Location: Windermere
Do Not Show Listings
9639 WESTOVER CLUB CIR, WINDERMERE, FL 34786
$847,500Listed 04/24/2026 2:03PM MLS ID: O6401787
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3248 Built: 2001Monthly Fee: $115 Tax: $11,000 (2025)Community: Westover Club Ph 01 44/139Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,000
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2025
Middle School: Gotha Middle
Remarks: There's room for everyone here. Nearly 3,300 square feet with five beds, three baths, a three-car garage, a pool, and no rear neighbors tucked behind the gates of Westover Club in Windermere. TStep inside and the house opens up. Soaring ceilings, a two-story family room with a fireplace stretching up the wall, a catwalk overhead, and sightlines that carry all the way through to the pool. Gorgeous Allen & Roth tile and baseboards run throughout the downstairs, tying it all together. The kitchen anchors the middle of it all with a 10-foot granite island, GE Café dishwasher, Kraus 60/40 sink, and Moen Motionsense faucet, with deep bar-height cabinets on the back doubling the storage. Living, family, and dining rooms all flow from here under the same vaulted roofline. Cook, entertain, collapse on the couch. Homes like this one don't come around often. Two sets of oversized sliders pull you onto the screened lanai, repainted and re-screened in 2024. Covered seating, a pool, and patio space beyond the cage. The downstairs primary suite stretches long enough for a true sitting area or home office, with its own sliders to the patio. The en-suite is a full retreat: dual vanities, a walk-in shower, a soaking tub, a private water closet, and two separate walk-in closets. A second bedroom and full pool bath sit across the home in a split plan, with a French door nearby to the patio. The right setup for guests, in-laws, or a long-stay visitor who wants their own door. Upstairs, three more bedrooms, one currently styled as a dedicated theater room with an 8-foot built-in screen, Epson projector, surround sound, and staggered seating. A full bath serves the upper floor. The laundry room has cabinets above and below the sink, and deep storage tucks under the stairs. Big-ticket updates are done. New roof, new upstairs HVAC, and new black metal fencing, all in 2023. Westover Club is gated, tree-lined, and quiet, with community tennis, a playground, and a sand volleyball court. You're minutes from the Walmart Fresh Market on Apopka-Vineland, ten to Restaurant Row on Sand Lake, fifteen to Disney and Universal, and twenty to downtown Orlando. Winter Garden Village and the Mall at Millenia are easy runs from here. Zoned for Thornebrooke Elementary, Gotha Middle, and Olympia High. Windermere gates, Dr. Phillips dining, Disney minutes away.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Brad Young (407-897-5400)
8323 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$590,00023 Days on yellowkey MLS ID: O6393407
REDUCED by $9,999 (1.7%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2633 Built: 2016Monthly Fee: $75 Tax: $9,688 (2025)Community: Windermere Trls Ph 3BSingle Family
Taxes:$9,688
Elementary School: Bay Lake Elementary
High School: Windermere High School
Middle School: Horizon West Middle School
Remarks: Beautiful 4 bedroom, 3.5 bath home located in the highly sought-after subdivision of Windermere Trails. The first floor has tile flooring and a spacious kitchen equipped with granite countertops, 42'' cabinets, a center island, and a walk-in pantry. Step through the dining room to a beautifully finished courtyard, complete with a private fence and elegant stone pavers. Upstairs, you'll find an additional room with double doors, perfect for a gathering space or home office. The primary bedroom features a large walk-in closet for ample storage. All interior has recently been painted, all carpets upstairs in the main home are new, as well as the AC unit is brand new, ensuring comfort and efficiency. This beautiful home layout provides the opportunity to convert this four bedroom home into six bedrooms. One of the rooms downstairs can easily be converted, as it’s already closed off; you just need to add a closet. Additionally, the loft upstairs is also closed off and simply missing a closet, offering another potential bedroom. This home has a separate private one - bedroom apartment above the garage, featuring a kitchenette, walk in closet, private entrance, and its own washer and dryer with a four month old A/C unit. Conveniently located off Winter Garden Vineland Rd. This home provides easy access to I-4, 429, and is just a short distance from all Disney Theme Parks. Enjoy the benefits of low HOA fees and being close to exceptional A+ schools.
Listing is courtesy of: WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC (407-922-9169)
Listing Agent: Ricardo Diaz (407-922-6196)
6820 THORNHILL CIR, WINDERMERE, FL 34786
$520,0005 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
Elementary School: Sunset Park Elem
Remarks: Beautiful Two-Story Home in The Lakes of Windermere 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. 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.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Maria Galindez (305-803-3799)
12699 HAWKSTONE DR, WINDERMERE, FL 34786
$2,125,000Listed 04/24/2026 12:05AM MLS ID: O6401293
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3751 Built: 2006Monthly Fee: $80 Tax: $22,152 (2025)Community: Lakes Windermere Ph 01 49 108Spa: YesSingle Family
Taxes:$22,152
Remarks: Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and 5 baths, lives large at 3751 sq ft (4936 total), and is ideally situated on pristine shoreline frontage with some of the lake’s most expansive water views. Showcasing fine craftsmanship and opulent elegance in every detail, Chalet du Lac serves up a host of amenities ideal for Florida lakeside living. At the entry, the handcrafted metal and glass doors open to a stunning foyer, capturing sensational pool and lake views from the formal living room. A distinctive formal dining area and generous study greet, then to the large great room overlooking the pool oasis and lake. The kitchen features new appliances, a gas cooktop, a luxurious ogee edged stone island with farmhouse sink plus a huge walk-in pantry. A built-in Miele espresso machine as well as a beverage cooler and even more cabinet space. The primary suite features his and her walk-in custom closets, luxurious spa tub, spacious walk-in shower, oversized double vanities, and an inviting bedroom lounge that opens to the pool area. Poolside, enjoy the elevated patio over the lake, along with Lakeside, the boathouse includes an electric boat lift, with the entire dock made of composite decking, accessed by the walkway dressed with a nautical balustrade. Evenings are enjoyed at the poolside outdoor kitchen and patio, complete with a fireplace to sit by while taking in the moonlight. Verdant, lush landscaping fosters relaxation and inspires reflection and rejuvenation. Lake Sawyer is both a water sports paradise and a prime opportunity for pristine Florida lakefront living. Lake Sawyer features a certified competition water ski slalom course for those who love to ski and is even home to a float plane on the lake. At the north end, Lake Sawyer connects to Little Lake Sawyer, availing more beautiful water to explore. Chalet du Lac is ideally situated with immediate proximity to Windermere Prep and Windermere High School, and only minutes from downtown Windermere, downtown Winter Garden, Walt Disney World and the world-famous attractions of Orlando.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
10624 REAMS RD, WINDERMERE, FL 34786
$487,000246 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
Taxes:$5,459
Tax Year: 2024
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)
13237 FOSSICK RD, WINDERMERE, FL 34786
$599,00063 Days on yellowkey MLS ID: O6382389
1 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2516 Built: 2004Monthly Fee: $110 Tax: $7,347 (2024)Community: Providence Ph 01 50 03Single Family
Taxes:$7,347
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Searching for a single story, 4-bed home in Windermere near Walt Disney World with space, convenience, and long term value? Nestled between Winter Haven and Lake Wales with all the conveniences nearby, 13237 Fossick Rd offers 4 bedrooms, 2 full baths, 2,516 square feet of living space, a NEW ROOF from 2022, new WATER HEATER from 2022, and a 0.21 acre corner lot in the Providence community, minutes from Disney, Winter Garden Village, and major commuter routes. The concrete block and stucco construction provides durability and classic, easy to maintain Florida curb appeal. From the moment you arrive, the covered front porch with column detail, stone accents, and paver driveway creates a warm first impression. Inside, a light filled formal living room off the foyer offers flexibility as a sitting room, home office, or quiet retreat separate from the main living areas. The kitchen is centrally positioned and overlooks the informal dining space and spacious family room, creating seamless flow for daily living and entertaining. Granite countertops, stainless steel appliances, abundant cabinetry, breakfast bar seating, and a center island provide both function and gathering space. Open sight lines keep everyone connected. The primary suite is generously sized with room for a seating area and direct access to the screened lanai. The ensuite bath features dual vanities, a soaking tub, separate glass shower, and walk in closet. Three additional bedrooms offer ideal flexibility for guests, remote work, or multigenerational living. Step outside to a covered screened lanai that extends your living space year round. The backyard offers green space and mature trees, creating privacy and room to relax after a day exploring Orlando’s attractions. The single level design appeals to buyers seeking long term convenience without stairs. The Providence neighborhood is perfectly located and is zoned for Windermere Elementary, Bridgewater Middle and Windermere High. If you are looking for space, location, and long-term upside in Windermere, this home deserves a closer look. Schedule your private tour today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Michael Collier (407-863-3401)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,00094 Days on yellowkey MLS ID: O6373065
REDUCED by $17,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1876 Built: 2014Monthly Fee: $81 Tax: $6,733 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,733
Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Renan Serretiello (407-415-7317)
325 MAGNOLIA ST, WINDERMERE, FL 34786
$2,475,00038 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
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)
3130 BUTLER BAY DR N, WINDERMERE, FL 34786
$1,725,00021 Days on yellowkey MLS ID: O6395307
2 Days Off yellowkey (back on 4/24/2026)
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 4490 Built: 1985Monthly Fee: $199 Tax: $21,502 (2025)Community: Butler BaySingle Family
Taxes:$21,502
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PALATIAL ESTATE in the heart of Windermere offers LUXURY living on an exclusive ONE ACRE LOT with mature landscaping among pines and palms for the ultimate in PRIVACY and SERENITY. A true estate in GATED Windermere Club, this pristine single story oasis offers extraordinary curb appeal with an expansive paver driveway, a grand drive through porte-cochere, three car garage, and professionally manicured grounds. This custom built home features true craftsmanship and offers quality details - a blank canvas just waiting for YOUR personal style AND PRICED BELOW APPRAISAL! You will feel like you are living in a Mediterranean villa in Windermere! The kitchen island was custom designed for the home with seating and two sinks so the chef can entertain while creating masterpieces with the 6 burner GAS cooktop, grill and double Monogram oven. The cabinets are truly a work of art custom made with rich wood planks. The pantry is elegantly hidden behind an artisan designed sliding door and is not only huge but well equipped with electrical outlets. The living and dining room share a double faced MASONRY FIREPLACE. Archways lead into every room and expertly finished plaster style walls make your palazzo a stylish retreat - DEFINITELY NOT A COOKIE CUTTER - THIS ESTATE IS SPECIAL. Lighting has been updated to give a bright, elegant and contemporary vibe. Each bedroom has its own ensuite bath! There is a finished “bonus room/in law suite” (2020) with a private exterior door and plenty of adjacent unfinished space, wired and plumbed for easy installation of a kitchen and bathroom - THIS WOULD BE AN IDEAL IN LAW OR TEEN SUITE! Three additional bedrooms, each with an ensuite bathroom are located in a wing of the home that can be closed from common area, creating privacy and comfort for family and guests. The Primary/Master suite, located on the other side of the home, is a private oasis overlooking the flower filled garden, resort style pool, pines and pristine green space on the sprawling ONE ACRE lot with NO REAR NEIGHBORS! There is a small office with a door connected to the primary suite. The primary/master bathroom has a walk around shower, an indulgent soaking tub, double vanities, high end finishes, TWO WALK IN CLOSETS with designer lighting and custom built ins, and a second hot water heater. The custom designed home has everything you’d expect for a LUXURY LIFESTYLE. The laundry room has granite, a sink, custom cabinets, and plenty of space. Likewise, the oversized three car garage has a sink, potting shed/room, epoxy floor and built in cabinets. No expense was spared as the owner installed thousands of dollars in exterior uplighting and two fountains creating a world class private resort ambience. Among meandering paver paths lined with flowers and bougainvillea arches, you’ll have an abundance of outdoor lounging space, including a sparkling heated pool and spa adjacent to a screen enclosed summer kitchen with commercial style built in grill, sink, built in refrigerator - all of this is steps from the pool cabana bath and outdoor shower. Windermere Club is zoned for award winning public and private schools. The Windermere Recreation Center is less than one mile away and features a boardwalk onto Lake Crescent, playground, kayak launch, pavilions, sand volleyball court, tennis courts and walking trails for residents. While all measurements are believed to be correct, buyer is encouraged to confirm all.
Listing Agent: Denise Crabbe (407-592-0692)
7137 BEEK ST, WINDERMERE, FL 34786
$550,0008 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
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 Agent: Jacquie Sosa (407-340-9793)
14014 EDEN ISLE BLVD, WINDERMERE, FL 34786
$507,0003 Days on yellowkey MLS ID: O6400224
1 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1794 Built: 2004Monthly Fee: $93 Tax: $2,957 (2025)Community: Eden Isle 52/9 Lot 173Spa: NoSingle Family
Taxes:$2,957
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your next chapter in one of Windermere’s most desirable gated communities. This beautifully maintained single-story home offers the perfect balance of comfort, functionality, and lifestyle. With 3 bedrooms, 2 bathrooms, and 1,794 sq ft, the layout is thoughtfully designed to feel open, bright, and effortlessly livable from the moment you walk in. Natural light fills the home, enhancing the spacious feel and creating a warm, inviting atmosphere that buyers instantly connect with. Every space flows seamlessly, making daily living and entertaining feel easy and intuitive. Step outside and you’ll discover one of the home’s most valuable features: a private backyard, surrounded by mature trees, offering both privacy and tranquility. Whether it’s morning coffee, family time, or simply unwinding at the end of the day, this outdoor space becomes a true extension of the home. Perfectly positioned, the home sits directly in front of the community playground, creating a unique sense of openness and convenience ideal for families, yet equally appealing for those who enjoy a peaceful, well-maintained environment without rear neighbors disrupting privacy. This home is especially well-suited for: - Buyers starting a family seeking safety, space, and community - Those looking to downsize without compromising comfort or outdoor living - Anyone who values a gated community lifestyle in a prime Windermere location Located just minutes from top-rated schools, shopping, dining, and major access roads, this is where convenience meets quality of life. Homes like this don’t just check boxes, they create a feeling. And this one feels like home. Contact us today for more information or to schedule a private showing! Attention: the home is not being sold furnished. The furniture shown is virtually staged only.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcella Reginato (407-725-9180)
12640 SALOMON COVE DR, WINDERMERE, FL 34786
$1,295,00044 Days on yellowkey MLS ID: O6388605
REDUCED by $5,000 (0.4%) on 04/24/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3694 Built: 2018Monthly Fee: $133 Tax: $13,961 (2024)Community: Westside VillageSpa: YesSingle Family
Taxes:$13,961
High School: Horizon High School
Remarks: Luxurious contemporary residence featuring 5 bedrooms, including the primary suite on the main floor. The main level with porcelain tile and marble staircase add sophistication, while the upper level with luxury vinyl flooring provides comfort and durability. Gourmet kitchen with custom cabinetry, waterfall island, premium stone countertops, and Samsung appliances. Walk-in closets in every bedroom and spa-inspired bathrooms with custom vanities, frameless glass showers, rainfall showerheads, and matte-black fixtures. Dramatic double-height entry with modern chandelier and glass railing. Staircase with motion-activated LED lighting. Elegant wine bar perfect for entertaining. Resort-style outdoor living with heated pool, spa, and screened lanai, offering privacy, relaxation, and style.
Listing is courtesy of: WEBB FLORIDA REALTY LLC (407-779-4695)
Listing Agent: Ramon Brandao (407-779-4695)
WINDERMERE, FL 34786
$359,000Listed 04/23/2026 5:09PM 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)
11438 ARBORSIDE BEND WAY, WINDERMERE, FL 34786
$629,9001 Day on yellowkey MLS ID: O6395080
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2019 Built: 2002Monthly Fee: $170 Tax: $4,648 (2025)Community: Glenmuir 48 39Single Family
Taxes:$4,648
Remarks: Welcome to 11438 Arborside Bend Way in the desirable gated GLENMUIR communitym or Windermere, a move-in ready home that blends stylish updates, beautiful curb appeal, and inviting outdoor living. From the moment you arrive, you’ll notice the long-lasting tile roof, freshly refreshed landscaping with tree and shrub trimming, new sod, and new topsoil, plus fresh interior paint in 2026 that gives the home a bright, clean feel. The private fenced backyard is a true highlight, designed for both relaxing and entertaining with brick pavers, a fire pit, and a stunning vinyl plank fence that adds both beauty and privacy. This exceptional outdoor space is perfect for entertaining guests, enjoying quiet evenings, and making the most of Florida living year-round. Inside, the updated kitchen is sure to impress with stainless steel appliances, updated granite countertops, a stylish backsplash, white cabinets, ample storage space, and a convenient breakfast bar that opens to the living areas for easy everyday living and entertaining. The spacious primary suite offers a relaxing retreat, while the primary bathroom features a Roman soaking tub, separate standing shower, and updated dual sinks and countertops, creating a spa-like feel. Located in the sought-after GLENMUIR community, residents enjoy a gated entrance and amenities including a community park and playground adding even more lifestyle appeal to this beautifully updated home. With its move-in ready condition, updated kitchen, primary suite, fenced backyard, outdoor entertaining space, and exceptional community amenities, this home checks all the boxes buyers are searching for. Close to major highways such as FL 429 making commute to downtown Winter Garden, major theme parks, Orlando International Airport, beaches and more a breeze. Come see today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Christina Rampersad (407-995-6788)
4309 SALTMARSH SPARROW DR, WINDERMERE, FL 34786
$810,00021 Days on yellowkey MLS ID: O6396295
REDUCED by $15,000 (1.8%) on 04/22/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3697 Built: 2015Monthly Fee: $130 Tax: $8,724 (2025)Community: Stillwater Xings Prcl Sc-13 PhSpa: NoSingle Family
Taxes:$8,724
Elementary School: None
High School: None
Middle School: None
Remarks: Check out 4309 Saltmarsh Sparrow Dr, a residence featuring a partial flooring replacement that enhances its overall presentation. The kitchen is equipped with all stainless steel appliances and includes a functional island. The primary bedroom provides a walk in closet, while the primary bathroom contains double sinks and a separate tub and shower. An exterior covered patio extends to a fully fenced in backyard, creating defined outdoor space. This property includes updated finishes and functional living spaces. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00055 Days on yellowkey MLS ID: S5144606
REDUCED by $10,000 (0.7%) on 04/12/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $8,883 (2024)Community: Windsor HillSingle Family
Taxes:$8,883
Remarks: Situated on a premier half-acre lot in highly desirable area of Windermere, this fully renovated 4-bedroom, 4-bath home offers a hard to find 'like-new' living experience. Every detail has been thoughtfully updated, featuring a chef’s kitchen with brand-new Thermador appliances, custom cabinetry, luxury vinyl plank flooring, and designer lighting throughout. The versatile floor plan includes an oversized upstairs bonus room, perfect for a media retreat or home office. Modern systems provide complete peace of mind, including a 2021 roof, dual high-efficiency A/C units, new water heater, and new sliding doors opening to the expansive backyard. An epoxy-finished garage adds style and convenience. Just minutes from the Butler Chain of Lakes, top-rated schools, and world-class golf, this move-in-ready home blends refined design with modern comfort.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Jessica Oliveira (407-925-9768)
11472 PARK AVE NE, WINDERMERE, FL 34786
$1,125,000101 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)
4 CHASE RD, WINDERMERE, FL 34786
$875,00063 Days on yellowkey MLS ID: O6384257
0 Days Off yellowkey (back on 4/23/2026)
REDUCED by $25,000 (2.8%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2386 Built: 1971 Tax: $7,637 (2024)Community: Windermere TownSingle Family
Taxes:$7,637
Remarks: Under contract-accepting backup offers. FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Matthew Hughes (407-619-4717)
1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,380,00025 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
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
$2,200,000282 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)
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