Location: Windermere
Do Not Show Listings
13339 ROSKIN LN, WINDERMERE, FL 34786
$680,000159 Days on yellowkey MLS ID: S5141148
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2947 Built: 2012Monthly Fee: $82 Tax: $8,674 (2024)Community: Lake Sawyer South Ph 01Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,674
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: Welcome to a standout opportunity in WINDERMERE , offering closing cost assistance and positioned for a timely sale. This 4 bedroom, 2.5 bath, two-story home with 2,947 sq ft delivers the space, layout, and location today’s buyers are searching for. The thoughtfully designed floor plan includes a first-floor den/office, expansive upstairs loft, and generously sized bedrooms throughout. The oversized primary suite provides a comfortable retreat with ample space to relax. Every room offers flexibility for a variety of living needs. Step outside to a fully fenced backyard featuring an OUTDOOR KITCHEN AND BRICK OVEN, ideal for entertaining and enjoying Florida living year-round. A key highlight of this home is the solar energy system, providing reduced monthly electric costs This translates to significant annual savings and protection against rising utility rates, making it a valuable long-term benefit. Located just 4 minutes from WINDERMERE HIGH School and approximately 15 MINUTES rom Walt DISNEY World and major attractions, the home offers convenient access to dining, shopping, and entertainment. The community features LOWHOA fees and NO CDD. With relocation season underway, homes offering space, efficiency, and location are in high demand. This property is centrally located, well-positioned, and ready for its next owner. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Karla Price (407-761-7764)
11923 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$1,630,000385 Days on yellowkey MLS ID: O6311003
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2238 Built: 1985 Tax: $12,907 (2024)Community: Lake Butler EstatesSingle Family
Taxes:$12,907
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!
Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)
Listing Agent: Bo Julian (407-694-5843)
12533 CRAGSIDE LN, WINDERMERE, FL 34786
$575,00041 Days on yellowkey MLS ID: O6405628
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2151 Built: 2004Monthly Fee: $82 Tax: $8,484 (2025)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$8,484
Tax Year: 2025
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 Lakes of Windermere, where comfort, thoughtful upgrades, and an unbeatable Central Florida location come together in one beautifully maintained home. Inside, you’ll love the inviting layout with formal living and dining spaces accented by custom crown molding, flowing into a kitchen designed for both function and style with marble countertops, stainless steel appliances, and a large pantry—all open to the family room so everyone stays connected. Step outside to the screened patio, the perfect spot for morning coffee, weekend grilling, or winding down in the evenings. The primary suite feels like a private retreat with a tray ceiling, spacious walk-in closet, and an en-suite bath featuring dual vanities, a soaking tub, and a separate walk-in shower, while three additional bedrooms present flexible space for guests, a home office, or growing households. Major updates have already been taken care of, including a new roof (May 2022), HVAC (2021), water heater (2022), plus fresh interior paint, baseboards, and newer ceiling fans, giving you true move-in-ready peace of mind. Enjoy resort-style community amenities like tennis courts, a playground, a community pool, and a pier on Lake Sawyer, all conveniently located near shopping, dining, major highways, theme parks, and everyday essentials.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Tyler Somers (561-713-8728)
11636 WATER RUN ALY, WINDERMERE, FL 34786
$408,000244 Days on yellowkey MLS ID: S5136888
REDUCED by $17,000 (4.0%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $332 Tax: $5,634 (2024)Community: Ashlin Park Ph 2Townhouse
Taxes:$5,634
Elementary School: None
High School: None
Middle School: None
Remarks: This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a private interior patio between the main home and the detached two-car garage with epoxy flooring, perfect for relaxing or entertaining. Residents benefit from community amenities including a pool, clubhouse, playground, and walking trails. Conveniently situated near top-rated schools, shopping, dining, and major highways, this property combines modern comfort with an unbeatable location in the heart of Windermere.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jose Jimenez (407-394-6379)
5145 LATROBE DR, WINDERMERE, FL 34786
$3,299,000123 Days on yellowkey MLS ID: O6382287
REDUCED by $150,000 (4.3%) on 05/17/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4512 Built: 1991Monthly Fee: $1,224 Tax: $27,776 (2025)Community: IsleworthSpa: NoSingle Family
Taxes:$27,776
Middle School: Chain of Lakes Middle
Remarks: Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
14341 CREST PALM AVE, WINDERMERE, FL 34786
$1,130,64333 Days on yellowkey MLS ID: G5112469
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3153 Built: 2026Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Elementary School: Bay Lake Elementary
Remarks: One or more photo(s) has been virtually staged. Under Construction. Arlington Floorplan – 3,153 Sq. Ft. | 4 Beds | 4 Baths | 2.5-Car Garage | Arlington with Bonus Room – a thoughtfully designed, 1-story home plus a Bonus Room on the 2nd floor that perfectly blends luxury, functionality, and comfort. This brand new 3,153 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space. Features: 4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet. 4 Full Bathrooms: Modern finishes with quartz countertops, tile flooring, and upgraded fixtures throughout.Gourmet Kitchen: A chef’s dream featuring built-in stainless steel appliances, a large center island, upgraded cabinetry, quartz countertops, a walk-in pantry, and designer lighting – perfect for hosting or everyday meals.Open-Concept Living: The heart of the home flows seamlessly from the kitchen to the dining area and large family room, all overlooking the covered lanai for indoor-outdoor living. 2.5-Car Garage: Ample space for two vehicles plus additional storage or hobby area. Projected Completion August/September. Preferred Lender incentives apply.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
12863 HOLDENBURY LN, WINDERMERE, FL 34786
$539,00085 Days on yellowkey MLS ID: O6393781
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 2006Monthly Fee: $82 Tax: $7,361 (2024)Community: Lakes Of WindermereSingle Family
Taxes:$7,361
High School: West Orange High
Middle School: Bridgewater Middle
Remarks: LOCATION! LOCATION! $5,000 CONCESSION FOR BUYER'S CLOSING COSTS. Experience refined living in this BEAUTIFUL upgraded residence located in Lakes of Windermere. OFFERING 3-bedroom, 2-bathroom home, 2 CAR GARAGE AND BACK PATIO. Showcases a seamless blend of modern sophistication and everyday comfort, featuring a thoughtfully designed split floor plan and no carpet throughout for a clean, contemporary aesthetic. From the moment you enter, you’re welcomed by light-filled living spaces enhanced by luxury wood-look flooring and freshly painted interiors in soft alabaster tones, creating a warm yet upscale ambiance. The primary suite is a private retreat, offering generous proportions, a spacious walk-in closet, and a beautifully appointed en-suite bath complete with stone countertops, a soaking garden tub, and a separate glass-enclosed shower—designed for relaxation and indulgence. At the heart of the home, the designer kitchen impresses with brand-new quartz countertops, an expansive island with breakfast bar, premium stainless-steel appliances, and a large pantry. The open-concept layout flows effortlessly into the family room and breakfast nook, ideal for both intimate gatherings and entertaining. Step outside to an extended covered lanai, where you can unwind in privacy with no rear neighbors, offering a tranquil outdoor setting perfect for morning coffee or evening relaxation. Residents of Lakes of Windermere enjoy access to resort-style amenities, including a sparkling community pool, tennis and basketball courts, and beautifully maintained green spaces. The home is ideally located near top-rated schools, upscale shopping, fine dining, and world-renowned attractions just minutes away. A rare opportunity to own a home that embodies style, comfort, and location—schedule your private tour today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Maria Castro Aversano, Pa (201-694-3982)
8179 MARITIME FLAG ST #101, WINDERMERE, FL 34786
$325,00063 Days on yellowkey MLS ID: O6399551
0 Days Off yellowkey (back on 5/16/2026)
REDUCED by $5,000 (1.5%) on 05/05/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,106 (2025)Community: Lakeside/Lks/WindermereCondo
Taxes:$4,106
Remarks: Under contract-accepting backup offers. 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)
9011 PINNACLE CIR, WINDERMERE, FL 34786
$2,250,00059 Days on yellowkey MLS ID: O6400872
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 6546 Built: 2002Monthly Fee: $172 Tax: $23,090 (2025)Community: Lake Down CrestSpa: YesSingle Family
Taxes:$23,090
Elementary School: Thornebrooke Elem
Remarks: Majestic and stately, this castle inspired residence sits on a 1.2 acre homesite within the privately gated enclave of Lake Down Crest. Its commanding presence is defined by patterned stone and brickwork, gabled rooflines, slate accents, wooden beams, and a shimmering grand fountain that sets an unforgettable first impression. Double front doors open to an impressive foyer flanked by formal living and dining rooms, while a step down home theater or richly paneled den—with custom built ins—creates a dramatic focal point. The well appointed kitchen features an island with prep sink, stainless appliances, gas cooktop, pantry, and a bright breakfast nook, making it ideal for both entertaining and everyday living. The inviting family room showcases a fireplace, custom millwork, and wood flooring, with French doors that lead to a Travertine patio overlooking the pool, elevated spa with waterfall, iron fencing, and paver decking. The primary retreat is a sanctuary of its own, complete with a private entrance foyer, bedroom with ceiling niche, fireplace, alcove, separate den or nursery, and a luxurious bath featuring a double headed pass through shower, jetted tub, marble topped vanities, and a spacious walk in closet. A secondary guest suite is also conveniently located on the main level. Upstairs, three additional bedrooms accompany a massive bonus room over the garage—perfect as a game room, theater, sixth bedroom, or private guest wing. A rare Florida feature, the finished basement offers exceptional flexibility for a game room, office, or substantial storage. A four and a half car drive through garage provides entrances on both sides and abundant storage. The home is nestled within an exclusive 32 residence community in East Windermere, offering top tier schools and effortless access to SR 408, downtown Orlando, I 4, Mall at Millenia, Walt Disney World, Universal Orlando, and Central Florida’s premier attractions.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786
$1,500,00063 Days on yellowkey MLS ID: O6399697
1 Days Off yellowkey (back on 5/15/2026)
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: Under contract-accepting backup offers. 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 Agent: Jeffrey Funk, Pa (407-285-9672)
2219 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,299,00060 Days on yellowkey MLS ID: O6400508
REDUCED by $50,000 (3.7%) on 05/04/2026
Bed: 6 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3364 Built: 1997Monthly Fee: $218 Tax: $10,027 (2024)Community: Estates At WindermereSingle Family
Taxes:$10,027
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable. Inside, soaring ceilings and natural light highlight detailed millwork and thoughtfully designed living spaces that balance character with livability. The kitchen delivers where it counts—gas cooktop, stainless steel appliances, and rich wood cabinetry—anchoring both everyday life and effortless entertaining. Formal and casual spaces connect seamlessly, creating flow without sacrificing definition. The primary suite is privately positioned on the main floor, featuring a recently refreshed, spa-inspired bath. A secondary downstairs bedroom offers flexibility for guests or a true work-from-home setup, while four additional bedrooms upstairs provide the space today’s buyers are searching for. And then—the lot. Set on a rare .63 acres, outdoor living feels like a private retreat. A saltwater pool, lush landscaping, and multiple areas to unwind create a setting that’s equal parts peaceful and functional. It’s the kind of backyard that’s increasingly hard to find in Windermere. Location seals it: gated privacy just minutes from top-rated schools, parks, dining, shopping, farmers markets, hospitals, major highways and everything that makes Windermere one of Central Florida’s most sought-after places to live. Distinctive. Hard to replicate. Worth seeing in person.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
212 W 1ST AVE, WINDERMERE, FL 34786
$3,900,00052 Days on yellowkey MLS ID: S5148430
INCREASED by $2,300,000 (143.8%) on 05/13/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3800 Built: 2026 Tax: $12,463 (2025)Community: Windermere TownSpa: NoSingle Family
Taxes:$12,463
Remarks: Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Eric Powell (407-720-1833)
14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786
$360,00073 Days on yellowkey MLS ID: O6396784
0 Days Off yellowkey (back on 5/14/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 2013Monthly Fee: $541 Tax: $3,885 (2025)Community: Oasis Cove Ii/Lakeside Village #XiSpa: NoCondo
Taxes:$3,885
Remarks: Don't miss 14368 Desert Haven St, recently enhanced with a partial flooring replacement, providing an updated surface throughout. The kitchen is equipped with stainless steel appliances for functional meal preparation. This residence includes a primary bedroom with a spacious walk-in closet, and its connecting bathroom provides double sinks and a separate tub and shower, contributing to its practical design. 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)
2127 LILYPAD LN, WINDERMERE, FL 34786
$1,250,00048 Days on yellowkey MLS ID: O6403899
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3349 Built: 1989Monthly Fee: $122 Tax: $10,870 (2025)Community: Willows At Lake Rhea Ph 01Spa: YesSingle Family
Taxes:$10,870
Remarks: Under contract-accepting backup offers. Welcome to a rare opportunity in the highly sought-after Willows at Lake Rhea, where incredible design, extensive upgrades, and an elevated Windermere lifestyle come together on a private ½-acre cul-de-sac lot in one of Central Florida’s most desirable luxury communities. This exceptional 4-bedroom, 3-bath residence features a thoughtfully designed split floor plan with two dedicated home offices and a versatile flex space complete with a built-in bar, currently designed as a sports and media room with multiple TVs, soundbar, and its own independent AC, creating the perfect balance of productivity and entertainment. At the center of the home, a fully reimagined custom designer kitchen flows seamlessly into the main living areas and showcases premium finishes, high-end appliances, and a reverse osmosis system, all complemented by architectural details like shiplap ceilings, barn doors, and curated lighting that add warmth and sophistication throughout. The outdoor living space is a beautifully landscaped setting with mature trees and a heated inground saltwater pool and spa featuring a color-changing LED lighting system, designed for both relaxation and hosting. This home has been meticulously upgraded with over $400,000 in improvements including a new roof, windows, doors, gutters, AC, smart WiFi thermostats, a smart WiFi hybrid hot water heater, smart WiFi Sprinkler controller, interior and exterior paint, pool equipment, and a Tesla charger, offering true peace of mind and move-in confidence, along with AT&T fiber internet delivering 1G/1G speeds for seamless connectivity. A side-entry 3-car garage, plantation shutters, and too many other details to list complete the home, while the location delivers unmatched convenience with walking distance to the Windermere Farmer’s Market, zoning for top-rated Windermere High School, and quick access to Winter Garden Village, the 408, and 429. Residents also enjoy community amenities including a park, basketball, and pickleball courts, all surrounded by the charm of Windermere and the lifestyle of the Butler Chain of Lakes, making this more than a home, it is a refined living experience that checks all the boxes in a community that truly offers it all. You have found your forever home.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Angela Jaspon (407-235-0093)
8866 HERENCIA ALY, WINDERMERE, FL 34786
$430,00036 Days on yellowkey MLS ID: O6407518
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1577 Built: 2021Monthly Fee: $240 Tax: $5,532 (2025)Community: Legado 95/47 Lot 100Townhouse
Taxes:$5,532
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious loft area perfect for a home office, media room, or play space. This move-in ready property offers an open-concept layout, stylish finishes, abundant natural light, and comfortable living spaces throughout. Located in the highly desirable Windermere area, this home offers easy access to top-rated schools, shopping, dining, major highways, and Orlando attractions. Enjoy the perfect blend of comfort, convenience, and Florida living in a great location!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Priscila Lima (321-442-7790)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00092 Days on yellowkey MLS ID: O6390327
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4471 Built: 2016 Tax: $25,043 (2025)Community: DiamondheadSingle Family
Taxes:$25,043
Remarks: Experience elevated lakefront living in this one-of-a-kind estate, offering breathtaking views of Lake Bessie and unforgettable Florida sunsets. A private gated entry welcomes you to this exceptional residence, featuring 3 bedrooms and 3.5 bathrooms, plus a private in-law suite with its own full bath bringing the total to 4 bedrooms and 4.5 bathrooms. Thoughtfully designed for both everyday living and elegant entertaining, this home offers the perfect blend of comfort, privacy, and sophistication. The main level features formal living and dining rooms with a fireplace, along with a private office just off the foyer. The gourmet kitchen is a chef’s dream, showcasing custom cabinetry, built-in wine rack, wine refrigerator, Sub-Zero refrigerator, custom lighting, gas range, and a spacious pantry. A convenient half bath and oversized laundry room are also located on the main floor. Upstairs, you’ll find two private suites, each with its own full bathroom, plus the luxurious owner’s retreat offering stunning lake views, custom tile floors and walls, a separate walk-in shower, jetted soaking tub, custom lighting, and a large walk-in closet with built-in cabinetry. Step outside to your resort-style oasis featuring large pool with expansive deck and water feature. Two additional outdoor entertaining areas include a dedicated space with an outdoor kitchen. The pool house offers large windows with panoramic views, custom cabinetry, granite countertops, upgraded tile flooring, a Murphy bed, and a full custom bathroom, perfect for guests. Complete with a covered boat dock and located just a few blocks from downtown Windermere and nearby shopping, this extraordinary home blends luxury, comfort, and the ultimate Florida lifestyle.
Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)
Listing Agent: Maria Sarmiento Webel (305-793-6614)
7503 LAKE ALBERT DR, WINDERMERE, FL 34786
$1,650,00041 Days on yellowkey MLS ID: S5149564
3 Days Off yellowkey (back on 5/11/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4329 Built: 2015Monthly Fee: $180 Tax: $17,734 (2025)Community: Lake Burden South Phase 1Single Family
Taxes:$17,734
Remarks: 7503 Lake Albert Drive presents a beautifully renovated residence in the Lake Burden South community of Windermere. Completely renovated in 2023, the home showcases modern finishes, soaring ceilings, abundant natural light, and an open-concept layout designed for both everyday living and entertaining. Interior features include porcelain tile flooring, designer lighting, updated bathrooms, a modern kitchen, and refined details throughout. The spacious floor plan offers seamless indoor-outdoor living with a stunning backyard featuring a private pool, screened enclosure, and generous outdoor living space ideal for enjoying Florida living year-round. Additional highlights include a whole-house reverse osmosis water filtration system and beautifully updated living spaces throughout the home. Conveniently located near shopping, dining, major highways, Horizon West, and Windermere area amenities.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Mariana Haddad (858-829-7578)
5603 MARLEON DR, WINDERMERE, FL 34786
$27,000,00038 Days on yellowkey MLS ID: O6404938
Bed: 7 Bath: 9.0 Gar: 10 Liv Area Sq Ft: 22108 Built: 2008 Tax: $138,635 (2025)Community: NaSpa: YesSingle Family
Taxes:$138,635
Remarks: A rare legacy estate of extraordinary scale and architectural significance, this magnificent lakefront compound spans over 22,000 square feet across more than 11 private acres with over 440 feet of pristine frontage on Cypress Lake. Masterfully designed to deliver the ultimate blend of grandeur, privacy, and resort-inspired living, the residence is statement of uncompromising luxury. Beyond the gated entrance, a sweeping motor court and dramatic porte-cochère introduce the home’s commanding Mediterranean-inspired architecture, where turreted wings, natural stone detailing, and elegant arched windows create an unforgettable arrival experience. Inside, a breathtaking 28-foot grand foyer unfolds beneath soaring ceilings, anchored by a spectacular double staircase with intricate custom ironwork that evokes the elegance of a world-class villa. Flooded with natural light through towering arched windows, the space immediately establishes the scale and sophistication that define the estate. Designed for intimate living and large-scale entertaining, the interiors blend timeless craftsmanship with modern refinement. The gourmet chef’s kitchen is a showpiece of its own, featuring custom wood cabinetry, expansive stone countertops, professional-grade appliances, a dramatic custom range hood, oversized center island, hidden pantry and richly detailed ceiling treatments that elevate the space into a culinary centerpiece. Adjacent gathering areas showcase exposed wood beams, designer lighting and seamless indoor-outdoor connectivity, creating warm yet grand living environments ideal for entertaining on any scale. Every amenity within the residence has been thoughtfully curated to rival the finest luxury resorts. Highlights include a state-of-the-art theater, golf simulator, multiple game rooms, an expansive wine room, private elevator, smart home automation system and a fully equipped fitness center. Elegant fireplaces and sophisticated entertaining spaces add warmth and intimacy throughout the home. A private guest wing with two bedrooms, its own living room, and separate entrance offers luxurious accommodations for extended family, guests or staff. The outdoor experience is nothing short of spectacular. The rear elevation unfolds around a breathtaking 125,000-gallon resort-style pool complete with cascading waterfalls, bordered by natural stones, a water slide, diving board and expansive terraces that rival five-star destinations. At twilight, the towering palms and illuminated architecture reflect across the shimmering water, creating a setting reminiscent of an exclusive private resort with intimate lounge settings that invite grand entertaining and quiet moments of retreat. For the automotive enthusiast, the estate includes a 10-car garage equipped with two vehicle lifts. Recreational amenities continue across the grounds with a private basketball court, boat dock and private community boat ramp, which provide effortless access to the desired Butler Chain of Lakes for world-class boating and waterfront living. Surrounded by expansive lawns, mature landscaping and unmatched privacy, this extraordinary residence represents a once-in-a-generation opportunity to own a waterfront legacy estate, a property designed not only to impress, but to endure for generations to come.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Llin Lu, Pa (954-907-3868)
5421 TILDENS GROVE BLVD, WINDERMERE, FL 34786
$1,999,90048 Days on yellowkey MLS ID: O6402594
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5922 Built: 2005Monthly Fee: $317 Tax: $17,783 (2025)Community: Tildens GroveSpa: YesSingle Family
Taxes:$17,783
Remarks: Welcome to one of Windermere’s finest offerings — an impressive 5-bedroom, 4.5-bath estate spanning almost 6,000 sq ft on a premium 0.62-acre direct water-view lot in the exclusive 24-hour guard-gated community of Tildens Grove. This is a luxury build that combines sophistication with fun and accommodates an active lifestyle for family and entertaining: a custom private movie theater, resort-style pool with spa and panoramic screen overlooking the water, gourmet kitchen, a dedicated gym, plus two generous family / entertainment spaces upstairs and down… all create a floor plan that handles both grand entertaining and relaxed everyday living. Updates to HVAC, lighting, fixtures, media systems, and wood flooring throughout. Soaring ceilings with architectural features, and elegant architectural details define every room. Bedroom layout creates a lot of options with one of the downstairs bedrooms featuring a separate side entry just off of the driveway with direct access to a full bathroom - ideal for guests and multi-generational living. Three-car garage, paver driveway, lush mature landscaping. Tildens Grove offers larger homesites and amenities including tennis, pickleball, basketball, playground, and a scenic park. Minutes to Disney World, Restaurant Row, Windermere Chain of Lakes boat ramp access, top-rated schools, quick SR-429 access for easy day trips to the beach, and approximately 30 minutes to Orlando International Airport. Luxury, privacy, and convenience — all in one remarkable home. Owners have this priced right so don’t delay in setting up your private showing today.
Listing is courtesy of: DERENTHAL REALTY (321-662-8014)
Listing Agent: Mike Derenthal (321-662-8014)
11686 WATER RUN ALY, WINDERMERE, FL 34786
$409,90097 Days on yellowkey MLS ID: O6390542
REDUCED by $2,000 (0.5%) on 04/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $332 Tax: $6,025 (2025)Community: Ashlin Park Ph 2Spa: NoTownhouse
Taxes:$6,025
Remarks: Welcome to this beautiful townhome located at 11686 Water Run Aly in the desirable Windermere community of Ashlin Park. Built in 2017, this well-maintained 3-bedroom, 2.5-bath home offers approximately 1,584 sq ft of comfortable living space with a modern open-concept layout.The kitchen features granite countertops, stainless steel appliances, and ample cabinetry overlooking the bright living and dining areas—perfect for everyday living and entertaining. New laminate flooring has been installed throughout the first floor, adding a fresh and modern touch. The spacious primary suite includes a walk-in closet and private bath, while two additional bedrooms provide flexibility for family, guests, or a home office. A private courtyard connects to the detached two-car garage, which features a newly painted floor.Residents enjoy community amenities including a pool, clubhouse, playground, tennis courts, and walking trails. Conveniently located near shopping, dining, major roadways, and top-rated schools, this home offers comfort and convenience in one of Central Florida’s most sought-after areas.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
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