Displaying: For Sale
Location: Windermere
Property Type(s): Single Family
Beds: 3 to 3
Do Not Show Listings
Windermere - 29 properties found
13324 LONGACRE DR, WINDERMERE, FL 34786
$510,000Listed 06/09/2026 12:06PM MLS ID: S5151263
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2058 Built: 2013Monthly Fee: $115 Tax: $7,924 (2025)Community: Windermere TerraceSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,924
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Welcome to this beautifully maintained and exceptionally spacious one-story home located in the highly desirable Windermere Terrace community in the heart of Windermere. Offering 3 bedrooms, 2 bathrooms, plus a large dedicated office/flex room, this home provides the perfect blend of comfort, functionality, and style for today's lifestyle. From the moment you enter, you'll appreciate the open and inviting floor plan designed for both everyday living and entertaining. The spacious living and dining areas are filled with natural light, creating a warm and welcoming atmosphere throughout the home. The well-appointed kitchen features 42-inch cabinetry, granite countertops, stainless steel appliances, ample counter space, and abundant storage, making it a dream for both home chefs and entertainers alike. The oversized primary suite serves as a private retreat, complete with a spacious en-suite bathroom and generous closet space. Two additional bedrooms provide flexibility for family members or guests, while the large office can easily be used as a home office, media room, playroom, or even a potential fourth bedroom. One of the standout features of this home is the oversized laundry room, complete with a convenient utility sink and additional storage space rarely found in similar homes. Step outside and enjoy the Florida lifestyle with outdoor living space perfect for relaxing, grilling, or spending quality time with family and friends. Residents of Windermere Terrace enjoy access to outstanding community amenities, including a resort-style swimming pool with cabana, playground, walking paths, and beautifully maintained common areas. The location is second to none—just minutes from shopping, dining, entertainment, and everyday conveniences. You'll love being approximately 10 minutes from Walt Disney World Resort, with easy access to major highways including SR-429, SR-408, CR-535, and Florida's Turnpike, making commuting throughout Central Florida simple and convenient. Families will appreciate the proximity to highly rated schools and the convenience of nearby shopping destinations, restaurants, golf courses, and recreational opportunities. With its desirable Windermere address, spacious one-story layout, flexible office space, excellent community amenities, and motivated seller offering potential closing cost assistance, this home represents an incredible value in today's market. Opportunities like this are becoming increasingly rare in Windermere. Don't miss your chance to make this beautiful home yours. Click the virtual tour button for a complete walkthrough and schedule your private showing today!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: James Song (407-405-3140)
9072 WOODBREEZE BLVD, WINDERMERE, FL 34786
$549,90034 Days on yellowkey MLS ID: O6403789
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
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Chain of Lakes Middle
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)
11155 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$850,0004 Days on yellowkey MLS ID: O6414373
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1935 Built: 1972 Tax: $3,589 (2025)Community: Wauseon RidgeSingle Family
Taxes:$3,589
Middle School: Gotha Middle
Remarks: Rare Opporunity to own a property in Windermere that is in Move In Condition anywhere near this price * 3 Bedroom 2 Bath Open Concept with a remodeled Kitchen and Baths * Large Lot * County Water * Natural Gas * Lake Butler Blvd is the Perfect Road for Exercise & Enjoying the Outdoors * This Home Includes A Gated Private Park & Boat Ramp with a Fishing Pier & Wood Dock to tie up your Boat or Jet Ski * Walk to Windermere Elementary * Downtown Windermere has Friday Farmer's Market and Monthly Food Trucks * Convenient Location with a 10 Minute Drive to All your Shopping, Restaurants, Banking and Professional needs
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
13836 BLUEBIRD POND RD, WINDERMERE, FL 34786
$675,00042 Days on yellowkey MLS ID: TB8502779
REDUCED by $23,000 (3.3%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2108 Built: 2004Monthly Fee: $100 Tax: $3,052 (2025)Community: SummerportSpa: NoSingle Family
Taxes:$3,052
Elementary School: Keene Crossing Elementary
Middle School: Bridgewater Middle
Remarks: Step into this impeccably maintained, move-in ready home in Summerport—one of Windermere’s most sought-after communities. With its high ceilings and elegant crown molding, the home feels both grand and inviting. The kitchen features quartz countertops, a hot water dispenser, a cozy café area, and a walk-in pantry. Recent updates include a new HVAC system and water heater, a 2021 roof, and R-38 attic insulation. Fiber optic cable is available, and the property offers room for a pool along with a one-year home warranty. Low HOA. Enjoy the spacious lanai accessible from both the family room and the primary bedroom. Start your mornings on the charming front porch overlooking the park. Summerport community amenities include a pool, fitness center, tennis, volleyball, and basketball courts, as well as a playground. Additional highlights include a rear-access two-car garage with storage shelves. Conveniently located just minutes from top-rated schools, dining, entertainment, and theme parks. Schedule your showing today and experience this beautiful home set in a garden-like setting.
Listing is courtesy of: GETMOREOFFERS (727-942-2929)
Listing Agent: Keith Gordon (727-610-8041)
6315 CLEARMEADOW CT, WINDERMERE, FL 34786
$618,00056 Days on yellowkey MLS ID: O6398505
0 Days Off yellowkey (back on 5/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 2002Monthly Fee: $170 Tax: $3,701 (2024)Community: Glenmuir 48 39Single Family
Taxes:$3,701
Tax Year: 2024
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the gated community of Glenmuir in Windermere. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld Orlando, and the charming downtown areas of Winter Garden and Downtown Windermere, this location offers both luxury and convenience. Tucked away on a quiet cul-de-sac, this freshly painted 3-bedroom, 2-bath home offers 2,077 sq. ft. of move-in ready living space. The open-concept great room features retractable sliding glass doors that lead to a 350 sq. ft. covered and enclosed outdoor retreat, creating the perfect space for relaxing or entertaining. The spacious kitchen includes solid wood cabinetry, quartz countertops (2022), stainless steel appliances, and a new dishwasher (2025), along with a cozy breakfast nook. The primary suite offers a large walk-in closet and a spa-like bath with dual vanities, garden tub, and private water closet. Major upgrades include a brand-new Spanish tile roof (2025), sprinkler system upgrade (2025), hot water heater (2020), A/C (2017), new blown insulation, and new carpet throughout. The extended driveway fits six or more vehicles, ideal for hosting guests. Residents enjoy a beautiful tree-lined community with a park, playground, basketball courts, and convenient access to major highways including Interstate 4 and Florida's Turnpike. A rare opportunity to own a move-in ready home with luxury upgrades, a private cul-de-sac location, and an exceptional outdoor retreat in one of Windermere’s most desirable communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Jessica Otero, Pa (407-780-1663)
8272 BRYCE CANYON AVE, WINDERMERE, FL 34786
$509,00091 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
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)
4718 BLUE MAJOR DR, WINDERMERE, FL 34786
$520,0006 Days on yellowkey MLS ID: O6410820
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1911 Built: 2005Monthly Fee: $143 Tax: $7,296 (2025)Community: Summerport Ph 05Single Family
Taxes:$7,296
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 4718 Blue Major Dr, a beautifully maintained 3-bedroom, 2-bathroom home offering 1,911 square feet of comfortable living space in the highly sought-after Windermere area. This move-in ready home features fresh interior paint, a newer A/C system that is only 2 years old, brand-new grass, and an updated sprinkler system that helps keep the landscaping lush and vibrant year-round. Inside, you’ll find a spacious and functional open floor plan perfect for both everyday living and entertaining. The home offers generous living spaces, abundant natural light, and a layout designed for comfort and convenience. Located in the highly desirable Summerport community, residents enjoy resort-style amenities including a clubhouse, community pool, tennis courts, basketball courts, volleyball courts, parks, playgrounds, walking trails, and scenic green spaces that create an active Florida lifestyle. Conveniently located near Winter Garden Village, Hamlin Town Center, Disney attractions, shopping, dining, and major highways, this location offers the perfect combination of convenience and community living. Families will appreciate being zoned for highly rated schools including Keene's Crossing Elementary, Bridgewater Middle School, and Windermere High School. Whether you’re looking for your primary residence or a fantastic investment opportunity, this home offers exceptional value in one of Central Florida’s most sought-after communities.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Matt Paul (407-350-9031)
11861 VERMILLION AVE, WINDERMERE, FL 34786
$475,0007 Days on yellowkey MLS ID: O6410430
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1600 Built: 2015Monthly Fee: $363 Tax: $6,340 (2025)Community: Windermere Trls Prcl 3Single Family
Taxes:$6,340
Remarks: TOP RATED SCHOOLS. NO CARPET throughout the home!! Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community! This spacious two-story home features an open-concept layout with a modern kitchen offering stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas — perfect for entertaining. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bathroom. Enjoy the convenience of a rear-entry 2-car garage and low-maintenance living in one of Windermere’s most desirable locations. Community amenities include a resort-style pool, playgrounds, walking trails, dog park, and scenic green spaces. Ideally located near top-rated schools, shopping, dining, major highways, and Disney attractions. Don’t miss this incredible opportunity!
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Frederico Hexsel (407-745-8841)
4906 AVIVA GARDEN CT, WINDERMERE, FL 34786
$4,590,00050 Days on yellowkey MLS ID: O6400218
REDUCED by $100,000 (2.1%) on 06/01/2026
Bed: 3 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6236 Built: 2016Monthly Fee: $1,146 Tax: $48,425 (2025)Community: Gardens/Isleworth Un #2Spa: YesSingle Family
Taxes:$48,425
Remarks: Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere. Thoughtfully designed for both everyday comfort and elevated entertaining, the home features a versatile layout including a spacious primary suite, multiple guest bedrooms, an oversized office/playroom, and a dedicated theater room. Expansive living areas flow seamlessly, creating a warm yet Elegant atmosphere throughout—all easily accessible via a private elevator connecting the home’s levels. The home delivers a true turnkey experience with modern finishes and enhancements, including a fully upgraded Crestron smart home system providing whole-home audio and video distribution for effortless control and convenience. A standout feature is the exceptional garage capacity, offering four individual single-car garages two of which are equipped with vehicle lifts. The outdoor living experience is a true highlight, featuring a resort-style pool, generous covered entertaining spaces, and serene water views that create a peaceful and private backdrop. Whether enjoying quiet mornings by the water or hosting guests in the evening, the setting is both inviting and unforgettable. Located within Isleworth—renowned for its championship golf course, world-class amenities, and guard-gated privacy—residents enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes and beautifully manicured grounds. This is a rare opportunity to own a fully updated, move-in ready home that seamlessly combines luxury, technology, and exceptional outdoor living in one of Orlando’s most sought-after communities.
Listing is courtesy of: CAMPBELL CUSTOM HOMES INC (407-947-4392)
Listing Agent: William Campbell (407-947-4392)
1924 DOWN HOLLOW LN, WINDERMERE, FL 34786
$1,680,00012 Days on yellowkey MLS ID: O6398100
0 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1962 Built: 1999 Tax: $8,460 (2025)Community: AcreageSpa: YesSingle Family
Taxes:$8,460
Elementary School: Thornebrooke Elem
Remarks: Under contract-accepting backup offers. Escape the ordinary! This charming Windermere cottage on the Butler Chain, is set on a beautiful and private wooded lot with a rare opportunity for lake and boat frontage on Lake Down! This inviting residence is nestled on nearly two acres in a serene, Florida-style setting, offering the perfect blend of privacy and convenience. Thoughtfully renovated, this 3-bed, 2.5-bath, 2-car garage home embraces a warm, relaxed style with timeless cottage appeal and inviting indoor-outdoor living. A welcoming front porch entry sets the tone for a spacious great room with a cozy fireplace, an eat-in kitchen with natural light, ample cabinets and counter top space, perfect for everyday living and hosting. The first-floor primary suite includes a walk-in closet and a private bath, featuring a dual vanity and a separate shower. The sunroom sitting areas open to an expansive deck with a recessed spa and TV, creating the perfect setting for entertaining or quiet evenings surrounded by nature. A true retreat, with a private walkway and dock leading directly to Lake Down, offering seamless access to the Butler Chain of Lakes and all the recreation the 13 interconnected lakes have to offer. Conveniently located near Downtown Windermere, top-rated schools, shopping, and dining, with easy access to major roadways and airports, delivers the best of both tranquility and accessibility.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
6820 THORNHILL CIR, WINDERMERE, FL 34786
$520,00051 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: Lakes Of WindermereSingle Family
Taxes:$7,228
Remarks: Welcome to this stunning 2-story residence featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus area—ideal for a home office, gym, or playroom at The Lakes of Windermere. The expansive primary suite boasts vaulted ceilings, creating a bright and airy retreat, along with a generous walk-in closet. The primary bathroom includes a relaxing jacuzzi tub, perfect for unwinding. Upstairs, enjoy wood flooring throughout—no carpet, offering both elegance and easy maintenance. Wooden plantation shutters throughout the home. Designed for comfort and efficiency, this home includes Impact Windows, stainless steel appliances, a new washer and dryer, and ceiling fans in both the living room and primary bedroom. Step outside to a fully fenced backyard, perfect for entertaining, relaxing, or enjoying time with pets. The outdoor space features a mature mango tree and a charming pergola, creating your own private retreat. An irrigation system using reclaimed water keeps the landscaping lush and eco-friendly. The extended rear driveway, with alley access, provides ample guest parking. The 2-car garage is thoughtfully upgraded with epoxy flooring, built-in storage cabinets, an extra refrigerator, and a new garage door opener—perfect for organization and convenience. Located in the highly desirable Lakes of Windermere community, residents enjoy beautifully maintained parks, scenic lake views, playgrounds, and a community pool. The home is situated on a quiet single-entry loop, surrounded by a mix of elegant and lakefront custom homes. Just minutes from shopping, dining, Disney resorts, and more—this home offers the perfect blend of comfort, style, and location. Tenant's Lease ends July 15/ 2026
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Maria Galindez (305-803-3799)
9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786
$4,450,00061 Days on yellowkey MLS ID: O6397842
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5004 Built: 2019Monthly Fee: $1,146 Tax: $35,432 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$35,432
Remarks: Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.
Listing is courtesy of: MEGAN DOWDY REALTY, LLC (407-509-9279)
Listing Agent: Megan Dowdy (407-509-9279)
6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$550,00010 Days on yellowkey MLS ID: O6412095
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1984 Built: 2012Monthly Fee: $130 Tax: $6,210 (2025)Community: Windermere Lndgs Ph 02Single Family
Taxes:$6,210
Remarks: RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School. Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price point. The result is a flexible floor plan ideal for families, remote work, guests, or a growing household. Pride of ownership shines throughout this one-owner home. Elegant porcelain tile flooring, custom wood accent walls, designer finishes, and abundant natural light create a sophisticated yet welcoming atmosphere. Every detail has been carefully maintained and thoughtfully enhanced. The location is simply unmatched. Enjoy a short walk to the community pool and playground, while being just minutes from top-rated schools, shopping, dining, and everyday conveniences. Disney, major attractions, and Orlando's world-class entertainment are only a short drive away. Whether you're searching for a primary residence, a relocation home, or an investment in one of Central Florida's most sought-after areas, this property delivers the perfect combination of location, upgrades, functionality, and value. Homes offering this level of quality, flexibility, and proximity to Windermere Prep rarely become available. Schedule your private showing today.
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Jose Rojo (786-502-6162)
11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$495,00012 Days on yellowkey MLS ID: O6409301
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1829 Built: 2014Monthly Fee: $85 Tax: $6,641 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,641
Remarks: Meticulously maintained, this 3-bedroom, 2.5-bathroom two-story home sits in an unbeatable location directly across from Bay Lake Elementary. The first level features a welcoming front porch, an open-concept living area with brand-new LVP flooring, an updated half bath, and a beautifully appointed kitchen boasting stone countertops, a walk-in pantry, and a breakfast bar. Upstairs, a versatile spacious loft leads to two guest bedrooms and a primary suite complete with newly installed carpet, updated bathroom with dual vanities, a tile shower, and a walk-in closet. Big-ticket upgrades offer total peace of mind, including a new roof (2022) and a new hybrid water heater (2025). Windemere Trails community offers excellent amenities and is ideally situated just minutes from Lakeside Village Center and Westside Shoppes (Publix, dining, fitness, and more) and a short drive to Orlando's Theme Parks, World Class Dining, Shopping, and Golf. This low-maintenance home offers exceptional accessibility and turnkey living!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: John Callahan (407-716-3541)
825 OAKDALE ST, WINDERMERE, FL 34786
$792,50063 Days on yellowkey MLS ID: O6396351
5 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1664 Built: 1935 Tax: $9,799 (2025)Community: Windermere TownSingle Family
Taxes:$9,799
Remarks: Under contract-accepting backup offers. Back on the market no fault of the home! ONLY HOME ON WINDERMERE’S ICONIC SANDY STREETS UNDER $800,000 — DON’T MISS YOUR CHANCE. Back on the market and better than ever, this charming traditional cottage now features thoughtful exterior enhancements that further showcase its incredible homesite and future potential. Nestled along one of Windermere’s signature sandy streets, this property offers the perfect blend of nostalgia, community, and convenience—just steps from the Farmers Market, Town Hall, Windermere Library, the new Ace Hardware plaza, and beloved town events. Set on an expansive .38-acre lot beneath beautiful mature trees, this 3-bedroom, 2-bath home now features a freshly cleared and improved backyard. Select trees and brush have been professionally trimmed and removed, creating a more open, usable space ideal for recreation, entertaining, or future expansion. Whether you envision a pool, home addition, or simply the ultimate setting for flag football and weekend gatherings, the groundwork has been laid. Inside, the home welcomes you with a vaulted-ceiling great room and kitchen featuring newly refinished REAL wood floors, exposed beams, and abundant natural light. A cozy adjacent living room offers built-in shelving and a double closet. The quaint kitchen blends character and function with tile and wood countertops, vintage-style paneled appliances, and nearby laundry. A separate dining room with REAL wood floors comfortably seats eight and opens through French doors to a refreshed screened rear porch—perfect for relaxing evenings overlooking your newly enhanced backyard. From here, updated wood steps lead directly into the fully fenced yard. The bedroom wing includes two secondary bedrooms with a shared hall bath, while the private primary suite features its own en-suite bath and French doors opening to a secluded outdoor porch. Major updates provide peace of mind: Brand-New Roof & Skylights (11/2025), HVAC (May 2024), Natural Gas Water Heater (Oct 2021), Exterior Paint (Jan 2024), Wired for High Speed Fiber by ATT and more. The home also includes a transferable annual termite bond, recent septic service (June 2025), and ongoing maintenance including tree care and exterior improvements. An oversized carport with a large enclosed storage/workshop space completes this exceptional Windermere opportunity. BACK ON MARKET BY CHOICE — NOT CONDITION. YOUR SECOND CHANCE IS HERE.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mildred Hershiser (407-758-5263)
6673 DUNCASTER ST, WINDERMERE, FL 34786
$530,000121 Days on yellowkey MLS ID: O6378820
REDUCED by $9,000 (1.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 2005 Tax: $3,351 (2024)Community: Lakes/Windermere Ph 02ASpa: NoSingle Family
Taxes:$3,351
Remarks: One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends the living space outdoors. Situated within a well-established community with a low HOA fee of $230 quarterly and no CDD, this property offers long-term cost efficiency compared to many newer developments. The Windermere location provides convenient access to major roadways, shopping, dining, retail centers, and entertainment throughout Central Florida.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Lilyan Machuca (407-738-7463)
111 MAIN ST, WINDERMERE, FL 34786
$889,00028 Days on yellowkey MLS ID: O6407060
2 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2272 Built: 1984 Tax: $9,734 (2025)Community: Windermere TownSingle Family
Taxes:$9,734
Remarks: Prime Windermere Location! Fully Renovated and Move-In Ready! Don't miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms perfect for comfortable family living and entertaining. Recent Upgrades Include: Fresh interior and exterior paint. Brand-new luxury vinyl flooring Stunning 2x4 porcelain tile in the kitchen, foyer, and dining room. Sleek European-style kitchen cabinets with quartz countertops. Modern interior doors throughout. Stylishly renovated bathrooms. Energy-efficient LED recessed lighting throughout the home. As a Windermere resident, you'll also enjoy exclusive access to the community lakes perfect for boating, fishing, and relaxing outdoors.
Listing is courtesy of: CENTURY 21 CARIOTI (407-770-0322)
Listing Agent: Sammy Nakhleh (407-360-4435)
5225 LEMON TWIST LN, WINDERMERE, FL 34786
$499,90025 Days on yellowkey MLS ID: O6406747
1 Days Off yellowkey (back on 5/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2006Monthly Fee: $130 Tax: $4,397 (2025)Community: Summerport Ph 03Single Family
Taxes:$4,397
Remarks: Under contract-accepting backup offers. Welcome to Summerport, one of Windermere's most sought-after communities! This charming 3 bedroom, 2 bath single-story home offers nearly 1,700 heated square feet of well-designed living space with a split bedroom floor plan, 2-car garage, and some of the most beautiful curb appeal on the street — complete with a brick paver walkway and low maintenance landscaping. Inside, gorgeous wood flooring flows through the main living areas and an abundance of natural light complements the open floor plan, making it ideal for both everyday living and entertaining. A multi-functional flex space off the foyer offers endless possibilities — formal dining, home office, gym, or playroom. The kitchen was fully remodeled in 2021 and features 42" white shaker cabinetry, subway tile backsplash, stainless steel appliances including a gas stove, a center island with bar seating, closet pantry, and an eating space — all open to the main living area. The primary suite is a true retreat, boasting tray ceilings, a generous walk-in closet, and a beautifully remodeled bathroom (2024) with dual sinks, soaking tub, walk-in shower, private water closet, and striking tile work. Step outside to your screen-enclosed lanai with brick pavers and an extended deck, all set within a fully fenced backyard with vinyl fencing — perfect for pets, play, or simply unwinding. Additional highlights include interior paint (2021) and AC (2019). Zoned for A-rated schools including Windermere High School, with the elementary school just a short distance away. Summerport's resort-style amenities are second to none — clubhouse, fitness center, pool, playground, beach volleyball, basketball and tennis courts, a fishing dock, sandy beach area, and miles of sidewalks winding past scenic ponds and beneath mature oak tree canopies perfect for walking and running. Whether you're a growing family, looking to downsize, or searching for a second home, this one checks all the boxes. Grocery, shopping, dining, and major highway access all just minutes away — this is Florida living at its finest!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Ruiz (407-608-0086)
6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786
$575,000150 Days on yellowkey MLS ID: G5106279
REDUCED by $10,000 (1.7%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2139 Built: 2012Monthly Fee: $125 Tax: $7,649 (2024)Community: Windermere Lndgs Ph 02Single Family
Taxes:$7,649
Remarks: Short Sale. Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much more. New refrigerator is 2022, water heater replaced in 2020, AC replaced in October 2021. This home is a great money saver! It is equipped with fully warranted solar panels that pays just $30.00 in electric bills. These panels are not your average solar panels; they are German technology USA made panels with top notch microinverter systems saving you thousands of dollars in utilities throughout the years!! Whether you are a first-time home buyer, investor, or a starter family this home checks all of the boxes. Wonderful Location, A Rated Schools, Shopping & Restaurants will meet all of your buyer's needs. Located within a short distance to Sunset Park Elementary, minutes to Windermere High School, CR 535, Windermere preparatory, Windermere villages, the Butler Chain of Lakes, and just 15 minutes to Disney. Book your showing today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Yindy Reyes (732-277-2828)
9648 MCCORMICK PL, WINDERMERE, FL 34786
$3,800,000256 Days on yellowkey MLS ID: O6346918
1 Days Off yellowkey (back on 5/20/2026)
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4751 Built: 1988Monthly Fee: $1,224 Tax: $33,873 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$33,873
Remarks: Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level. Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. A striking glass wall encases the pool area, maximizing panoramic views of both the golf course and the lake. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brand-new heater, or unwind in the extended backyard, which offers an additional 15 feet added to one side of the property. Every detail of this outdoor transformation has been designed to enhance both beauty and livability, making this property the perfect retreat for year-round enjoyment.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Michelle Corbin (407-491-2690)
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