Location: Windermere, Windermere
Do Not Show Listings
10624 REAMS RD, WINDERMERE, FL 34786
$487,000248 Days on yellowkey MLS ID: O6338130
REDUCED by $12,000 (2.4%) on 04/24/2026
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,459
Elementary School: Bay Lake Elementary
High School: Windermere High School
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: 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 connects the spacious living and with the kitchen, perfect 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, office, or media area. Recent updates include a new A/C (2022) and water heater (2023). 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. Don’t miss this opportunity—schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jeff Taulbee (407-622-2122)
325 MAGNOLIA ST, WINDERMERE, FL 34786
$2,475,00040 Days on yellowkey MLS ID: O6391047
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3975 Built: 1954 Tax: $21,080 (2025)Community: Windermere TownSingle Family
Taxes:$21,080
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: 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 and walkability to town. 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 500 block with shops and dining. Inside, the home is both comfortable and thoughtfully updated, with travertine flooring in the main living areas and new luxury vinyl plank in bedrooms two and three—no carpet. The kitchen features a gas cooktop with vented exhaust and a brand-new all-in-one convection oven, microwave, and air fryer. The large dining room provides a pleasurable dining experience with lake views. The theater room can be a flexible space used for movies, a guest bedroom, or a game room. It can also work as an office, playroom, or just a place to sit and relax. 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—no HOA.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Rebekkah Boskovich (321-438-3307)
7137 BEEK ST, WINDERMERE, FL 34786
$550,00010 Days on yellowkey MLS ID: O6398814
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1910 Built: 2013Monthly Fee: $120 Tax: $7,932 (2025)Community: Windermere TerraceSingle Family
Taxes:$7,932
Elementary School: Sunset Park Elem
Remarks: Under contract-accepting backup offers. BUYER FAILED TO DEPOSIT ESCROW - BACK ON MARKET - Welcome to Windermere Terrace. This home offers a rare combination of privacy, location, and lifestyle that is difficult to find in Central Florida. Set on a premium lot, the property overlooks a pond with a conservation area beyond that means you will never have rear neighbors! This buffer creates a peaceful and private setting that enhances everyday living. This well-designed home features 3 bedrooms, 2 bathrooms, and approximately 1,910 square feet of living space. The kitchen is both functional and stylish and includes 42-inch cabinets, granite countertops, stainless steel appliances, pendant lighting, and ample pantry storage. The split-bedroom floor plan offers privacy and flexibility. The primary suite features dual vanities, a walk-in shower, and a spacious closet. Meanwhile, the secondary bedrooms and full bathroom are positioned on the opposite side, making them ideal for guests or family members. Step outside to a screened patio that extends your living space. Here, you can relax while enjoying tranquil water and conservation views. Residents of Windermere Terrace enjoy community amenities that include a pool and scenic walking paths. Perfect location too with convenient access to shopping and dining at Winter Garden Village, as well as outdoor recreation at Tibet-Butler Nature Preserve. Major roadways are also easily accessible, simplifying your daily commute. This home delivers a rare blend of privacy, views, and proximity to Central Florida’s top attractions, including Universal Orlando Resort and SeaWorld Orlando. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jacquie Sosa (407-340-9793)
WINDERMERE, FL 34786
$359,0003 Days on yellowkey MLS ID: O6400745
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1429 Built: 2006Monthly Fee: $200 Tax: $5,436 (2025)Community: Lakes/Windermere-Lk Reams TwhmSpa: NoTownhouse
Taxes:$5,436
Remarks: Welcome to this beautifully maintained 2-bedroom, 2½-bathroom corner lot townhome in the highly desirable Windermere area! Located at 8905 Newmarket Drive, this home offers the perfect blend of comfort, style, and convenience. The spacious open floor plan is filled with natural light and designed for both everyday living and entertaining. The kitchen features clean white appliances, ample cabinetry, and a layout that flows seamlessly into the living and dining areas.The primary suite provides a relaxing retreat with a well-appointed ensuite bathroom. The second bedroom and additional baths offer flexibility for guests, home office use, or hobbies. Enjoy a private backyard and the added benefits of a corner lot, providing extra privacy and space.Situated in a sought-after community, residents enjoy easy access to top-rated schools, shopping, dining, and major roadways, with quick access to Walt Disney World. Nearby golf courses and Windermere’s charm make this location truly exceptional.Don’t miss the opportunity to own this charming corner lot townhome in a prime location—schedule your private showing today!
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
11472 PARK AVE NE, WINDERMERE, FL 34786
$1,125,000103 Days on yellowkey MLS ID: G5105731
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3166 Built: 1985Monthly Fee: $21 Tax: $5,774 (2025)Community: WindermereSingle Family
Taxes:$5,774
Remarks: Approximately 3,000 sq ft home in a desirable Windermere location within FEMA Flood Zone X. Buyer is responsible for verifying all measurements, dimensions, and square footage The residence offers a flexible layout with multiple living areas and is fully livable, presenting an excellent opportunity for buyers seeking long-term value and equity potential in one of Central Florida’s most established and highly regarded residential markets. Nearby Schools & Community Amenities Conveniently located near Windermere Elementary School on Park Avenue and the Windermere Recreation Center (Butler Bay), which offers lake access, a boardwalk, playground, picnic areas, and open green space along the Butler Chain of Lakes. Luxury Market Areas & Subdivision Context The Property is surrounded by well-established luxury residential communities with home values frequently exceeding $1,000,000. Nearby communities include Isleworth, Casabella at Windermere, and the Butler Bay / Windermere Club area, reinforcing the strong market fundamentals and long-term desirability of the Park Avenue corridor. Recreation, Shopping & Location Benefits The property offers easy access to area golf courses, parks, walking trails, marinas, and everyday conveniences. Located minutes from dining, shopping, and entertainment along International Drive, with convenient connections to major roadways serving Windermere, Orlando, and surrounding communities. Recent price improvement reflects the seller’s decision to position the property competitively within the current Windermere market Showings available upon request
Listing is courtesy of: WEICHERT, REALTORS-HALLMARK PR (352-536-9948)
Listing Agent: Ralph Vock (734-928-8181)
1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,380,00027 Days on yellowkey MLS ID: S5146178
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5108 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. This home is being offered fully furnished, providing a truly turnkey, move in ready experience. 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, fully furnished, move in ready home in one of Windermere’s most desirable neighborhoods.
Listing Agent: Catalina Gomez (407-289-9029)
1020 OAKDALE ST, WINDERMERE, FL 34786
$2,200,000284 Days on yellowkey MLS ID: O6322270
1 Days Off yellowkey (back on 11/1/2025)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3994 Built: 2025 Tax: $7,202 (2024)Community: Windermere TownSpa: YesSingle Family
Taxes:$7,202
Remarks: Under contract-accepting backup offers. Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space. From the moment you step inside, you're enveloped in elevated elegance, soaring ceilings, rich custom millwork, and engineered hardwood flooring set the tone for this amazing home. The state-of-the-art chef’s kitchen is a true culinary masterpiece, featuring a full suite of premium Thermador appliances, stunning quartz countertops, custom cabinetry, and an oversized island designed for both function and entertainment. The luxurious primary suite is a true sanctuary, featuring a spa-inspired soaking tub, an oversized walk-in shower, a private office, and an expansive boutique-style walk-in closet that redefines elevated living. The open-concept layout seamlessly blends indoor and outdoor living, with expansive sliding glass doors leading to a resort-caliber backyard oasis. The expansive backyard features a sparkling pool and spa, a fully equipped summer kitchen, and a generously sized covered lanai, perfect for luxurious outdoor living and year-round entertaining. Ideally located within walking distance to Windermere’s boutiques, award-winning schools, weekly farmer’s markets, and scenic lakefront parks you have unlimited access to everything Windermere has to offer. With close proximity to Winter Garden Village, Restaurant Row, and all the area attractions you are truly in the heart of it all. This is more than a home, it’s a statement of luxury, lifestyle, and taste.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Christopher Christensen (407-312-8003)
6897 NORTHWICH DR, WINDERMERE, FL 34786
$579,9004 Days on yellowkey MLS ID: O6400673
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2229 Built: 2003Monthly Fee: $82 Tax: $7,925 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$7,925
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to the highly desirable Lakes of Windermere! Where comfort, convenience, and thoughtful updates come together in one of Central Florida’s most sought-after communities. This move-in ready 4-bedroom, 3-bathroom home offers a functional, open layout perfect for both everyday living and entertaining. Step inside to find upgraded flooring installed in 2023, creating a warm, modern feel throughout the main living areas. The kitchen has been refreshed with newer appliances, including a refrigerator (2025) and electric stove and microwave (2025), along with major systems such as roof (2018), and AC (2020) - giving buyers peace of mind and a clean, updated look from day one. Complementing the space is updated tile flooring in the kitchen (2023), blending durability with style. Major updates continue with a hot water heater (2023), adding to the home’s overall value and reducing big-ticket concerns for future homeowners. With four well-sized bedrooms and three full bathrooms, the layout offers flexibility for families, guests, or a dedicated home office. Located in the heart of Windermere, residents of Lakes of Windermere enjoy access to community amenities including a pool, playground, volleyball & tennis courts - conveniently across the street from your home. All while being just minutes from top-rated schools, shopping, dining, and major roadways. Your community now has fiber internet as an option! Don't miss out on one of the best values in Central Florida's most sought communities of Windermere!!
Listing is courtesy of: REALTY ONE GROUP INSPIRATION (321-233-2300)
Listing Agent: Blake Blahut (407-748-0484)
13048 LAKE ROPER CT., WINDERMERE, FL 34786
$1,890,000226 Days on yellowkey MLS ID: O6342354
REDUCED by $60,000 (3.1%) on 04/22/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4130 Built: 2002Monthly Fee: $333 Tax: $14,738 (2025)Community: Windermere PointeSingle Family
Taxes:$14,738
Remarks: Back on the market. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage. Lake Roper is renowned for its water sports, water skiing, jet skiing and fishing only acceded by the surrounding houses (No Public Ramps). This is one of the largest lots in the community. Location: Only minutes from Winter Garden Village and Downtown Windermere, minutes from main roads like 429 and 408 and a short distance from Theme Parks and Shopping Areas. Great School District. Kitchen: Totally renewed, custom-built cabinetry, high-end stainless still appliances, built in induction cook top, built in microwave and oven, huge island built with one piece of quartz, no sims. Pop-out outlets, touchless faucet and built in hood. Bathrooms: Contemporary look with porcelain tiles, quartz tops, custom made cabinetry and modern metals. Pool area: The pool was resurfaced, surrounded by new pavers overviewing the lake and a brand-new equipped summer kitchen just built. Dock: Wood dock and fishing pier with Electric Boat lift. The house was completely renovated from top to bottom including new engineering hardwood floors, 3 new A/Cs, new water heater, new irrigation system, fresh painted and new roof installed in 2020. Important Notice: "Seller is willing to accept a smaller house as part of the payment".
Listing is courtesy of: WOODSTONE INVESTMENTS LLC (407-300-4727)
Listing Agent: Fernando Teixeira (407-300-4727)
8632 ABBOTSBURY DR, WINDERMERE, FL 34786
$609,99996 Days on yellowkey MLS ID: O6374937
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2720 Built: 2004Monthly Fee: $167 Tax: $8,567 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$8,567
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8632 Abbotsbury Drive, a beautifully situated 4-bedroom, 3.5-bath residence offering 2,720 square feet of heated living space in the heart of Windermere, one of Central Florida’s most desirable communities. This well-maintained home features an open floor plan that creates a bright, airy feel and allows for effortless flow between the main living areas, making it ideal for both everyday living and entertaining. Spacious rooms are filled with natural light, enhancing the home’s inviting atmosphere. The property includes a 2-car garage, providing convenience and ample storage. At the rear of the home, a screened-in patio offers a peaceful outdoor retreat, surrounded by mature trees and lush, well-maintained landscaping that delivers privacy and a serene setting. Located in a well-established neighborhood, this home offers easy access to top-rated schools, shopping, dining, and nearby attractions. With its open layout, mature landscaping, and prime Windermere location, 8632 Abbotsbury Drive is a wonderful opportunity to enjoy comfortable Florida living at its best.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1002 OAKDALE ST, WINDERMERE, FL 34786
$975,00012 Days on yellowkey MLS ID: TB8495717
1 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 3516 Built: 1973 Tax: $8,799 (2025)Community: Windermere TownSingle Family
Taxes:$8,799
Remarks: Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is offering up to a $25,000 closing cost credit, providing added flexibility and value for buyers. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Frank Smith (401-644-4762)
12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786
$1,490,00010 Days on yellowkey MLS ID: O6399958
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3487 Built: 1997Monthly Fee: $130 Tax: $6,661 (2025)Community: Isles WindermereSpa: YesSingle Family
Taxes:$6,661
Remarks: Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The outdoor living area is designed for true Florida living, featuring a sparkling pool and spa, perfect for relaxing or entertaining. Adding to the sense of tranquility, one side of the property has no direct neighbors—only beautifully maintained green space and a scenic bridge, creating gorgeous views and a rare feeling of serenity. Inside, the home features generously sized rooms filled with comfort and charm, including an oversized family room with a wood-burning fireplace. The primary suite is a private retreat, complete with a luxurious bath featuring dual sinks, a jetted garden tub, a large walk-in shower, and a full vanity area. Every detail has been thoughtfully updated with style and functionality in mind. Additional highlights include a three-car garage with ample space for parking and storage, as well as a prime location within a top-rated public school district, just minutes from Windermere’s premier shopping, dining, and recreation. A rare opportunity to own a beautifully updated home in one of Central Florida’s most desirable communities.
Listing Agent: Patricia Zimath, Llc (321-318-1050)
13013 OVERSTREET RD, WINDERMERE, FL 34786
$669,99459 Days on yellowkey MLS ID: O6380917
REDUCED by $10,000 (1.5%) on 04/21/2026
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 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 Agent: Omar Andreasen (407-883-2989)
11922 ANGLE POND AVE, WINDERMERE, FL 34786
$760,000282 Days on yellowkey MLS ID: O6328443
1 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3382 Built: 2013Monthly Fee: $81 Tax: $8,155 (2024)Community: Windermere Trls Ph 1BSpa: NoSingle Family
Taxes:$8,155
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained four-bedroom, three-and-a-half-bath home in the highly sought-after Windermere Trails community, located less than two minutes from Walt Disney World. The front of the home offers multiple flexible living spaces ideal for a home office, sitting room, or hobby area. The open family room flows into a spacious kitchen featuring a large quartz island, brand-new stainless steel appliances, ample cabinetry, and tasteful modern finishes. An additional flex space near the kitchen can serve as formal dining or an additional gathering area. Upstairs, the primary suite provides a peaceful retreat with two walk-in closets and a spa-style bathroom with dual vanities and an oversized walk-in shower. Two bedrooms share a Jack-and-Jill bathroom, while the fourth bedroom has its own private, upgraded bath. A large bonus room with a built-in movie screen adds extra space for entertainment. Step onto the upstairs balcony to enjoy morning coffee or evening breezes. The fully fenced backyard features a screened patio and mature banana, mango, lemon, and orange trees, creating a private tropical setting. Luxury vinyl flooring runs throughout the home, with no carpet. Major updates include a new HVAC system in 2023, whole-home water softener, and fresh interior and exterior paint in 2025. Windermere Trails offers walking trails, lakes, and a resort-style pool. Lakeside Village is less than a mile away with grocery stores, shopping, and restaurants, along with close proximity to downtown Windermere, top-rated A schools, boat ramps, major highways, and Orlando’s best dining and entertainment.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
13430 HOPKINTON CT, WINDERMERE, FL 34786
$585,000212 Days on yellowkey MLS ID: O6346406
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1732 Built: 2005Monthly Fee: $167 Tax: $7,277 (2024)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$7,277
Remarks: ***Charming Windermere Home in Lakes of Windermere – Peachtree! *** Welcome to this beautifully maintained 3-bedroom, 2-bath single-story home located on a quiet cul-de-sac in the desirable Lakes of Windermere – Peachtree community, behind the famous Walt Disney World Magic Kingdom! This home combines comfort, convenience, and style in one of Central Florida’s most sought-after locations. Step inside to find a bright and open floor plan with a spacious great room, dining area, and a well-appointed kitchen featuring ample cabinetry and counter space and kitchen eat in nook. The primary suite includes a walk-in closet and an en-suite bath, while two additional bedrooms and a full bath provide plenty of room for family or guests. Outside, enjoy a large screened in patio perfect for relaxing or entertaining. The home also features a finished garage, new roof, recent exterior painting, storage racks in the garage, central heating & cooling, and fresh curb appeal. Located just minutes from Disney, shopping, dining, top-rated schools, and major highways, this property offers the ideal balance of convenience and community living. The HOA includes access to neighborhood amenities and ensures a well-kept environment. Don’t miss the opportunity to make this charming Windermere home yours!
Listing Agent: Lynn London (410-206-0952)
713 MAIN ST, WINDERMERE, FL 34786
$2,235,000129 Days on yellowkey MLS ID: O6368185
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5031 Built: 2013 Tax: $9,559 (2025)Community: WindermereSpa: NoSingle Family
Taxes:$9,559
Remarks: Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024) and windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. The property also offers the opportunity to add a FRONT GATE for enhanced privacy and security, and allows for a FUTURE POOL ADDITION, giving buyers flexibility to further customize the outdoor living experience. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new redevelopment complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
8236 PROCIDA ISLE LN, WINDERMERE, FL 34786
$1,100,00065 Days on yellowkey MLS ID: O6383546
REDUCED by $90,000 (7.6%) on 04/15/2026
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4176 Built: 2018Monthly Fee: $299 Tax: $12,887 (2025)Community: Windermere Isle Ph 2Spa: NoSingle Family
Taxes:$12,887
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light-filled foyer with a private office at the front of the home. Beautiful wood-look tile flooring flows seamlessly throughout the main level. The stunning gourmet kitchen features 42” cabinets, gas appliances, light granite countertops, subway tile backsplash, a unique coffee bar nook with extra storage, and a spacious walk-in pantry with upgraded shelving—perfect for organization and functionality. Downstairs also offers a private bedroom and full bath with an oversized walk-in shower, ideal for guests or multigenerational living. Upstairs, you’ll find a versatile lounge area and four additional spacious bedrooms. The luxurious primary suite boasts a spa-like shower, upgraded vanity with extra storage, and a large walk-in closet complete with custom shelving. The upstairs laundry room includes enhanced shelving for optimal organization. Step outside to your screened-in private lanai overlooking a sparkling saltwater pool with heater, surrounded by mature landscaping that creates your own backyard oasis. Additional premium upgrades include EV outlet and charger, upgraded garage flooring, and a saltwater pool system for easy maintenance. Located in a vibrant community offering social events, a community pool, and playground—and situated near top-rated schools—this home is just a short drive from Disney property, making it perfect as a primary residence or vacation retreat.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Babi Hennemann (407-633-0777)
825 OAKDALE ST, WINDERMERE, FL 34786
$792,50019 Days on yellowkey MLS ID: O6396351
0 Days Off yellowkey (back on 4/19/2026)
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 Agent: Mildred Hershiser (407-758-5263)
6965 TETTENHALL LN, WINDERMERE, FL 34786
$679,000207 Days on yellowkey MLS ID: O6340538
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2972 Built: 2007Monthly Fee: $75 Tax: $4,946 (2024)Community: Lakes/Windermere Ph 04Single Family
Taxes:$4,946
Remarks: Reduced for a quick Sale . Welcome to own this beautiful home in lakes of windermere . 5 bedrooms 3 full bathrooms that has been remodeled . Marble floor through downstairs and laminate upstairs and a lot of upgrades throughout the house . The house is looking over a stunning view of a pond with a water fountain and looking everyday at the Disney fireworks . Perfectly situated minutes from all the attractions Disney , universal , and SeaWorld and also close to all shopping , Dining and major Highways . Walking distance to top rated schools . Fenced backyard with A screened pool .The community offers incredible amenities including a pool,Tennis court , Sand volleyball and Basketball court and two playgrounds . Schedule your showing today . The listing agent is the owner .
Listing is courtesy of: VISION HOME REAL ESTATE, LLC (407-902-6236)
Listing Agent: Nabil Chakrouni (407-963-8548)
8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786
$330,00010 Days on yellowkey MLS ID: O6399551
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,106 (2025)Community: Lakeside/Lks/WindermereCondo
Taxes:$4,106
Remarks: Located just 10 minutes from Disney's Magic Kingdom and Transportation and Ticket Center, welcome to this beautifully maintained FIRST FLOOR END UNIT in the highly sought after Lakeside at Lakes of Windermere. Move in ready and thoughtfully updated, this home offers a bright, open split floor plan with high ceilings and a light, neutral palette throughout. The home has been wired with high speed fiber optic internet, and association included valet trash, sewer, and water completes living with convenience. The kitchen has been tastefully upgraded with new FRIGIDAIRE GALLERY STAINLESS STEEL appliances, including a luxury INDUCTION RANGE, complemented by 42 inch wood cabinetry, a stainless steel backsplash, pantry, and bar seating that is perfect for everyday living or entertaining. The spacious owner’s suite is filled with natural light and offers a peaceful retreat, complete with a large walk in closet and an en suite bath featuring double sinks and a garden tub and shower combo. Secondary bedrooms are generously sized with one having an ensuite/shared bathroom, and the full size laundry closet adds everyday convenience. One of the standout features is the wraparound screened in porch where you can relax and enjoy the lush landscaping and mature oak trees, plus easy access to explore the beautifully maintained grounds or go fishing on Lake Burden. The amenities here truly stand out. Residents enjoy a resort style pool, tennis courts, fishing dock to LAKE BURDEN, clubhouse with full kitchen and gathering spaces, fitness center, beach volleyball court, outdoor fireplace, walking paths, playground, and more. With assigned parking, plus plenty of guest parking, and a prime location just across the street from Publix, dining options such as My French Cafe, Piesanos Stone Fired Pizza, Boteco do Manolo, and other great dining, shopping, top rated schools, and just minutes to Orlando’s world renowned theme parks, this is low maintenance living at its best.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Chris Sartwell (321-427-7678)
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