Location: Windermere
Do Not Show Listings
9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786
$1,859,00098 Days on yellowkey MLS ID: O6390656
1 Days Off yellowkey (back on 6/17/2026)
REDUCED by $40,000 (2.1%) on 05/29/2026
Bed: 6 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5430 Built: 1997Monthly Fee: $267 Tax: $12,735 (2025)Community: BalmoralSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,735
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive ¾-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water fountain, creating a grand sense of arrival. The residence also features a spacious four-car garage equipped with two EV charging stations, offering modern convenience for today’s lifestyle. Custom front entry doors open to an impressive grand foyer with elegant marble tile flooring, introducing the refined finishes that define the home. Inside, the residence has been beautifully transformed with brand-new flooring throughout, custom recessed lighting, upgraded designer fixtures, and crown molding across the main level. At the heart of the home is a stunning designer gourmet kitchen featuring custom white cabinetry, granite countertops, a striking tile mosaic accent wall, and premium KitchenAid stainless steel appliances, including a built-in oven, microwave, and cooktop. Perfect for entertaining or multi-generational living, the home also features a fully rebuilt second kitchen with granite countertops, custom cabinetry, and stainless steel appliances with direct access to the outdoor entertaining area. The home offers two luxurious primary suites, each thoughtfully designed as a private retreat. The upstairs primary suite features a spa-inspired bathroom with dual vanities, custom cabinetry, a dedicated makeup vanity, an oversized jacuzzi soaking tub, and a beautifully tiled walk-in shower. Outdoor living is equally impressive with a custom outdoor kitchen complete with built-in grill, professional venting, and built-in speakers, creating the perfect setting for entertaining and relaxation. Three brand-new sliding glass doors upstairs open to a private balcony, enhancing the home’s seamless indoor-outdoor lifestyle. Recent upgrades provide comfort and peace of mind, including a new Carrier 5-ton air conditioning system, new 50-gallon water heater, whole-home water purification system, and a new pool pump installed within the last six months. With extensive renovations, luxurious finishes, and exceptional indoor-outdoor living, this remarkable residence offers the sophistication, comfort, and lifestyle expected of a premier luxury estate.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ryan Rogers (407-492-0674)
11234 RAPALLO LN, WINDERMERE, FL 34786
$520,0005 Days on yellowkey MLS ID: O6416987
0 Days Off yellowkey (back on 6/16/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2236 Built: 2003Monthly Fee: $136 Tax: $3,973 (2025)Community: Belmere Village G2 48 65Single Family
Taxes:$3,973
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Located in the highly sought-after gated community of Belmere in Windermere, this beautifully maintained 4-bedroom, 2.5-bath home offers 2,236 square feet of comfortable living space and a thoughtfully designed floor plan. Filled with natural light, the home features spacious living and dining areas, a well-appointed kitchen that opens to the family room, and generously sized bedrooms, including a private primary suite. One of the home's standout features is the beautiful low-maintenance backyard courtyard, creating a private outdoor retreat perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine without the upkeep of a large yard. Residents of Belmere enjoy an exceptional amenity package including a clubhouse, fitness center, resort-style pool, tennis court, basketball court, playground, and walking areas, all within a secure gated setting. Conveniently located near top-rated schools, shopping, dining, major highways, and area attractions, this home offers the perfect combination of comfort, convenience, and community living.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kyle Grafton (203-246-8512)
11564 MIZZON DR #930, WINDERMERE, FL 34786
$325,00047 Days on yellowkey MLS ID: O6404607
2 Days Off yellowkey (back on 6/16/2026)
REDUCED by $10,000 (3.0%) on 05/31/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,561 (2025)Community: Lakeside/Lks/Windermere CondoCondo
Taxes:$4,561
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Lovely 3rd floor (Corner unit on top floor) In sought after Lakes at Lakeside of Windermere. Well-appointed 3 Bedrooms and 2 bathrooms Condo, Spacious feel. Offering an excellent layout. Newer carpets, home is ready to move in. Dine in kitchen has 42" dark cherry wood cabinets and granite countertops, stainless range and dishwasher, laminate flooring throughout the living areas and new carpet in bedrooms. Master bedroom Features walk-in closet, and Master bathroom 2 further bedrooms and other full bathroom. Step out from sliding doors to the Spacious covered/screened balcony. Elevators and stairs access to the unit. Superb community amenities. Resort style recreation, Olympic swimming pool, sand volleyball court, state-of-the-art fitness center, playground, large community clubhouse, BBQ area, & cozy outdoor fireplace! With easy access to all major highways including I-4, 429, & SR 535…Close to Disney theme parks & Restaurants, Dining, Shopping & School. Maintenance, carefree Florida living, in this well-maintained community
Listing is courtesy of: RE REALTY (321-363-6345)
Listing Agent: Reeta Gulati (321-363-6345)
2 CHASE RD, WINDERMERE, FL 34786
$2,200,000276 Days on yellowkey MLS ID: O6345197
REDUCED by $1,000,000 (31.3%) on 06/16/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3889 Built: 2026 Tax: $3,100 (2024)Community: WindermereSingle Family
Taxes:$3,100
Elementary School: Windermere Elem
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!
Listing Agent: Matthew Hughes (407-619-4717)
11536 CLAYMONT CIR, WINDERMERE, FL 34786
$1,175,00086 Days on yellowkey MLS ID: O6392958
REDUCED by $75,000 (6.0%) on 05/26/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2882 Built: 2002Monthly Fee: $298 Tax: $8,766 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Spa: YesSingle Family
Taxes:$8,766
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Virtually Staged. Price Improvement! Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and lifestyle. Beautifully remodeled throughout, this is truly move-in ready, showcasing a fresh, modern aesthetic while maintaining timeless architectural appeal. From the moment you enter, you’re welcomed by marble tile flooring, newly refinished wood floors, fresh interior paint, and thoughtfully selected modern light fixtures that elevate every space. The home features both a traditional dining room and formal living room, complemented by custom window treatments that add warmth and sophistication. At the heart of the home, the completely remodeled kitchen shines with all-new appliances, a gas stove, double oven, quartz countertops, and a large walk-in pantry, all wrapped in a clean, contemporary design that seamlessly opens to the family room—where a decorative modern fireplace creates the perfect gathering space. The expansive primary suite is a true retreat, featuring wood floors, direct pool access, a dedicated mini-split system for enhanced comfort and efficiency, and a spa-inspired bathroom with a stunning new garden tub, separate shower, and an oversized walk-in closet. Additional bedrooms lend to stylish comfort with new herringbone tile flooring and share a convenient Jack-and-Jill bathroom. All bathrooms throughout the home have been fully remodeled with high-end finishes. A large private office with a built-in desk provides the ideal work-from-home environment. Step outside to a spacious, fenced backyard featuring a newly repainted pool and patio—perfect for enjoying Florida living year-round. Additional highlights include a 2020 roof, paver driveway, and an oversized 3-car garage. Every detail has been thoughtfully updated, making this home completely turn-key. Residents of Keene’s Pointe enjoy 24-hour guard-gated security and a lifestyle centered around both recreation and natural beauty. The community offers private access to the Butler Chain of Lakes, ideal for boating, skiing, and sunset cruises, along with scenic walking paths, tranquil green spaces, and a peaceful, well-maintained setting throughout. There is even the opportunity for boat storage, adding convenience for those looking to fully embrace the lake lifestyle. Optional membership to the Golden Bear Club unlocks a premier lifestyle experience with championship golf, tennis, fitness, a resort-style pool, dining, and a vibrant calendar of social events. The neighborhood also features community parks, playgrounds, and gathering spaces, creating a welcoming environment that blends luxury living with everyday convenience and community connection through regular neigborhood events. Whether you're relaxing poolside, entertaining guests, or enjoying the unmatched lifestyle of this premier golf and lakefront community, this home delivers the very best of Central Florida living.
Listing is courtesy of: MATT ALLEN REAL ESTATE LLC (321-228-5555)
Listing Agent: Matt Allen (321-228-5555)
7719 ANSELMO LN, WINDERMERE, FL 34786
$375,00088 Days on yellowkey MLS ID: O6392007
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $7,000 (1.8%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2008Monthly Fee: $375 Tax: $5,537 (2025)Community: Lake Sawyer South Ph 03Townhouse
Taxes:$5,537
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Virtually Staged. Move-in ready townhome offering a clean, functional layout with abundant natural light throughout. Upon entry, you’re welcomed into a spacious living room that provides a comfortable and defined gathering space separate from the kitchen and dining areas. Toward the rear of the home, the kitchen and dining area are thoughtfully positioned for everyday functionality and ease of use. The kitchen features granite counters, stainless steel appliances, ample cabinetry, and a breakfast bar that offers additional seating and prep space. The adjacent dining area provides direct access to a private, fenced paver patio, creating a low-maintenance outdoor space ideal for relaxing or entertaining. Recent updates include new interior paint, new carpet, and a new water heater, enhancing both comfort and long-term value. A/C unit was replaced with a brand new unit in 2021. Upstairs, all bedrooms feature fresh carpet flooring and generous closet space. The primary suite offers a spacious layout with an en suite bathroom that includes dual sinks and a walk-in shower. Additional bedrooms are well-sized and versatile for guests, office space, or hobbies. A convenient upstairs laundry area and a main-level half bath add to the home’s practical appeal. With neutral finishes, thoughtful updates, and a well-maintained interior, this property is a strong option for buyers seeking low-maintenance living with functional space and modern touches.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Stephanie Pitts (407-353-6132)
9312 BLANCHE COVE DR, WINDERMERE, FL 34786
$12,350,00019 Days on yellowkey MLS ID: O6407102
Bed: 7 Bath: 9.5 Gar: 4 Liv Area Sq Ft: 11465 Built: 2022Monthly Fee: $1,224 Tax: $116,012 (2025)Community: Isleworth 5Th AmdSpa: NoSingle Family
Taxes:$116,012
Remarks: Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,000 square feet, the residence is thoughtfully positioned to capture sweeping views across the lakefront, with walls of glass framing the water from nearly every room and filling the interiors with natural light. Beauty and modernity define the home, where sleek architectural lines are complemented by elegant oak wood flooring throughout. The main living areas flow effortlessly, creating both an impressive setting for entertaining and a comfortable environment for everyday living. At the heart of the home, a striking kitchen features distinctive Viking appliances, a Miele espresso machine, two wine refrigerators, and a seamless connection to the family room, patio, and surrounding living and dining spaces.The estate offers 7 spacious bedrooms and 9.5 baths, with each suite designed for privacy and comfort. Multiple levels—including a rooftop terrace—provide an array of vantage points from which to enjoy the lake and surrounding grounds. Additional highlights of the estate include a private home theater; a versatile lakefront bonus room ideal for a game room, wellness studio, or creative space; and two adjoining offices with custom built-ins that can be closed off for quiet focus. A standout feature of the property is the expansive guest residence on the lower level, complete with its own full kitchen, living room, two en-suite bedrooms, laundry room, and private patio—perfect for extended family or long-term guests. Practicality meets luxury with three laundry rooms throughout the estate, an elevator servicing multiple levels, and a four-bay garage. Outdoors, the expansive grounds offer both privacy and possibility, anchored by a spacious yard that leads to a private dock along the shores of Lake Blanche. A covered lanai with summer kitchen and screened living area creates an inviting setting for year-round entertaining, seamlessly blending indoor and outdoor living. This is a home that delivers on every level—scale, setting, and sophistication—offering a truly exceptional lakefront lifestyle within one of the finest golf club communities in the world.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
9832 LAUREL VALLEY DR, WINDERMERE, FL 34786
$13,900,0009 Days on yellowkey MLS ID: O6416194
Bed: 6 Bath: 8.5 Gar: 4 Liv Area Sq Ft: 11100 Built: 2004Monthly Fee: $1,167 Tax: $93,184 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$93,184
Remarks: Virtually Staged. https://iframe.videodelivery.net/7c8847db18d8a7617d27c5577c88508f A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most well known communities. This statement home features six bedrooms, seven full bathrooms, and three half bathrooms, a newly installed bespoke theater room with custom seating, an infrared sauna and dedicated wellness and fitness area, two full bars, a private pub and game room, an elegant pool and spa, a fully equipped summer kitchen, and multiple levels of outdoor living and lounge space overlooking the lake. Complemented by countless additional spaces designed for both grand-scale entertaining and everyday enjoyment, every room exudes elegance and has been meticulously designed and expertly executed down to the finest detail. Beyond its unmatched location and architecture, the home has benefited from several million dollars’ worth of enhancements and upgrades, further elevating an already impressive estate into something truly magnificent. The result is a residence that blends timeless luxury with modern comfort while offering one of the most desirable waterfront settings in Central Florida. Not all lakefront homes are created equal, and Laurel Valley is a shining example of that. More than a home, 9832 Laurel Valley Drive is a statement. A trophy estate befitting a legacy. A rare opportunity to own one of Florida’s most compelling waterfront properties ever. The home may be negotiated to include select furniture, a brand-new pontoon boat, two new Sea-Doo jet skis, and a golf cart.
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Nicholas Taylor (407-810-9680)
12720 JACOB GRACE CT, WINDERMERE, FL 34786
$2,750,000107 Days on yellowkey MLS ID: TB8476930
REDUCED by $95,000 (3.3%) on 06/16/2026
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2005Monthly Fee: $300 Tax: $13,298 (2024)Community: Tildens Grove Ph 01 47/65Spa: YesSingle Family
Taxes:$13,298
Remarks: Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central Florida living. A long, winding driveway welcomes you, framed by mature trees and sweeping lawns. Tucked away on a quiet cul-de-sac within a 24-hour guard-gated neighborhood with a manned guard station, the property offers both grandeur and seclusion — a rare combination in today’s luxury market. Thoughtfully designed to maximize natural light and panoramic water views, the home features soaring ceilings, expansive picture windows, and seamless indoor-outdoor flow. The grand foyer opens to a spectacular living room anchored by tranquil lake vistas. The chef’s kitchen is appointed with custom cabinetry, high-end appliances, and an oversized island, effortlessly connecting to spacious dining and living areas — ideal for both intimate evenings and large-scale entertaining. The primary suite, located on the main level, is a private sanctuary with serene lake views and direct access to the outdoor living areas. The spa-inspired bath offers a soaking tub, dual vanities, walk-in shower, and generous closet space. Four additional bedrooms of which two of them include their own en-suite bath, ensuring comfort and privacy for family and guests. A detached in-law suite with private entrance, living area, bedroom, and bath provides exceptional flexibility for multigenerational living, long-term guests, or a private executive office. Step outside to your own outdoor oasis. The resort-style pool overlooks the lake, creating a stunning backdrop for entertaining or quiet relaxation. A charming pool house complete with a Murphy bed offers additional guest accommodations and enhances the estate’s resort-like ambiance. At the water’s edge, a private dock provides access to a private ski lake — perfect for boating, skiing, paddleboarding, or sunset cruises. As evening falls, the magic begins. From your backyard, dock, or expansive windows, enjoy nightly fireworks illuminating the sky above Disney — a spectacular private show reflected across the water. With nearly two acres of lakefront land, six bedrooms, six and a half baths, a detached suite, pool house, long private driveway, and location within one of Windermere’s most prestigious guard-gated communities, 12720 Jacob Grace Ct is more than a home — it is a destination, a sanctuary, and a stage for life’s most extraordinary moments.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Adrian Jacob (832-381-4670)
14005 SPARKLING COVE LN, WINDERMERE, FL 34786
$370,00030 Days on yellowkey MLS ID: O6409827
REDUCED by $5,000 (1.3%) on 06/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1647 Built: 2007Monthly Fee: $539 Tax: $1,943 (2025)Community: Oasis Cove 1 At Lakeside Village Condo Ph 1Townhouse
Taxes:$1,943
Elementary School: Bay Lake Elementary
Remarks: Welcome to resort-style living in the gated community of Oasis Cove in the heart of Windermere! This beautifully maintained three-bedroom, 2.5-bath townhome with a two-car garage also features a spacious loft and a versatile bonus room/home office, offering flexible living space beyond the traditional bedroom layout. Tucked away on a quiet dead-end street with minimal traffic, the home enjoys peaceful wooded and lake views with no rear neighbors, creating a tranquil retreat to come home to each day. Inside, soaring ceilings and an open-concept layout create a bright and spacious feel. The updated kitchen features granite countertops, ample cabinetry and overlooks the main living area, ideal for entertaining or everyday living. The primary suite is conveniently downstairs and offers serene wooded views for a relaxing escape. Upstairs, you’ll find additional bedrooms along with the loft and bonus room, ideal for remote work, hobbies, a media room, playroom or guest overflow space. The laundry room is also conveniently upstairs. Sellers are offering a $5,000 carpet allowance with an acceptable offer, giving buyers the opportunity to personalize the flooring to their taste. Enjoy Florida living year-round from the screened patio and open patio deck, both with attractive stone pavers in the front walkway and rear of the home. Additional upgrades include a 2020 HVAC system with UV lighting and an air filtration system for enhanced comfort and air quality. The home is also wired for surround sound, and the speakers are available should buyers wish to reconnect them after the freshly painted downstairs interior. Residents of Oasis Cove enjoy exceptional amenities, including a resort-style pool with lake views, fitness center, clubhouse, playground and beautifully maintained grounds. HOA fees include exterior maintenance, water, cable, internet, and grounds maintenance for added convenience and value. Just minutes from shopping, dining and everyday conveniences, this home also offers quick access to SR 429, Florida’s Turnpike, and Interstate 4. Enjoy being approximately 20 minutes from Walt Disney World, EPCOT and Disney's Animal Kingdom Theme Park while enjoying the peaceful charm of Windermere living. Nearby attractions also include Hamlin Town Center, golf courses, scenic lakes, restaurants and top-rated schools.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Carrie Bantel (321-217-8750)
5500 W LAKE BUTLER RD, WINDERMERE, FL 34786
$4,700,00033 Days on yellowkey MLS ID: O6408637
0 Days Off yellowkey (back on 6/9/2026)
Bed: 8 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 7000 Built: 1997 Tax: $17,387 (2025)Community: West Lake Butler EstatesSpa: YesSingle Family
Taxes:$17,387
Remarks: Under contract-accepting backup offers. Experience the pinnacle of lakefront luxury breathtaking acres in the heart of Windermere, offering an extraordinary 320 feet of pristine ski lake frontage and an unmatched resort-style lifestyle. This one-of-a-kind waterfront compound features a stunning 6-bedroom, 5-bathroom main residence encompassing 12,323 gross square feet with 7,000 heated square feet, thoughtfully designed to maximize comfort, elegance, and breathtaking water views from nearly every angle. Adding to the property’s exceptional versatility is a private 2-bedroom, 1-bathroom guest house and separate garage apartment, creating incredible multigenerational living potential or the ideal setup for extended guests, private offices, or luxury accommodations. The showstopping covered dock pavilion is truly in a class of its own, featuring an expansive over-water lounge, designer outdoor kitchen, bar seating, dining area, and private boat slip, creating the ultimate lakeside retreat. Every detail of this estate has been curated to deliver a private luxury resort experience unlike anything else on the market. The grounds are equally spectacular with a custom screened pool and heated spa overlooking the lake, a private sandy beach, mature canopy trees, waterfront firepit lounge, multiple entertaining spaces, and beautifully manicured landscaping that creates total serenity and privacy. The property’s incredible resort-style entertaining infrastructure makes it ideal for hosting intimate gatherings or large-scale events with ease. Perfectly positioned just minutes from charming downtown Windermere, and conveniently located near Horizon West and downtown Winter Garden, this extraordinary estate also offers easy access to Orlando’s world-renowned attractions — including approximately 25 minutes to Disney and Central Florida’s premier theme parks, and only 30 minutes to Orlando International Airport (MCO). Whether enjoying peaceful mornings on the water, sunset cruises from your private dock, or entertaining on a grand scale, this extraordinary Windermere estate offers a rare opportunity to own one of Central Florida’s most impressive waterfront compounds. A true WOW property that must be experienced in person to fully appreciate its scale, setting, and lifestyle.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Julie Sanchez (817-807-3117)
6558 HELMSLEY CIR, WINDERMERE, FL 34786
$635,0009 Days on yellowkey MLS ID: S5151342
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2575 Built: 2009Monthly Fee: $129 Tax: $4,553 (2025)Community: Preston SquareSingle Family
Taxes:$4,553
Remarks: Immaculately maintained, move in ready, 4 bed, 3 bath family home in the highly sought after Preston Square community, an established Windermere community. The home feels warm and welcoming, but also luxurious with the 10ft ceilings, crown molding and plantation shutters. The kitchen features a dining area and boasts upgraded appliances, granite countertops and 42" cabinets. The primary bedroom is conveniently located on the first floor, a lovely refuge with tray ceiling, large walk in closet with built ins and en suite bathroom. The large upstairs bedroom, bathroom and bonus room would make a great teenager space, in law suite or entertainment area. Roof was replaced in 2022 and to save on high power bills, a complete, FULLY PAID, solar system installed in 2023!! Other upgrades include new interior paint and light fixtures in 2025, exterior painted in 2019 and a water purification system. For easy maintenance, the sod in the back yard has been replace with turf, is fully fenced and has a spacious screened patio - a serene, private place to relax with your favorite coffee or cocktail! Located in a top-rated school district and zoned for Windermere High School, this home combines luxury, convenience, and peace of mind in one of Central Florida’s most desirable communities. square has a charming atmosphere and features its own community pool, park, playground and sport court, all located just minutes from shopping, dining, and theme parks. A short drive to historic Windermere Town with its weekly farmers market, monthly food carts, historic town hall and old school house. Don't miss the opportunity to live the Florida lifestyle in this gorgeous home located within a great school district!
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Sue Webb (407-361-6425)
9620 MAYWOOD DR, WINDERMERE, FL 34786
$2,349,00066 Days on yellowkey MLS ID: O6399315
REDUCED by $51,000 (2.1%) on 06/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3004 Built: 1979 Tax: $20,433 (2025)Community: Lake Down ShoresSpa: NoSingle Family
Taxes:$20,433
Remarks: Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a setting that feels refined and relaxed. From sunrise to sunset, the backdrop is nothing short of extraordinary. Sweeping views stretch across Lake Down, where calm morning waters give way to vibrant evening skies, and a nightly Disney fireworks view adds a subtle sense of wonder to the horizon. The property is thoughtfully oriented to take full advantage of its surroundings, featuring a private beach area, a two-story dock and direct access to the Butler Chain, one of Central Florida’s sought-after and interconnected lake systems, known for its recreational appeal and timeless value. Inside, the home offers a layout designed for everyday living and effortless entertaining. Spacious living and family rooms are complemented by an open kitchen appointed with granite countertops and stainless steel appliances, creating a central gathering space that flows naturally to the outdoors. A dedicated office or den provides flexibility for work or quiet retreat, while an upstairs loft captures elevated, panoramic views of Lake Down, an ideal setting for a secondary lounge, media space or creative studio. The outdoor experience is equally compelling. A resort-style pool anchors the backyard, accompanied by a screened porch and expansive lawn that extends toward the water’s edge. The setting invites relaxed afternoons and large-scale gatherings, with ample room to further enhance or personalize the landscape. A greenhouse and additional storage add charm and functionality, supporting a variety of lifestyle needs. A second-story balcony offers yet another vantage point, where elevated lake views and evening fireworks create a memorable daily backdrop. Whether enjoying a quiet morning coffee or winding down at sunset, this space reinforces the home’s seamless connection to its environment. Positioned in a peaceful and private location, yet just moments from renowned restaurants, shopping and everyday conveniences, the property offers a rare balance of seclusion and accessibility. Its location on one of the desirable stretches of Lake Down further underscores its long-term appeal. This is a compelling opportunity to enjoy the home as it exists today or to reimagine the site as an exceptional custom waterfront estate. In a setting defined by natural beauty, established luxury and enduring demand, properties of this caliber and positioning are increasingly rare.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Linda O'Grady (407-970-6880)
11539 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$3,800,0005 Days on yellowkey MLS ID: O6416913
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5018 Built: 2017 Tax: $14,654 (2025)Community: Lake Butler EstatesSpa: NoSingle Family
Taxes:$14,654
Remarks: Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. Nestled on a sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort. Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with wide plank wood flooring, tongue & groove ceilings, and exposed timber beams that create a warm, inviting atmosphere. The impressive 1st floor primary suite features a huge closet offering ultimate storage and style. Guests will enjoy complete privacy in the generously sized 1st floor guest suite. The gourmet kitchen is a chef’s dream, having Natural Gas & equipped with high-end Thermador appliances and crowned by stunning quartz countertops—perfect for preparing meals or entertaining. Step outside to the fully appointed summer kitchen and enjoy the screen-enclosed swimming pool on your expansive wrap-around porch, enhanced by elegant stacked stone columns. Car enthusiasts and hobbyists will appreciate the oversized 42 x 30 - 4 car garage with 10-foot tall doors, providing ample space for all your toys and vehicles. Additional modern comforts include natural gas for efficiency and convenience throughout the home. Laundry Rooms on each Floor - Located on the most sought-after street in Windermere, this masterpiece offers privacy, style, and unparalleled craftsmanship. Truly, this is everyone’s dream home—ready for you to create lasting memories.
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
6648 HELSTON LN, WINDERMERE, FL 34786
$665,0005 Days on yellowkey MLS ID: O6413354
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3072 Built: 2005Monthly Fee: $82 Tax: $9,709 (2025)Community: Lakes/Windermere Ph 02ASingle Family
Taxes:$9,709
Remarks: Beautiful two-story residence offering 4 bedrooms and 3.5 bathrooms, plus an upstairs multi purpose bonus room with full bathroom, that can easily be converted into a 5th bedroom, perfectly positioned on an oversized lot in the highly desirable Lakes of Windermere community. This home combines comfort, space, and an exceptional Florida lifestyle in one of the area’s most sought-after neighborhoods.A welcoming front porch leads into a bright and spacious open-concept layout featuring formal living and dining areas, along with a generous family room designed for both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing a large center island, breakfast bar, breakfast nook, recessed lighting, 42” dark mahogany cabinetry, solid surface countertops, designer tile backsplash, and a convenient butler’s pantry for added storage and functionality. The primary suite offers a peaceful retreat with a tray ceiling, expansive walk-in closet, dual sink vanity, and a relaxing garden tub. Secondary bedrooms are well-sized and thoughtfully positioned, complemented by a versatile upstairs bonus room ideal for a media room, office, or additional living space. Major improvements include a brand-new roof installed in August 2024, along with HVAC updates (upstairs unit replaced in 2016 and downstairs unit in 2017), providing added value and peace of mind.Enjoy outdoor living with covered front and rear porches, offering great space to relax and enjoy the surrounding neighborhood atmosphere (rear porch is not screened/enclosed). Lakes of Windermere is a beautifully maintained master-planned community known for its mature landscaping, scenic surroundings near Lake Sawyer, and exceptional amenities including a clubhouse, resort-style pool, tennis courts, basketball courts, soccer field, beach volleyball, and fishing pier. Ideally located in one of Central Florida’s most desirable areas, with access to top-rated schools, nearby shopping centers, dining options, parks, and major roadways, and just a short drive to world-famous attractions.
Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)
Listing Agent: Isabel Sirizzotti (407-361-8236)
6897 NORTHWICH DR, WINDERMERE, FL 34786
$574,90059 Days on yellowkey MLS ID: O6400673
0 Days Off yellowkey (back on 5/18/2026)
REDUCED by $5,000 (0.9%) on 05/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2229 Built: 2003Monthly Fee: $82 Tax: $7,925 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$7,925
Remarks: Under contract-accepting backup offers. Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel throughout the main living areas. The kitchen has been refreshed with newer appliances, including a refrigerator (2025) and electric stove and microwave (2025), along with major systems such as roof (2018), and AC (2020) - giving buyers peace of mind and a clean, updated look from day one. Complementing the space is updated tile flooring in the kitchen (2023), blending durability with style. Major updates continue with a hot water heater (2023), adding to the home’s overall value and reducing big-ticket concerns for future homeowners. With four well-sized bedrooms and three full bathrooms, the layout offers flexibility for families, guests, or a dedicated home office. Located in the heart of Windermere, residents of Lakes of Windermere enjoy access to community amenities including a pool, playground, volleyball & tennis courts - conveniently across the street from your home. All while being just minutes from top-rated schools, shopping, dining, and major roadways. Your community now has fiber internet as an option! Don't miss out on one of the best values in Central Florida's most sought communities of Windermere!!
Listing is courtesy of: REALTY ONE GROUP INSPIRATION (321-233-2300)
Listing Agent: Blake Blahut (407-748-0484)
9621 WINDY RIDGE RD, WINDERMERE, FL 34786
$12,999,99961 Days on yellowkey MLS ID: O6400740
REDUCED by $430,001 (3.2%) on 06/15/2026
Bed: 9 Bath: 13.0 Gar: 8 Liv Area Sq Ft: 20445 Built: 2025 Tax: $13,931 (2025)Community: Windsor HillSingle Family
Taxes:$13,931
Remarks: Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool with a spa and massage room ! Highlights: • Custom-built mansion in progress — secure it now to choose your colors, flooring, cabinetry, countertops, lighting, and finishes • Private helicopter pad for seamless arrival and departure • Luxury bowling alley in development — your private entertainment retreat of turn into extra car show storage garage area ! • Grand open floor plan, soaring ceilings, and estate-level architecture • Massive gourmet kitchen + walk-in pantry, ideal for chef-level entertaining • Space for home theater, gym, wine cellar, or guest quarters • Oversized garages and motor court • For our equestrian lovers, you are permitted one horse for each acre. Location Perks: • Situated in one of Windermere’s most coveted neighborhoods • Minutes to Lake Butler Chain, championship golf, and elite private schools • Close to Winter Garden Village and exclusive dining/shopping This is a rare opportunity to own a truly bespoke estate before completion — where every detail is yours to design, and your view is forever protected. Inquire now for private plans, customization walkthrough, and completion timeline. Step into your own private paradise with this one-of-a-kind resort-style property featuring every amenity for ultimate relaxation and recreation. Highlights include: • Lagoon-style pool with a swim-up bar, perfect for hosting or unwinding in luxury • Private spa sanctuary with a designated massage room and indoor heated pool, offering year-round wellness experiences • Full-size tennis court for active days and fun with friends or family • Charming barn – ideal for equestrian use, storage, or a stunning rustic event space Whether you’re dreaming of daily spa treatments, evening swims under the stars, or tennis matches followed by cocktails poolside, this property delivers the ultimate blend of luxury and leisure.
Listing is courtesy of: CITARELLI REALTY GROUP LLC (321-607-3586)
Listing Agent: Natalie Citarelli (321-607-3586)
12555 CRUXBURY DR, WINDERMERE, FL 34786
$350,00025 Days on yellowkey MLS ID: O6410796
2 Days Off yellowkey (back on 6/15/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1211 Built: 2005Monthly Fee: $200 Tax: $4,443 (2025)Community: Lakes Of Windermere - Lake Reams TownhomesTownhouse
Taxes:$4,443
Remarks: Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 12555 Cruxbury Drive in Windermere, a well-maintained 2-story townhouse offering 2 bedrooms, 2.5 bathrooms, and a practical layout in a convenient Central Florida location. Set on a quieter street with a conservation area across the way, the home offers a more open surrounding feel with added privacy. The main level features comfortable living and dining areas designed for everyday use, along with a kitchen that has a pantry closet and connects easily to the shared spaces. The home has been thoughtfully improved with a number of recent upgrades, including replaced toilets, faucets, bathroom fixtures, dishwasher, washing machine, dryer, kitchen light fixture, and exterior lighting. Additional updates include a new kitchen backsplash, LED flood lights, epoxy-coated bathroom walls, and electrical improvements completed following the previous inspection. The mirrored bathroom walls were also removed, giving the spaces a cleaner and more updated appearance. Upstairs, both bedrooms are separated from the main living area, creating a practical setup for privacy, guests, roommates, or a home office arrangement. With 2 full bathrooms upstairs and a half bath on the first floor, the layout works well for both daily living and entertaining. Outside, the patio offers a manageable area for seating, plants, or a small outdoor dining setup. The exterior lighting adds function and curb appeal, while the conservation area across the way contributes to the home’s quieter setting. The exterior of the home was also freshly repainted last year through the HOA, helping maintain a clean and updated appearance. Adding to the home’s appeal is the low-maintenance lifestyle provided by the HOA, which handles roof repairs, exterior painting (touchup 2025), and landscaping maintenance, allowing for easier day-to-day ownership and added peace of mind. Located in Windermere, the property is close to restaurants, daycare options, nearby elementary schools, Disney University, shopping, parks, area employers, and major Central Florida roadways. With its low-maintenance layout, recent updates, HOA-covered exterior maintenance, patio space, and well-connected location, 12555 Cruxbury Drive offers a solid opportunity in a desirable Windermere area.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00036 Days on yellowkey MLS ID: O6407352
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $9,227 (2025)Community: Windsor HillSingle Family
Taxes:$9,227
Remarks: Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
9072 WOODBREEZE BLVD, WINDERMERE, FL 34786
$549,90045 Days on yellowkey MLS ID: O6403789
1 Days Off yellowkey (back on 6/15/2026)
REDUCED by $12,600 (2.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1721 Built: 1985Monthly Fee: $30 Tax: $3,899 (2025)Community: Silver WoodsSpa: NoSingle Family
Taxes:$3,899
Remarks: Best price Improvement.. Welcome to 9072 Woodbreeze Blvd, a beautifully maintained and thoughtfully updated home nestled in the highly desirable Silver Woods community of Windermere. This charming single-story residence offers 3 bedrooms, 2 bathrooms, and 1,728 square feet of comfortable living space, perfectly blending classic character with modern improvements. Set on a spacious quarter-acre lot, the property showcases mature landscaping and a serene pond view that creates a peaceful backyard retreat. Inside, the home is filled with natural light and designed for both relaxation and everyday living. The kitchen and family room flow seamlessly together, offering inviting spaces to gather while enjoying picturesque views of the lush yard and water beyond. A standout feature is the added Florida room—an ideal spot to unwind, entertain, or simply take in the tranquil surroundings year-round. This home has been lovingly cared for, with key updates already completed for peace of mind. Recent improvements include a newer A/C system, newer hot water heater, updated exterior lighting and door hardware, and consistent professional grounds maintenance. Major systems have also been addressed, with the septic system replaced in 2019 and the roof replaced in 2020. The kitchen, updated in 2010, features full-sized cabinetry and durable Corian countertops, offering both functionality and timeless appeal. Silver Woods is known for its welcoming, family-friendly atmosphere and remarkably low HOA dues of just $364 annually. Residents enjoy access to community amenities including tennis and pickleball courts, all while being conveniently located within walking distance to local middle and high schools, as well as the Grove Publix shopping center with its variety of restaurants, shops, and fitness options. The location is truly exceptional—just minutes from Sand Lake Road’s renowned dining and entertainment, with easy access to major highways including I-4, the Turnpike, 528, and the 408. Downtown Orlando is only about 20 minutes away, and Orlando International Airport is approximately a 25-minute drive. This home offers a rare combination of comfort, updates, location, and community charm. It’s a place where you can truly settle in and enjoy the best of Central Florida living!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Charles Kohlinger (407-421-9188)
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