Location: Windermere, Windermere
Do Not Show Listings
12633 HADDON DR, WINDERMERE, FL 34786
$650,00018 Days on yellowkey MLS ID: O6411199
0 Days Off yellowkey (back on 6/11/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3000 Built: 2003Monthly Fee: $82 Tax: $7,410 (2025)Community: Lakes WindermereSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,410
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Sitting on a premium corner lot with mature landscaping, this beautiful Kensington model by Ashton Woods is located in the highly sought-after Lakes of Windermere community! Offering nearly 3,000 sq ft, this move-in ready home has been meticulously cared for and features room for a future pool. Recent updates include a new roof (2024), new downstairs A/C (2026), upstairs A/C (2023), upgraded Stainmaster PetProtect carpet (2026), quartz countertops, marble backsplash, cabinet lighting, paver patio, aluminum fencing, and updated landscaping. Inside, you’ll love the open split-bedroom floor plan, crown molding, upgraded flooring, and spacious kitchen with tons of cabinet space and stainless steel appliances overlooking the family room with custom built-in entertainment center wired for home theater. Upstairs 5th bedroom with full bath could also make the perfect theater room, game room, and guest suite. Lakes of Windermere offers a welcoming small-town atmosphere with resort-style amenities including a fishing dock, junior Olympic-size community pool, tennis courts, playgrounds, and organized recreational activities. Ideally located just minutes from Disney, Winter Garden Village, I-4, SR 408, and the Florida Turnpike.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Amy Brown (443-851-1508)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$649,994109 Days on yellowkey MLS ID: O6380917
REDUCED by $15,000 (2.3%) on 05/12/2026
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
Tax Year: 2024
Remarks: Welcome to 13013 Overstreet Rd — a beautifully upgraded 4-bedroom, 2.5-bath home located in one of Windermere’s most desirable and sought-after communities. This property combines modern living, elegant design, and the true Florida lifestyle you’ve been searching for. Step inside to an open, bright floor plan featuring gorgeous wood floors, a spacious living area, and a modern kitchen with sleek cabinetry, stainless steel appliances, island, and plenty of storage — perfect for everyday cooking or entertaining friends and family. The primary suite includes a luxurious bathroom with his-and-her sinks and an upgraded California closet with premium built-ins for maximum organization. Enjoy Florida weather year-round in the screened-in patio with a retractable electric screen, extending your living space and providing the perfect spot for morning coffee or evening relaxation. The large, fully fenced backyard features extended brick pavers, offering plenty of room for gatherings, grilling, pets, or future customization. Additional features include a front balcony, a 2-car garage, and an oversized driveway with great curb appeal. This home sits in a prime Windermere location surrounded by some of the best amenities in Central Florida. Just minutes away you’ll find top-rated Windermere schools, scenic lakes, nature trails, Bay Hill, The Butler Chain of Lakes, playgrounds, and community parks. Nearby you’ll enjoy endless shopping, popular restaurants, cafés, breweries, local markets, and everyday conveniences. You’re also close to the Winter Garden Village, Downtown Windermere, major highways, theme parks, and world-class entertainment. The community itself offers resort-style amenities including a sparkling community pool and clubhouse — perfect for relaxing weekends and social gatherings. If you’re looking for a move-in-ready home with modern finishes, incredible outdoor space, and a location that simply can’t be beat, this is the one. Homes like this in Windermere don’t last long — schedule your private showing today! *** 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)
8409 VIVARO ISLE WAY, WINDERMERE, FL 34786
$1,187,00035 Days on yellowkey MLS ID: G5112154
0 Days Off yellowkey (back on 6/10/2026)
REDUCED by $48,000 (3.9%) on 06/03/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4176 Built: 2019Monthly Fee: $299 Tax: $9,493 (2025)Community: Windermere IsleSpa: YesSingle Family
Taxes:$9,493
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Under contract-accepting backup offers. Welcome to 8409 Vivaro Isle Way, an exceptional move-in ready luxury residence located in the highly desirable community of Windermere Isle in Windermere. This impressive home offers 4,176 square feet of living space featuring 6 bedrooms, 4.5 bathrooms, and a dedicated office space. Perfectly positioned approximately 2.5 miles from Magic Kingdom Park at Walt Disney World Resort, this elegant home offers the ideal combination of luxury, comfort, and the sought-after Central Florida lifestyle. Surrounded by conservation areas, residents enjoy privacy, tranquility, and a connection to nature while remaining close to premier golf courses, Hamlin Town Center, Horizon West, upscale dining, shopping, and major roadways. Recently painted inside and out, this energy-efficient smart home was thoughtfully designed with both functionality and sophistication in mind. The expansive open-concept floor plan features elegant 9'4" ceilings on the first floor and 9'0" ceilings on the second level, creating a spacious and airy feel throughout the home. The gourmet kitchen showcases upgraded cabinetry, stainless steel appliances, a walk-in pantry, and generous preparation and gathering space ideal for entertaining. Additional highlights include spacious living and dining areas, beautifully designed finishes throughout, and a private office space ideal for remote work or study. The functional layout includes two bedrooms conveniently located on the first floor, offering flexibility for guests, multigenerational living, or private workspace options. Upstairs, enjoy an ample loft filled with natural daylight, perfect for family gatherings, media space, game room, or flexible living area. The second floor also features a conveniently located laundry room and an additional junior suite with its own private full bathroom. All appliances are included, making this home truly move-in ready. The spacious owner’s suite offers a true private retreat featuring an in-suite bathroom with a generous walk-in closet, relaxing garden tub, and separate shower designed for comfort and relaxation. Step outside into your own private outdoor oasis featuring an extended covered and screened pool, spa, lanai, and travertine deck area designed for entertaining and year-round Florida living. The saltwater, gas-heated pool and spa combined with the spacious outdoor gathering areas create the perfect setting to relax and entertain. The fully fenced backyard and screened enclosure further enhance the outdoor experience. With no rear neighbors and surrounded by conservation, this home offers exceptional privacy and peaceful views. Enjoy breathtaking nightly Disney fireworks and connect with nature from your own backyard. Additional exterior highlights include future outdoor kitchen utility connections already available and newly finished epoxy garage floors that enhance both appearance and functionality. Residents of Windermere Isle enjoy resort-style amenities including a community pool, cabana, playground/tot lot, scenic conservation surroundings, and beautifully maintained streetscapes while remaining close to Disney, golf, shopping, dining, and everyday conveniences. Located within a highly rated school zone, this home presents a rare opportunity to own an exceptional property in one of Windermere’s most desirable communities. Experience the lifestyle, location, elegance, privacy, and convenience that make 8409 Vivaro Isle Way truly exceptional.
Listing is courtesy of: WATSON REALTY CORP., REALTORS (352-243-7374)
Listing Agent: Katherine Figueroa Santiago (407-417-4227)
7612 FAIRGROVE AVE, WINDERMERE, FL 34786
$440,00040 Days on yellowkey MLS ID: S5149402
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1742 Built: 2016Monthly Fee: $347 Tax: $6,515 (2025)Community: Windermere Sound Ph 2Townhouse
Taxes:$6,515
Elementary School: None
High School: None
Middle School: None
Remarks: Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool, tennis and basketball courts, playgrounds, and scenic ponds, all with lawn care included. Ideally situated just minutes from Disney World, premium shopping, fine dining, and top-rated schools such as Windermere High School, this home perfectly blends comfort, convenience, and luxury living in one of Orlando's most sought-after areas.
Listing is courtesy of: FLORIDA FANTASY REAL ESTATE INC (407-397-9039)
Listing Agent: Maribel Minarro (407-908-3522)
8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$1,150,0007 Days on yellowkey MLS ID: O6413196
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3971 Built: 2016Monthly Fee: $8 Tax: $13,647 (2025)Community: Windermere Trls Ph 3BSpa: YesSingle Family
Taxes:$13,647
Remarks: FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll immediately notice the attention to detail. Inside, exquisite marble floors, crown moulding, upgraded lighting, and a dramatic staircase create a timeless first impression. The recently renovated kitchen is truly the heart of the home. Crisp white cabinetry adorned with traditional millwork, glass display cabinets, brushed gold pendant lighting, and an oversized island blend beauty and function effortlessly. Quartzite, granite, and other fine stone finishes have been thoughtfully incorporated throughout, creating a refined yet comfortable atmosphere. Designed for both entertaining and everyday living, the home features a formal dining room, spacious eat-in kitchen, and multiple gathering spaces overlooking the pool and Lake Reams beyond. Two sets of French doors open to the covered lanai, seamlessly connecting indoor and outdoor living. With five bedrooms, four bathrooms, and a dedicated office on the main level, there is flexibility for growing families, remote work, guests, or multigenerational living. Wake up to water views and enjoy evening sunsets from your private backyard retreat featuring a sparkling pool and covered lanai. The upstairs loft also offers the same beautiful view! Residents of Windermere Trails enjoy miles of walking trails, a community pool, playground, picnic pavilion, and some of the area's most desirable schools. Located just minutes from shopping, dining, and approximately 10 minutes from Disney, this location offers convenience without sacrificing the charm and character that make Windermere so special.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$322,000151 Days on yellowkey MLS ID: TB8465266
0 Days Off yellowkey (back on 6/8/2026)
REDUCED by $3,000 (0.9%) on 05/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Taxes:$4,422
Remarks: Under contract-accepting backup offers. Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing Agent: Erin Aaron (727-422-1688)
9257 OUTLOOK ROCK TRL, WINDERMERE, FL 34786
$879,999127 Days on yellowkey MLS ID: S5143447
REDUCED by $19,991 (2.2%) on 05/28/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3619 Built: 2017 Tax: $488 (2024)Community: Windermere Trls Ph 4BSingle Family
Taxes:$488
Elementary School: Bay Lake Elementary
Remarks: Under contract-accepting backup offers. In the Highly Desirable Windermere Trails community we have this Stunning 5-Bedroom, 4.5-Bathroom. This luxurious and spacious residence is located in one of Windermere’s most privileged and sought-after areas. It features open-concept living spaces, a gourmet kitchen with premium finishes, and a beautiful and cozy primary suite with a spa-style bathroom and a large walk-in closet. Step outside to a beautifully landscaped backyard, perfect for family gatherings and weekend BBQs—offering both comfort and style. The Windermere Trails community offers amazing amenities, including walking trails, dog parks, and playgrounds—designed for an active, family-friendly lifestyle. Enjoy the convenience of being just minutes from top-rated schools, fine dining, shopping centers, and Orlando’s world-class attractions. Luxury, comfort, and a prime location—all in one place. Move-in ready and waiting for you!
Listing is courtesy of: PRIMUS CRE GROUP (305-988-7978)
Listing Agent: Macarena Jimenez (407-943-4558)
7174 BEEK ST, WINDERMERE, FL 34786
$725,00042 Days on yellowkey MLS ID: O6402279
0 Days Off yellowkey (back on 6/1/2026)
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2464 Built: 2013Monthly Fee: $115 Tax: $5,627 (2025)Community: Windermere TerraceSingle Family
Taxes:$5,627
Remarks: Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 square feet of well designed living space, plus a 3 car garage and no rear neighbor as it backs to the brick wall of Windermere Terrace. Inside you'll find soaring 10' ceilings & 6-incht baseboards throughout, crown moldings in the family/kitchen area, ceramic tile in the kitchen & bathrooms and engineered wood floors in the foyer, dining & family rooms & carpet in the bedrooms. As you enter the foyer, the view draws you to the family room and kitchen/dining area plus the triple sliding doors to the large covered porch (21x15). The kitchen has all granite counters, a breakfast bar and plenty of cabinets & a closet pantry. The dining room is at the end of the kitchen with a view to the rear yard. The additional multiple purpose room with granite counters opens to the family room, and can be a computer room, mud room, dry bar or butler pantry, extra storage with the cabinets. It also opens to the inside laundry room then to the 3-car garage with brand new door openers (April 2026). The primary bedroom has an ensuite bathroom with dual sinks, granite counters, garden tub plus separate shower, and walk-in closet with built in custom made Italian clothes storage cabinets. The community pool is a short distance away exclusive for Windermere Terrace residents. The electric power to the home is efficiently supplied by the Leased Solar system in connection with Duke. Reduces the electric bill. The recent upgrades will greatly make this home worry free for your family, They are: (1) The 4 ton air conditioner was replaced on 3-30-2023. (2) The entire roof was replaced in October 2025 (3) The 50 gallon water heater was replaced on 11-12-2024. (4) Both garage door openers were replaced in April 2026. Great location and close to all shopping, major roads and more. Shop and compare, your family deserves this home. Click the tour button above for Virtual Tour and floor plan..
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Ron Hernquist (407-257-2700)
11861 VERMILLION AVE, WINDERMERE, FL 34786
$475,00013 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 3Townhouse
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)
715 MAGNOLIA ST, WINDERMERE, FL 34786
$1,175,00065 Days on yellowkey MLS ID: S5147648
REDUCED by $75,000 (6.0%) on 04/27/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3390 Built: 1999 Tax: $5,631 (2024)Community: Windermere TownSpa: NoSingle Family
Taxes:$5,631
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwood floors throughout, spacious living areas, and large sliding doors that open to a serene, beautiful backyard — ideal for both entertaining and unwinding. An added highlight is the fully equipped ADU, offering a private one-bedroom, one-bathroom living space perfect for in-laws, guests, or a dedicated home office. Situated just minutes from local shops, parks, boat ramps, and the renowned Windermere Chain of Lakes, this home places the best of the area right at your doorstep.
Listing is courtesy of: IRIS INTERNATIONAL (407-448-5085)
Listing Agent: Robert Trien (407-484-8474)
13542 GORGONA ISLE DR, WINDERMERE, FL 34786
$895,00094 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: One or more photo(s) has been 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: Jennifer Olmeda (407-547-9242)
1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,290,00077 Days on yellowkey MLS ID: S5146178
REDUCED by $90,000 (3.8%) on 05/29/2026
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5448 Built: 2019Monthly Fee: $250 Tax: $1,982 (2025)Community: Estancia/WindermereSingle Family
Taxes:$1,982
Middle School: Bridgewater Middle
Remarks: Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. Built in 2019 on an oversized homesite, this beautifully appointed residence showcases modern architecture, generous living areas filled with natural light, and high end finishes throughout. The open concept layout is ideal for both everyday living and entertaining, with a gourmet style kitchen, elegant dining spaces, and seamless flow to the outdoor living area. Enjoy Windermere’s signature lifestyle just minutes from top rated schools, charming downtown Windermere, and world class Orlando attractions, including Walt Disney World and Universal Studios. Estancia is a boutique community of luxury homes featuring a private, serene atmosphere with conservation surroundings, while still offering quick access to major highways, shopping, dining, parks, and the Butler Chain of Lakes. This is an outstanding opportunity to own a stylish, move in ready home in one of Windermere’s most desirable neighborhoods.
Listing Agent: Catalina Gomez (407-289-9029)
4474 BEGONIA CT, WINDERMERE, FL 34786
$1,170,00051 Days on yellowkey MLS ID: O6402227
REDUCED by $100,000 (7.9%) on 05/13/2026
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)
2509 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,460,00039 Days on yellowkey MLS ID: O6402522
0 Days Off yellowkey (back on 6/6/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3844 Built: 1998Monthly Fee: $220 Tax: $19,706 (2025)Community: Estates At WindermereSingle Family
Taxes:$19,706
Elementary School: Lake Whitney Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to 2509 Ridgewind Way, a timeless Southern estate tucked inside the gates of The Estates at Windermere—one of Windermere’s most beloved communities known for its oak-lined streets, oversized lots, and quiet charm. Set on a rare .75-acre homesite, this beautifully updated residence blends classic architecture with the functionality today’s buyers are searching for. A wraparound front porch, copper lanterns, and mature oaks create an immediate sense of arrival, while inside, nearly 3,900 square feet unfold with warmth, light, and thoughtful design. At the center of the home, the renovated kitchen was made for gathering—featuring an oversized island, built-in banquette seating, premium appliances, and seamless flow into both formal and casual living spaces. The floor plan lives exceptionally well with 4 bedrooms, 3.5 baths, TWO bonus rooms, TWO primary suites, a private office, custom drop zone, extensive storage, and a dream laundry room rarely found at this price point. The main-level primary suite offers a true retreat with porch access, a spa-inspired bath, clawfoot soaking tub, oversized walk-in shower, and custom boutique-style closet built-ins. Upstairs, spacious secondary bedrooms and flexible bonus spaces create endless options for media, fitness, play, or guests. Outside, the experience becomes resort-like. A screen-enclosed, solar-heated lagoon pool with waterfall feature is surrounded by lush, mature landscaping, while the expansive lanai was designed for entertaining—with a wood-burning fireplace, mounted TVs, built-in bar, and kegerator beneath glowing café lights. Mature mango and lemon trees complete the setting, while a private well keeps the landscaping green year-round. Additional highlights include a paver driveway, oversized three-car garage with epoxy floors and custom storage, EV charger, newer HVAC (2023), water heater (2022), and roof (2017). Residents of The Estates at Windermere enjoy a rare combination of privacy and community, with just 67 homes, plus tennis, pickleball, playground, and a location minutes from top-rated public and private schools, dining, shopping, major highways, and Orlando’s premier attractions.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
11903 CAVE RUN AVE, WINDERMERE, FL 34786
$750,00084 Days on yellowkey MLS ID: O6392757
0 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3413 Built: 2014Monthly Fee: $81 Tax: $10,874 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$10,874
Remarks: Under contract-accepting backup offers. Stunning move-in ready home in the highly sought-after Windermere Trails community, located in a top-rated school district and just 2 miles from Walt Disney World! This beautifully upgraded 4-bedroom, 3.5-bath home features a gourmet kitchen with an oversized center island, custom solid wood cabinetry, granite countertops, built-in ovens, and a spacious walk-in pantry — perfect for entertaining and everyday living. Brand new carpet has just been installed, offering a fresh, clean feel throughout the home. The first floor offers a dedicated office/den, ideal for working from home. Upstairs, a large bonus/media room provides flexible space for family gatherings, a playroom, or home theater. The spacious layout, combined with thoughtful upgrades, creates both comfort and functionality for modern living. Enjoy resort-style community amenities including a pool, dog parks with wash stations, cabana, walking/running trails, and playgrounds — all in one of Windermere’s most desirable neighborhoods. Zoned for highly rated schools, this home is perfect for families seeking both lifestyle and location.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Yan Zheng (407-279-8417)
325 MAGNOLIA ST, WINDERMERE, FL 34786
$2,450,00090 Days on yellowkey MLS ID: O6391047
REDUCED by $25,000 (1.0%) on 05/30/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3975 Built: 1954 Tax: $24,094 (2025)Community: Windermere TownSingle Family
Taxes:$24,094
Remarks: Under contract-accepting backup offers. Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid-back lake living with walkability to town, and a bike ride to Windermere Elementary. The Town of Windermere has much to offer. Walk to the local park and tennis courts just a few blocks from your home. It’s an easy stroll or bike ride to Main Street—home to local spots like Dixie Cream, Paloma Coffee, Windermere Brewing Company, the Friday farmer’s market, and the newly updated shops and dining on the 500 Block. Inside, the home is both comfortable and thoughtfully updated, with travertine flooring in the main living areas and new luxury vinyl plank in two bedrooms —no carpet. The kitchen features a gas cooktop with vented exhaust, a new Dacor refrigerator and a newer all-in-one convection oven, microwave, and air fryer. The large dining room provides a pleasurable dining experience with lake views. The 4th bedroom/theater room is a flexible space that can be used as a guest bedroom, theatre room, workout room or a game room. It can also work as a large office, playroom, or just a place to sit and relax with views of the lake. The bright open Florida room, equipped with three full glass French doors with side panels, a wet bar and views of your outdoor lakefront oasis, opens up to the pool and overlooks the water, creating an easy space to relax or entertain. A great opportunity to enjoy the convenience of the Butler Chain lifestyle in the heart of Windermere—with no HOA.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Rebekkah Boskovich (321-438-3307)
12319 CRUXBURY DR, WINDERMERE, FL 34786
$405,00017 Days on yellowkey MLS ID: O6411226
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $1,935 (2025)Community: Lakes/Windermere-Lk Reams TwhmTownhouse
Taxes:$1,935
Remarks: Approximately 1,429 square feet of well-designed living space await in this attractive 3-bedroom, 2.5-bathroom home. Situated in a sought-after Windermere community, this turnkey home offers an inviting layout with a harmonious flow. The home showcases hardwood laminate flooring that extends throughout, including the staircase which has solid oak treads creating a cohesive aesthetic. The kitchen, which opens to the dinette and family room, is equipped with stainless steel appliances and a breakfast bar, making it an ideal space for meal preparation and casual gatherings. Upstairs, the primary suite boasts an upgraded walk-in shower, providing a private and rejuvenating retreat. Two additional bedrooms and a full bathroom complete the upper level, ensuring ample space and comfort for residents. The home is further enhanced by upgraded high-efficiency Renewal by Anderson windows for better energy savings, upgraded garage floor coating, providing a durable and attractive surface and ceiling fans throughout. The rear entry two-car garage with an automatic door opener offers convenient access, while the private fenced courtyard and paver patio offers a delightful outdoor space. Residents can enjoy evening Walt Disney World fireworks from the backyard, adding a touch of enchantment to the property. The community amenities include a well-maintained junior Olympic-sized pool and cabana, situated just minutes from the Walt Disney World employee entrance, offering residents a harmonious blend of convenience and recreation. With its well-thought-out design, quality finishes, and desirable location, this residence presents an ideal opportunity for those seeking a turnkey, move-in-ready home in a charming community, conveniently close to shopping, dining, major attractions and zoned for A-rated schools.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Dee Lund (407-925-7781)
728 FOREST ST, WINDERMERE, FL 34786
$10,200,00011 Days on yellowkey MLS ID: O6411906
Bed: 6 Bath: 8.5 Gar: 3 Liv Area Sq Ft: 6457 Built: 2026 Tax: $18,799 (2025)Community: Windermere TownSpa: YesSingle Family
Taxes:$18,799
Remarks: An extraordinary brand-new contemporary lakefront estate on prestigious LAKE BUTLER, part of the renowned Butler Chain of Lakes, offering an exceptional blend of architectural sophistication, modern luxury, and unparalleled waterfront living. Situated on approximately 0.83 acres with 114 feet of pristine lake frontage, this remarkable residence was designed to capture breathtaking panoramic water views, spectacular sunrises, and unforgettable sunsets from nearly every major living space. Encompassing 6,457 square feet of heated living area, the home seamlessly integrates architecture and landscape through expansive walls of glass, soaring ceilings, refined finishes, and an abundance of natural light. Every space was carefully oriented to maximize the connection between the interior and the surrounding waterfront setting. The designer chef’s kitchen showcases premium Sub-Zero and Wolf appliances, custom European cabinetry, an oversized waterfall island, Italian marble accents, and contemporary finishes, making it both a stunning focal point and an ideal space for entertaining. Designed for flexibility and comfort, the residence features six private bedroom suites, including two luxurious primary suites—one conveniently located on the main level and another on the second floor. Both primary retreats offer spa-inspired bathrooms with elevated finishes, expansive custom closets, premium TOTO fixtures, and living spaces that blend comfort and sophistication. The home also includes eight full bathrooms, one half bath, a dedicated wine room with elegant Italian marble detailing, wide-plank engineered hardwood flooring throughout, designer lighting, dual laundry rooms, a natural gas fireplace, and fully integrated Control4 smart home automation. Control4 home automation allows seamless control of lighting, audio, security cameras, pool equipment, and HVAC systems, creating a connected living experience. Outdoor living is equally impressive, featuring expansive covered lanais, a summer kitchen, saltwater pool and spa, and a private two-level covered dock equipped with water, electricity, and a boat lift. Designed for the ultimate waterfront lifestyle, the dock accommodates a 25-foot boat and two jet skis while providing direct access to the Butler Chain of Lakes, one of Central Florida’s most sought-after boating destinations. Constructed with exceptional attention to detail, the residence features concrete block construction on the main level, metal-frame construction on the second floor, DensGlass exterior sheathing for enhanced durability and weather resistance, energy-efficient TPO roofing, advanced spray foam insulation, four Daikin variable-speed HVAC systems with a combined 20-ton capacity, and natural gas tankless water heaters with recirculation technology. The garage is also equipped with dual 220V outlets for future EV charging capability. Located within the historic Town of Windermere, residents enjoy a unique golf-cart-friendly lifestyle with access to community parks, tennis courts, playgrounds, private lake amenities, and charming tree-lined streets, and the added benefit of no HOA, all while being just minutes from Orlando’s finest dining, shopping, world-class golf, and top-rated private schools. A rare offering on Lake Butler, where architectural excellence, luxury finishes, advanced technology, and one of Central Florida’s most coveted waterfront settings come together to create an exceptional living experience.
Listing is courtesy of: S2J REALTY, LLC (407-745-6023)
Listing Agent: Soraya Resende (407-745-6023)
9150 OUTLOOK ROCK TRL, WINDERMERE, FL 34786
$915,00095 Days on yellowkey MLS ID: S5145642
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2988 Built: 2015Monthly Fee: $13 Tax: $10,964 (2024)Community: Windermere Trls Ph 5BSingle Family
Taxes:$10,964
Remarks: Welcome to this exquisite and impeccably maintained home filled with natural light and elegant open spaces. As you step inside, you are greeted by a soaring ceiling in the grand foyer that immediately sets the tone for the home’s impressive design. The first floor features a versatile bedroom with a full bath, perfect for guests or multi-generational living, along with a formal dining room that can easily serve as a home office. The beautifully remodeled kitchen is a true showpiece, boasting 42” warm white -colored cabinetry, granite countertops. A walk-in pantry, vented built-in microwave, and two full double ovens provide both convenience and functionality. The spacious island is illuminated with elegant pendant lighting, while a butler’s pantry conveniently located between the kitchen and garage adds extra storage and practicality. The home also features brand-new flooring, adding a fresh and modern touch throughout. The main living areas are finished with neutral tile, while the stairwell and entire second floor—including all bedrooms—showcase new Lifeproof wood-look luxury vinyl flooring. The expansive owner’s suite serves as a private retreat, offering two large walk-in closets, a relaxing soaking tub, separate shower, and dual vanities. Each additional bedroom also includes walk-in closets and TV cable feed-throughs for added convenience. Upstairs you’ll also find a spacious bonus/media room pre-wired for A/V components, perfect for movie nights, gaming, or entertaining. Step outside to your private outdoor oasis, featuring a screened lanai and sparkling saltwater pool with a sun shelf, surrounded by elegant glass mosaic tiles in soothing ocean-blue tones. The property has also been recently enclosed with a newly installed vinyl privacy fence, creating the perfect setting for relaxing afternoons or weekend barbecues. This home is not only beautiful but also energy efficient, featuring R-38 insulation, a 15 SEER HVAC system, and a hybrid water heater, helping keep utility costs low while earning an ENERGY STAR rating. Located in the highly desirable Windermere Trails community, surrounded by scenic green spaces and ponds, and just minutes from shopping, dining, and top attractions. Residents enjoy exceptional amenities including a lakeside pool with splash pad, playgrounds, and a running and biking trail. Don’t miss the opportunity to make this stunning home yours. Schedule your private showing today and experience the lifestyle it offers.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Andrea Munoz (407-989-2021)
7011 NOBLETON DR, WINDERMERE, FL 34786
$580,00015 Days on yellowkey MLS ID: O6412101
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2460 Built: 2003Monthly Fee: $82 Tax: $9,209 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$9,209
Remarks: TOP RATED SCHOOLS!!! Welcome to this beautifully maintained Craftsman-style home in the highly sought-after Lakes of Windermere community. Perfectly positioned on a premium homesite overlooking tranquil conservation views, this 4-bedroom, 2.5-bath residence combines timeless charm with modern upgrades and exceptional indoor-outdoor living. Inside, you’ll find a light-filled floor plan featuring hardwood flooring, elegant transom windows, custom built-ins, and spacious living and dining areas ideal for both everyday living and entertaining. The upgraded kitchen offers granite countertops, solid wood cabinetry, stainless steel appliances, a butler’s pantry, and ample prep and storage space. This is the one you’ve been waiting for—schedule your private showing today.
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