Location: Windermere
Do Not Show Listings
84 OAKDALE ST, WINDERMERE, FL 34786
$1,875,00095 Days on yellowkey MLS ID: O6372842
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3519 Built: 2020 Tax: $12,265 (2024)Community: Davis ShoresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,265
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: Welcome to 84 Oakdale Street, an exceptional luxury residence in the heart of Windermere, Florida, crafted by the renowned Element Home Builders—a rare opportunity to own one of their highly sought-after homes. Situated on a premium corner lot, this elegant 4-bedroom, 4 full and 2 half bath home showcases refined craftsmanship, a thoughtfully designed open floor plan, and sophisticated finishes throughout. The expansive living spaces are filled with natural light and flow seamlessly into a designer kitchen ideal for both entertaining and everyday living. The primary suite offers a serene private retreat with a spa-inspired bath, while additional bedrooms provide comfort and privacy for family and guests. Outdoor living is elevated with a private resort-style pool, creating the perfect setting for relaxing or entertaining year-round. Enjoy the convenience of being just a short golf cart ride to charming downtown Windermere, offering boutique shopping, dining, community events, and the weekly farmers market. Located in one of Windermere’s most desirable communities, just minutes from top-rated schools, upscale dining, golf, shopping, and the Butler Chain of Lakes, this home delivers timeless luxury, quality construction, and an unbeatable location. This exceptional home is a rare offering and will not last—schedule your private tour today.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Carolina Dumit (407-325-8963)
11449 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$1,730,000Listed 04/17/2026 7:34AM MLS ID: O6399319
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4648 Built: 1995 Tax: $19,423 (2025)Community: Lake Butler EstatesSpa: YesSingle Family
Taxes:$19,423
Tax Year: 2025
Remarks: Discover Windermere’s charm and classic style from this stunning Victorian-style pool home, set on a 1-acre lot with no HOA, on one of the most desirable streets. Under the canopy of majestic oaks, this 5-bedroom residence features a dedicated office space and a versatile bonus room ideal for a private apartment or guest suite. A charming wrap-around porch welcomes you into a classic foyer featuring rich wood floors, soaring ceilings, custom millwork, and a graceful grand staircase. Throughout the home, you’ll find exquisite traditional details including dental crown molding, chair rails, and beautifully crafted trim. The spacious formal dining room is filled with natural light and accented by warm wood flooring. The kitchen blends style and function with stainless steel appliances, granite countertops, an island, walk-in pantry, custom cabinetry, and a lovely view of the pool with newly installed screen enclosure. All main living areas are carpet-free, and every bathroom has been thoughtfully updated with travertine flooring, porcelain showers, and marble countertops. The owner’s suiteis located upstairs and features bay windows, wood floors, crown molding, and a walk-in closet. Its luxurious bath includes a frameless glass stone shower, dual vanities, and an elegant vessel tub. The expansive bonus room accessible off the primary bathroom offers an optional private entrance leading to the large backyard—complete with a sparkling pool, generous patio space, and room to store a boat. The oversized 3-car garage provides exceptional clearance for larger vehicles, golf carts, and lake toys. Town of Windermere residents have private access available to the Butler Chain via a town boat ramp plus town tennis courts. Home is walking distance to downtown and the weekly farmer’s market, monthly food trucks, and the quaint shopping district.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786
$14,250,000333 Days on yellowkey MLS ID: O6304800
0 Days Off yellowkey (back on 4/17/2026)
Bed: 5 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 9511 Built: 1999Monthly Fee: $1,224 Tax: $37,372 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$37,372
Middle School: Chain of Lakes Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with more than 2,200-bottle capacity—is a collector's dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida's most desirable enclaves.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
11866 CAMDEN PARK DR, WINDERMERE, FL 34786
$984,90043 Days on yellowkey MLS ID: O6381558
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3337 Built: 2006Monthly Fee: $298 Tax: $13,742 (2025)Community: Keenes PointeSingle Family
Taxes:$13,742
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Welcome. A new roof and one new AC System are being installed! Residing in the established, guard-gated community of Keene’s Pointe, this delightful five-bedroom, four-bathroom home features a functional two-story layout, with multiple living areas, spacious bedrooms, and modern finishes, creating an environment that is ready for life’s ever-changing needs. At the heart of the home, the gourmet kitchen showcases granite counters, plenty of cabinetry, a breakfast bar, and an island overlooking the family room and backyard, offering a cohesive main living space fit for relaxation and memorable gatherings. If practicality and privacy are aspects at the top of your list, the three-way split-bedroom floor plan allows for incredible flexibility and offers pristine privacy for all. On one side of the home, the large primary suite enjoys a tray ceiling, stylish flooring, a spacious closet, dual vanities, and a separate garden tub there to soothe you each day. On the other side of the home, the remaining bedrooms and bathrooms are designed to maximize privacy, with the ability to easily create en-suites, while the upstairs bonus room, bedroom, and bathroom provide a versatile and private space. High ceilings, crown molding, and ceiling accents throughout the home add a refined finish to the interior spaces. Venture outside to enjoy the sizable, covered lanai, providing a perfect retreat while remaining protected from the elements, or enjoy a journey through the lusciously landscaped community, with multiple parks and a community boat ramp accessing the Butler Chain of Lakes deliver regular delight. If the country club lifestyle is for you, The Golden Bear Club offers social and golf membership for an additional fee, which grants access to the renowned Golden Bear Golf Course and practice facilities, as well as the resort-style pool, tennis courts, state-of-the-art fitness center, and dining. The community’s location delivers unmatched convenience with proximity to well-rated schools, along with The Grove, Westside Shoppes, Cornerstone at Summerport, and Downtown Windermere for daily essentials, local dining, and shopping adventures. Entertainment options abound with easy access to Disney, Universal, and the famed Restaurant Row in Dr. Phillips. Schedule your private showing today to experience the full charm of this practical home.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
4029 ISABELLA CIR, WINDERMERE, FL 34786
$3,299,000Listed 04/16/2026 11:38PM MLS ID: O6400064
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 7217 Built: 2018Monthly Fee: $480 Tax: $30,300 (2025)Community: CasabellaSpa: YesSingle Family
Taxes:$30,300
Remarks: Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak finish with bathrooms featuring porcelain floors and walls. Tech enthusiasts will marvel at the Lutron smart home system's ability to control power shades and lighting throughout the home. enterprise-grade 10Gbps networking backbone. Cinema lovers will find no equal in the custom movie theater, boasting a 133” anti-reflection screen, Sony 4K 3D projection, and a commercial-grade Dolby Atmos 11.2 3D sound system within a fully soundproofed environment. The backyard is a tropical paradise featuring imported African white marble flooring, a custom smart pool, and a professional Alfresco summer kitchen. The centerpiece is a magnificent 20,000-gallon Obsidian & Natural Stone Koi garden, fully equipped with UV/scrub filters and gas heating to protect its world-class inhabitants. Located minutes from top-rated Windermere schools, Orlando Health Central, and Dr. P. Phillips Hospital, with easy access to Downtown Orlando. This is not just a home; it is a high-tech fortress and a private resort
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Drew Frahm (407-996-4656)
9011 CHAPMAN OAK CT, WINDERMERE, FL 34786
$649,0001 Day on yellowkey MLS ID: S5148031
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 1987Monthly Fee: $31 Tax: $8,592 (2025)Community: Silver Woods Ph 05Single Family
Taxes:$8,592
Elementary School: None
High School: None
Middle School: None
Remarks: Great opportunity to own a beautifully updated home in the highly desirable Windermere area! This property features a private pool that has been recently resurfaced, along with a new pool pump, offering the perfect space to enjoy Florida living year-round. The home also includes a new roof (2024), fresh interior paint, a fully updated kitchen, and new appliances, making it move-in ready with modern upgrades throughout. Ideally located in a prime area, just minutes from shopping centers, fitness facilities, and top-rated schools. Nearby community tennis courts, adding to the lifestyle this home offers. Perfect for homeowners or investors looking for a well-located and upgraded property in one of Central Florida’s most sought-after communities.
Listing is courtesy of: TOWNE CENTER REALTY (407-447-7700)
Listing Agent: Shiran Moyal (407-716-0224)
5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786
$1,500,0001 Day on yellowkey MLS ID: O6399697
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4319 Built: 2002Monthly Fee: $183 Tax: $16,530 (2025)Community: Oxford MoorSpa: YesSingle Family
Taxes:$16,530
Remarks: Completely Remodeled 2022 | Single Story |Gated Windermere Community | Set on nearly three-quarters of an acre in the gated Oxford Moor community, this fully remodeled single-story home delivers the kind of space and finish level that's genuinely hard to find. Wide-open living areas, high ceilings, oversized rooms, and a modern aesthetic. The kitchen provides a large island, full stone backsplash, Bosch appliances with induction cooktop and double ovens, and a dedicated coffee bar. The split floorplan separates the primary suite from the secondary bedrooms, each generously sized, while the living areas flow directly to the covered lanai and saltwater pool. The primary suite includes a sitting area, expanded closet, and a fully renovated bath. A large private office comfortably fits dual workstations. Outdoor living space includes the saltwater pool running on updated equipment and automation, surrounded by a spacious fenced yard framed by mature landscaping and fruit trees that actually produce. Oxford Moor is one of Windermere's quieter gated communities comprised of 85 Estate Homes. Top-rated schools including Windermere Elementary, Bridgewater Middle, Windermere High school, and less than 1 mile from Windermere Prep, convenient SR 429 access, and a short drive to Walt Disney World round out the location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeffrey Funk, Pa (407-285-9672)
8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786
$330,0001 Day 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
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
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)
9663 GOTHA RD, WINDERMERE, FL 34786
$1,400,0001 Day on yellowkey MLS ID: O6399130
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3731 Built: 2000 Tax: $8,425 (2025)Community: Gotha TownSpa: NoSingle Family
Taxes:$8,425
Elementary School: Thornebrooke Elem
Remarks: Experience refined Florida living in this extensively upgraded estate nestled in the sought-after Windermere–Gotha enclave. Set on a rare and private 0.55-acre homesite with no HOA, this 4-bedroom, 2.5-bath residence offers a seamless blend of luxury, comfort, and versatility. No detail has been overlooked—from the 2023 metal roof and full hurricane-impact windows to brand-new A/C systems, upgraded insulation, and a state-of-the-art water treatment system. Interiors are enhanced with modern finishes, custom window treatments, and fully remodeled spa-inspired bathrooms featuring premium upgrades. Step into your private resort-style retreat, complete with a newly built saltwater pool, expansive paved driveway, and a beautifully designed outdoor living space. The custom gazebo with outdoor kitchen creates the perfect setting for entertaining, while the fully enclosed, air-conditioned patio extends your living space year-round. A standout feature is the detached 1-bedroom, 1-bath guest residence, complete with a full kitchen—ideal for multigenerational living, a private office, or an income-producing opportunity. Located just minutes from Orlando Hospital, Orlando’s premier dining, shopping, and entertainment, including Walt Disney World and Universal Studios Florida, this exceptional property offers the ultimate balance of privacy and convenience.
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)
Listing Agent: Reza Shirzad (407-234-1515)
1420 DINGENS AVE, WINDERMERE, FL 34786
$1,600,00078 Days on yellowkey MLS ID: O6376538
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4072 Built: 2018 Tax: $13,393 (2025)Community: GothaSingle Family
Taxes:$13,393
Remarks: One or more photo(s) has been virtually staged. No HOA custom pool home on over half an acre, offering rare space and privacy in a central Windermere location just minutes from top schools, dining, and 20–30 minutes to Disney, Universal, and Orlando International Airport. Set on 0.63 acres, the outdoor space is set up to be used, with a fully fenced yard, gas-heated saltwater pool with sunshelf, covered lanai, and outdoor kitchen. Inside, the main living area flows into a kitchen designed to anchor the home, featuring a large island, custom cabinetry, walk in pantry, natural gas cooktop with pot filler, and double wall ovens. The layout is designed to work without wasted space. The primary suite is set apart with backyard views and a well finished en suite with dual vanities, a freestanding tub, walk in shower with dual heads, and a custom closet. Secondary bedrooms are generously sized and share a well designed bath, while a fourth bedroom with direct pool access, a dedicated office with built ins, and a separate bonus room provide flexibility for guests, work, or additional living. Additional features include a mudroom and laundry space with built ins, an oversized three car garage with epoxy flooring, a large paver driveway, outdoor lighting, a security system, a fully fenced yard and paid off 20kW solar panels. Zoned for A rated Thornebrooke Elementary and just minutes from Windermere Prep, the home brings together space, layout, and location in a way that is hard to replicate in this area.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
3328 WAX BERRY CT, WINDERMERE, FL 34786
$925,000171 Days on yellowkey MLS ID: O6355868
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2636 Built: 1984Monthly Fee: $21 Tax: $10,867 (2024)Community: Lake Butler EstatesSingle Family
Taxes:$10,867
Remarks: One or more photo(s) has been virtually staged. Located in Lake Butler Estates, one of Windermere’s most private established communities, this 4-bedroom, 4-bath single-family pool home sits on a 1-acre cul-de-sac lot surrounded by mature oak trees and lush landscaping, with only 11 neighboring homes and access to the Butler Chain of Lakes through the community’s private boat ramp. Built in 1959 and renovated in 2022, this single-story residence offers an open split floor plan, combining luxury finishes with functional everyday living. Interior features include marble flooring throughout the main living areas and engineered hardwood flooring in all bedrooms, high ceilings, crown molding, recessed LED lighting. The living room features a textured accent wall, skylights, and a wood-burning stone fireplace with gas connection that anchors the main living space. The kitchen was redesigned with sealed butcher block counters, stainless steel Samsung appliances, pantry storage, breakfast bar seating, reverse osmosis water treatment system, Samsung dishwasher, Samsung smart oven, pot filler, and a Fotile range hood with self-adjusting capture shield, with both kitchen water and irrigation supplied by well water. A dry bar adds additional entertaining appeal in the living room, while remote-controlled ceiling fans and lights are installed in every bedroom, with new chandeliers in the living and dining rooms. The spacious primary suite includes custom walk-in closet storage with overhead recessed lighting, sliding glass shower enclosure, Kohler rainfall shower, three-head body sprayers with jets, pebble flooring, marble backsplash, dual vanities, soft-close cabinetry, and bidet hookup. The shared bath offers dual sinks, LED anti-fog mirror, pool access, marble finishes, accent wall tile, pebble flooring, and dual shower heads. A newly added full guest bath includes Swiss Madison pedestal sink, Hansgrohe faucet, medicine cabinet, marble finishes, pebble flooring, and Kohler dual shower sprayers, while the en-suite bath in the first bedroom features sliding glass shower doors, marble backsplash, skylight, LED anti-fog mirror, and soft-close cabinetry. Smart-home and energy efficient features include Ecobee smart thermostat, myQ garage opener, smart front door lock, remote-controlled lighting systems and upgraded electrical outlets throughout. Exterior highlights include a screen-enclosed in-ground pool, covered lanai, outdoor workshop, circular driveway, side-entry two-car garage, extended parking pad, and additional rear concrete parking for RV or boat storage. The backyard offers expansion flexibility, allowing room for privacy fencing, a future mother-in-law suite, or an addition. The annual HOA is only $253 and includes access to the adjacent Windermere Recreation Center, offering 3 lighted tennis courts, fenced playground, pet parks, lakefront boardwalk, kayak launch, sand volleyball court, grills, picninc tables and large entertaining pavilion. Zoned for A-rated Windermere schools. Location second to none as this home is within 10 minutes of downtown Windermere where you can enjoy the weekly Farmers Market. Easy access to Interstate 4, Florida Turnpike, local hospitals, and within 30 minutes of Orlando International Airport, Disney World, and Universal Studios. This move-in-ready Windermere property delivers privacy, acreage, and premier community access in one of Central Florida’s most desirable residential corridors. Schedule your showing today!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Ferris Kassar (407-284-8384)
4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,699,000226 Days on yellowkey MLS ID: O6339134
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4262 Built: 2007Monthly Fee: $1,146 Tax: $45,888 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$45,888
Remarks: Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a private courtyard featuring a glistening pool adorned with a cascading waterfall from the pergola. An expansive covered patio houses a summer kitchen, pool bath, and attached third bedroom accessed only from the courtyard. The heart of this home is a chef's dream, with a gourmet kitchen featuring top-of-the-line Wolf appliances, striking custom cabinetry, and an open design that seamlessly connects to the family room and dining areas. The grand primary suite offers a private sitting area overlooking the peaceful pond, double walk-in closets, and a spa-like bath complete with a Jacuzzi tub and an expansive walk-in shower. The third garage was converted into a gym with air conditioning and can be converted back to additional garage space. Garden villas offer carefree living with exterior grounds maintenance included in the separate monthly fees. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
11434 JASPER KAY TER #1120, WINDERMERE, FL 34786
$315,00064 Days on yellowkey MLS ID: O6382035
0 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1332 Built: 2007Monthly Fee: $489 Tax: $2,663 (2024)Community: Lakeside/Lks/WindermereCondo
Taxes:$2,663
Remarks: Beautifully maintained condo located in the highly desirable Lakeside Lakes of Windermere community. Situated on the third floor with elevator access, this residence features a spacious split floor plan offering both privacy and functionality. The open concept living and dining area flows seamlessly to a private balcony perfect for enjoying your morning coffee or relaxing evenings. The generous primary suite includes a walk in closet and an en suite bath with dual sinks. Wood flooring runs throughout the main living areas, with ceramic tile in wet areas for added durability. Residents enjoy an array of resort style amenities including a community pool, fitness center, outdoor grilling areas, sand volleyball courts, and more. Conveniently located near Disney, Winter Garden Village, shopping, dining, and zoned for top rated schools, this property is ideal for first time buyers, investors, or as a second home. Schedule your private showing today.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Alonso Delgado, Pa (407-592-8306)
13302 ROSKIN LN, WINDERMERE, FL 34786
$849,90069 Days on yellowkey MLS ID: O6380701
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3424 Built: 2011Monthly Fee: $82 Tax: $10,244 (2024)Community: Lake Sawyer South Ph 1Single Family
Taxes:$10,244
Remarks: Welcome to this impeccably maintained former model home in Windermere, beautifully positioned on a premium corner lot in a quiet, highly desirable community and zoned for top-rated schools. Offering over 3,400 square feet with 4 bedrooms and 3.5 bathrooms, this home stands out for its smart use of space, generous room sizes, and the refined “model home” presentation that feels clean, polished, and truly move-in ready. From the moment you arrive, the corner-lot setting provides a more open feel and excellent curb appeal, complemented by mature landscaping and a wide driveway. The exterior was fully repainted in 2025, adding a fresh, updated look. Inside, you’ll appreciate a bright, well-planned layout with spacious living and dining areas and clear separation of rooms that keeps daily life organized while still feeling connected. Multiple gathering spaces allow you to host comfortably, work from home, and enjoy everyday living without wasted square footage. A major highlight is the first-floor primary suite, offering privacy and convenience, along with a dedicated first-floor study/office that works perfectly as a home office, library, homework room, or flex space. A convenient half bath on the main level is ideal for guests. The home lives comfortably with practical flow and strong functionality, and the bedroom and bathroom count makes routines smoother for busy households and visiting guests alike. At the center of the home, the kitchen is designed for both function and gatherings. It features granite countertops, stainless steel appliances, a center island, breakfast bar, pantry, and abundant wood cabinetry, all positioned to stay open to the main living area so the cook is never separated from the conversation. Recent updates include a new kitchen hood, new refrigerator, and a new kitchen faucet, giving the space a refreshed, turnkey feel. Upstairs, you’ll find three additional bedrooms and two full bathrooms, plus a bonus/media room that easily becomes a second living area, movie room, playroom, fitness space, or guest retreat. The upstairs layout is thoughtfully arranged for privacy and flexibility, making the space ideal for family living and guests. Step outside to enjoy a backyard designed for easy outdoor living and low-stress entertaining, offering a private outdoor area and an outdoor kitchen/BBQ setup that creates a natural gathering spot for weekend cookouts and casual dinners. The corner-lot placement adds extra breathing room and a more spacious feel outdoors. The home also features major improvements already completed, including a NEW roof (2024), two AC units replaced (2025), new solid hardwood flooring (2024), and plumbing updates completed in 2021. A spacious 3-car garage with upgraded finished flooring and ample driveway parking completes the package. Ideally located in a top-rated Windermere school zone with excellent public and private options, the community features a pool, playground, walking trails, and year-round neighborhood events. Enjoy the added backdrop of nearby conservation areas and community amenities, with Disney fireworks often visible in the distance. Just minutes to Disney, major highways, Publix, Lakeside Village, shopping, dining, and everyday conveniences, this home combines a peaceful setting with exceptional convenience throughout Central Florida.
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Xiaoyu Su (352-216-1257)
17514 BLACK RAIL ST, WINDERMERE, FL 34786
$725,00082 Days on yellowkey MLS ID: O6376756
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2373 Built: 2014Monthly Fee: $167 Tax: $8,578 (2025)Community: EnclaveSingle Family
Taxes:$8,578
Remarks: New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and durability. The layout includes 4 bedrooms and 2 bathrooms, plus a large dedicated office, ideal for working from home or for those seeking a quiet, flexible space. Designed for comfortable single-level living, this home is perfect for buyers who appreciate the convenience of no stairs while still enjoying an open and grand feel. Located in the heart of Windermere, the property offers outstanding accessibility, with shopping, dining, and daily amenities just minutes away. AC WAS INSTALLED IN 2022,3.5 TONS. The primary suite is a true retreat, featuring an elegant tray ceiling, serene pond views with screen patio, and direct access to the backyard, allowing you to step outside and enjoy the peaceful water scenery at any time. Both the primary bedroom and the living room overlook the pond, bringing nature and calm into everyday living. This is an ideal home for those seeking privacy, convenience, and refined single-story living in a prime Windermere location.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: He Gao (407-955-0138)
713 MAIN ST, WINDERMERE, FL 34786
$2,235,000120 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)
6799 HELMSLEY CIR, WINDERMERE, FL 34786
$658,000151 Days on yellowkey MLS ID: O6361417
REDUCED by $12,000 (1.8%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2615 Built: 2011Monthly Fee: $129 Tax: $9,339 (2024)Community: Preston SquareSingle Family
Taxes:$9,339
Remarks: Windermere Lake View Home with Disney Fireworks - Best Value in the Area! Recent price improvement - now one of the best opportunities in Windermere. Welcome to your dream home! This beautiful 4-bedroom, 3.5-bathroom residence offers the perfect blend of elegance, comfort, and convenience — ideally located in one of Windermere’s most sought-after communities with top-rated “A” schools. Enjoy breathtaking views of the lake and conservation area right from your spacious covered screened lanai, with a large backyard ready for your future pool. The open-concept kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and entertainment. On the first floor, you’ll find a guest suite with a full bath, a private office, and a welcoming foyer. Upstairs features a massive loft — perfect as a media room, playroom, or second family room — along with the master suite and two additional bedrooms. The home also features a newer air conditioning system replaced just two years ago, offering added comfort and peace of mind. Enjoy the exclusive community amenities, including a clubhouse, pool, playground, and sports court. From your backyard, you can even watch the Disney fireworks at night! Conveniently located near shopping centers, dining, and entertainment, this home truly combines luxury, location, and lifestyle — the perfect place for your family in Windermere! Seller willing to consider offers.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Maqueli Gewehr (863-258-5656)
8552 POWDER RIDGE TRL, WINDERMERE, FL 34786
$680,00051 Days on yellowkey MLS ID: S5144276
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2612 Built: 2016Monthly Fee: $82 Tax: $8,150 (2024)Community: Windermere Trls Ph 3BSingle Family
Taxes:$8,150
Remarks: Located in the highly desirable area of Windermere, this spacious 4-bedroom, 2.5-bath home offers comfort, functionality, and added income potential. The property features an open and inviting floor plan, perfect for both everyday living and entertaining. Upstairs above the garage, you’ll find a private apartment—ideal for guests, extended family, a home office, or rental income opportunity. Enjoy living in one of Central Florida’s most sought-after communities, known for its charm, excellent schools, and convenient access to shopping, dining, and major highways.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Andrea Munoz (407-989-2021)
8796 PEACHTREE PARK CT, WINDERMERE, FL 34786
$979,9991 Day on yellowkey MLS ID: O6399023
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3299 Built: 2014Monthly Fee: $218 Tax: $9,513 (2025)Community: Peachtree ParkSingle Family
Taxes:$9,513
Elementary School: Bay Lake Elementary
Remarks: Come live in paradise!! Minutes from the Magic Kingdom with amazing fireworks view from front porch and private pool. This exceptional builder model offers an unmatched combination of luxury upgrades, thoughtful design, and a premier location in the coveted Peachtree Park community. Perfectly positioned with conservation views and no rear neighbors, this home delivers privacy, style, and a true Windermere lifestyle. Step inside to discover custom upgrades throughout the house, including beams, shiplap accents, built-ins, and designer finishes that elevate every room. The first-floor features engineered hardwood flooring and a beautifully upgraded powder room, while the second floor offers upgraded carpet, a spacious loft with custom built-in shelving and a cushioned bench overlooking the backyard, and a fully outfitted laundry room with soft-close cabinetry and a farmhouse sink. The gourmet kitchen is a showstopper with a quartz island, open shelving, built-in appliances, a stainless steel vent hood, and a stylish backsplash. A custom cushioned bench at the kitchen table seats 8+ and stays with the home. Retreat to the luxurious primary suite featuring a custom shiplap wall, large pendant lighting, and a mounted TV, along with a spa-inspired bath offering dual vanities and a large walk-in shower. The expansive California Closets–designed primary closet is large enough to function as a second office, and the desk remains with the home. Outdoor living shines with a heated electric pool with water fountains, upgraded landscaping including a turfed backyard, bamboo and hedging for privacy, and extensive black rock accents. The pavered lanai features a motorized awning, a mounted TV, and a cedar tongue-and-groove ceiling, mirrored on the charming front porch. Professional landscape lighting enhances both the front and back yards. Insulated garage door, quiet side-winder opener, and a temperature-controlled storage closet with a keypad lock. Epoxy flooring and ceiling storage racks in the garage. Custom plantation shutters, curtains, blinds, and motorized shades. The HOA also takes care of the lawn, trees, fertilizer and hedge trimming. This home is zoned for A+ Windermere schools and offers the rare opportunity to own a meticulously upgraded, model-quality residence in one of the area’s most desirable neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Lee Goldberg (407-223-6965)
6840 HELMSLEY CIR, WINDERMERE, FL 34786
$719,99970 Days on yellowkey MLS ID: S5142930
1 Days Off yellowkey (back on 4/16/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2847 Built: 2009Monthly Fee: $129 Tax: $5,044 (2024)Community: Preston SquareSpa: NoSingle Family
Taxes:$5,044
Remarks: Under contract-accepting backup offers. Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago — an exceptional offering in a premier Windermere community. Owner relocated .motivated seller. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.
Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)
Listing Agent: Eleanor Desimone (845-796-6951)
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