Location: Windermere
Do Not Show Listings
7271 SUNNY MEADOW ALY, WINDERMERE, FL 34786
$675,00022 Days on yellowkey MLS ID: O6392619
1 Days Off yellowkey (back on 3/28/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2280 Built: 2015Monthly Fee: $107 Tax: $7,200 (2025)Community: Ashlin Park Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,200
Elementary School: Sunset Park Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: This meticulously maintained contemporary home is ideally situated on a premium FENCED corner lot just steps from the resort style community pool and clubhouse in sought after Ashlin Park in Windermere. Your family will enjoy the private and large fenced yard! This home is like new and features a long list of amazing upgrades - including recently installed luxury vinyl plank flooring and designer lighting. The entire home has a clean and contemporary design aesthetic with smooth walls and ceilings in serene colors, quartz countertops, flat panel 42” cabinets, tumbled marble and glass backsplash, and designer lighting. Tons of windows and double French doors provide abundant natural light for a bright and airy ambience. The kitchen is the heart of every home and this one offers a large island with seating, stainless appliances and an open flow into the family room, dining room and large screened lanai offering the ultimate space to entertain family and friends. The screened lanai is plumbed for a summer kitchen and offers a tranquil space to enjoy your outdoor oasis. The FENCED yard has mature privacy landscaping with room for your family and pets to run and play. Professionally landscaped with a well manicured lawn, the property is the envy of the neighborhood. Upstairs, the master suite is a harmonious retreat with French doors to a private balcony, a huge walk-in closet and a luxurious bath suite featuring a rain shower and jetted tub. The additional bedrooms are ample and elegantly appointed and ALL bedrooms feature luxury vinyl plank floors. The bathrooms are upgraded with premium cabinetry and quartz countertops. Ashlin Park is conveniently located for easy access to highways, theme parks, dining and shopping. The community pool and clubhouse are an easy walk from your front door and there are walking trails and park space throughout this tranquil neighborhood for exercise and leisurely strolls. Enjoy the charm of Windermere with easy access to the Butler Chain of Lakes, world class dining and entertainment, golfing, boating, fishing and more. Known for top-rated schools, Windermere truly offers a wonderful quality of life! This house is truly a MUST SEE! All information intended to be accurate but BUYER SHOULD VERIFY ALL MEASUREMENTS, SQ. FOOTAGE, HOA RESTRICTIONS AND FEES.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Denise Crabbe (407-592-0692)
12879 EMERSONDALE AVE, WINDERMERE, FL 34786
$399,00057 Days on yellowkey MLS ID: O6383280
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1565 Built: 2010Monthly Fee: $185 Tax: $5,505 (2024)Community: Wickham Park 04 05 06 09 10 11 12 01Townhouse
Taxes:$5,505
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Welcome home to this beautiful END-UNIT 3-bedroom, 2.5-bath townhome, thoughtfully designed to maximize space, comfort, and natural light. With abundant windows throughout, the home is filled with sunshine, creating a bright and inviting atmosphere from the moment you step inside. The open-concept floor plan is ideal for both everyday living and entertaining. Enjoy tile flooring in the kitchen, dining, and living areas, complemented by engineered hardwood floors in all bedrooms for a warm and cohesive feel. The spacious primary suite features a large walk-in closet with custom built-ins, while two additional bedrooms share a convenient Jack-and-Jill bathroom, perfect for family or guests. Step outside to your private patio, offering direct access to a detached 2-car garage—a rare and valuable feature. Additional peace of mind comes with a NEW AC system installed in 2025, adding value and energy efficiency. The community offers an impressive array of amenities, including multiple parks, scenic walking trails, a gazebo, clubhouse, and a resort-style pool, all while maintaining a LOW HOA. Ideally located minutes from shopping, dining, major roadways, and popular attractions, and zoned for top-rated schools, this home truly has it all. Schedule your private showing today and experience the perfect blend of comfort, convenience, and community living.
Listing is courtesy of: UNIONE REALTY INC (407-808-9080)
Listing Agent: Kyle Li (407-808-9080)
9319 WOODBREEZE BLVD, WINDERMERE, FL 34786
$574,99552 Days on yellowkey MLS ID: O6384930
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1798 Built: 1986Monthly Fee: $30 Tax: $3,384 (2024)Community: Silver WoodsSingle Family
Taxes:$3,384
Elementary School: None
High School: None
Middle School: None
Remarks: WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you will notice the details: beveled glass front door, split floorplan, large dining and living (open concept) and well-appointed kitchen. The kitchen overlooks the Livingroom and dining room, and boost upgrades you are sure to love. Cherrywood cabinets with pullout shelves, glass doors, pantry, under cabinet lighting, decorative lighting in cabinets, stainless steel appliances and upgraded granite counters. Additional cabinets were added to create workspace or an eat in kitchen space. Just off the kitchen if the laundry area with matching cabinets. The spacious living room is positioned with views of the kitchen and dining space with sliders leading to the massive patio space. Two additional bedrooms are located just off the living room with the hall bath set up for a pool bath if you decided to add one. Just off the dining room you will find the primary bedroom with French doors leading to a private patio space. The primary bath includes a walk in closet space, cherrywood cabinets and a walk in shower. The rear patio has just as many endless options as the front courtyard does...dining spaces or entertaining or both! All this in a home and still just minutes to restaurants, entertainment, shopping, the parks and so much more. Land, Site, and Tax Information
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786
$479,00023 Days on yellowkey MLS ID: O6392752
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1980 Built: 2008Monthly Fee: $315 Tax: $3,248 (2025)Community: Preston SquareTownhouse
Taxes:$3,248
Remarks: Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Morgan Horsley (256-283-8747)
5538 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,495,00078 Days on yellowkey MLS ID: O6376859
Bed: 6 Bath: 5.5 Liv Area Sq Ft: 6000 Built: 1982Monthly Fee: $67 Tax: $25,546 (2025)Community: Kelso On Lake ButlerSingle Family
Taxes:$25,546
Elementary School: Windermere Elem
Middle School: Bridgewater Middle
Remarks: Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated access to Kelso's private boat ramp on the prestigious Butler Chain of Lakes. This convergence of private waterfront with chain-of-lakes connectivity creates unparalleled boating and recreational opportunities found in few lakefront estates. The expansive grounds and recent outdoor enhancements create an entertainer's paradise that is second to none! A newly upgraded outdoor bar and grill area, resort-caliber pool and spa, and sweeping lawn frame breathtaking sunset views over the water. Boasting 6 bedrooms, 6 bathrooms, 3 car garage, and more than 6,000 square feet of living space, this custom estate offers privacy, scale, and unforgettable lakefront views from nearly every room. From the moment you arrive, the chic coastal architecture, circular drive, and sprawling presence command attention. Step inside to dramatic 25-foot ceilings in the living room with a two story stacked stone fireplace and walls of glass that dissolve the boundary between interior luxury and lakefront beauty. An adjacent sun-filled flex room provides tranquil views of Lake Davis, while the completely remodeled chef's kitchen, with its oversized island, custom cabinetry, high end appliances, adjacent indoor bar and generous family room, is designed for both intimate moments as well as large scale entertaining. The main level's thoughtfully designed primary suite offers serene seclusion with a private sitting area, spa-inspired bathroom, and expansive walk-in closet, complemented by a convenient main-floor office. Upstairs, five additional oversized bedrooms, a versatile loft, dedicated gym, and stunning rooftop deck provide space for every lifestyle need. Recent upgrades give you the ultimate peace of mind, including upgraded lighting throughout, a new roof with GAF Golden Pledge 20 year workmanship warranty, three newer A/C units, updated water heater, Hayward pool heater, new dock motor, new sprinkler system with a lake-fed pump, and a transferable Massey termite bond. Minutes from Disney's back gates, top-tier schools, and Windermere's celebrated shopping and dining, yet completely private and serene—this is lakefront living without sacrifice. Your Kelso compound awaits!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
12784 GARRIDAN AVE, WINDERMERE, FL 34786
$550,00024 Days on yellowkey MLS ID: O6392486
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1970 Built: 2012Monthly Fee: $243 Tax: $5,000 (2025)Community: Wickham ParkSingle Family
Taxes:$5,000
Remarks: Welcome to this well-maintained 4-bedroom, 2.5-bath home in the desirable Wickham Park community in Windermere. Offering 1,970 square feet of living space, this home is move-in ready and has been thoughtfully cared for. The layout is both functional and comfortable, making it easy to enjoy everyday living as well as time with family and friends. It’s a home that simply feels right from the moment you walk in. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting, and landscaping. Residents also have access to a community pool and clubhouse. Additional features include a two-car garage, central air, and walkability to nearby Top rated schools, adding to the home’s overall convenience. Located just minutes from Walt Disney World Resort and close to Winter Garden Village, this home also offers convenient access to nearby grocery shopping, including Publix, along with a variety of dining and everyday essentials. This property offers the perfect balance of location, comfort, and ease of living. A/C was replaced in 2023.
Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)
Listing Agent: Maria Sarmiento Webel (305-793-6614)
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,199,00020 Days on yellowkey MLS ID: O6393659
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2599 Built: 2001Monthly Fee: $283 Tax: $8,252 (2025)Community: Keenes PointeSingle Family
Taxes:$8,252
Remarks: Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartz countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026). This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
12121 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$509,00036 Days on yellowkey MLS ID: O6388109
0 Days Off yellowkey (back on 3/28/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2035 Built: 2013Monthly Fee: $33 Tax: $7,699 (2025)Community: Windermere Trls Ph 1Single Family
Taxes:$7,699
Elementary School: Bay Lake Elementary
Remarks: Under contract-accepting backup offers. Enjoy over $35,000 in upgrades in this beautiful Windermere subdivision! This CORNER LOT home is move-in ready with FRESH INTERIOR AND EXTERIOR PAINT * REPLACED CARPETING * RENOVATED SECOND BATHROOM SHOWER * KITCHEN QUARTZ COUNTERTOP * APPLIANCES REPLACED * WASHER AND DRYER INLUDED * WATER SOFTENER/FILTRATION SYSTEM and more! Experience the bright and inviting atmosphere from the moment you enter. The updated kitchen features elegant quartz countertops, stainless steel appliances, and provides the perfect space for cooking, gathering, and entertaining. The secondary upstairs full bathroom has been updated with a newly renovated shower, offering a spa-like retreat within your own home. Additional upgrades include a water softener system, adding comfort and convenience to everyday living. This home is close to theme parks, major roadways, shopping, dining, and top area attractions! You'll enjoy the ideal balance of peaceful neighborhood living and easy access to everything Central Florida has to offer. From its stylish upgrades to its prime location, this home delivers exceptional value and comfort. Come experience everything this spectacular home has to offer!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
5036 LATROBE DR, WINDERMERE, FL 34786
$4,900,000195 Days on yellowkey MLS ID: O6346003
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 5548 Built: 1990Monthly Fee: $1,224 Tax: $17,326 (2024)Community: IsleworthSingle Family
Taxes:$17,326
High School: Olympia High
Middle School: Chain of Lakes Middle
Remarks: Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
13106 ORANGE ISLE DR, WINDERMERE, FL 34786
$815,000129 Days on yellowkey MLS ID: O6361057
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3312 Built: 2022Monthly Fee: $95 Tax: $11,893 (2025)Community: Sanctuary/Lks/WindermereSingle Family
Taxes:$11,893
Remarks: Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Victor De Oliveira (321-393-2772)
6109 ORTA CT, WINDERMERE, FL 34786
$4,495,00091 Days on yellowkey MLS ID: O6374125
1 Days Off yellowkey (back on 3/27/2026)
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 5895 Built: 2016Monthly Fee: $442 Tax: $65,510 (2025)Community: WaterstoneSingle Family
Taxes:$65,510
Remarks: Under contract-accepting backup offers. Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level. At the heart of the home is an expansive gourmet kitchen appointed with premium Thermador appliances and granite countertops, perfectly balancing form and function. The kitchen opens effortlessly to the grand family room, creating an ideal setting for both everyday living and entertaining. Soaring ceilings and clean, contemporary finishes throughout the residence underscore the home’s elevated design. Additional highlights include a dedicated wine room, ideal for showcasing a curated collection, and a private office suite that offers a quiet, productive retreat. Outdoor living is equally impressive, featuring a resort-style pool and spa, an outdoor kitchen, and a fireplace—designed for year-round enjoyment. Set on a generous 2.16-acre cul-de-sac lot, the property offers sweeping views of the ski-able Lake Cypress and includes a private dock capable of accommodating jet skis, delivering a truly exceptional waterfront lifestyle.
9508 WINDY RIDGE RD, WINDERMERE, FL 34786
$30,000,00030 Days on yellowkey MLS ID: O6388674
Bed: 7 Bath: 13.0 Liv Area Sq Ft: 51000 Built: 2011 Tax: $162,563 (2024)Community: N/ASingle Family
Taxes:$162,563
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple structures create an unrivaled lakefront compound. The walled entry opens to a grand foyer with a floating mahogany staircase, marble floors, paneled walls, and Murano chandeliers. An art gallery leads to a spacious living room featuring rich mahogany millwork and expansive lake vistas. Gourmet kitchen: salamander, dual double convection ovens, commercial icemaker, full-size refrigerator, and freezer. The main level includes one of two owners' suites, plus a library-lounge or a possible sixth bedroom. Dual staircases or a Thyssenkrupp elevator provide access to the upper level, which features four-bedroom suites, including the primary retreat. An 85-foot parlor with 20-foot ceilings, built-in bookshelves, and a wet bar provides a dramatic entertaining space. Screened porch captures southern lake views and Disney fireworks. Breezeway connects to a 5,600 SF rustic lodge with a bar, catering kitchen, entertainment hall, and locker facilities. Outdoor amenities: Junior Olympic pool, spa, decorative fountain, architectural lighting, direct lake access. Additional structures include a 4,000 SF paneled garage with 20-foot ceilings, an office, and a guest apartment; a 3,800 SF storage building; three separate garages accommodating motor coach and car collection; and staff quarters with a private courtyard. A rare fusion of Georgian grandeur, lakefront serenity, and equestrian potential—crafted for those who demand the extraordinary.
Listing is courtesy of: DOUGLAS ELLIMAN (305-695-6070)
Listing Agent: Christine Gelman (561-723-4545)
505 JENNIFER LN, WINDERMERE, FL 34786
$2,250,00048 Days on yellowkey MLS ID: O6384643
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3525 Built: 1989Monthly Fee: $333 Tax: $7,624 (2024)Community: Windermere OaksSingle Family
Taxes:$7,624
Remarks: Under contract-accepting backup offers. Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. Villa Casablanca was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this white-painted brick 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. Bay windows overlook the fountain and motor court, creating a balanced dialogue between arrival and retreat. 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, smooth drywall level 5 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)
325 MAGNOLIA ST, WINDERMERE, FL 34786
$2,475,00030 Days on yellowkey MLS ID: O6391047
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3975 Built: 1954 Tax: $21,080 (2025)Community: Windermere TownSingle Family
Taxes:$21,080
Remarks: Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid-back lake living and walkability to town. The Town of Windermere has much to offer. Walk to the local park and tennis courts just a few blocks from your home. It’s an easy stroll or bike ride to Main Street—home to local spots like Dixie Cream, Paloma Coffee, Windermere Brewing Company, the Friday farmer’s market, and the newly updated 500 block with shops and dining. Inside, the home is both comfortable and thoughtfully updated, with travertine flooring in the main living areas and new luxury vinyl plank in bedrooms two and three—no carpet. The kitchen features a gas cooktop with vented exhaust and a brand-new all-in-one convection oven, microwave, and air fryer. The large dining room provides a pleasurable dining experience with lake views. The theater room can be a flexible space used for movies, a guest bedroom, or a game room. It can also work as an office, playroom, or just a place to sit and relax. The bright open Florida room, equipped with three full glass French doors with side panels, a wet bar and views of your outdoor lakefront oasis, opens up to the pool and overlooks the water, creating an easy space to relax or entertain. A great opportunity to enjoy the convenience of the Butler Chain lifestyle in the heart of Windermere—no HOA.
Listing Agent: Rebekkah Boskovich (321-438-3307)
11536 CLAYMONT CIR, WINDERMERE, FL 34786
$1,250,00021 Days on yellowkey MLS ID: O6392958
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2882 Built: 2002Monthly Fee: $298 Tax: $8,766 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Single Family
Taxes:$8,766
High School: Winter Park High
Remarks: One or more photo(s) has been virtually staged. Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and lifestyle. Beautifully remodeled throughout, this is truly move-in ready, showcasing a fresh, modern aesthetic while maintaining timeless architectural appeal. From the moment you enter, you’re welcomed by marble tile flooring, newly refinished wood floors, fresh interior paint, and thoughtfully selected modern light fixtures that elevate every space. The home features both a traditional dining room and formal living room, complemented by custom window treatments that add warmth and sophistication. At the heart of the home, the completely remodeled kitchen shines with all-new appliances, a gas stove, double oven, quartz countertops, and a large walk-in pantry, all wrapped in a clean, contemporary design that seamlessly opens to the family room—where a decorative modern fireplace creates the perfect gathering space. The expansive primary suite is a true retreat, featuring wood floors, direct pool access, a dedicated mini-split system for enhanced comfort and efficiency, and a spa-inspired bathroom with a stunning new garden tub, separate shower, and an oversized walk-in closet. Additional bedrooms lend to stylish comfort with new herringbone tile flooring and share a convenient Jack-and-Jill bathroom. All bathrooms throughout the home have been fully remodeled with high-end finishes. A large private office with a built-in desk provides the ideal work-from-home environment. Step outside to a spacious, fenced backyard featuring a newly repainted pool and patio—perfect for enjoying Florida living year-round. Additional highlights include a 2020 roof, paver driveway, and an oversized 3-car garage. Every detail has been thoughtfully updated, making this home completely turn-key. Residents of Keene’s Pointe enjoy 24-hour guard-gated security and a lifestyle centered around both recreation and natural beauty. The community offers private access to the Butler Chain of Lakes, ideal for boating, skiing, and sunset cruises, along with scenic walking paths, tranquil green spaces, and a peaceful, well-maintained setting throughout. There is even the opportunity for boat storage, adding convenience for those looking to fully embrace the lake lifestyle. Optional membership to the Golden Bear Club unlocks a premier lifestyle experience with championship golf, tennis, fitness, a resort-style pool, dining, and a vibrant calendar of social events. The neighborhood also features community parks, playgrounds, and gathering spaces, creating a welcoming environment that blends luxury living with everyday convenience and community connection through regular neigborhood events. Whether you're relaxing poolside, entertaining guests, or enjoying the unmatched lifestyle of this premier golf and lakefront community, this home delivers the very best of Central Florida living.
Listing is courtesy of: MATT ALLEN REAL ESTATE LLC (321-228-5555)
Listing Agent: Matt Allen (321-228-5555)
436 E 7TH AVE, WINDERMERE, FL 34786
$2,175,000190 Days on yellowkey MLS ID: O6350454
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3136 Built: 2025Community: Windermere Town RepSingle Family
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Remarks: Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor shower, and an oversized 3-car garage. A dramatic two-story living area sets the tone with clean lines, expansive glass, and natural light throughout. The chef’s kitchen pairs performance and elegance, with a waterfall-edge quartz island, full-height book-matched backsplash, custom cabinetry, and high-end appliances including a Sub-Zero refrigerator, Wolf vent hood, and a full Thermador suite with double ovens and microwave drawer. A hidden walk-in pantry blends seamlessly into the design for added utility and clean aesthetics.Upstairs, the owner’s suite offers lake views, a spacious layout, and a sleek en-suite bath with a large walk-in shower and dual vanity. Secondary bedrooms include en-suite baths and reach-in closets. The home is finished with oversized rectangular porcelain tile throughout the entire main level including the expansive covered lanai and wide plank engineered wood flooring from the staircase through the second floor. Additional highlights include a glass-framed staircase and an abundance of natural light in every space. Located just blocks from Downtown Windermere, this home places you at the center of a highly coveted lakefront lifestyle. Enjoy tennis courts, playgrounds, boat ramps on both Lake Bessie and the Butler Chain, plus a vibrant local culture with weekly farmers markets, food truck nights, and seasonal events in Town Square. Cruise oak-lined sandy streets by golf cart, or explore nearby dining, shops, and fitness at The Grove and along Restaurant Row. World-class golf, theme parks, and the airport are all within easy reach and with the hard work already done, all that’s left is to move in and enjoy. Private showings by appointment only. Seller is Motivated and open to negotiate! We completed the closets upgrades in this beautiful home, thoughtfully designed for the family who will soon call this place home.
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Deniley Valdes (407-922-3870)
14285 CREST PALM AVE, WINDERMERE, FL 34786
$1,019,99082 Days on yellowkey MLS ID: G5107224
0 Days Off yellowkey (back on 3/25/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3100 Built: 2025Community: Palms At WindermereSingle Family
Remarks: One or more photo(s) has been virtually staged. Welcome to the Arlington with Bonus a stunning 4-bedroom, 4-bathroom home offering 3,123 square feet of beautifully designed living space. Thoughtfully crafted with an open-concept layout, this home is perfect for both everyday living and entertaining. Step inside to find soaring 10-foot ceilings on the first floor and durable laminate flooring throughout, creating a seamless and modern feel. The gourmet kitchen is a true centerpiece, featuring elegant quartz countertops, a large center island, and abundant cabinet space—ideal for hosting and meal preparation alike. The spacious floor plan includes a versatile second-floor bonus room complete with a full bath, perfect for a guest suite, media room, or home office. The elegant primary bathroom offers a spa-like retreat, featuring a spacious walk-in shower with a luxurious rain shower head and a dual vanity with ample counter space. Situated on a desirable conservation homesite, this property offers added privacy and serene natural views. The oversized garage provides ample room for vehicles, storage, or even a workshop. This home effortlessly combines style, functionality, and comfort.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Cindy Sapp (352-516-2843)
11802 WATERSTONE LOOP DR, WINDERMERE, FL 34786
$1,395,00042 Days on yellowkey MLS ID: O6387172
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3396 Built: 2012Community: WaterstoneSingle Family
Remarks: Under contract-accepting backup offers. Stunning Mediterranean courtyard-style estate offering 4 bedrooms, 4.5 Bathrooms and 3396 sq ft of living space--all thoughtfully designed on one spacious level by Siliman Homes! From the moment you enter, you'll appreciate the seamless indoor-outdoor flow, centered around a salt water pool, cabana and expansive brick paver patio--perfect for entertaining or enjoying Florida living all year round. The open concept kitchen opens effortlessly to the entire family room, where you'll enjoy a Cosmos gas fireplace and surround sound. Elegant travertine flooring runs throughout the main living areas, with engineered wood flooring in the master bedroom and plush carpeting in the secondary bedrooms. The 4th bedroom functions beautifully as a private IN-LAW suite, complete with its own separate entrance, living room, full bedroom and full bathroom--ideal for MULTI-GENERATIONAL living or guests. This residence also features throughout upgrades including tankless water heater, open-cell foam spray insulation, natural gas 5 burner stove, Low-E insulated glass windows and sliding doors! Located in a guard gated community Waterstone, known for its mature landscaping and privacy, the home is located within 10 mins to the Publix Shopping center and dining. Residents also enjoy PRIVATE ACCESS into Windermere Prep School! This is a rare opportunity to own in one of the area's most desirable gated communities!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Catherine Lambert Pa (407-908-2525)
84 OAKDALE ST, WINDERMERE, FL 34786
$1,875,00094 Days on yellowkey MLS ID: O6372842
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3519 Built: 2020Community: Davis ShoresSingle Family
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)
81 OAKDALE ST, WINDERMERE, FL 34786
$2,300,000150 Days on yellowkey MLS ID: S5138567
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 4284 Built: 2001Community: Davis ShoresSingle Family
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 bidets in both the primary and powder 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)
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