Location: Windermere
Do Not Show Listings
11472 PARK AVE NE, WINDERMERE, FL 34786
$1,125,000140 Days on yellowkey MLS ID: G5105731
5 Days Off yellowkey (back on 4/28/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3166 Built: 1985Monthly Fee: $21 Tax: $5,774 (2025)Community: WindermereSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,774
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Property is currently under contract; seller will consider backup offers Approximately 3,000 sq ft home in a desirable Windermere location within FEMA Flood Zone X. Buyer is responsible for verifying all measurements, dimensions, and square footage The residence offers a flexible layout with multiple living areas and is fully livable, presenting an excellent opportunity for buyers seeking long-term value and equity potential in one of Central Florida’s most established and highly regarded residential markets. Nearby Schools & Community Amenities Conveniently located near Windermere Elementary School on Park Avenue and the Windermere Recreation Center (Butler Bay), which offers lake access, a boardwalk, playground, picnic areas, and open green space along the Butler Chain of Lakes. Luxury Market Areas & Subdivision Context The Property is surrounded by well-established luxury residential communities with home values frequently exceeding $1,000,000. Nearby communities include Isleworth, Casabella at Windermere, and the Butler Bay / Windermere Club area, reinforcing the strong market fundamentals and long-term desirability of the Park Avenue corridor. Recreation, Shopping & Location Benefits The property offers easy access to area golf courses, parks, walking trails, marinas, and everyday conveniences. Located minutes from dining, shopping, and entertainment along International Drive, with convenient connections to major roadways serving Windermere, Orlando, and surrounding communities. Recent price improvement reflects the seller’s decision to position the property competitively within the current Windermere market Showings available upon request
Listing is courtesy of: WEICHERT, REALTORS-HALLMARK PR (352-536-9948)
Listing Agent: Ralph Vock (734-928-8181)
6606 SAWYER SHORES LN, WINDERMERE, FL 34786
$2,500,00096 Days on yellowkey MLS ID: O6386058
Bed: 5 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 5516 Built: 2025 Tax: $3,720 (2024)Community: Sawyer Shores SubSingle Family
Taxes:$3,720
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees or restrictions, you have the freedom to design and build your dream home exactly as you envision it or use the plans already available and variances approved — saving you time and expense. Offering approximately 5,516 SF of impeccably appointed living space and over 8,316 SF under roof, every detail has been curated to the highest standard of elegance and sophistication. Dramatic sightlines from the grand entry sweep through sun-drenched principal rooms to the resort-caliber outdoor living spaces beyond. The showstopping gourmet kitchen dazzles with extra-thick natural quartzite countertops, an oversized center island, pot filler, a fully integrated refrigerator and dishwasher with bespoke wood-panel cabinetry, and an oversized walk-in pantry — a culinary stage worthy of the most discerning chef. A soaring great room with designer tray ceilings and an elegant formal dining room set the scene for unforgettable entertaining, complemented by a private study and home office. The first-floor primary suite is a true sanctuary — a sumptuous walk-in closet, sculptural freestanding soaking tub, and a spa-inspired shower enclosure deliver five-star hotel indulgence at home. Upstairs, a second master suite, a spectacular lake-view recreation room with oversized balcony, three additional bedrooms, a chic loft with front balcony, and a second laundry suite elevate every aspect of daily life. Outside, a breathtaking covered lanai unfolds into a private lakeside paradise — summer kitchen, outdoor fireplace, alfresco dining, and a heated pool and spa framed by elegant paver decking and the glittering expanse of Lake Sawyer. A 4-car garage with EV charging, dual laundry rooms, impact-rated windows and doors, and bespoke designer finishes complete this extraordinary offering. Minutes from Windermere Prep School, shopping, dining and within minutes of Walt Disney World. *Images have been taken from a similar model home*
Listing is courtesy of: PREMIUM PROPERTIES R.E. SERVICE (407-380-2800)
Listing Agent: Nick Khela (407-308-9995)
6560 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786
$1,890,000103 Days on yellowkey MLS ID: O6381835
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3687 Built: 2006Monthly Fee: $298 Tax: $24,050 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$24,050
Middle School: Bridgewater Middle
Remarks: Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil water views, creating an inspiring workspace. Inside, expansive windows frame the sparkling pool and spa, filling the living spaces with natural light and creating a seamless indoor-outdoor ambiance. Contemporary interior updates lend a true “jewel box” feel, with luxury finishes throughout. Neutral designer tones, upgraded Viking appliances, two newer A/C units, and custom iron Cantera double entry doors add both elegance and sophistication. The spacious three-car garage is discreetly tucked at the rear of the property, allowing the home’s striking front elevation and exceptional curb appeal to shine. Situated on an oversized one-third-acre lot overlooking the Camden River, the property offers generous green space and picturesque water views that enhance its impressive setting. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
3629 LAKE BUYNAK RD, WINDERMERE, FL 34786
$1,200,000313 Days on yellowkey MLS ID: G5099846
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2618 Built: 1973 Tax: $8,533 (2024)Community: Lake Buynak EstatesSingle Family
Taxes:$8,533
Remarks: Back on market—buyer withdrew for personal reasons, not due to any home-related issues. Set on 1.3 acres in the Lake Buynak Estate community, this 4-bedroom, 3.5-bath home presents an outstanding opportunity for investors, builders, or buyers wanting space and a Windermere-area address with NO HOA. Offering over 2,600 square feet, two ensuite bedrooms, a split layout, multiple screened porches, and a wood-burning fireplace, the home provides a solid framework for renovation, rental use, multigenerational living, or a future custom build. Upgrades include energy-efficient double-paned windows and a dual septic system with an expanded drain field, enhancing functionality and long-term value. The expansive 1.3-acre lot allows for substantial expansion, an ADU, or complete redevelopment in an area surrounded by high-end homes near Lake Butler. With optional HOA membership and no Windermere city restrictions, the property offers freedom that is rarely available in this ZIP code. Located minutes from Disney, Universal, shopping, dining, and major roadways, it combines convenience with the space and privacy acreage buyers crave. Owner financing may be considered. Explore the potential this unique property provides and imagine the possibilities.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tania Matthews (407-497-9660)
9237 SABAL PALM CIR, WINDERMERE, FL 34786
$769,99559 Days on yellowkey MLS ID: G5110005
REDUCED by $20,000 (2.5%) on 05/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2469 Built: 1985Monthly Fee: $32 Tax: $3,444 (2025)Community: Silver Woods Ph 01Single Family
Taxes:$3,444
Remarks: Nestled in the charming and highly desirable Silverwoods subdivision of Windermere, this beautifully maintained home offers the perfect blend of comfort, convenience, and community living. Ideally situated between Bay Hill and Isleworth, Silverwoods is a sought-after neighborhood of just over 250 homes, known for its tree-lined streets, sidewalks, street lighting, and welcoming atmosphere. Residents enjoy access to tennis courts and the ease of walkable surroundings, all while being just minutes from shopping, dining, grocery stores, churches, and everyday conveniences. This inviting residence features three bedrooms and two bathrooms in a thoughtfully designed layout, enhanced by an impressive 650-square-foot addition that includes a spacious sunroom, bar area, and den—creating versatile living spaces ideal for both everyday comfort and entertaining. Originally built in 1985, the home has been extensively updated with a remodeled kitchen featuring new cabinetry, a standalone island, and updated appliances, all complemented by wood and tile flooring throughout. Additional upgrades include high-efficiency windows, a new 4-ton HVAC system with Nest thermostat, new ductwork and attic insulation, and a new 50-gallon water heater—offering both comfort and energy efficiency. Interior improvements such as new doors, refinished ceilings with LED recessed lighting, and a beautifully refinished stone fireplace add to the home’s modern appeal. The expansive Florida room provides a bright and relaxing retreat with year-round enjoyment of the backyard, while exterior enhancements include premium architectural shingles, a new septic field, a 7-zone irrigation system, and a water softener system. Fiber optic internet is also available, supporting today’s connected lifestyle. This is more than a home—it is an opportunity to experience elevated living in one of Windermere’s most desirable and conveniently located communities.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Chelsea Murphy (407-373-8101)
8272 BRYCE CANYON AVE, WINDERMERE, FL 34786
$509,00084 Days on yellowkey MLS ID: O6389547
REDUCED by $6,000 (1.2%) on 05/07/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1888 Built: 2016Monthly Fee: $71 Tax: $7,459 (2024)Community: Windermere Trls Ph 3BSingle Family
Taxes:$7,459
Elementary School: Bay Lake Elementary
Middle School: Horizon West Middle School
Remarks: 3BR/2.5BA bungalow-style home in the Windermere Trails community. This well maintained residence offers an open floor plan with high ceilings, and premium tile flooring throughout the main level. The home includes a gourmet kitchen, upgraded cabinetry in the laundry room. Upstairs, a versatile loft provides the perfect space for an office or media room, alongside a spacious master suite and two additional bedrooms. Perfectly located near Publix, dining, and banking, and zoned for A-rated schools with Bay Lake Elementary situated right at the community entrance.
Listing is courtesy of: ON ME REALTY (321-370-1474)
Listing Agent: Eduardo Pavone (407-232-1241)
8525 BOWDEN WAY, WINDERMERE, FL 34786
$999,00027 Days on yellowkey MLS ID: O6405195
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2357 Built: 2000Monthly Fee: $298 Tax: $5,825 (2025)Community: Keenes PointeSpa: NoSingle Family
Taxes:$5,825
Remarks: Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and garden tub. Enjoy peaceful evenings in the private back yard with spacious lanai, screened oversized pool and large yard. The fourth bedroom is currently being used as a den with French doors. NEW ROOF IN 2022, WATER HEATER 2020, two car garage with storage, and much more. Discover all this community has to offer, including The Golden Bear Club, a private 18-hole golf course designed by Jack Nicklaus offering golf, tennis, swimming, dining and clubhouse. Located close to shopping, dining, expressways and top-rated public and private schools, this home is perfect as a primary home or vacation home. Call today for you private viewing.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
13420 BONICA WAY, WINDERMERE, FL 34786
$1,875,000249 Days on yellowkey MLS ID: O6347722
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4489 Built: 2006Monthly Fee: $297 Tax: $19,325 (2025)Community: Tildens GroveSpa: YesSingle Family
Taxes:$19,325
Remarks: Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new dual-zoned AC system in August 2025 including Nest smart thermostat. Situated across from the community park and tennis on one of the best waterfront lots in sought-after gated Tildens Grove, offering a perfect blend of privacy and serene panoramic views. Step into elegance in the light and bright formal Living Room enhanced by a stunning Fireplace, Pool and Lanai views, and high Coffered Ceiling. The equally exquisite Formal Dining Room is also adorned with a Coffered Ceiling and ample natural lighting. A beautiful open Island Kitchen at the center of this home, perfectly situated for accommodating and entertaining friends and family, boasts Granite Counters, built-in Wall Oven and microwave, granite back splash, abundant storage in 42" wood cabinetry with pull outs, tray ceiling, 5 burner Gas Stove, effortless ventilation with a modern exhaust hood for a fresh kitchen environment, high-end stainless-steel appliances, and a concealed 11x5 Walk-in Pantry through cabinetry passage. The Kitchen opens to the Dinette area with large picture window overlooking the Lanai and Pool, and Family Room ideal for entertaining with Built-Ins, storage and gorgeous details with French Doors leading to the outdoor living space. Relax, play, or entertain outdoors in the voluminous Pool with Spa and expansive covered Lanai, providing shaded space perfect for enjoying refreshments as you gaze across the water. The spacious Owner’s Suite is a true retreat tucked away on one side of the home, including an elegant bedroom with Sitting Area, stately entertainment wall unit, Double-Tray Ceiling, handsome wood flooring, French Door access to Lanai, and a generous walk-in California Closet system with dressing area. The finely appointed, light-filled Ensuite Bath boasts split sink vanities, large walk-through dual-head shower, Jetted Garden Tub, and private water closet. On the opposite end, the 2nd and 3rd bedrooms share a convenient Jack and Jill bathroom. The private 4th bedroom with Ensuite Bath is perfect for your visiting guests. The 5th bedroom adjacent to the Foyer is currently utilized as a den/home office. Enjoy a home cinema experience in the fabulous 6-seat Theater Room, equipped with great acoustical audio, large movie screen, leather recliner seating, gorgeous Custom Millwork with concealed column storage, all overlooking the Scenic Pond. Located in the hallway between the Kitchen and Dining Room is an extravagant built-in Mahogany glass-front cigar Humidor including Wine Storage to display and preserve cherished collections. High ceilings and Crown Molding accents throughout exude a sense of grandeur. French Doors from multiple rooms let you open the home to the outdoors space. Large, covered Lanai with a built-in grill, sink and counter space, screen enclosed Pool and heated Spa with a panoramic pond view. The Tildens Grove community is quiet and private, with 140 luxury homes, in the top school districts, in a low-traffic area, centrally located for convenience to Windermere's dining, shopping and culture, local theme parks, 429, I-4, and Florida's Turnpike. Whether you're entertaining or seeking a peaceful retreat, this home delivers on every level.
Listing is courtesy of: FERRELL REALTY, INC. (407-628-3200)
Listing Agent: Frank Ferrell (407-227-2753)
WINDERMERE, FL 34786
$359,00040 Days on yellowkey MLS ID: O6400745
2 Days Off yellowkey (back on 5/6/2026)
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $5,436 (2025)Community: Lakes/Windermere-Lk Reams TwhmSpa: NoTownhouse
Taxes:$5,436
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 2-bedroom, 2½-bathroom corner lot townhome in the highly desirable Windermere area! Located at 8905 Newmarket Drive, this home offers the perfect blend of comfort, style, and convenience. The spacious open floor plan is filled with natural light and designed for both everyday living and entertaining. The kitchen features clean white appliances, ample cabinetry, and a layout that flows seamlessly into the living and dining areas.The primary suite provides a relaxing retreat with a well-appointed ensuite bathroom. The second bedroom and additional baths offer flexibility for guests, home office use, or hobbies. Enjoy a private backyard and the added benefits of a corner lot, providing extra privacy and space.Situated in a sought-after community, residents enjoy easy access to top-rated schools, shopping, dining, and major roadways, with quick access to Walt Disney World. Nearby golf courses and Windermere’s charm make this location truly exceptional.Don’t miss the opportunity to own this charming corner lot townhome in a prime location—schedule your private showing today!
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
5070 DOWN POINT LN, WINDERMERE, FL 34786
$4,995,00096 Days on yellowkey MLS ID: O6385276
Bed: 6 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 7349 Built: 1998Monthly Fee: $229 Tax: $58,446 (2025)Community: Sunset BaySpa: YesSingle Family
Taxes:$58,446
Middle School: Chain of Lakes Middle
Remarks: Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless entertaining, the residence offers six bedrooms, six full baths, and a powder bath — including a fully equipped private guest apartment ideal for extended family or long-term visitors. From the moment you arrive, the home’s striking architectural presence is undeniable. A dramatic entry with soaring ceilings and intricate iron detailing introduces expansive living spaces crafted with both grandeur and comfort in mind. Walls of glass and retractable doors blur the line between indoors and out, inviting natural light and panoramic lake vistas into nearly every room. The main level showcases elegant formal spaces, a richly appointed study, and a music room, along with a stunning lakefront family room and game room complete with a stylish wet bar. At the heart of the home, the gourmet kitchen features premium finishes, abundant workspace, and seamless flow for hosting gatherings large or intimate. The primary suite and an additional guest suite are thoughtfully positioned on the first floor for privacy and convenience. Upstairs, guests are treated to elevated lake views from a spacious lounge with kitchenette, multiple bedroom suites, a private theater with adjoining sitting area, and a spectacular balcony overlooking the water. Outdoor living is simply extraordinary. A heated saltwater pool and spa anchor the expansive terrace, complemented by a summer kitchen, bar seating, and a fireplace — the perfect setting for sunset evenings on the water. A private boathouse offers direct access for boating, paddleboarding, or fishing along one of Central Florida’s most coveted waterways. Despite its serene setting, the home is just minutes from upscale shopping, dining, and world-class attractions, including Walt Disney World, and approximately 20 minutes to Orlando International Airport. With the owners preparing for their next chapter, this extraordinary waterfront retreat presents a rare opportunity to own on the Butler Chain at a compelling value. A lifestyle of privacy, beauty, and convenience awaits.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Isis Sarcos (407-749-2130)
9121 TIBET POINTE CIR, WINDERMERE, FL 34786
$14,500,00032 Days on yellowkey MLS ID: O6403217
0 Days Off yellowkey (back on 5/6/2026)
Bed: 6 Bath: 10.0 Gar: 6 Liv Area Sq Ft: 11071 Built: 2006Monthly Fee: $298 Tax: $51,573 (2025)Community: Keenes Pointe 46/104Spa: YesSingle Family
Taxes:$51,573
Remarks: Experience the Ultimate in Luxury Living — Immerse yourself in a world of elegance, privacy, and unparalleled entertainment across four and a half acres of gated perfection within the community of Keene's Pointe on the coveted Butler Chain of Lakes in Windermere. This extraordinary estate showcases a breathtaking resort-style pool and outdoor living experience—complete with slide, waterfall, diving rock, swim-up seating, and a fireside lounge—paired with front-row views of Disney’s nightly fireworks, enjoyed from your private terrace or poolside retreat. Designed for those who live life at the highest level, the residence is rich in craftsmanship and architectural detail, featuring all custom-designed cabinetry, wood windows, extensive molding, intricate inlays, and striking beam work throughout. A grand winding staircase sets the tone upon entry, while hand-scraped wood floors, polished travertine, and dramatic stone interior walls create a warm yet elegant ambiance. Entertain effortlessly with a circular bar and additional tasting wine bar in the game room, along with a private home theater complete with its own candy lobby for a true cinematic experience. At the heart of the home, a professional chef’s kitchen impresses with luxury high-end appliances, custom cabinetry, a hidden pantry, dedicated coffee room, and a statement mahogany wood island. A temperature-controlled wine cellar further enhances the home’s refined lifestyle offerings. Wellness and recreation are thoughtfully elevated with a fully equipped fitness center, private cigar lounge, lit tennis court, and a state-of-the-art indoor basketball court rivaling a professional training facility. Two interior fireplaces, two outdoor fireplaces, along with an outdoor fire pit, create inviting spaces to gather and unwind throughout the property. Whether hosting intimate dinners under the stars, enjoying resort-style amenities, or taking in the spectacular evening skyline illuminated by Disney fireworks, every moment here feels effortless and exceptional. This is more than a home—it is a lifestyle reserved for those who demand the very best in luxury, privacy, and performance.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jay Martin (407-496-8613)
14155 ANCILLA BLVD, WINDERMERE, FL 34786
$399,00028 Days on yellowkey MLS ID: O6404896
0 Days Off yellowkey (back on 5/5/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1629 Built: 2006Monthly Fee: $318 Tax: $5,974 (2024)Community: SummerportTownhouse
Taxes:$5,974
Elementary School: Keene Crossing Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to 14155 Ancilla Blvd, a charming three-bedroom, two-and-a-half-bathroom townhouse in the desirable Windermere community. This 1,629 square foot home offers a comfortable layout with a convenient ground-floor primary bedroom suite, perfect for easy living or hosting guests. The property features a bright colonial design with well-maintained landscaping that creates great curb appeal. Inside, you'll find recently updated flooring throughout, giving the home a fresh, modern feel. The upstairs loft provides flexible space that works well as a home office, playroom, or additional living area. Recent improvements include a 2022 roof replacement and a brand-new 2024 AC unit, providing peace of mind for years to come. The home's location puts you just steps away from fantastic community amenities including a clubhouse, resort-style pool, tennis and basketball courts, and a fitness center. Pet owners will appreciate the on-site dog park, while the fishing pier offers a peaceful spot to relax. The community also features convenient services like a salon, pizzeria, ice cream shop, and even a veterinary clinic, making daily life easier. The location provides easy access to Windermere High School, located just over a mile away, and local shopping at Publix Super Market at Cornerstone. With excellent schools, convenient amenities, and a prime Windermere address, this townhouse offers the perfect blend of comfort and community living in one of Central Florida's most sought-after areas.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Maritza Saint Hilaire (407-953-6765)
9349 TIBET POINTE CIR, WINDERMERE, FL 34786
$7,400,00028 Days on yellowkey MLS ID: O6404415
Bed: 5 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 7529 Built: 2003Monthly Fee: $298 Tax: $41,495 (2024)Community: Keenes PointeSpa: YesSingle Family
Taxes:$41,495
High School: West Orange High
Remarks: Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated lakefront living. Spanning over 7,500 square feet, every detail has been thoughtfully curated to balance grandeur with comfort. A dramatic foyer makes a lasting first impression, overlooking formal living and dining spaces defined by architectural ceilings, designer lighting, and rich travertine flooring. At the heart of the home, the gourmet kitchen is both stunning and functional—featuring professional-grade appliances, custom cabinetry, stone countertops, and an expansive island that seamlessly connects to the dining area and inviting family room. Designed for entertaining, a showstopping game room features a 2,000-gallon saltwater aquarium—famously showcased in The Wall Street Journal—while French doors throughout the main living areas open to a fully screened resort-style patio. Here, a spa, fireplace, and summer kitchen create the ultimate indoor-outdoor living experience. The owner’s suite offers a true private retreat, complete with a fireplace, sitting area, wet bar, and dual dressing rooms—including a two-story boutique-style closet with an adjoining massage room. The spa-inspired bath features a soaking tub and steam shower, delivering a serene, resort-like escape. The main level also includes a private guest suite, a dedicated office with built-in safe, and an oversized laundry and utility space designed for both efficiency and versatility. Upstairs, a fully equipped fitness room and three additional en-suite bedrooms with sleek, modern finishes provide comfort and privacy for family and guests. Outdoors, lush landscaping and mature trees frame a tranquil setting designed for both relaxation and connection to nature. Meandering pathways lead past fountains and gardens to a secluded fire pit beside a gentle stream, while a charming bridge guides you to a private dock on the lake—enhanced with a Trex system for lasting durability. Located within the guard-gated community of Keene’s Pointe—home to the Jack Nicklaus Signature Golf Course at Golden Bear Club and offering direct access to the Butler Chain of Lakes—this residence represents a rare opportunity to own a true legacy property. Recent updates include a new tile roof (August 2024) and upgraded dock system, ensuring both beauty and peace of mind for years to come.
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
$5,500,00038 Days on yellowkey MLS ID: O6401757
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4330 Built: 1994Monthly Fee: $1,224 Tax: $19,599 (2025)Community: IsleworthSpa: YesSingle Family
Taxes:$19,599
High School: Olympia High
Remarks: Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
436 E 7TH AVE, WINDERMERE, FL 34786
$2,175,000237 Days on yellowkey MLS ID: O6350454
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3136 Built: 2025 Tax: $13,016 (2025)Community: Windermere Town RepSingle Family
Taxes:$13,016
Remarks: Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor shower, and an oversized 3-car garage. A dramatic two-story living area sets the tone with clean lines, expansive glass, and natural light throughout. The chef’s kitchen pairs performance and elegance, with a waterfall-edge quartz island, full-height book-matched backsplash, custom cabinetry, and high-end appliances including a Sub-Zero refrigerator, Wolf vent hood, and a full Thermador suite with double ovens and microwave drawer. A hidden walk-in pantry blends seamlessly into the design for added utility and clean aesthetics.Upstairs, the owner’s suite offers lake views, a spacious layout, and a sleek en-suite bath with a large walk-in shower and dual vanity. Secondary bedrooms include en-suite baths and reach-in closets. The home is finished with oversized rectangular porcelain tile throughout the entire main level including the expansive covered lanai and wide plank engineered wood flooring from the staircase through the second floor. Additional highlights include a glass-framed staircase and an abundance of natural light in every space. Located just blocks from Downtown Windermere, this home places you at the center of a highly coveted lakefront lifestyle. Enjoy tennis courts, playgrounds, boat ramps on both Lake Bessie and the Butler Chain, plus a vibrant local culture with weekly farmers markets, food truck nights, and seasonal events in Town Square. Cruise oak-lined sandy streets by golf cart, or explore nearby dining, shops, and fitness at The Grove and along Restaurant Row. World-class golf, theme parks, and the airport are all within easy reach and with the hard work already done, all that’s left is to move in and enjoy. Private showings by appointment only. Seller is Motivated and open to negotiate! We completed the closets upgrades in this beautiful home, thoughtfully designed for the family who will soon call this place home.
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Deniley Valdes (407-922-3870)
12264 MONTALCINO CIR, WINDERMERE, FL 34786
$5,760,00029 Days on yellowkey MLS ID: O6404587
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 7872 Built: 2017Monthly Fee: $495 Tax: $85,351 (2024)Community: Casa Del Lago RepSpa: YesSingle Family
Taxes:$85,351
Elementary School: Sunset Park Elem
Remarks: Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere, located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. with over eight expertly designed rooms, this home was carefully customized by the builder down to the smallest detail — from the finishes to the overall design. With four suites, four full bathrooms, and three powder rooms, this home was designed to delight at every turn. Upon entering, you're welcomed by a grand entry hall with soaring ceilings over 10 feet high and elegant porcelain tile flooring, enhancing the space’s refined atmosphere. The living room, complete with a fireplace, offers a cozy yet sophisticated ambiance, while the kitchen is a showstopper: spacious, quartz countertops, a large island with a waterfall design, and impeccably finished custom cabinetry. The master suite, located on the second floor, is a true retreat. It features a private sitting area, a fireplace, and a spa-like bathroom with a double shower, dual sinks, and a sophisticated design focused on your comfort. In addition to the master suite, the second floor includes additional bedrooms and a versatile living area, ideal for use as a home theater or game room. On the ground floor, a guest suite provides the perfect space for entertaining visitors. The home also offers expansive balconies on both floors with panoramic lake views, seamlessly connecting indoor living areas to a breathtaking outdoor setting. Outdoor features include a terrace, a deck, a pool with a resort-style spa, and a gourmet area — perfect for entertaining friends and family. The entire home is hurricane-proof, offering maximum safety and peace of mind for your family. Located in one of Florida's most desirable areas, you'll be near fine dining, luxury shopping, premier entertainment, and, of course, just minutes from the Disney Parks. Don’t miss this unique opportunity to live in style at one of Windermere’s most prestigious addresses. Schedule your visit today and experience this true gem in person!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
5151 LATROBE DR, WINDERMERE, FL 34786
$3,900,00074 Days on yellowkey MLS ID: O6392380
REDUCED by $200,000 (4.9%) on 05/05/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5301 Built: 2000Monthly Fee: $1,224 Tax: $23,020 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$23,020
Remarks: Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.
13430 HOPKINTON CT, WINDERMERE, FL 34786
$585,000249 Days on yellowkey MLS ID: O6346406
1 Days Off yellowkey (back on 5/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1732 Built: 2005Monthly Fee: $167 Tax: $7,277 (2024)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$7,277
Remarks: ***Charming Windermere Home in Lakes of Windermere – Peachtree! *** Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations. Step inside to find a bright and open floor plan with a spacious great room, dining area, and a well-appointed kitchen featuring ample cabinetry and counter space and kitchen eat in nook. The primary suite includes a walk-in closet and an en-suite bath, while two additional bedrooms and a full bath provide plenty of room for family or guests. Outside, enjoy a large screened in patio perfect for relaxing or entertaining. The home also features a finished garage, new roof, recent exterior painting, storage racks in the garage, central heating & cooling, and fresh curb appeal. Located just minutes from Disney, shopping, dining, top-rated schools, and major highways, this property offers the ideal balance of convenience and community living. The HOA includes access to neighborhood amenities and ensures a well-kept environment. Don’t miss the opportunity to make this charming Windermere home yours!
Listing Agent: Lynn London (410-206-0952)
9055 LEGADO DR, WINDERMERE, FL 34786
$425,00032 Days on yellowkey MLS ID: O6403350
0 Days Off yellowkey (back on 5/4/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2019Monthly Fee: $240 Tax: $6,408 (2025)Community: LegadoTownhouse
Taxes:$6,408
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Under contract-accepting backup offers. Welcome to this beautiful former model townhome in the outstanding Legado community in Windermere, Florida with your own view of the Disney Fireworks! Legado is perfectly positioned near Winter Garden, Horizon West, and just minutes from Disney! Whether you're searching for a private Disney getaway, a smart investment property, or a place to call home, this location truly delivers. Offering 3 bedrooms, 2.5 baths, and 1,584 square feet, this residence showcases upscale finishes throughout, reflecting its status as the original model. The first floor features stunning porcelain wood-look tile and a spacious, open layout ideal for both everyday living and entertaining. The kitchen is a standout with a large peninsula that comfortably seats four, accented by three stylish pendant lights, warm wood cabinetry, including glass-front accents, a beautiful backsplash, and elegant quartz countertops. All appliances convey, including a high-end stainless steel refrigerator. The home is complete with blinds and custom window treatments throughout, and the staircase is enhanced with upgraded iron spindles, adding an additional touch of sophistication. Upstairs, the generous primary suite offers a relaxing retreat with a spa-like bathroom featuring upgraded cabinetry, counters, and a tiled shower. Secondary bedrooms are well-sized with ample storage. At the upstairs landing there is a private balcony overlooks a peaceful pond with no rear neighbors. A two-car garage adds convenience, and the home is ideally located directly across from the community amenities, including a pool and playground, making this property as functional as it is inviting. WELCOME HOME!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Amy Kidwell Pa (407-848-8042)
2 CHASE RD, WINDERMERE, FL 34786
$3,200,000258 Days on yellowkey MLS ID: O6345197
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3889 Built: 2026 Tax: $3,100 (2024)Community: WindermereSingle Family
Taxes:$3,100
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 is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Matthew Hughes (407-619-4717)
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