Location: Windermere, Windermere
Do Not Show Listings
2617 BUTLER BAY DR N, WINDERMERE, FL 34786
$1,649,00015 Days on yellowkey MLS ID: O6420023
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3086 Built: 1990Monthly Fee: $216 Tax: $10,025 (2025)Community: Windermere ClubSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,025
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Rare opportunity to own one of the most private lakefront settings on Lake Crescent in Windermere, featuring approximately 165 feet of shoreline, breathtaking water views, and a resort-style waterfront lifestyle on a private ski lake known for its exceptional water quality. This beautifully designed custom residence offers approximately 3,086 square feet, 4 bedrooms, and 4 bathrooms, thoughtfully positioned to maximize natural light, privacy, and panoramic lake views from nearly every main living space. From the moment you arrive, the setting speaks for itself, tranquil water vistas, expansive outdoor living, and an immediate sense of calm that defines this exceptional waterfront property. A grand entrance with custom glass double doors opens into a spectacular great room where soaring vaulted ceilings and a dramatic wall of windows frame uninterrupted panoramic lake views, filling the home with natural light and creating a stunning first impression that defines the entire residence. The open concept layout seamlessly connects the living room, dining area, and spacious kitchen, creating an inviting flow ideal for both relaxed everyday living and effortless entertaining, all while the lake remains the backdrop from nearly every main living space. A truly distinctive feature of the home is its extraordinary collection of handcrafted stained glass art installations. Rich jewel tones and custom artistic designs transform sunlight into ever changing displays of color throughout the home, adding a level of artistry, warmth, and individuality rarely found in lakefront properties. The primary suite is positioned as a private sanctuary, offering soaring ceilings, peaceful lake views, and direct visual connection to the covered, screened lanai and lake beyond. The spa-inspired bath is designed for comfort and relaxation, featuring generous space and soft natural light. The expansive screened lanai overlooks the sparkling pool, spa, and poolside summer kitchen, creating a seamless indoor-outdoor living experience designed for year round Florida enjoyment. Whether entertaining guests, enjoying quiet mornings, or unwinding at sunset, this outdoor space becomes an extension of the home itself. A private dock offers direct access to Lake Crescent, where boating, skiing, paddleboarding, kayaking, and fishing become part of everyday life. Set on a beautifully landscaped homesite offering privacy and exceptional waterfront exposure, this property combines single-story convenience with one of Windermere’s most captivating lakefront settings. Located just minutes from downtown Windermere, boutique shopping, dining, golf, and top-rated schools, it offers both seclusion and convenience in one of Central Florida’s most sought after communities. Rare opportunities on Lake Crescent are limited and homes offering this level of waterfront frontage, architectural character, artistic detail, and true resort-style lake living are seldom available. This is more than a home, it is a lakefront lifestyle designed to be experienced.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Jenny Ramirez (321-946-8555)
1700 LAKE ROBERTS CT, WINDERMERE, FL 34786
$1,400,00051 Days on yellowkey MLS ID: O6410847
REDUCED by $50,000 (3.4%) on 07/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3929 Built: 2002Monthly Fee: $216 Tax: $10,637 (2025)Community: Butler Bay,Windermere ClubSingle Family
Taxes:$10,637
Remarks: Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully appointed bathrooms, and 3,929 square feet of refined living space on an expansive homesite of over half an acre. Perfectly positioned in a highly sought-after location, this stunning property combines elegance, comfort, and privacy with resort-style outdoor living. Surrounded by lush, mature landscaping, the home makes a striking first impression and provides a serene setting for everyday living. Inside, thoughtfully designed interiors feature generous living and entertaining spaces, abundant natural light, and sophisticated finishes throughout. The spacious layout seamlessly accommodates both intimate family gatherings and large-scale entertaining. The outdoor retreat is equally impressive, highlighted by a sparkling pool and expansive patio areas ideal for relaxation and year-round enjoyment. The oversized lot offers exceptional privacy while providing ample space for outdoor activities and future enhancements. Residents enjoy access to outstanding community amenities and the convenience of a prime location close to premier shopping, dining, entertainment, top-rated schools, and major transportation routes. Offering an unparalleled blend of luxury, space, and lifestyle, this remarkable property presents a rare opportunity to own a distinguished home in one of the area’s most desirable communities. You're also nestled within a well-established community, this property enjoys an enviable location close to major highways, ensuring convenient access to all amenities. Just minutes away, residents can indulge in excellent shopping opportunities, dine at a variety of luxury and casual eateries, and explore nearby theme parks for entertainment. The neighborhood benefits from proximity to brand-new, state-of-the-art hospitals and a top notch school system, providing peace of mind for residents seeking quality healthcare services and high end education for their family. This vibrant community offers an abundance of options to suit every lifestyle need and preference. Call today to schedule a private tour.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: David Johnston (407-398-3295)
6820 THORNHILL CIR, WINDERMERE, FL 34786
$520,00088 Days on yellowkey MLS ID: V4948591
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1725 Built: 2009Monthly Fee: $82 Tax: $7,228 (2025)Community: Lake SawyerSingle Family
Taxes:$7,228
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: MOVING READY ! Seller very Motivated to sell . This exceptional home is now available for showings! Welcome to this stunning 2-story home in the highly desirable Lakes of Windermere, featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus room that can easily serve as a home office, gym, media room, or playroom. The expansive primary suite offers soaring vaulted ceilings, a large walk-in closet, and a spa-inspired in-suite bathroom with a relaxing jacuzzi tub. Upstairs, you'll find beautiful wood flooring throughout—no carpet—along with elegant plantation shutters that add warmth and timeless style to every room. Thoughtfully updated for comfort and peace of mind, this home features impact windows, stainless steel appliances, Laundry room with washer and dryer, and ceiling fans in both the living room and primary suite. Step outside to your private, fully fenced backyard—perfect for entertaining, family gatherings, or simply relaxing. Enjoy a mature mango tree, a charming pergola, and an irrigation system using reclaimed water to keep the landscaping lush while conserving resources. The extended rear driveway with alley access provides generous guest parking, while the 2-car garage offers epoxy flooring, built-in storage cabinets, an extra refrigerator, and a new garage door opener for added convenience. Located in the sought-after Lakes of Windermere community, residents enjoy beautifully maintained parks, scenic lake views, playgrounds, and a community pool. Nestled on a quiet single-entry loop surrounded by elegant homes, this property is just minutes from shopping, dining, top-rated schools, Disney, and major roadways.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Maria Galindez (305-803-3799)
2230 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,259,00055 Days on yellowkey MLS ID: O6410264
REDUCED by $90,000 (6.7%) on 06/24/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3064 Built: 1999Monthly Fee: $220 Tax: $8,790 (2025)Community: Estates At WindermereSpa: YesSingle Family
Taxes:$8,790
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: One or more photos has been virtually staged. Welcome to this updated and meticulously maintained home in the intimate, 64-home community of Estates of Windermere, where spacious rooms, thoughtful updates, and sought-after Florida living come together on a beautiful ½-acre fenced homesite backing to neighborhood green space. From the moment you arrive, you'll appreciate the home's outstanding curb appeal, highlighted by a freshly painted exterior, architectural details, updated exterior lighting, and a desirable 3-car garage. The private backyard setting and expansive lot provide the perfect backdrop for outdoor living and entertaining. Inside, the owners' pride of ownership is evident throughout. Recent improvements include fresh interior paint, porcelain tile flooring throughout the main living areas, and new carpeting in the bedrooms. Large windows fill the home with natural Florida sunshine, creating a bright and inviting atmosphere. The welcoming floor plan features a formal dining room and a versatile front room with French doors, ideal as a home office, living room, or study. At the heart of the home is the beautifully updated kitchen, showcasing warm wood-tone cabinetry with modern hardware, granite countertops, a new stove, dishwasher, and a newer microwave. A separate breakfast area and the kitchen itself overlook the screened lanai, sparkling oversized pool with water feature, and the lush green space beyond the backyard. Open to the kitchen, the spacious family room offers a custom built-in wall unit and provides the perfect gathering space for family and friends. The thoughtfully designed split-bedroom floor plan offers privacy for everyone, with well-positioned bathrooms throughout the home, including a convenient pool bath with direct access to the lanai. The private primary suite is tucked away in the rear of the home and features a spacious ensuite bath with a large soaking tub, walk-in shower, double sink vanity with drawers and an oversized walk-in closet with abundant storage space. A standout feature is the versatile fifth bedroom located just off the garage entry hallway. This flexible space is ideal for guests, multigenerational living, a nanny suite, game room, playroom, craft room, sewing room, fitness space, or a second home office. Residents of Estates of Windermere enjoy more than just beautiful homes. The community offers a neighborhood park, playground, and sports courts, along with resident gatherings and community events held throughout the year, creating a welcoming atmosphere and strong sense of community. Families will appreciate the home's zoning for highly regarded area schools. The location is also exceptionally convenient, with easy access to Winter Garden's popular Fowler's Grove area for extensive shopping, dining, and entertainment. In the other direction, charming downtown Windermere awaits with its beloved Friday Farmers Market, food truck events, local shops, hardware store, café-style dining options, and community library. Offering a wonderful combination of updates, generous living spaces, outdoor enjoyment, community amenities, and a prime Windermere-area location, this home is ready for its next owners to enjoy the very best of Central Florida living.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Tim Frush (407-284-9222)
4474 BEGONIA CT, WINDERMERE, FL 34786
$1,070,00082 Days on yellowkey MLS ID: O6402227
REDUCED by $50,000 (4.5%) on 07/14/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4380 Built: 1998Monthly Fee: $133 Tax: $7,670 (2025)Community: Magnolia Park WindermereSingle Family
Taxes:$7,670
Remarks: Beautifully maintained estate in a small, private gated community in Windermere, zoned for some of the area's best school- you can even walk to Windermere High School. Situated on a quiet cul-de-sac with no rear neighbors, the property offers exceptional privacy along with generously sized lots compared to many surrounding Windermere communities. Master bedroom and one additional room are located on the first floor, ideal for guests or multigenerational living. No carpet throughout the entire home! This 5-bedroom, 4.5 bath home offers a screened pool, extensive system upgrades and efficient well and septic utilities- meaning no water or sewer bills. Recent improvements include a new roof and water heater (2026), a new chlorine injection pump (2026), and two main A/C units replaced in 2020. Additional comfort is provided by two mini-split A/C and heating systems, installed in the master bedroom (2024) and an extra room (2025). Ideally located just minutes from SR-429, SR-535, and just minutes from Publix, Walmart, Target and nearby hospitals. This home offers the perfect blend of comfort, convenience, and luxury. If this home interests you, schedule your showing today!
Listing is courtesy of: SOGO REAL ESTATE SERVICES LLC (407-730-3100)
Listing Agent: Ranah Nam (321-277-3482)
2503 BUTLER BAY DR N, WINDERMERE, FL 34786
$1,750,00043 Days on yellowkey MLS ID: O6413242
REDUCED by $49,000 (2.7%) on 07/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3297 Built: 1990Monthly Fee: $199 Tax: $16,376 (2025)Community: Windermere ClubSpa: YesSingle Family
Taxes:$16,376
Remarks: Set behind the gates of Windermere Club, this lakefront residence delivers everyday comfort with a resort-style backdrop on beautiful Lake Crescent. Offering 4 bedrooms and 3 baths, the home is designed for easy living and effortless entertaining, with bright, open gathering spaces that keep the water views front and center. At the heart of the home, the kitchen pairs generous prep space with a welcoming bar and an adjacent dining area that comfortably seats six, while a separate formal dining room adds flexibility for holidays and special occasions. The main living area is wrapped in expansive windows, filling the home with natural light and framing tranquil lake scenery throughout the day. Step outside to a covered lanai and screened pool area ideal for quiet mornings, sunset dinners, and everything in between. Take a dip in the saltwater pool, now enhanced with a new pool heater and an Aqua Link pool & spa control system for simple, modern management. The primary suite is a private retreat with captivating lake views and a spa-like bath featuring large windows overlooking a secluded courtyard. Three additional bedrooms provide plenty of space for family, guests, or a home office setup. For true lakefront living, enjoy the newer dock with a covered boat lift, perfect for skiing, cruising, kayaking, or paddle boarding whenever the mood strikes. Upgrades and highlights include double pane windows and sliding glass doors, Shark Coating garage floors, a water purifier, Paradise Grill outdoor kitchen with cover and TV, new pool heater, two brand new AC units, a new water heater, plus additional notable improvements throughout. This is the Windermere waterfront lifestyle, refined, relaxed, and ready to enjoy. Be sure to click on the virtual tour links.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
109 E 12TH AVE, WINDERMERE, FL 34786
$1,195,00092 Days on yellowkey MLS ID: O6394569
REDUCED by $3,000 (0.3%) on 07/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2791 Built: 1989 Tax: $18,865 (2025)Community: Windermere TownSpa: YesSingle Family
Taxes:$18,865
High School: Olympia High
Middle School: Gotha Middle
Remarks: SELLER WILL CONTRIBUTE $20,000 TOWARD INTEREST RATE BUY DOWN OR DECORATING ALLOWANCE. Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with NO HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2022), a/c (2016), plumbing, flooring, drain field and water filtration system. Inside, sun drenched living and dining spaces flow seamlessly, anchored by a warm inviting fireplace setting the tone for relaxed living and effortless entertaining. The kitchen serves as the heart of the home, featuring soft gray shaker cabinetry, quartz countertops, a generous island with induction cooktop, hood, double wall ovens, mosaic glass backsplash and all new stainless appliances. Sliding doors open to a sparkling pool with sun deck and pergola, surrounded by lush landscaping in a private, fenced courtyard. Whether hosting gatherings or enjoying quiet evenings at home, this outdoor space delivers the true Florida lifestyle. Upstairs, the primary suite features a spa inspired bath with a freestanding soaking tub, rainfall shower, dual sinks, and elegant finishes. Additional bedrooms include an oversized fourth bedroom with its own fireplace and built-ins which easily can be used as a media room, office, or home gym. Located just a short walk or golf cart ride to Windermere shops, restaurants, lakefront parks, weekly farmers markets, library and more, this home places you at the center of it all. Surrounded by the Butler Chain of Lakes and close to renowned golf, fine dining and premium shopping. Windermere offers small town charm yet convenient to major roadways, area attractions and the International Airport. The location is as exceptional as the home itself. This is more than a residence; it is a refined Windermere lifestyle defined by comfort connection and enduring style. SELLER WILL CONTRIBUTE $20,000 TOWARD INTEREST RATE BUY DOWN OR DECORATING ALLOWANCE.
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Judy Black (407-810-1803)
10624 REAMS RD, WINDERMERE, FL 34786
$475,000329 Days on yellowkey MLS ID: O6338130
0 Days Off yellowkey (back on 7/14/2026)
REDUCED by $12,000 (2.5%) on 05/28/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2092 Built: 2014Monthly Fee: $81 Tax: $5,459 (2024)Community: Windermere Trls Ph 1CSingle Family
Taxes:$5,459
Elementary School: Bay Lake Elementary
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design seamlessly connects the spacious living area with the kitchen, creating the perfect space for entertaining. The primary suite offers a walk-in closet, dual-sink vanity, and walk-in shower, while the upstairs loft provides a versatile space for a playroom, home office, or media room. Recent updates include a new A/C (2022), water heater (2023), and fresh interior paint and updated light fixtures completed this year. Windermere Trails offers fantastic community amenities, including a resort-style pool, playground, picnic areas, and scenic walking trails. Located near top-rated (A+) schools, beautiful parks, and a variety of dining and entertainment options, this home combines comfort, convenience, and lifestyle. Schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jeff Taulbee (407-622-2122)
8662 ABBOTSBURY DR, WINDERMERE, FL 34786
$500,00034 Days on yellowkey MLS ID: O6416099
REDUCED by $25,000 (4.8%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1877 Built: 2004Monthly Fee: $170 Tax: $2,511 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$2,511
Remarks: Welcome home to this charming single story, 3-bedroom, 2-bath home located in the highly desired gated community, Lakes of Windermere – Peachtree. Step inside to an inviting open layout with brand new carpet, abundant natural light, spacious living and dining areas ideal for everyday living and entertaining. The kitchen features ample cabinetry, a kitchen island, and stunning views of the serene backyard. The split-bedroom floor plan provides a private primary suite with a walk in closet and en-suite bath, while two additional bedrooms and a full bath offers flexibility for family, guests, or a home office. Enjoy outdoor living in the fully fenced backyard and a screen enclosed patio overlooking lush conservation with no rear neighbors — a perfect setting for relaxing, gardening, or play. For added peace of mind, a NEW ROOF WILL BE INSTALLED PRIOR TO CLOSING, offering exceptional value to the next owner. Residents of Lakes of Windermere enjoy access to community amenities including a community pool, playground, and beautifully maintained green spaces, all just minutes from top-rated schools, dining, shopping, and the best of Windermere and Horizon West. Move in ready with meaningful updates and a premium lot — this home is the ideal blend of comfort, convenience, and Florida living. GET YOUR RATE BOUGHT DOWN by using SELLERS PREFERRED LENDER.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Paul Donovan (407-785-7070)
14371 CREST PALM AVE, WINDERMERE, FL 34786
$1,049,990101 Days on yellowkey MLS ID: G5110664
REDUCED by $64,999 (5.8%) on 06/17/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 2025Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Remarks: Virtually Staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in.Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, large center island, upgraded cabinetry, quartz countertops, walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living.2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden,—ideal for entertaining or relaxing outdoors.Move-In Ready: No waiting required.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Cindy Sapp (352-516-2843)
8316 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$1,075,00022 Days on yellowkey MLS ID: S5152477
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4332 Built: 2016Monthly Fee: $8 Tax: $14,774 (2026)Community: Windermere Trls Ph 3BSingle Family
Taxes:$14,774
Tax Year: 2026
Remarks: Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The gourmet kitchen showcases stainless steel appliances, a 36-inch cooktop, 42-inch cabinetry with crown molding, quartz countertops, upgraded backsplash, and a spacious walk-in pantry. The primary suite includes a large walk-in closet and a luxurious bathroom with dual vanities and a private water closet. An upgraded home theater with fiber-optic illuminated ceiling and wall panels creates a unique entertainment experience. Step outside to enjoy a beautifully landscaped, fully fenced backyard with dual gate access, a tranquil water feature, and an extended covered lanai perfect for relaxing or entertaining. Residents enjoy access to community amenities including walking trails, a resort-style pool, playground, dog park, pavilions, and fitness areas. The property is being offered partially furnished, with many of the furnishings and features shown in the photos included in the sale.
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Gian Balsamo (407-844-4563)
13303 PENSHURST LN, WINDERMERE, FL 34786
$669,9003 Days on yellowkey MLS ID: O6423867
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2959 Built: 2015 Tax: $8,999 (2025)Community: Windermere SoundSingle Family
Taxes:$8,999
Remarks: Prime Windermere location just a couple miles from luxury, million-dollar estates and minutes from Windermere Downtown. Families appreciate access to top-rated schools, while the home’s proximity to world-class Disney Parks and Disney Springs adds exceptional lifestyle convenience. The property features two updated AC systems — one replaced in 2020 for the separate mother-in-law suite and another brand-new unit installed in 2024 for the main house. The detached mother-in-law residence offers outstanding flexibility, providing a private, comfortable space ideal for extended family or young adults learning independence, or even long-term guests who benefit from having their own dedicated living area. The community includes professional landscaping through the HOA, ensuring a clean, well-maintained environment year-round. With quick access to major roadways, shopping, dining, and Windermere’s charming lakeside town center, this home delivers exceptional value in one of Central Florida’s most desirable areas.
Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)
Listing Agent: Ernesto Lopez (863-337-8264)
12912 DROXFORD RD, WINDERMERE, FL 34786
$650,00013 Days on yellowkey MLS ID: O6422064
0 Days Off yellowkey (back on 7/13/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2966 Built: 2006Monthly Fee: $82 Tax: $9,868 (2025)Community: Lakes/Windermere Ph 02ASpa: YesSingle Family
Taxes:$9,868
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a brand-NEW ROOF currently being installed for added value and peace of mind. Designed with both comfort and functionality in mind, the home features a bright, open floor plan with spacious living and dining areas, tile flooring throughout the main living spaces, and flexible room to accommodate everyday living, entertaining, working from home, or hosting guests. The well-appointed kitchen showcases wood cabinetry, granite countertops, stainless steel appliances, a center island, and seamless flow into the main living areas, making it the heart of the home. The spacious primary suite serves as a relaxing retreat with a large walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. Step outside to enjoy Florida living year-round in the screened lanai overlooking the private pool, brick paver deck, and fully fenced backyard—perfect for entertaining, family gatherings, or simply unwinding in your own backyard oasis. Located in the desirable Lakes of Windermere community, residents enjoy access to a playground, covered picnic area, and convenient proximity to top-rated schools, shopping, dining, Disney, major highways, and everything Southwest Orlando has to offer.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Phat Nguyen (407-452-8751)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$639,994140 Days on yellowkey MLS ID: O6380917
REDUCED by $10,000 (1.5%) on 06/17/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 2009Monthly Fee: $82 Tax: $3,146 (2024)Community: Lakes/WindermereSpa: NoSingle Family
Taxes:$3,146
Remarks: Welcome to one of the best opportunities in Windermere's highly sought-after Lakes of Windermere community! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, convenience, and the Florida lifestyle buyers are searching for. Step inside to discover a thoughtfully designed floor plan featuring spacious living areas, abundant natural light, and stylish updates throughout. The well-appointed kitchen opens seamlessly to the main living spaces, creating an ideal setting for everyday living and entertaining. Upstairs, the generous primary suite provides a private retreat, while three additional bedrooms offer flexibility for family, guests, a home office, or fitness space. Outside, enjoy your own private backyard oasis with plenty of room to relax, dine, and enjoy Florida's year-round sunshine. Whether you're hosting friends, grilling on the patio, or simply unwinding after a long day, this outdoor space is designed for making memories. Located in the heart of Windermere, residents of Lakes of Windermere enjoy resort-style amenities including a community pool, playgrounds, parks, walking trails, sports courts, and scenic green spaces. Just minutes from Disney, Horizon West, Winter Garden Village, Hamlin Town Center, top-rated schools, championship golf, dining, shopping, and major highways, this location offers unmatched convenience while maintaining the charm and character that make Windermere one of Central Florida's most desirable places to live. Whether you're searching for a primary residence, relocating to Central Florida, or looking to enjoy the highly coveted Windermere lifestyle, this move-in-ready home delivers exceptional value in an unbeatable location. Schedule your private showing today and discover why so many buyers are choosing to call Windermere home. *** A/C and Water Heater replaced in 2024. Roof replaced in 2025. Exterior of home repainted in 2022 ***
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Omar Andreasen (407-883-2989)
13525 GORGONA ISLE DR, WINDERMERE, FL 34786
$1,095,000150 Days on yellowkey MLS ID: O6377789
REDUCED by $3,000 (0.3%) on 07/11/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4625 Built: 2018Monthly Fee: $268 Tax: $9,351 (2025)Community: Windermere IsleSpa: NoSingle Family
Taxes:$9,351
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space. Seller is providing a credit towards a 2-1 RATE BUY DOWN with full price offer. Inquire for more details.
Listing Agent: Roo Klaers (407-493-5615)
13542 GORGONA ISLE DR, WINDERMERE, FL 34786
$895,000125 Days on yellowkey MLS ID: O6390582
REDUCED by $55,000 (5.8%) on 04/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2018Monthly Fee: $268 Tax: $9,762 (2024)Community: Windermere IsleSingle Family
Taxes:$9,762
Remarks: Virtually Staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From the moment you arrive, the well-maintained landscaping and inviting front porch set a warm and welcoming tone. The home features 4 bedrooms and 3 full bathrooms, with a thoughtfully designed open-concept layout that seamlessly connects the living room, kitchen, and dining area. The gourmet kitchen is a true highlight, equipped with stainless steel appliances, custom cabinetry, quartz countertops, a double oven, and a spacious pantry—perfect for those who love cooking and entertaining. Sliding glass doors open to the outdoor space, where a private pool and summer kitchen are currently being completed and will be ready within one month, creating the perfect setting for relaxing or entertaining guests while enjoying the lake view. The primary suite is spacious and comfortable, featuring vinyl flooring, a generous walk-in closet, and a beautifully designed bathroom with dual vanities. The additional bedrooms also feature vinyl flooring, providing both comfort and easy maintenance throughout the home. The two-car garage offers ample space and convenience. Located in the desirable Windermere Isle community, residents enjoy resort-style amenities including a community pool, cabana, playground, and scenic walking trails. The home is also located near top-rated schools, as well as shopping, restaurants, and all the attractions and magic of Walt Disney World just minutes away. If you are looking for quality of life, a prime location, and a beautiful home for your family, this is the perfect opportunity. Schedule your private showing today and come fall in love with this exceptional home.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Thiago De Ataide (407-745-9283)
14353 CREST PALM AVE, WINDERMERE, FL 34786
$1,039,09182 Days on yellowkey MLS ID: G5111542
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Remarks: Virtually Staged. Under Construction. Sample Image Arlington Floorplan – 2,740 Sq. Ft. | 4 Beds | 3 Baths | 2.5-Car Garage a thoughtfully designed, 1-story home by Dream Finders Homes that perfectly blends luxury, functionality, and comfort. This brand new 2,740 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in. Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.3 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, a large center island, upgraded cabinetry, quartz countertops, a walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living. 2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area.Oversized Lot: Extra space for a garden—ideal for entertaining or relaxing. Projected Completion July/August. Preferred Lender incentives apply.
2053 WOODY DR, WINDERMERE, FL 34786
$679,00013 Days on yellowkey MLS ID: O6421738
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2177 Built: 1973Monthly Fee: $88 Tax: $4,023 (2025)Community: Windermere DownsSingle Family
Taxes:$4,023
Elementary School: Thornebrooke Elem
Remarks: Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019
Listing Agent: Vivian Saavedra (772-332-9318)
14422 CREST PALM AVE, WINDERMERE, FL 34786
$1,100,00026 Days on yellowkey MLS ID: O6418503
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3140 Built: 2025Monthly Fee: $245 Tax: $2,889 (2025)Community: Palms At WindermereSingle Family
Taxes:$2,889
Remarks: Why wait months for new construction when you can move into this stunning, like-new home today? Located in the desirable Windermere area, this beautifully designed residence offers the perfect blend of luxury, comfort, and convenience. Step through the welcoming foyer and immediately appreciate the thoughtful layout. To the right, you'll find the first spacious bedroom, followed by a full bathroom and a second generously sized bedroom. As you continue through the home, you'll be greeted by an expansive open-concept living area designed for gathering with family and friends. The gourmet kitchen overlooks the living and dining spaces, creating the ideal setting for entertaining and everyday living. The main level features four spacious bedrooms and four full bathrooms, providing comfort and privacy for everyone. The luxurious primary suite serves as a private retreat, complete with a spa-like bathroom designed for relaxation and tranquility. Step outside to the covered lanai and unwind while enjoying peaceful water views. Whether you're sipping your morning coffee or watching the sunset, this serene outdoor space offers the perfect place to relax and recharge. Upstairs, you'll find a versatile bonus room with its own full bathroom, ideal for a guest suite, home office, media room, or playroom. Conveniently zoned for top-rated schools, including Windermere High School, this exceptional home is just minutes from shopping centers, restaurants, entertainment, and world-famous Walt Disney World attractions. Don't miss this incredible opportunity to own a move-in-ready home that offers the benefits of new construction without the wait!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Lan Lee (541-287-0919)
9117 OUTLOOK ROCK TRL, WINDERMERE, FL 34786
$1,125,00041 Days on yellowkey MLS ID: O6413948
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4936 Built: 2014Monthly Fee: $94 Tax: $15,179 (2025)Community: Windermere Trls Ph 5ASingle Family
Taxes:$15,179
Remarks: Experience ELEVATED LUXURY LIVING in this exceptional WINDERMERE TRAILS ESTATE, where timeless elegance, and RESORT-STYLE AMENITIES combine to create an unforgettable place to call home. Offering 5 bedrooms, 3 full bathrooms, 2 half bathrooms, a private office, expansive loft, *DEDICATED MOVIE THEATER*, sparkling POOL, and an OVERSIZED 3-car garage, this remarkable residence spans nearly *5,000 SQUARE FEET* of thoughtfully designed living space. From the moment you arrive, the beautiful TILE ROOF and impressive curb appeal set the tone for the sophistication found throughout. Evening views are made even more *MAGICAL with DISNEY FIREWORKS* visible nightly from the front of the home. Inside, you will find SOARING CEILINGS and exquisite coffered ceiling details that guide you through the elegant dining area and into the heart of the home. Designed for both entertaining and everyday living, the expansive open-concept floorplan seamlessly connects the living room, breakfast nook, and gourmet kitchen. The chef-inspired kitchen is a true showpiece, featuring stainless steel appliances, granite countertops, 42-inch wood cabinetry, an oversized center island, breakfast bar seating, and an abundance of cabinet and counter space. The kitchen has also been enhanced with newer appliances, including the refrigerator and dishwasher, offering both style and convenience. The FIRST-FLOOR PRIMARY SUITE is a luxurious retreat, complete with tray ceilings and a SPA-LIKE EN-SUITE bath featuring dual vanities, a soaking tub, walk-in shower, and generous closet space, and HIGH-END newer bidets that add an extra touch of comfort and luxury. A PRIVATE OFFICE and spacious laundry room complete the main level. Upstairs, an EXPANSIVE LOFT provides the perfect space for a GAME ROOM, LOUNGE, or SECONDARY LIVING AREA. The second level is thoughtfully designed to accommodate family and guests alike, featuring four additional spacious bedrooms, including two connected by a CONVENIENT JACK-AND-JILL BATHROOM. The crown jewel awaits behind closed doors: YOUR VERY OWN PRIVATE MOVIE THEATER, delivering a true cinematic experience without ever leaving home. Outside, discover your personal backyard oasis, where a LARGE SCREENED LANAI overlooks the STUNNING RESORT- STYLE POOL with elegant water features, creating the perfect setting for sunset gatherings, weekend entertaining, or peaceful relaxation. The pool has been *UPGRATED SALTWATER CONVERSION SYSTEM*, enhancing the swimming experience while simplifying maintenance. Beyond its luxurious finishes, the home has also been thoughtfully *UPDATED with NEW HVAC UNITS* and a *WHOLE-HOUSE WATER SOFTENER SYSTEM*, providing added efficiency, comfort, and peace of mind for years to come. Perfectly positioned in THE HEART OF WINDERMERE, this extraordinary residence is surrounded by picturesque lakes, premier dining, upscale shopping, renowned public and private schools, and offers CONVENIENT ACCESS TO DISNEY, DOWNTOWN ORLANDO, AND ORLANDO INTERNATIONAL AIRPORT. Combining *LUXURY, CONFORT, AND EXECEPTIONAL LOCATION*, this is a rare opportunity to own one of Windermere Trails' most impressive residences.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Rosanna Rivera (407-708-9747)
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