Location: Windermere
Do Not Show Listings
11486 MISTY OAK ALY, WINDERMERE, FL 34786
$549,00040 Days on yellowkey MLS ID: S5148331
3 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1950 Built: 2016Monthly Fee: $107 Tax: $7,492 (2025)Community: Ashlin Park Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,492
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Beautiful two-story single-family home with a pond view in the Ashlin Park neighborhood of Windermere. Open floor plan includes large living room, dining, and kitchen, with ceramic tile throughout the first floor. Kitchen has quartz countertops, stainless steel appliances, large island, and ample cabinet space. Living room faces pond and peaceful walking trail with lovely indoor or porch water view. First floor also has a half bathroom and a large storage room, as well as an attached two-car-garage. All three bedrooms on second floor with carpet flooring, along with two full bathrooms and a spacious laundry room. Ashlin Park is quiet neighborhood located between the world-famous Walt Disney World and FL535, with great access to theme parks, a variety of restaurants and shops, major highways, golf courses, etc., Minutes’ walk to the community clubhouse and pool. Make this lovely home yours and enjoy Central Florida living.
Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)
Listing Agent: Kikuko Moribe, Pa (321-246-0066)
12720 JACOB GRACE CT, WINDERMERE, FL 34786
$2,845,00087 Days on yellowkey MLS ID: TB8476930
REDUCED by $50,000 (1.7%) on 05/18/2026
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2005Monthly Fee: $300 Tax: $13,298 (2024)Community: Tildens Grove Ph 01 47/65Spa: YesSingle Family
Taxes:$13,298
Elementary School: Windermere Elem
Tax Year: 2024
Middle School: Bridgewater Middle
Remarks: Nestled within one of **Windermere**’s most exclusive communities, this extraordinary custom-built lakefront estate with an almost 2 acres lot offers an elegant lifestyle defined by privacy, prestige, and breathtaking nightly views of the **Walt Disney World** fireworks. With nearly 6,000 square feet, six bedrooms, and six and a half baths, this residence is the pinnacle of refined Central Florida living. A long, winding driveway welcomes you, framed by mature trees and sweeping lawns. Tucked away on a quiet cul-de-sac within a 24-hour guard-gated neighborhood with a manned guard station, the property offers both grandeur and seclusion — a rare combination in today’s luxury market. Thoughtfully designed to maximize natural light and panoramic water views, the home features soaring ceilings, expansive picture windows, and seamless indoor-outdoor flow. The grand foyer opens to a spectacular living room anchored by tranquil lake vistas. The chef’s kitchen is appointed with custom cabinetry, high-end appliances, and an oversized island, effortlessly connecting to spacious dining and living areas — ideal for both intimate evenings and large-scale entertaining. The primary suite, located on the main level, is a private sanctuary with serene lake views and direct access to the outdoor living areas. The spa-inspired bath offers a soaking tub, dual vanities, walk-in shower, and generous closet space. Four additional bedrooms of which two of them include their own en-suite bath, ensuring comfort and privacy for family and guests. A detached in-law suite with private entrance, living area, bedroom, and bath provides exceptional flexibility for multigenerational living, long-term guests, or a private executive office. Step outside to your own outdoor oasis. The resort-style pool overlooks the lake, creating a stunning backdrop for entertaining or quiet relaxation. A charming pool house complete with a Murphy bed offers additional guest accommodations and enhances the estate’s resort-like ambiance. At the water’s edge, a private dock provides access to a private ski lake — perfect for boating, skiing, paddleboarding, or sunset cruises. As evening falls, the magic begins. From your backyard, dock, or expansive windows, enjoy nightly fireworks illuminating the sky above Disney — a spectacular private show reflected across the water. With nearly two acres of lakefront land, six bedrooms, six and a half baths, a detached suite, pool house, long private driveway, and location within one of Windermere’s most prestigious guard-gated communities, 12720 Jacob Grace Ct is more than a home — it is a destination, a sanctuary, and a stage for life’s most extraordinary moments.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Adrian Jacob (832-381-4670)
2806 WINDSOR HILL DR, WINDERMERE, FL 34786
$1,099,00052 Days on yellowkey MLS ID: O6385977
1 Days Off yellowkey (back on 5/18/2026)
REDUCED by $51,000 (4.4%) on 05/02/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3181 Built: 1989Monthly Fee: $111 Tax: $13,057 (2024)Community: Windsor HillSpa: YesSingle Family
Taxes:$13,057
Elementary School: Thornebrooke Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Step into this stunning 4-bedroom, 3-bathroom pool home nestled on nearly half an acre in the highly desirable Windsor Hill community of Windermere. From the moment you enter, you’ll appreciate the bright, open floor plan designed for both comfort and effortless entertaining. At the heart of the home is a beautifully updated kitchen featuring rich walnut cabinetry, quartz countertops, a mosaic tile backsplash, touch faucet and a spacious island that seamlessly connects to the dining and living areas. Equipped with a gas range, stainless steel appliances, and ample counter space, this kitchen is perfect for gathering with family and friends. The expansive media room offers the ultimate entertainment experience, complete with a built-in media center, kitchenette, wine refrigerator, and full-size refrigerator—ideal for movie nights or hosting guests in style. Step outside to your private backyard oasis, where a sparkling heated pool and spa await. Enjoy modern features including a heater, LED lighting with remote control, and a newer pool pump. The covered outdoor living area, complete with a sink and cabinetry, creates the perfect setting for al fresco dining and relaxation. Inside, every bathroom has been thoughtfully renovated with updated vanities, mirrors, bidets, and sleek shower stalls. The luxurious primary suite boasts a spa-inspired bath with a 67-inch freestanding soaking tub, smart mirror with defog function, and dual vanities. Major system upgrades provide peace of mind, including a new roof and skylight (2021), whole-home re-plumbing (2022), water heater (2022), and pool pump (2023). Garage features an electric car charger. Combining the tranquility of suburban living with convenient access to major roadways, shopping, dining, and downtown Orlando, this move-in ready home truly has it all. The HOA features a play ground and tennis courts for neighborhood enjoyment! Don’t miss your opportunity to own this exceptional property—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Candace Hebert (321-246-0068)
12533 CRAGSIDE LN, WINDERMERE, FL 34786
$575,00023 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
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 Agent: Tyler Somers (561-713-8728)
11208 LEDGEMENT LN, WINDERMERE, FL 34786
$999,950243 Days on yellowkey MLS ID: O6325096
1 Days Off yellowkey (back on 5/17/2026)
REDUCED by $50 (0.0%) on 05/09/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2788 Built: 2002Monthly Fee: $140 Tax: $6,561 (2024)Community: Glenmuir 48 39Spa: YesSingle Family
Taxes:$6,561
Remarks: Under contract-accepting backup offers. Welcome to this beautifully upgraded one-story home in a desirable gated community, offering nearly 3,000 sq. ft. of thoughtfully designed living space.Feature, NEW ROOF, CORNER LOT, LOCATED NEAR DISNEY: With five bedrooms, 3.5 baths, and a three-car garage, this home blends comfort, style, and functionality. Upon entry, you’ll be captivated by the high-end finishes and open layout. The formal dining and living areas flow seamlessly together, while sliding glass doors bring the outdoors in, filling the space with natural light. The heart of the home is the oversized kitchen, featuring an island, coffee or wine bar, and direct access to the spacious family room—perfect for entertaining. Large sliding doors open to your own private oasis: a saltwater pool surrounded by lush palm trees, ideal for relaxing or hosting guests. Additional highlights include: • Split floor plan for added privacy • Second bedroom with full ensuite, perfect for guests • Fifth bedroom at the front of the home, ideal for a home office or flex space • Tankless water heater • New A/C system • New pool pump and water filtration system • Wood flooring throughout • Tile floors in the garage * Car Charger *. Surge Protector on Electrical Box *. Attic access via the floor trusses support attic flooring. • Located on an oversized corner lot * appliances 4 years old * * Smart home This move-in-ready home has it all—space, style, and modern upgrades—ready for you to enjoy. Ideally situated in heart of Central Florida, this exceptional home offers effortless access to the area'smost sought after attractions, including the convenient back entrance to Walt Disney World, Disney Springs. Including nearby Universal Orlando, City Walk, SeaWorld,Ocon Park and the renowned dining destinations along Restarant Row. If you've been searching for a beautifully updated home with space, sophistication and an unbeatable location.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Ruthanne Martin (407-721-6420)
5145 LATROBE DR, WINDERMERE, FL 34786
$3,299,000105 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
$1,130,64315 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
$539,00067 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
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)
8796 PEACHTREE PARK CT, WINDERMERE, FL 34786
$949,99946 Days on yellowkey MLS ID: O6399023
REDUCED by $30,000 (3.1%) on 05/16/2026
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
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)
9011 PINNACLE CIR, WINDERMERE, FL 34786
$2,250,00041 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
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)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00016 Days on yellowkey MLS ID: O6407352
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $9,227 (2025)Community: Windsor HillSingle Family
Taxes:$9,227
Remarks: Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
505 JENNIFER LN, WINDERMERE, FL 34786
$2,199,00093 Days on yellowkey MLS ID: O6384643
4 Days Off yellowkey (back on 5/15/2026)
REDUCED by $51,000 (2.3%) on 04/28/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3525 Built: 1989Monthly Fee: $333 Tax: $7,624 (2024)Community: Windermere OaksSpa: YesSingle Family
Taxes:$7,624
Remarks: Under contract-accepting backup offers. Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside. What unfolds within is architectural theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive double-pane windows flood the interiors with natural light. A sculptural chandelier crowns the volume, while a full-height stone fireplace ascends as the focal point. French glass doors frame panoramic views of the private rear oasis — pool, pergola, and mature canopy beyond — creating a seamless connection between interior grandeur and outdoor serenity. The chef’s kitchen commands attention. A grand Taj Mahal quartzite island defines the center. White oak cabinetry spans floor to ceiling. The Thor range and sculpted hood rise against a full-height stone backdrop. pot filler., Viking refrigerator. Glass pendants hover overhead -- Every finish carries presence. The scullery unfolds unexpected, elevated, and unforgettable — Deep olive custom cabinetry, textured tile, LED-lit shelving, beverage refrigeration, and layered storage make it as functional as it is striking. A split plan introduces the primary suite — vaulted, private, composed. A sculptural chandelier anchors the ceiling while tailored wall moldings define the room. Dual concealed walk-in closets preserve symmetry. The primary bath is a statement of design: matte stone soaking tub beneath clerestory light, full-height stone extending into a curbless marble shower, dual tailored vanities with brushed brass accents, and patterned marble floor grounding the space in immersive opulence. An adjoining vaulted extension captures pool views and opens to the lanai. The powder room shifts tone — charcoal paneled walls, sculptural marble sink, polished brass fittings, arched mirror, and bold tile creating a rich, moody presence. A formal office behind glass French doors offers focused productivity and polished presentation. An arched corridor leads to the secondary wing where three additional bedrooms offer privacy and versatility. One suite provides direct exterior access, functioning as a cabana retreat with its own en suite bath — ideal for guests or seamless indoor-outdoor living. Outdoors, the property transforms into a private compound. A covered veranda spans the rear with classical columns and herringbone flooring. The fully equipped summer kitchen, custom wood pergola lounge, expansive lawn, fresh sod, rear gate access, and lush landscaping offer scale impossible to replicate in today’s market. Villa Casablanca is not comparable to new construction. It is rarer. Extensively renovated inside out with a long list of brand new finishes - Roof, HVAC, Double pane windows, plumbing, pool refinish, level 5 drywall smooth finish and much more. Schedule your showing today.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Ahmad Hassan, Pa (718-641-9358)
5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786
$1,500,00045 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 is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeffrey Funk, Pa (407-285-9672)
2219 RIDGEWIND WAY, WINDERMERE, FL 34786
$1,299,00042 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 Agent: Hilary Hall (407-902-9311)
212 W 1ST AVE, WINDERMERE, FL 34786
$3,900,00034 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)
2127 LILYPAD LN, WINDERMERE, FL 34786
$1,250,00030 Days on yellowkey MLS ID: O6403899
0 Days Off yellowkey (back on 5/14/2026)
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)
81 OAKDALE ST, WINDERMERE, FL 34786
$2,300,000195 Days on yellowkey MLS ID: S5138567
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4284 Built: 2001 Tax: $24,940 (2025)Community: Davis ShoresSingle Family
Taxes:$24,940
Remarks: Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step inside to an open, grand gathering space framed with natural wood beams, a gas fireplace, and a seamless flow into a chef-inspired kitchen. Featuring state-of-the-art GE Monogram appliances, a Taj Mahal quartzite island, restaurant-quality crushed ice, a 100+ bottle wine cooler, a full bar and coffee lounge, and a spacious walk-in kitchen pantry—this home invites effortless entertaining. Throughout, new wide-plank laminate wood floors set a refined, cohesive tone. Additional highlights include professional designer wallpaper in the dining room and powder bath, smart bidet in the primary bath, and a fully integrated smart-home lighting, shade, and security system. The primary suite is a private sanctuary, complete with a fully reimagined spa bath wrapped in marble and porcelain, a freestanding soaking tub, and two custom-designed closets. There are three more en suite bedrooms offering privacy and convenience. This corner-lot haven is framed by mature oak trees and newly installed landscaping and irrigation. A beautiful outdoor deck and built-in fire pit creates a cozy retreat for gatherings. Follow the canal behind the home to access the world-renowned Butler Chain of Lakes. The boathouse features an electric lift, dual Sea-Doo floating docks, and instant access to some of Florida’s most coveted waterways.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: David Warzycha (863-860-3365)
13609 ANCILLA BLVD, WINDERMERE, FL 34786
$749,999107 Days on yellowkey MLS ID: O6381542
0 Days Off yellowkey (back on 5/12/2026)
REDUCED by $39,001 (4.9%) on 04/14/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3360 Built: 2005Monthly Fee: $130 Tax: $9,521 (2024)Community: Summerport Ph 03Single Family
Taxes:$9,521
Elementary School: Keene Crossing Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony, providing a serene retreat, as well as a dedicated home office perfect for remote work or study. Generous living areas are filled with natural light and create a seamless connection between indoor and outdoor living. Step outside to enjoy the covered patio and expansive backyard, offering ample space for entertaining, relaxing, or future customization. The property sits on a well-sized lot and is part of a community that features amenities such as a pool, park, playground, and sidewalks. Conveniently located near top-rated schools, shopping, dining, and major roadways, this home delivers an exceptional combination of location, space, and lifestyle. A rare opportunity to own a lake-view property in one of Windermere’s most desirable areas. Schedule your private showing today. SOME IMAGES HAVE BEEN VIRTUALLY STAGED AND/OR DIGITALLY ENHANCED TO ILLUSTRATE THE PROPERTY'S POTENTIAL AFTER UPDATES OR RENOVATIONS.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Fernanda Soares Santos De Oliveira (407-840-0734)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,000131 Days on yellowkey MLS ID: O6373065
1 Days Off yellowkey (back on 5/13/2026)
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)
606 E 6TH AVE, WINDERMERE, FL 34786
$2,350,00074 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)
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