of Lakes in Windermere. This custom-built masterpiece by Goehring & Morgan is inspired by Andrea Palladio, one of the most influential architects in history, celebrated for his elegant country houses and villas. The design draws inspiration from the diverse regions of Italy, with the finest imported materials hand-selected to ensure authenticity. Every finish and detail was thoughtfully curated, showcasing refined craftsmanship, exquisite design elements and seamless indoor-outdoor living enhanced by stunning water views. Offering 14,068 square feet of living space on more than four acres, this remarkable residence enjoys one of the most breathtaking lake views in the area. Thoughtfully designed with Palladian principles, the rear elevation is every bit as impressive as the front, maximizing the beauty of its exceptional waterfront setting. With six bedrooms and eight-and-a-half baths plus guest house, this home offers every luxury amenity imaginable. The floor plan includes formal living and dining rooms, an open-concept kitchen and family room that flow effortlessly into the outdoor living spaces, a climate-controlled wine room, an office, a library, two bonus rooms, a fitness room and a private attached guest suite. The backyard retreat evokes the feeling of Lake Como, with picturesque sightlines, expansive lake views and covered outdoor living areas featuring fireplaces that surround the resort-style pool. Mature landscaping provides exceptional privacy while enhancing the ambiance of this extraordinary outdoor oasis. Artistry is evident throughout every space, highlighted by exposed wood beams with hand-painted details, frescoed ceilings, Old World tumbled brick floors and ceilings, inlaid marble and wood accents, barrel-vaulted ceilings, Venetian plaster finishes and countless other custom architectural elements. Within the guard-gated community of Keene's Pointe, this estate enjoys access to an exceptional lifestyle. Lake Tibet is one of the largest lakes on the Butler Chain, offering privacy and connectivity through the navigable canal system. The Butler Chain of Lakes, also known as the Windermere Chain of Lakes, consists of 13 interconnected lakes encompassing more than 5,000 acres of spring-fed water. Residents of Keene's Pointe enjoy access to the renowned Golden Bear Club, featuring a 250-acre Jack Nicklaus Signature Golf Course, a resort-style pool, tennis courts, a fitness center, multiple playgrounds and a clubhouse for private events. Combining small-town charm with unparalleled convenience, Windermere is just minutes from downtown Orlando and offers easy access to fine dining, world-class shopping, championship golf courses, top-rated schools, international and private airports, and world-famous theme parks. The Butler Chain of Lakes spans more than 4,900 acres of crystal-clear, spring-fed water and is renowned for its pristine sand bottoms, exceptional water quality and designation as an "Outstanding Florida Water."

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 14030 SPARKLING COVE LN #603, WINDERMERE, FL - MLS# O6424774

    OASIS COVE I/LAKESIDE VILLAGE PH 01 - O6424774 - 14030 SPARKLING COVE LN #603, WINDERMERE, FL 34786
    3 Days on yellowkey

    $330,000 | Townhouse | 2 beds | 2.5 baths | 1 gar

    Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhome-style condominium nestled in the gated community of Oasis Cove at Lakeside Village in the heart of Windermere. Offering the perfect blend of comfort, style, and convenience, this move-in ready home features an open-concept floor plan with abundant natural light, creating an inviting space for both everyday living and entertaining. Residents of Oasis Cove enjoy resort-style amenities, including a community pool, fitness center, playground, clubhouse, and beautifully maintained grounds, all within a secure gated entrance. In addition to the resort-style amenities the association fees also include water, internet, cable, ground maintenance and exterior maintenance for all homes. Ideally located just minutes from Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools, this home offers easy access to everything Central Florida has to offer. Whether you're looking for your primary residence, a second home, or an investment opportunity, this exceptional property checks all the boxes. Don't miss your chance to own a beautiful home in one of Windermere's most desirable communities—schedule your private showing today! *New Roof + New HVAC!!*

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 13303 PENSHURST LN, WINDERMERE, FL - MLS# O6423867

    WINDERMERE SOUND - O6423867 - 13303 PENSHURST LN, WINDERMERE, FL 34786
    3 Days on yellowkey

    $669,900 | Single Family Home | 5 beds | 4.5 baths | 2 gar

    Prime Windermere location just a couple miles from luxury, million-dollar estates and minutes from Windermere Downtown. Families appreciate access to top-rated schools, while the home’s proximity to world-class Disney Parks and Disney Springs adds exceptional lifestyle convenience. The property features two updated AC systems — one replaced in 2020 for the separate mother-in-law suite and another brand-new unit installed in 2024 for the main house. The detached mother-in-law residence offers outstanding flexibility, providing a private, comfortable space ideal for extended family or young adults learning independence, or even long-term guests who benefit from having their own dedicated living area. The community includes professional landscaping through the HOA, ensuring a clean, well-maintained environment year-round. With quick access to major roadways, shopping, dining, and Windermere’s charming lakeside town center, this home delivers exceptional value in one of Central Florida’s most desirable areas.

    Contact Yellowkey Agent

    Listing is courtesy of: UNITED REALTY GROUP INC

  • 9225 MCDAVID CT, WINDERMERE, FL - MLS# O6424617

    ROBERTS LANDING - O6424617 - 9225 MCDAVID CT, WINDERMERE, FL 34786
    3 Days on yellowkey

    $799,999 | Single Family Home | 4 beds | 2.0 baths | 3 gar

    Nestled on a private one-acre homesite in the established community of Roberts Landing, this meticulously maintained custom pool home offers the perfect blend of space, comfort, and timeless design. Featuring 4 bedrooms, 2 bathrooms, over 2,700 square feet, and a desirable 3-car side-entry garage, this home has been lovingly cared for by its original owners. Inside, soaring vaulted ceilings, abundant natural light, and a flowing open floor plan create an inviting atmosphere for everyday living and entertaining. The spacious kitchen overlooks the family room with a cozy wood-burning fireplace and offers generous cabinetry, ample prep space, and a casual dining area. The oversized primary suite provides a peaceful retreat, while the expansive Florida room seamlessly extends your living space and overlooks the screened pool and private backyard—perfect for year-round Florida living. Thoughtful upgrades include a metal roof, whole-home water filtration and softener system, private well and septic, and an oversized garage with dedicated workshop space. Every inch of this home reflects exceptional pride of ownership. Located just minutes from top-rated schools, shopping, dining, and major roadways, this is a rare opportunity to own a beautifully maintained home with the privacy of country living and the convenience of Windermere. Homes with this level of care, space, and setting don't come along often. Schedule your private showing today.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 13419 LEMON ORCHARD BND, WINDERMERE, FL - MLS# TB8528688

    LAKE CAWOOD COVE - TB8528688 - 13419 LEMON ORCHARD BND, WINDERMERE, FL 34786
    3 Days on yellowkey

    $599,990 Reduced | Townhouse | 3 beds | 2.5 baths | 2 gar

    Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living.

    Contact Yellowkey Agent

    Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC

  • 1629 HEMPEL AVE, WINDERMERE, FL - MLS# O6418226

    GOTHA TOWN - O6418226 - 1629 HEMPEL AVE, WINDERMERE, FL 34786
    5 Days on yellowkey

    $2,500,000 | Single Family Home | 6 beds | 4.0 baths | 3 car

    Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximately 88-acre, spring-fed lake with private access. Located in the desirable Gotha/Windermere area, this exceptional property offers rare peace and privacy while remaining convenient to Southwest Orlando’s renowned theme parks, premier shopping, Downtown Orlando, Orlando International Airport, highly regarded schools, and the Florida Turnpike. Mature trees, lush gardens, and thoughtfully designed outdoor spaces create a setting that feels secluded, established, and distinctly Florida. An antique church door provides a memorable entrance, setting the tone for a residence that blends refined finishes, distinctive character, and comfortable everyday living. The main residence features four bedrooms, two full bathrooms, and an expansive open-concept living area designed for entertaining while showcasing beautiful lake views. The oversized great room offers multiple gathering spaces, including a billiards area, a large television and game-day space, a generous dining area, and an impressive chef-inspired kitchen. At the center of the kitchen is an abundant quartz-topped island offering extensive workspace, seating, and a natural gathering place where guests can connect while meals are prepared. High-end flooring throughout the main home includes polished ceramic tile, travertine, and solid wood, while newer energy-efficient windows and doors enhance comfort and efficiency. The primary suite is a magazine-worthy addition created as a private lakeside sanctuary. Cathedral ceilings, polished ceramic tile flooring, expansive lake views, and a flexible sitting or exercise area create an open and relaxing environment. Two oversized custom closets provide exceptional storage. The luxurious bathroom features floor-to-ceiling ceramic tile, quartz countertops, an oversized porcelain soaking tub, and a spacious walk-in shower room. Four distinctive outdoor living areas invite you to enjoy the property throughout the year. Gather around the fire in the stone-paver garden area, relax within the private walled courtyard surrounded by potted plants and the soothing sound of a water fountain, or spend the day along the expansive backyard and private boat dock. The recently updated infinity-edge pool and heated spa overlook the lake, creating a resort-style setting for relaxing, entertaining, and enjoying unforgettable sunsets. A separate guest residence adds tremendous flexibility and privacy. Complete with two bedrooms, two bathrooms, a kitchen, and a living area, it is ideal for multigenerational living, extended guests, or an on-site caretaker. A private gated driveway and abundant parking accommodate multiple vehicles with ease. Combining two complete residences, more than an acre of lakefront land, exceptional outdoor living, mature landscaping, and private access to Lake Olivia, this one-of-a-kind estate offers a lifestyle rarely available in Central Florida.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 13328 OVERSTREET RD, WINDERMERE, FL - MLS# O6423949

    LAKE SAWYER SOUTH - O6423949 - 13328 OVERSTREET RD, WINDERMERE, FL 34786
    6 Days on yellowkey

    $639,900 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Situated on a distinguished homesite in one of Windermere's most sought after locations, 13328 Overstreet Road impresses right when you pull into the oversized 6+ CAR PAVER DRIVWAY with parking for up to six vehicles. If any of those vehicles are electric, you can charge them using the installed TESLA CAR CHARGER and save $$ on the electric bill with the PAID-OFF SOLAR PANELS. This home defines exceptional value and modern efficiency. At the heart of the home, the GOURMET KITCHEN is an entertainer's dream, with not one, but two center islands, ample solid WOOD CABINETS with crown molding, granite counters, and a tile backsplash. A stainless steel appliance package complements these features. A spacious dining area, family room, a mini mudroom off the garage, and a multipurpose space with additional cabinetry perfect for a small office, coffee bar, or wine bar. If you are looking for some multigenerational space, take advantage of the downstairs ensuite, which includes built-in closet organizers, a new vanity and toilet and a walk in shower. There is no carpet; the entire first floor has ceramic tile and the stairs and upstairs feature newly installed hardwood flooring. Luxurious master suite provides ELECTRIC BLINDS to let the light in and out at your fingertips, a perfectly organized walk in closet with custom built ins plus a double sink vanity with vessel sinks, modern light framed mirrors and a remodeled huge walk in shower complete with a shower wand, RAINHEAD SHOWER  and pebble stone floor. The second floor also offers a tremendous bonus/game room, media lounge, office or fitness studio along with 2 additional bedrooms, a full bath, and a laundry room with its own built-in sink and cabinet. Additional interior upgrades include plantation shutters on the first floor, an electric blind to the exterior and a digital thermostat. Exterior features include a SCREEN ENCLOSED LANAI  overlooking the fully fenced backyard for quiet comfort, privacy and shade from the yard's mature landscaping. Pavers line the back patio, making it possible to step right outside to both grill and dine al fresco during the temperate fall, winter, and spring months here in Central Florida. Additional features include YEAR ROUND HOLIDAY LIGHTING installed on the home making you ready for every season with the flip of a switch. Neighborhood features include a community pool complete with lounge chairs and a covered pavilion, a basketball court, a tennis court, a putting green, playgrounds covered from the sun or rain, and plenty of green space. LOCATION BENEFITS include easy access to DISNEY, SR 429, SR 408 to Downtown Orlando, Florida Turnpike, I4, shopping, restaurants and much more! Combining sophisticated finishes, versatile living spaces, and cutting-edge energy-conscious upgrades, this exceptional Windermere residence offers a lifestyle as impressive as the home itself.

    Contact Yellowkey Agent

    Listing is courtesy of: RE/MAX PRIME PROPERTIES

  • 9433 PALM TREE DR, WINDERMERE, FL - MLS# O6423262

    SILVER WOODS PH 03 - O6423262 - 9433 PALM TREE DR, WINDERMERE, FL 34786
    7 Days on yellowkey

    $560,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    WELCOME HOME! Nestled beneath majestic oak trees in one of Windermere's most desirable communities, this well-maintained 3-bedroom, 2-bath home sits on a quarter of an acre and offers the perfect blend of comfort, privacy, and location. Situated in the highly sought-after 34786 zip code, this exceptional residence features a popular split-bedroom floor plan with 1,819 square feet of thoughtfully designed living space. Silver Woods is located in the center of SW Orlando, close to Downtown Windermere, Restaurant Row, Winter Garden Village, Downtown Winter Garden, churches, schools, shopping, and more. As you enter the front door, you will be impressed with the open floor plan. New paint, new carpet, and neutral tile create a light and bright environment. Step inside to discover spacious living and dining areas that flow seamlessly into the heart of the home. The living room looks out onto the huge patio and backyard. The kitchen offers abundant cabinetry, granite countertops, ample workspace, and overlooks the main living areas, making it ideal for everyday living. Enjoy the family room, which opens to a covered, screened lanai via sliding doors, creating an incredible outdoor living space perfect for relaxing, entertaining, or simply enjoying the tranquil backyard surrounded by mature trees. The oversized, park-like shared fenced backyard provides exceptional privacy and plenty of room for gardening, play, or creating your own outdoor oasis. Let your imagination create the perfect Pool/Spa area with a summer kitchen, fire-pit, and more. The primary bedroom features sliding doors to the expansive lanai, and the en-suite features a Tub, a newer double-sink vanity, and a walk-in shower. A split-bedroom plan is perfect for today's busy family, featuring two bedrooms and a hall bath with a shower/tub. Recent improvements, including a NEW ROOF, HVAC (2016), New Garage Door (2016), Septic (2021), Electric Panel (2017), Interior paint (2026), Front Sod (2026), and Carpet (2026) in the main living areas, make this home move-in ready while still offering opportunities for a new owner to personalize and add value over time. The community offers a park and a tennis court for the residents. Ideally located just minutes from top-rated Windermere schools, shopping, dining, churches, world-famous theme parks, major highways, and Orlando's many entertainment destinations, this home offers the perfect balance of peaceful neighborhood living and everyday convenience. Don't miss your chance to make this Windermere gem your next home- schedule your private showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 4642 RIVER GEM AVE, WINDERMERE, FL - MLS# O6422241

    SUMMERPORT PH 05 - O6422241 - 4642 RIVER GEM AVE, WINDERMERE, FL 34786
    7 Days on yellowkey

    $825,000 | Single Family Home | 5 beds | 5.0 baths | 3 gar

    Discover refined living in one of Windermere's most sought-after communities. This exceptional 5-bedroom, 5-bath residence in Summerport perfectly blends timeless elegance, everyday comfort, and an unmatched location. Offering an ideal floor plan for both everyday living and entertaining, this beautifully maintained home features a dedicated office, formal dining room, spacious living room, family room, and thoughtfully designed living spaces throughout. The entire first floor showcases upgraded luxury vinyl flooring, while the gourmet kitchen is appointed with beautiful granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast bar with seating, perfect for casual dining and gathering with family and friends. Situated on an oversized homesite, the backyard has been thoughtfully upgraded to create the perfect outdoor retreat. Enjoy a spacious covered lanai, an extended paver patio, and a fire pit, offering the ideal setting for entertaining or relaxing under the shade of the mature Trees. Upstairs, you'll find all 5 generously sized bedrooms, each complemented by access to a full bathroom, providing exceptional comfort and privacy for family members and guests alike. The first floor features a spacious private office that can easily be converted into a media room or 6th bedroom, complemented by a full bathroom for added flexibility. A spacious 3-car garage offers abundant room for vehicles, storage, and recreational equipment. Designed with efficiency in mind, the home is equipped with solar panels producing approximately 22–23 MWh annually, delivering substantial energy savings while reducing utility costs. Summerport is one of Windermere's most desirable communities, offering residents an exceptional lifestyle with resort-style amenities, including a community pool, fitness center, tennis courts, sand volleyball courts, playgrounds, scenic walking trails, and beautiful lakes. Families will appreciate being zoned for highly rated schools, including the sought-after Windermere High School. Ideally located just minutes from Walt Disney World, Winter Garden Village, Publix, premier shopping, dining, and major highways, this home presents a rare opportunity to enjoy luxury living in one of Central Florida's most prestigious communities.

    Contact Yellowkey Agent

    Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES

  • 13431 BELLARIA CIR, WINDERMERE, FL - MLS# P4939244

    BELLARIA - P4939244 - 13431 BELLARIA CIR, WINDERMERE, FL 34786
    7 Days on yellowkey

    $3,250,000 | Single Family Home | 4 beds | 4.5 baths | 3 gar

    BREATHTAKING WINDERMERE ESTATE!!! Situated on nearly 1.5 acres in the gated/guarded community of Bellaria, this custom built 4BR/4.5BA pool residence is the pinnacle of detail and design. Follow the long drive winding amongst the towering Italian Cypress to your expansive motor court and magnificent entry. Upon opening the massive custom double doors, you will see elegance, functionality, and breathtaking detail in every corner. Features include: over 5500SqFt of living area, soaring ceiling heights, top-notch molding and finish work, travertine floors, NEW carpet, NEW interior paint, massive kitchen with bar seating and island, walk-in pantry, game room with full bar and refrigeration, over 3000SqFt of rear pool and patio space with hot tub, outdoor bar/kitchen with vent fan and refrigeration, patio shower, multiple gas fireplaces, corner sliding pocket doors opening onto patio, NO REAR NEIGHBORS, gigantic privacy hedge, spacious primary suite with seating area and pool access, dual walk-in closets, exquisite primary bath with enormous soaking tub, spacious guest bedrooms and beautifully appointed guest bathrooms, sauna, three car garage with a hydraulic lift for a fourth vehicle, generous utility room, 22kw natural gas generator installed in 2021, office with built-ins and fireplace, fully equipped theatre with elevated seating, A BRAND NEW TILE ROOF, ample storage opportunities, and the list goes on!!! This is all just minutes from Winter Garden Village with easy access to SR429, downtown, and all the attractions!!! Schedule your showing and prepare to be amazed, this property is special. Call today!!!

    Contact Yellowkey Agent

    Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC

  • 8342 BOYLA CT, WINDERMERE, FL - MLS# O6422852

    KEENES POINTE - O6422852 - 8342 BOYLA CT, WINDERMERE, FL 34786
    9 Days on yellowkey

    $6,700,000 | Single Family Home | 8 beds | 8.5 baths | 4 gar

    Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden. Offering 8,133 square feet under air and 10,971 total square feet, this exceptional home features 8 bedrooms, 7 full bathrooms, and 3 half bathrooms with unparalleled craftsmanship and luxury finishes throughout. A grand marble foyer welcomes you with soaring ceilings, designer lighting, wood beams, and rich solid oak flooring. The stunning chef’s kitchen features custom solid wood cabinetry, stunning countertops, Thermador paneled refrigerator and freezer with white wine refrigeration, Wolf range, built-in convection oven, microwave, and a custom exhaust hood. The expansive great room showcases a natural stone fireplace and wall to wall sliders that open to breathtaking views of the infinity edge saltwater pool, spa, backyard oasis, and Lake Burden. The luxurious primary suite offers panoramic water views, custom illuminated walk-in closets, a spa inspired bathroom with a massive shower, designer fixtures, and a freestanding soaking tub. Additional highlights include a temperature controlled wine cellar, hidden elevator, executive study with custom built-ins, five spacious main level bedrooms, and a spectacular second floor featuring a private gym with reinforced insulation, custom theater, loft with kitchenette, balcony overlooking the water, and three ensuite bedrooms. Outdoor living is designed for entertaining with your summer kitchen including a heavy duty grill and hood, motorized screens for the entire lanai, multiple gathering areas, fire pit, private putting green, and a nature path leading to your covered boat dock with boat lift for endless Lake Burden adventures on a 125 acre skiable lake. A four-car garage with built in ceiling lighting tracks and electric vehicle charging completes this exceptional residence. Keene’s Pointe offers an unmatched lifestyle with the Golden Bear Club, featuring a championship golf course, clubhouse, fitness center, tennis courts, resort-style pool, and numerous parks and recreation areas. Ideally located just minutes from Walt Disney World, world class dining, shopping, and top rated schools, with close proximity to Windermere Preparatory School. This rare never been lived in lakefront estate is being offered for the first time and represents a unique opportunity to own one of Central Florida’s finest custom homes. Be sure to click on the virtual tour links.

    Contact Yellowkey Agent

    Listing is courtesy of: THE SIMON SIMAAN GROUP

  • 11564 MIZZON DR #102, WINDERMERE, FL - MLS# O6423023

    LAKESIDE/LKS/WINDERMERE - O6423023 - 11564 MIZZON DR #102, WINDERMERE, FL 34786
    9 Days on yellowkey

    $295,000 | Condo | 2 beds | 2.0 baths

    **Windermere Renovated First-Floor Condo | Resort-Style Amenities | Minutes from Disney & Winter Garden Village** Beautifully renovated and move-in ready, this light-filled **first-floor** condo offers the perfect combination of comfort, convenience, and low-maintenance living in one of Windermere's most desirable gated communities. Ideally located just minutes from Disney, Winter Garden Village, and directly across from Lakeside Village Center, you'll enjoy easy access to shopping, dining, and everyday conveniences. Designed with an open-concept layout, this well-maintained residence features **laminate flooring throughout the living areas and bedrooms**, creating a seamless, modern look with no carpet. The updated kitchen is equipped with **stainless steel appliances**, granite countertops, and ample cabinet space, making it both stylish and functional. The spacious primary suite includes a walk-in closet, while the private screened patio provides the perfect space to relax and enjoy Florida's year-round weather. Enjoy a truly carefree lifestyle with the **monthly condominium fee covering water, trash collection, exterior maintenance, and access to outstanding community amenities**. Residents have access to a resort-style swimming pool, clubhouse, fitness center, volleyball court, playground, BBQ and picnic areas, scenic walking trails, and valet trash service. One reserved parking space is included. The community has been exceptionally maintained, with significant exterior improvements completed in recent years, including roof replacement, asphalt resurfacing with updated striping, and exterior building repainting, helping preserve both curb appeal and long-term value. Fiber-optic internet service is also available, providing reliable high-speed connectivity for working from home or streaming. Whether you're looking for a primary residence, a seasonal getaway, or an investment opportunity, this beautifully updated condo offers exceptional value in one of Central Florida's most convenient locations.

    Contact Yellowkey Agent

    Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS

  • 7231 SANGALLA DR, WINDERMERE, FL - MLS# O6422598

    CASA DEL LAGO-REPLAT - O6422598 - 7231 SANGALLA DR, WINDERMERE, FL 34786
    9 Days on yellowkey

    $1,300,000 | Single Family Home | 5 beds | 4.5 baths | 3 gar

    Tucked away within the private gates of Casa Del Lago, one of Windermere’s most desirable communities, this exceptional home offers a rare opportunity to enjoy luxury living just moments from everything Central Florida has to offer. With only 88 residences surrounding the shores of Lake Burden, Casa Del Lago provides an intimate neighborhood setting close to top-performing schools, major roadways, Orlando International Airport, upscale shopping, dining, and the area’s famous attractions. Crafted by renowned builder David Weekley Homes, this impressive residence spans almost 4,000 square feet and has been designed with both comfort and functionality in mind. The main level features four generously sized bedrooms, including a unique wing where two bedrooms are connected by a versatile flex space, perfect as a playroom, study area, or media room. Each bedroom benefits from its own private bathroom, providing comfort and privacy for family members and guests alike. The heart of the home is the open-concept living area, complemented by a dedicated office for remote work and a formal dining room for special occasions. A conveniently located pool bath provides easy access from both the interior living spaces and outdoor entertaining areas. Upstairs, you’ll find an expansive bonus room that can serve as a game room, home theater, fitness space, or second living area. Also on this level is a private guest suite complete with its own full bathroom, ideal for visitors, older children, or extended family. Step outside to your own backyard oasis where a screened swimming pool, oversized paver deck which could be a great basketball or play area, and maintenance-free turf create the perfect environment for relaxing or entertaining throughout the year. For added convenience and security, the home is equipped with an extensive CCTV system featuring 21 cameras. Residents of Casa Del Lago also have the option to join the nearby Golden Bear Club at Keene’s Pointe, offering championship golf, dining, social events, and premium recreational amenities. With homes in this sought-after community seldom available, this is a chance to secure a property in one of Windermere’s most coveted gated neighborhoods.

    Contact Yellowkey Agent

    Listing is courtesy of: THE AGENCY FL

  • 6241 BLAKEFORD DR, WINDERMERE, FL - MLS# O6417788

    KEENES POINTE - O6417788 - 6241 BLAKEFORD DR, WINDERMERE, FL 34786
    10 Days on yellowkey

    $1,795,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar

    Something unexpected! Something unique! An amazing space! Welcome to 6241 Blakeford Drive, where the charm, character, and glamour of this custom-built jewel box home are sure to impress. Designed to capture natural light and stunning water views, this residence offers a floor plan that is both functional and unforgettable. At the heart of the home is a spectacular Great Room featuring soaring 30-foot ceilings and dramatic picture windows that frame breathtaking views of the pool, pond, and colorful Florida sunsets. Abundant natural light fills the space, creating an inviting atmosphere that seamlessly connects the main living areas. The thoughtfully designed split floor plan places the spacious primary suite in its own private wing, complete with French doors opening to the pool and a luxurious spa inspired bath showcasing exquisite custom tilework that is truly a work of art. On the opposite side of the home, you'll find a bright office or fifth bedroom with adjacent full bath, an additional guest bedroom, and a rear bedroom overlooking the garden and water, also with convenient pool access. The boutique-style kitchen is a showpiece, highlighted by a dramatic stacked-stone exhaust wall that beautifully complements the matching stone fireplace in the great room. Together, these elements create a warm and cohesive gathering space perfect for everyday living and entertaining. The formal dining room offers flexibility as a sitting room or entertaining space, while the breakfast nook is perfectly positioned to enjoy tranquil pond views and unforgettable sunsets. Upstairs, a spacious bonus room, fourth bedroom, full bath, and stackable washer/dryer closet create a private retreat ideal for guests, extended family, or multigenerational living. Situated on just over one-third acre with 90 feet of waterfront frontage, the property enjoys long pond views and stunning sunset vistas. The oversized three-car garage and prime location just steps from the Golden Bear Clubhouse add to the home's appeal. Move-in ready and worry free with new ACs and roof (2024) new quartz countertops (2023 & 2026), new flooring (2023) and newly painted exterior (2025).

    Contact Yellowkey Agent

    Listing is courtesy of: KEENE'S POINTE REALTY

  • 2009 WOODY DR, WINDERMERE, FL - MLS# O6422132

    WINDERMERE DOWNS - O6422132 - 2009 WOODY DR, WINDERMERE, FL 34786
    10 Days on yellowkey

    $1,200,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by canopy-shaded, oak tree-lined streets. A walkway lined with custom pavers leads to the front door, where you're welcomed by the formal living and dining rooms on the right. Large bay windows let in plenty of natural light, creating a bright and inviting space. A barn door opens to the kitchen, which features travertine flooring, a gas stove, and stainless steel appliances—great for home cooking or entertaining. The living room is a cozy gathering space, with three skylights bringing in extra light and an Authentic Old Chicago Brick fireplace that adds warmth and character. The primary bedroom is spacious, with French doors that open to the screened-in pool lanai, offering easy access to outdoor living. The primary bathroom includes a Kohler clawfoot tub and Kohler fixtures, adding a touch of quality and comfort. Out back, the screened-in pool with travertine deck and patio provides a great spot to relax, while the larger open travertine patio off of the kitchen is perfect for hosting family and friends. The backyard is full of greenery, offering both beauty and privacy and an irrigation well. Home includes a 1,000 Underground Large Gas Tank and Full House Propane Generator and a hybrid water heater. A two-car attached garage is complemented by a large detached deep second two-car garage, perfect for extra parking, storage, or keeping your favorite lake-living toys. Living in Windermere Downs means access to a private community boat ramp, where you can launch your boat and explore Lake Down and the Butler Chain of Lakes. The community amenities include a dock with a roped-off swim area, tennis courts, pickleball courts, community park, playground—plenty of options for outdoor fun. Recent updates include whole house re-pipe (2026), freshly painted exterior and new soffit (2026).

    Contact Yellowkey Agent

    Listing is courtesy of: REVEL REALTY LLC

  • 7060 VENTNOR DR, WINDERMERE, FL - MLS# S5153025

    PRESTON SQUARE - S5153025 - 7060 VENTNOR DR, WINDERMERE, FL 34786
    13 Days on yellowkey

    $444,900 | Townhouse | 3 beds | 2.5 baths | 2 gar

    BEST VALUE TOWNHOUSE IN WINDERMERE! OUTSTANDING HOME AND LOCATION in the desirable community of Preston Square in Windermere FL. This amazingly unique 3 bedroom, 2,5 bath feels like a single family home with its large kitchen and attached 2-car garage. When you enter, you will be welcomed by the beautiful columns, hardwood floors, separate dining room, separate living room and a great paved private courtyard. Wonderful front porch overlooks the park, community pool and basketball areas. Other awesome features include crown molding, sliding door with built-in blinds, retractable ceiling fans, plantation shutters and curved archways. Expansive kitchen has plenty of 42" wood cabinets and granite countertops with backsplash and an additional eat-in-kitchen space. Master suite has large walk-in closet, tray ceiling and spacious master bath with double sink, granite countertops, wood cabinets, jetted tub and shower. Wonderfully kept community maintains ground maintenance. Close to Disney, Publix, restaurants, retail stores, major roads and excellent Windermere schools. MOVE-IN-READY. Room measurements are approximate. Must see!

    Contact Yellowkey Agent

    Listing is courtesy of: AGENT TRUST REALTY CORPORATION

  • 13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL - MLS# O6421552

    SUMMERPORT TRAIL PH 2 - O6421552 - 13845 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786
    13 Days on yellowkey

    $474,900 Reduced | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Welcome to this beautifully maintained home in the highly desirable community of Summerport Trail in Windermere. This spacious residence offers a functional open floor plan with abundant natural light, generous living and dining areas, and a well-appointed kitchen featuring ample cabinetry, granite countertops, stainless steel appliances, and a large island perfect for entertaining. Throughout the home, you'll find updated luxury vinyl plank (LVP) and tile flooring, providing a modern look that's both stylish and easy to maintain. The primary suite provides a relaxing retreat with a spacious walk-in closet and an en suite bathroom featuring dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms offer flexibility for family, guests, or a home office. Conveniently located near top-rated schools, shopping, dining, major highways, and Orlando's world-famous attractions, this home offers the perfect blend of comfort, style, and convenience. Don't miss this incredible opportunity to own a beautiful home in one of Windermere's most sought-after communities. Schedule your private showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS

  • 12912 DROXFORD RD, WINDERMERE, FL - MLS# O6422064

    LAKES/WINDERMERE PH 02A - O6422064 - 12912 DROXFORD RD, WINDERMERE, FL 34786
    13 Days on yellowkey

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

    Under contract-accepting backup offers. Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a brand-NEW ROOF currently being installed for added value and peace of mind. Designed with both comfort and functionality in mind, the home features a bright, open floor plan with spacious living and dining areas, tile flooring throughout the main living spaces, and flexible room to accommodate everyday living, entertaining, working from home, or hosting guests. The well-appointed kitchen showcases wood cabinetry, granite countertops, stainless steel appliances, a center island, and seamless flow into the main living areas, making it the heart of the home. The spacious primary suite serves as a relaxing retreat with a large walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. Step outside to enjoy Florida living year-round in the screened lanai overlooking the private pool, brick paver deck, and fully fenced backyard—perfect for entertaining, family gatherings, or simply unwinding in your own backyard oasis. Located in the desirable Lakes of Windermere community, residents enjoy access to a playground, covered picnic area, and convenient proximity to top-rated schools, shopping, dining, Disney, major highways, and everything Southwest Orlando has to offer.

    Contact Yellowkey Agent

    Listing is courtesy of: LPT REALTY, LLC

  • 2053 WOODY DR, WINDERMERE, FL - MLS# O6421738

    WINDERMERE DOWNS - O6421738 - 2053 WOODY DR, WINDERMERE, FL 34786
    13 Days on yellowkey

    $679,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar

    Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019

    Contact Yellowkey Agent

    Listing is courtesy of: LPT REALTY, LLC

  • 11429 BROWNSTONE ST, WINDERMERE, FL - MLS# O6421245

    LAKE BURDEN SOUTH PH 2 - O6421245 - 11429 BROWNSTONE ST, WINDERMERE, FL 34786
    13 Days on yellowkey

    $460,000 | Townhouse | 4 beds | 2.5 baths | 2 gar

    Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Enjoy the best of Windermere living in this beautifully maintained 4-bedroom, 2.5-bath townhome with a rear facing 2-car garage in the sought-after Lake Burden South community! Offering a spacious, LOW MAINTENANCE LIFESTYLE, this home combines an ideal SPLIT BEDROOM floor plan with timeless finishes and an unbeatable location just steps from shopping, dining, and everyday conveniences. A charming covered front entry, attractive landscaping, and durable concrete TILE ROOF create welcoming CURB APPEAL. Inside, TILE & WOOD LAMINATE FLOORING flow throughout the home, while the light-filled OPEN CONCEPT design makes everyday living and entertaining effortless. FRENCH DOORS extend the living space to a private COURTYARD PAVER PATIO, creating the perfect spot to unwind, grill, or gather with friends. The kitchen is designed to be both functional and inviting, featuring rich cabinetry, granite countertops, a tiled backsplash, STAINLESS STEEL APPLIANCES, pantry storage, and a breakfast bar that overlooks the living and dining areas. The highly desirable MAIN FLOOR PRIMARY SUITE offers privacy and convenience with a generous WALK-IN CLOSET and a well-appointed en-suite bath. Upstairs, a versatile LOFT provides the perfect flex space for a home office, media room, or play area, while three additional bedrooms, a full bath, and upstairs laundry offer plenty of room for family, guests, or hobbies. Residents of Lake Burden South enjoy a COMMUNITY POOL and one of Windermere's most convenient locations, with easy access to Winter Garden Vineland Road, the area's beautiful lakes, Downtown Windermere, Disney, Winter Garden, Restaurant Row, shopping, dining, and major roadways. Whether you are looking for a full-time residence, a seasonal getaway, or a smart investment in one of Central Florida's most desirable communities, this exceptional townhome is ready to impress. Call today to schedule your tour and fall in love with Brownstone Street!

    Contact Yellowkey Agent

    Listing is courtesy of: WEMERT GROUP REALTY LLC

  • 2512 TRYON PL, WINDERMERE, FL - MLS# O6422154

    MANORS AT BUTLER BAY PH 02 - O6422154 - 2512 TRYON PL, WINDERMERE, FL 34786
    13 Days on yellowkey

    $1,190,000 Reduced | Single Family Home | 4 beds | 3.0 baths | 2 gar

    Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters of an acre and a corner lot. This impressive single-story residence offers 3,478 square feet of thoughtfully designed living space with 4 bedrooms, 3 full bathrooms, a side-entry 2-car garage, an extended driveway, and a screen-enclosed pool and spa. Step through the front door into a grand foyer that opens to a spacious, flowing floor plan. The formal living room sits adjacent to the formal dining room, creating ideal space for entertaining. The expansive family room features soaring ceilings, a cozy wood-burning fireplace, and french doors that lead to the fully enclosed florida room. The oversized primary suite is a true retreat, featuring double-door entry, high ceilings, ample room for a sitting area, a walk-in closet, and french doors opening to the florida room. The spacious primary bath was remodeled approximately four years ago and offers dual vanities, a garden tub, separate shower, and a private toilet room. The open layout provides privacy and flexibility. Two secondary bedrooms share a full bathroom, while the fourth bedroom is tucked away on the opposite side of the home with its own ensuite bath, ideal for guests or multigenerational living. The kitchen is designed for both everyday living and entertaining with granite countertops, a center island with cooktop, built-in oven, dinette area, and more french doors leading to the florida room. The laundry room includes a utility sink and built-in cabinetry for added convenience. Wood-look tile flooring extends throughout the home, with carpet only in the enclosed florida room. One of the home's standout features is the expansive L-shaped florida room that wraps around the side and rear of the home, creating an abundance of bright, versatile space perfect for relaxing, entertaining, a home office, hobby room, fitness area, or additional living space, all while enjoying year-round comfort. Additional updates include an approximately 4-year-old HVAC system and 7-year-old roof, offering peace of mind for the next owner. The Manors at Butler Bay is an intimate community nestled along the shores of beautiful Lake Crescent in southwest Orange County. Residents enjoy a low HOA, golf cart friendly streets, a park with picnic area and access to Lake Crescent for launching non-motorized watercraft such as kayaks and canoes. As a resident of the Town of Windermere, you'll also enjoy access to town amenities including tennis courts and the Lake Butler boat ramp, providing entry to the renowned Butler Chain of Lakes (also known as the Windermere Chain), a 5,000-acre network of 13 interconnected lakes. Renowned for crystal-clear waters, prime bass fishing, luxury waterfront estates, and connects via 32 navigable canals for boating and water sports. The home is conveniently located within a top-rated school district and close to shopping, dining, and major roadways. This exceptional home offers the perfect combination of space, location, and lifestyle. Don't miss your opportunity to own this rare one-owner home in one of Windermere's most desirable communities!

    Contact Yellowkey Agent

    Listing is courtesy of: CENTURY 21 CARIOTI

  • 11446 JASPER KAY TER #103, WINDERMERE, FL - MLS# O6420653

    LAKESIDE AT LAKES OF WINDERMERE - O6420653 - 11446 JASPER KAY TER #103, WINDERMERE, FL 34786
    14 Days on yellowkey

    $330,000 | Condo | 3 beds | 2.0 baths

    Welcome to 11446 Jasper Kay Terrace, Unit 103, a beautifully updated first-floor condominium offering comfortable, low-maintenance living in a gated Windermere community. This move-in ready residence features a desirable split-bedroom floor plan with three bedrooms and two bathrooms, providing both privacy and functionality.The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating an inviting space for everyday living and entertaining. Recent updates include new kitchen countertops, newer kitchen appliances, updated bathrooms, recently replaced flooring throughout the main living areas, and a new HVAC system installed in 2025, providing added comfort and peace of mind. Abundant natural light creates a bright and welcoming atmosphere.The spacious primary suite features a walk-in closet and an updated en-suite bathroom. Two additional bedrooms provide flexibility for guests, a home office, or other lifestyle needs. Step outside to the private screened and covered patio, the perfect place to enjoy your morning coffee or relax at the end of the day.Residents enjoy access to a variety of community amenities, including a resort-style swimming pool, clubhouse, fitness center, playground, volleyball court, BBQ and picnic areas, scenic walking trails, water service, and valet trash. One reserved parking space is included.The community has recently completed extensive exterior improvements, including new roofs, freshly resurfaced and striped parking areas, and exterior building repainting, enhancing both curb appeal and long-term value. Fiber optic internet service is also available for high-speed connectivity.Conveniently located just minutes from Walt Disney World, Winter Garden Village, major highways, and directly across from Lakeside Village Center, this home offers easy access to shopping, dining, entertainment, and top-rated schools. Whether you’re looking for a primary residence, seasonal retreat, or investment opportunity, this updated condo offers the perfect combination of modern improvements, community amenities, and an exceptional location.

    Contact Yellowkey Agent

    Listing is courtesy of: SOUTHERN REALTY GROUP LLC

  • 13219 CHARFIELD ST, WINDERMERE, FL - MLS# O6420991

    LAKE SAWYER SOUTH PH 2 - O6420991 - 13219 CHARFIELD ST, WINDERMERE, FL 34786
    14 Days on yellowkey

    $565,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As you drive through the neighborhood, you'll immediately appreciate the mature landscaping, beautiful tree-lined streets, and peaceful atmosphere that make this communityso special. Upon arrival, you're greeted by a spacious covered front porch — the perfect place to relax and enjoy the Florida lifestyle. Step inside to a welcoming, wide foyer that opens to a bright and airy living room featuring soaring ceilings and an abundance of natural light. Two secondary bedrooms are thoughtfully positioned at the front of the home, offering privacy and flexibility for family members, guests, or a home office. The formal dining room is enhanced by a large window that fills the space with beautiful natural light, creating an inviting setting for entertaining. The open-concept kitchen overlooks the living room, making it ideal for gathering with family and friends. It also includes a cozy breakfast nook, perfect for casual everyday meals. Privately located at the rear of the home, the spacious primary suite is filled with natural light from three large windows. The en-suite bathroom features dual vanities, a soaking tub, a separate walk-in shower, a walk-in closet, and an additional linen closet for extra storage. Sliding glass doors from the living room lead to a covered and screened lanai and a fenced backyard with a paved patio, providing the perfect space for outdoor dining, entertaining, or simply unwinding. Offering 1,706 square feet of living space, this well-maintained home features 3 bedrooms, 2 bathrooms, a formal dining room, an open living room, a functional kitchen, a dedicated laundry room, and a two-car garage. Conveniently located just minutes from Publix, coffee shops, dinners, restaurants, shopping, personal storage facilities, and schools. This home combines comfort, convenience, and an exceptional Windermere location. Don't miss the opportunity to make this beautiful and welcoming home your own—schedule your private showing today! The existing solar panel financing is transferable to qualified buyers, offering the opportunity to enjoy energy savings without the upfront installation cost.

    Contact Yellowkey Agent

    Listing is courtesy of: DENIZ REALTY PARTNERS LLC

  • 2617 BUTLER BAY DR N, WINDERMERE, FL - MLS# O6420023

    WINDERMERE CLUB - O6420023 - 2617 BUTLER BAY DR N, WINDERMERE, FL 34786
    15 Days on yellowkey

    $1,649,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar

    Rare opportunity to own one of the most private lakefront settings on Lake Crescent in Windermere, featuring approximately 165 feet of shoreline, breathtaking water views, and a resort-style waterfront lifestyle on a private ski lake known for its exceptional water quality. This beautifully designed custom residence offers approximately 3,086 square feet, 4 bedrooms, and 4 bathrooms, thoughtfully positioned to maximize natural light, privacy, and panoramic lake views from nearly every main living space. From the moment you arrive, the setting speaks for itself, tranquil water vistas, expansive outdoor living, and an immediate sense of calm that defines this exceptional waterfront property. A grand entrance with custom glass double doors opens into a spectacular great room where soaring vaulted ceilings and a dramatic wall of windows frame uninterrupted panoramic lake views, filling the home with natural light and creating a stunning first impression that defines the entire residence. The open concept layout seamlessly connects the living room, dining area, and spacious kitchen, creating an inviting flow ideal for both relaxed everyday living and effortless entertaining, all while the lake remains the backdrop from nearly every main living space. A truly distinctive feature of the home is its extraordinary collection of handcrafted stained glass art installations. Rich jewel tones and custom artistic designs transform sunlight into ever changing displays of color throughout the home, adding a level of artistry, warmth, and individuality rarely found in lakefront properties. The primary suite is positioned as a private sanctuary, offering soaring ceilings, peaceful lake views, and direct visual connection to the covered, screened lanai and lake beyond. The spa-inspired bath is designed for comfort and relaxation, featuring generous space and soft natural light. The expansive screened lanai overlooks the sparkling pool, spa, and poolside summer kitchen, creating a seamless indoor-outdoor living experience designed for year round Florida enjoyment. Whether entertaining guests, enjoying quiet mornings, or unwinding at sunset, this outdoor space becomes an extension of the home itself. A private dock offers direct access to Lake Crescent, where boating, skiing, paddleboarding, kayaking, and fishing become part of everyday life. Set on a beautifully landscaped homesite offering privacy and exceptional waterfront exposure, this property combines single-story convenience with one of Windermere’s most captivating lakefront settings. Located just minutes from downtown Windermere, boutique shopping, dining, golf, and top-rated schools, it offers both seclusion and convenience in one of Central Florida’s most sought after communities. Rare opportunities on Lake Crescent are limited and homes offering this level of waterfront frontage, architectural character, artistic detail, and true resort-style lake living are seldom available. This is more than a home, it is a lakefront lifestyle designed to be experienced.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 8168 BOAT HOOK LOOP #724, WINDERMERE, FL - MLS# O6421614

    LAKESIDE/LKS/WINDERMERE - O6421614 - 8168 BOAT HOOK LOOP #724, WINDERMERE, FL 34786
    15 Days on yellowkey

    $325,000 | Condo | 3 beds | 2.0 baths

    Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt Disney World! This beautiful 3 Bed + 2 Bath top-floor unit is located in the highly sought-after Horizon West area of Windermere, where comfort, convenience, and an exceptional location come together. Perfectly situated directly across from the clubhouse with easy elevator access, this bright and spacious home offers relaxing views from the private screened balcony overlooking the community's extensive amenities. The open, split floor plan features tile flooring throughout the main living areas, carpet in the bedrooms, and gorgeous crown molding. The lovely kitchen has granite countertops, 42" maple cabinetry, quality appliances, upgraded fixtures, and a large walk-in pantry. Lakeside's amenities include two resort-style pools, fitness center, volleyball courts, and a spacious clubhouse. Located just minutes from Disney, Lake Side Shoppes, Hamlin Town Center, tons of restaurants and top-rated schools! Call today to schedule a viewing!

    Contact Yellowkey Agent

    Listing is courtesy of: ROMAN REALTY GROUP, LLC





Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.