Windermere Single Family Homes For Sale - 283 homes

Remarks: TOP RATED SCHOOLS!!! Welcome to this beautifully maintained Craftsman-style home in the highly sought-after Lakes of Windermere community. Perfectly positioned on a premium homesite overlooking tranquil conservation views, this 4-bedroom, 2.5-bath residence combines timeless charm with modern upgrades and exceptional indoor-outdoor living. Inside, you’ll find a light-filled floor plan featuring hardwood flooring, elegant transom windows, custom built-ins, and spacious living and dining areas ideal for both everyday living and entertaining. The upgraded kitchen offers granite countertops, solid wood cabinetry, stainless steel appliances, a butler’s pantry, and ample prep and storage space. This is the one you’ve been waiting for—schedule your private showing today.

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Frederico Hexsel (407-745-8841)

Remarks: 3BR/2.5BA bungalow-style home in the Windermere Trails community. This well maintained residence offers an open floor plan with high ceilings, and premium tile flooring throughout the main level. The home includes a gourmet kitchen, upgraded cabinetry in the laundry room. Upstairs, a versatile loft provides the perfect space for an office or media room, alongside a spacious master suite and two additional bedrooms. Perfectly located near Publix, dining, and banking, and zoned for A-rated schools with Bay Lake Elementary situated right at the community entrance.

Listing is courtesy of: ON ME REALTY (321-370-1474)

Listing Agent: Eduardo Pavone (407-232-1241)

Remarks: Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion foyer floor design, coffered ceilings, crown molding, and European-style ironwork boasts spectacular views of Lake Roper. The upstairs master bedroom has a beautiful view of Lake Roper. Master bath features an oversized tub and walk-in closet. This Grand Retreat has plenty of outdoor amenities including a basketball court, boat dock and boat lift. Heated family pool and spa. For all your family entertainment, a large open backyard leads to the dock with plenty of land. Stunning cedar and cypress trees surrender the property reminding you of FLORIDA living at its best. The ideal setting for privacy and serenity! Entertainment and fine shopping just minutes away. Close to major highways such as 429, 408 & the Turnpike. Easy access to the airport and Downtown Orlando yet secluded enough to give you a unique home in the heart of Windermere! Close to Windermere Prep school. Convenient to major highways, shops, restaurants, historic sites, major hospitals, and theme parks! Privacy awaits you! Schedule showing!

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Karolina Taylor (813-702-5478)

Remarks: Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a seamless blend of sophistication and comfort. Spanning a thoughtfully designed single-story layout, the residence features five bedrooms, four full baths, and two half baths, all curated with impeccable attention to detail. From the moment you enter, soaring ceilings and an abundance of natural light highlight exquisite porcelain marble flooring that flows seamlessly throughout the main living areas—completely carpet-free for a clean, modern aesthetic. The bedrooms feature rich hardwood flooring, adding warmth and contrast. The open-concept design creates an inviting yet refined atmosphere, ideal for both intimate living and grand entertaining. At the heart of the home, the gourmet chef’s kitchen is a true showpiece, appointed with premium Viking stainless steel appliances, rich granite countertops, and bespoke custom cabinetry. Whether hosting elegant gatherings or enjoying everyday moments, this space is designed to impress. Step outside to your private resort-style sanctuary. The covered lanai, complete with a fully equipped outdoor kitchen and grill, overlooks a beautifully redesigned pool framed by lush, mature landscaping—creating a serene and secluded backdrop for relaxation or entertaining under the Florida sun. This home has been extensively upgraded with no detail overlooked, including a complete pool renovation with new equipment, a new screen enclosure, fresh exterior paint and lighting, two new HVAC systems, updated garage interiors and openers, EV charging capability, a new septic system, and a whole-home reverse osmosis water treatment system. Residents of this distinguished community enjoy 24-hour guard-gated security, private fishing dock on Lake Butler, and impeccably maintained surroundings—all just minutes from world-class attractions, fine dining, upscale shopping, top-rated schools, and major thoroughfares. This is more than a home—it is a statement of refined living in one of Central Florida’s most coveted addresses. Schedule your private tour today and experience it for yourself.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Priced below appraised value, this extraordinary Windermere estate presents a rare opportunity to enjoy refined lakefront living on the Butler Chain of Lakes. Set along one of the area’s most desirable streets, the residence has undergone more than $350,000 in recent luxurious upgrades, including a reimagined kitchen and fireplace, new windows and doors, upgraded landscape lighting, refreshed landscaping, a freshly painted exterior and a new roof. Completing the offering is a newly constructed $85,000 private dock by Docks of Orlando, delivering direct access to the tranquil waters of Wauseon Bay. Spanning 5,639 square feet, the home showcases thoughtfully curated living spaces designed to capture sweeping views of one of the tranquil stretches of the Butler Chain. A dramatic two-story foyer opens to the formal living area, where expansive sightlines extend to the resort-style pool and spa. These views are beautifully complemented by a striking 650-gallon arched saltwater fish tank that creates a captivating visual connection to the bay beyond. The formal living room is further enhanced by a sculptural paneled feature wall accented with soft ambient lighting, lending an atmosphere of understated elegance. At heart of the home, the gourmet kitchen is sophisticated and functional, featuring a wet bar, wine refrigerator, oversized pantry with a custom swinging door, Wolf and Sub-Zero appliances, quartz countertops, bespoke cabinetry and updated designer lighting. Seamlessly connected is an inviting living space anchored by a dramatic fireplace clad in exotic stone and framed by custom cabinetry with refined wood detailing, creating a warm yet elevated focal point. The newly renovated primary suite on the main level serves as a serene retreat, offering panoramic views of Wauseon Bay. The luxurious en-suite bath is appointed with Christopher Guy lighting, dual vanities, a freestanding soaking tub and a Schonbek Da Vinci chandelier that crowns the space. Also on the first floor are a temperature-controlled wine cellar, a well-equipped laundry room, an additional bedroom and a full bath. A graceful staircase with curved glass railings leads to the second level, highlighted by an impressive 195-square-foot feature wall clad in custom copper patinated iron. The residence also includes a private residential elevator finished with rich wood paneling and a stainless steel SICIS tile floor. The custom cinema is exceptional, showcasing eucalyptus wood millwork, an illuminated glass bar top, Busby cabinetry, generous storage, Sub-Zero appliances, dual under-counter wine refrigerators and plush seating beneath a starlit ceiling. Go onto the expansive private balcony to enjoy sunrise views over the lake, framed by glass railings and finished with AstroTurf flooring. The second floor also offers three additional bedrooms, three full baths and a second laundry room, providing comfort and flexibility for family and guests. Outdoors, the living areas are designed for relaxation and entertaining, complete with a summer kitchen and ample space to enjoy Central Florida lifestyle. For the automotive enthusiast, the three-car air-conditioned garage features RaceDeck tile flooring and a custom storage system. An exclusive respite, this home represents a refined, opulent lifestyle inside and out.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Harif Hazera Llc (407-953-9098)

Remarks: Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades. This 4-bedroom plus office, 4-bath home features a highly functional, split-floorplan layout with nearly all living space on the main floor, including the primary suite and main living areas, with one bedroom and full bath upstairs. The home has been extensively updated throughout, beginning with all new interior paint and continuing into a fully renovated kitchen with updated finishes and appliances. All four bathrooms have been completely reimagined from floor to ceiling with today’s luxury buyer in mind, creating a cohesive and elevated feel throughout the home. Attention to detail is evident in every space, from the custom built-ins in the office and family room to the all-new lighting and chandeliers installed throughout both the interior and exterior, all integrated with a Lutron system for seamless control. Sonos in-ceiling speakers have been installed throughout the home, creating a whole-home audio experience. What truly sets this home apart is its advanced energy efficiency and independence. Equipped with a Tesla solar system, multiple Powerwalls and electricity backup, the home is designed to operate seamlessly even during outages while significantly reducing long-term energy costs. With the ability to sell excess power back to the grid and the convenience of EV charging at the ready, this is a rare blend of luxury and forward-thinking functionality. The primary suite offers a private retreat with French doors leading to the lanai, ample space for a sitting area, and a spa-inspired bath with dual vanities, soaking tub, walk-in shower, and generous closet space. Secondary bedrooms are well-positioned with direct bath access, providing both comfort and functionality. Outdoor living is equally impressive, featuring a screened pool and an expansive covered lanai designed for both relaxation and entertaining. The rear patio is equipped with an outdoor refrigerator, sink, and TV, creating the perfect setting for year-round enjoyment. The home is also equipped with a Ring security camera system covering the exterior. Ideally located directly across from The Golden Bear Club members' driving range from the front, with golf course views to the rear, this home also provides access to Keene’s Pointe amenities, such as parks and playgrounds, including community boat ramp to Lake Burden, and access to the Butler Chain of Lakes for recreation. Membership at The Golden Bear Club further allows for access to the Jack Nicklaus-designed golf course, tennis courts, fitness center, and restaurant. Residents of Keene's Pointe enjoy a lifestyle that blends privacy, recreation, and convenience, all just minutes from the world's best theme parks and entertainment, Winter Garden Village, Restaurant Row, and top-rated schools. This is a rare opportunity to own a fully updated, energy-efficient custom home in Keene’s Pointe that truly stands apart from the rest. Furniture designed specifically for the home is negotiable, offering a potential turnkey opportunity for the next owner.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Donna Calhoun (407-329-6253)

Remarks: Opportunities like this in Windermere rarely reach the open market and are often treasured for generations.Welcome to an extraordinary lakefront estate in the highly coveted community of Kelso on Lake Butler, where timeless architecture, unmatched privacy and the ultimate Florida lifestyle come together on over 2 pristine acres along the shores of private Lake Davis. This sprawling custom one-story estate offers almost 4000 square feet of thoughtfully designed living space with breathtaking sunset views, a private sandy shoreline,private boat ramp and covered boat dock on Lake Davis. Residents of Kelso on Lake Butler also enjoy exclusive access to a private community boat ramp, fishing pier and park on the world-renowned Butler Chain of Lakes,connecting you to 13 interconnected ski lakes and more than 5,000 acres of recreational paradise just moments from your front door. From the moment you arrive, the heavily landscaped grounds,massive brick paver driveway,lush tropical landscaping & mature oak trees create a commanding first impression.Oversized double entry doors open to soaring 14-foot ceilings and an incredible open-concept living space designed for both grand entertaining and everyday comfort.The impressive great room (34x25) is anchored by a dramatic wall of custom built-ins, stunning stonework and an electric fireplace that creates an incredible focal point. The chef’s kitchen is equally spectacular,featuring an oversized gathering island,separate Sub-Zero refrigerator and freezer,custom cabinetry and a showstopping Wolf freestanding range,vented hood and pot filler.This space was designed to bring people together and will quickly become the centerpiece of every gathering. The owner’s retreat is a true private sanctuary , massive custom walk-in closet with additional full sized W & D, massive spa and secluded outdoor shower. On the opposite side of the home, a bonus/flex room leads to an additional ensuite bedroom and two oversized secondary bedrooms connected by a Jack and Jill bath provide exceptional privacy and flexibility for family and guests. A secondary garage exit also allows this area to easily be converted into an in law suite. One of the home’s most captivating features is the massive pocketing glass wall that completely opens the interior to the enormous covered & screened lanai, creating a seamless indoor-outdoor living experience. Tongue & groove ceilings,a summer kitchen and panoramic lake views transform this space into the ultimate entertaining destination.Every evening feels special as you enjoy postcard-worthy sunsets over Lake Davis from the comfort of your own backyard. Additional highlights include a climate-controlled garage,irrigation sourced directly from the lake for reduced waterbill &a durable metal roof designed for decades of drama free ownership. Kelso on Lake Butler is one of Windermere’s most sought-after luxury lakefront communities,known for its canopy oak-lined streets,estate homes and unmatched access to the Butler Chain of Lakes.Tucked away in one of Windermere’s best-kept secrets,yet only minutes from top-rated schools, dining, shopping and major attractions,this location perfectly balances tranquility and convenience. This is more than a home,it is a rare legacy property and a true unicorn opportunity in the Windermere luxury real estate market. Opportunities like this are few and far between.Do not miss your chance to own one of Central Florida’s most special lakefront estates.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Ronald Ziolkowski (407-592-7653)

Remarks: Under contract-accepting backup offers. Discover the charm of the Town of Windermere, Tree City USA, where the sparkling lakes, mature tree canopies, and a quaint ambiance create an exceptional place to call home. Deeply committed to preserving its character while embracing thoughtful cultural progress, Windermere offers a vibrant community filled with playful events. Nestled within the town proper and the gates of Lake Crescent Reserve, this freshly painted, custom 4018 sf home rests on pristine a 1.06 acre lot, showcasing an outdoor oasis. Designed for seamless indoor-outdoor living, this home also features an impressive 1100 sf flex suite with a private entrance, full kitchen, sliding doors to the pool. This area is ideal for a pool party or game area, multigenerational living, private office and work area, fitness center, or other creative space that best suits your needs. From the moment you enter, you’re welcomed into the family room featuring the vaulted ceilings, a wondrous wood-burning fireplace and wet bar conveniently located by the sliding pocket doors to the pool and outdoor entertaining spaces. Overlooking a privately landscaped yard with a new firepit, this home invites you to the perfect balance of year-round entertaining and peaceful retreat, where indoor comfort meets outdoor beauty in effortless harmony. Thoughtful home design is exhibited by a split floor plan, providing flexible spaces for separate conversations, play areas, multigenerational living, or large, scale entertaining. The spacious, well-appointed kitchen features a large eat-in area, SubZero refrigerator, quartz and granite countertops, wood cabinetry, and a center island with a cooktop and countertop eating. The owner’s suite offers a luxurious, recently updated en-suite and generous walk-in closet. Take advantage of the flex-space opportunities, which include the 1100 sf private entrance suite and the expansive second-floor loft with natural light from skylights. Notable upgrades include a Gerard stone-coated metal roof, resurfaced pool, re-sealed patio deck, and oversized septic leach field. Additional features include two water heaters, three-zone HVAC, vaulted family room ceiling, a large, covered lanai with retractable sunscreens on those days you prefer a little shade, and two outdoor kitchen plumbing access points for future expansion of the outdoor living space. Located within the Town of Windermere, residents enjoy exclusive amenities, including access to tennis courts, boat ramps to the various lakes, events, food truck night, farmers market, art and holiday special events, and other exclusive Town of Windermere residents-only events, to mention a few. The recently approved project to enhance the already meaningful community, involves the development of the Windermere Ward Trail and pedestrian bridge to provide safe and convenient access for pedestrians, bicyclists, and golf carts, to safely connect to local recreational areas, businesses, and government.

Listing is courtesy of: REVEL REALTY LLC (407-876-6448)

Listing Agent: Christa Dinallo (561-702-2112)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details! This expansive two-story residence offers beautifully connected gathering spaces, multiple private retreats, and flexible rooms that adapt to your lifestyle. As you arrive, a welcoming entry and foyer set the tone for the home’s inviting layout. Just off the entrance, a dedicated office provides the ideal work-from-home space, library, or quiet study. Beyond the foyer, the floor plan opens into a spacious formal living room that creates a warm first impression and offers a natural transition into the heart of the home. At the center of the first floor, the kitchen is perfectly positioned for both daily life and entertaining, complete with a walk-in pantry, a generously sized island for seating, and a seamless connection to a separate dining room, providing an elegant setting for holidays, celebrations, and dinner parties. Natural lighting streams through multiple windows in the breakfast nook, which overlooks the outdoor living area, offering the perfect spot for casual morning coffee or relaxed meals. The family room creates an open concept gathering space where conversation flows effortlessly and allows for easy entertaining. A thoughtfully placed half bath with access to the outdoor patio area adds easy accessibility for guests and family alike, and the attached garage offers convenient parking and direct entry into the living space, enhancing both functionality and comfort. Upstairs, the home continues to impress with a thoughtfully designed second floor. The private primary suite is a true retreat, featuring generous proportions, multiple closet spaces, and a spa-inspired bath designed for relaxation. Two bedrooms provide comfort and privacy for siblings and share a Jack and Jill bathroom. An additional bedroom is ideal for family or guests with access to a covered balcony, creating a private outdoor escape to enjoy Florida evenings. A spacious flex room offers endless possibilities to create a home theater, game room, fitness studio, second office, or guest retreat to fit your needs. Completing the upper level is a third full bathroom with a walk-in shower and a laundry room, adding everyday convenience right where you need it most. Step outside to one of the home’s standout features, an oversized covered lanai and expansive brick-paver patio designed for true Florida outdoor living. Ample space for multiple seating and dining areas, this private backyard retreat is ideal for entertaining, weekend gatherings, outdoor dining, or simply relaxing under the shade of mature trees. Lush landscaping, privacy fencing, and natural greenery create a peaceful setting with room to enjoy year-round outdoor living. Residents enjoy a beautifully designed central gathering area featuring the community’s amenity center, resort-style pool, basketball court, playground, expansive open green space, and connected sidewalks for walking. The location is convenient, with nearby shopping, dining, and everyday essentials just minutes away at Westside Shoppes, Lakeside Village, and Windermere Village, plus additional retail and dining options throughout the surrounding Windermere area.

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Kathryn West (321-277-1999)

Remarks: Under contract-accepting backup offers. Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect blend of elegance and modern convenience. Home Features: • Total 4 suites Bedrooms, 5 Baths, a Gym & a Office. • 3 spacious suites on the first floor. • 1 converted in-law suite on the second floor. • Dedicated office space for work-from-home convenience. • 3 Car garage with a huge driveway/ parking. • Open-Concept Living with high-end finishes throughout including plantation shutters. Home also features a whole Home Water Filtration System. • Gourmet Kitchen: • Expansive granite island with seating. • Built-in appliances & wine bar. • Double-door dishwasher & trash compactor. • Touchless faucet & instant filtered boiling water. • Natural gas cooktop & pantry. Recent Replacements: • New Gas Water Heater (November 2024). • New Roof (September 2023). • Fairly New Air Conditioning Units (September/2019). Outdoor Oasis – Perfect for Entertaining! • Lanai with unobstructed picture screen for breathtaking views. • Heated pool with built-in bench & jets. • Full Summer Kitchen: • Ice maker, dishwasher, BBQ grill. • Hibachi Japanese grill & pizza oven. • Built-in Gas Fire Pit – perfect for cozy evenings • 5-Person Infrared Jacuzzi Sauna. • Outdoor Bath & Shower for convenience. Prime Location & Community Perks: • A-rated school zone. • Close to theme parks, fine dining, and shopping. • Keene’s Pointe Amenities: • Guarded gate, parks, trails, and clubhouse. • Optional Membership to The Golden Bear Club: • Championship golf course, tennis courts, gym, pool, restaurant & more. Stop searching—this home has it all! Experience luxury, privacy, and resort-style living in one of Windermere’s most exclusive communities. Schedule your private showing today! ****Feel free to Text Listing Agent asking the video of the property****

Listing is courtesy of: QUATTRO R E SOLUTIONS LLC (407-929-6120)

Listing Agent: Stella Freeman (407-285-1281)

Remarks: One or more photo(s) has been virtually staged. "HUGE PRICE REDUCTION" - Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized loft—ideal for a secondary living area, media room, or playroom. The owner’s suite is conveniently located on the first floor, providing privacy and easy access, one bedroom can be used as an office located in the first floor, while the remaining three bedrooms are upstairs, offering ample space for family or guests.Step inside to soaring high ceilings and luxurious travertine tile flooring that flows throughout the main living areas on the first floor, creating a seamless and elegant look. The master bedroom is carpeted for added warmth and comfort.The gourmet kitchen overlooks the open-concept living and dining spaces, making it perfect for entertaining. From the living area, step out onto the covered lanai, ideal for year-round outdoor enjoyment. The fenced backyard provides a secure and private retreat with room for pets, play, or future swimming pool or outdoor enhancements. New roof was just replaced (June 2025), new AC units replaced in 2023. Laundry room with cabinetry and utility sink. Residents of Keenes Pointe enjoy access to world-class amenities including The Golden Bear Club featuring a Jack Nicklaus-designed golf course, clubhouse, dining, fitness center, and lakeside parks. The community is zoned for top-rated schools and is conveniently located near Windermere, Winter Garden Village, major highways, and theme parks.

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Cynthia Noto (407-782-1878)

Remarks: Under contract-accepting backup offers. Set on an expansive, nearly half-acre lot and located just a short walk from Downtown Windermere, this brand-new construction residence delivers a level of space, design, and presence that is rarely found in Windermere. Framed by a large driveway and a three-car garage, the home makes an immediate impression before you even step inside. Through the grand double-door entry, you’re welcomed by a striking stone feature wall with LED backlighting, setting the tone for the refined design carried throughout. The main living area is both warm and beautiful, highlighted by rich wood beams, custom built-in shelving, and a statement wall anchored by a sleek electric fireplace. At the heart of the home, the chef’s kitchen is as functional as it is beautiful, featuring an oversized quartz island, a hidden walk-in pantry, and a full suite of Thermador appliances, including a paneled refrigerator for a seamless, custom look. The space flows effortlessly into the lanai through a wall of pocketing sliders, blurring the line between indoor and outdoor living. Just off the kitchen, the formal dining room makes a statement of its own with detailed millwork and a stunning wine wall that adds both style and sophistication. The primary suite is a true retreat, offering generous proportions and refined detailing, including custom millwork with soft LED uplighting. The spa-inspired bath features dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large custom closet. Also on the main level, a dedicated office with a substantial built-in provides a private and polished workspace. Upstairs, the home continues to impress with four additional bedrooms, along with a flex space that can serve as a fifth bedroom or second office. A sprawling bonus/game room anchors the upper level, complete with its own fireplace and a large island with bar seating. Outdoors is where this property truly sets itself apart. Rare for Windermere, the nearly half-acre homesite offers an extraordinary backyard framed by mature trees, creating both privacy and a sense of nature. The expansive covered lanai is equipped with a full summer kitchen, perfect for year-round entertaining. Beyond, a beautifully designed lap pool and spa are complemented by a dedicated deck area ideal for a fire pit or lounge seating, creating a resort-style environment that is almost impossible to replicate in this location. With its combination of walkability to Downtown Windermere, oversized lot, and thoughtfully curated architecture, this home represents a rare opportunity to own a truly exceptional new home in one of Central Florida’s most desirable areas.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Nestled within the exclusive enclave of Estancia at Windermere, this exceptional custom pool residence offers the perfect blend of sophisticated design, luxury finishes, and timeless Florida living. Built in 2019 and situated on a professionally landscaped homesite, this stunning two-story estate spans over 4,230 square feet of thoughtfully designed living space with 5 bedrooms and 5 bathrooms. The elegant interior showcases soaring ceilings, expansive living spaces, and a bright open-concept floor plan designed for both everyday comfort and grand-scale entertaining. A gourmet chef's kitchen serves as the heart of the home, featuring an oversized center island, premium built-in appliances, wine refrigerator, custom cabinetry, and generous gathering areas. The luxurious first-floor primary suite offers a private retreat with a spacious bedroom, spa-inspired bath, and oversized walk-in closet. Additional highlights include a dedicated office/den, formal dining room, loft-style secondary living area, media/flex space, oversized laundry room, and abundant storage throughout. High ceilings, designer finishes, custom window treatments, and expansive sliding glass doors enhance the home's sophisticated ambiance. Outdoor living is equally impressive. The resort-style backyard was designed for entertaining and relaxation, featuring a covered lanai, Travertine pool deck, sparkling heated pool, outdoor kitchen, grill station, and a fully fenced private backyard surrounded by mature landscaping. The three-car garage, concrete tile roof, and covered front porch further complement the home's exceptional curb appeal. This property has been upgraded with a $70,000 whole-home solar energy system and automatic backup generator. Whether lowering monthly energy expenses or maintaining power during storms and outages, this home is designed to deliver exceptional reliability, efficiency, and convenience. Located just minutes from charming downtown Windermere, residents enjoy one of Central Florida's most desirable luxury communities known for its tree-lined streets, lakeside setting, upscale estates, highly rated schools, and proximity to world-class golf, dining, shopping, and entertainment. Convenient access to the Butler Chain of Lakes, premier private schools, major highways, and the attractions of the Orlando area make this location as desirable as the home itself. Estancia offers an intimate luxury neighborhood atmosphere with beautifully maintained grounds and estate-sized homesites that provide both privacy and prestige. This extraordinary residence delivers the ultimate Windermere lifestyle—where luxury, comfort, and convenient living come together in one remarkable home.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Move-in ready! Situated in the Windermere community of Providence, this home offers spacious living across two floors. Upon entering, you are greeted by the formal living and dining rooms. The family room is open to the kitchen for easy entertaining. The primary suite along with three other bedrooms are on the first floor. On the second floor, there is a large loft with full bathroom and private guest bedroom. The 5 bedroom home scans over 3,500 Sq Ft and sits on 0.21 acres. The private, fenced backyard features a screened patio accessible by the primary suite and family room. Providence features a community pool, playground and sidewalks throughout offering scenic vistas whether you are jogging, walking your dog or strolling to take in the fresh Florida air.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Toni Cafferty (904-449-2184)

Remarks: Welcome to one of the lowest-priced single-family home in the highly desirable Summerport community in Windermere. This well-maintained home features 4 bedrooms, 3.5 baths, a formal dining room, a private office, and a versatile loft/bonus space. Recent updates include a new roof (2021), fresh interior paint, and two new HVAC units (2023). The open-concept layout offers a spacious kitchen with 42” maple cabinets, granite countertops, tile backsplash, and stainless-steel appliances with a natural gas range, flowing into the family room with high ceilings. A formal dining room and private office with French doors add flexibility. The first-floor primary suite includes wood flooring, a large walk-in closet, dual sink granite vanities, garden tub, and separate shower. Upstairs features an en-suite bedroom, two additional bedrooms, a full bath, and a loft. Spacious Indoor laundry room with a sink and additional storage for those trips to Costco. Enjoy the screened and covered lanai, perfect for outdoor living. Amenities include a resort-style pool, playgrounds, parks, beach volleyball, tennis and basketball courts, and a scenic pier overlooking the community lake. Conveniently located within 5 minutes of top-rated public schools, this home also offers easy access to everyday essentials and local favorites—just a short bike ride to Foxtail Coffee and Kelly’s Ice Cream, with multiple Publix locations nearby and quick access to the Winter Garden Village, major highways (SR 429, Turnpike, SR 408), and downtown Winter Garden. Lovingly maintained and offered as the sellers relocate to be closer to family.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Carmen Aridas (407-299-6942)

Remarks: Showcasing Central Florida’s most iconic lakefront estate: an 18-acre compound with 614 feet of pristine frontage on Lake Down on The Butler Chain of Lakes. The Windy Ridge Estate is comprised of multiple buildings spanning 51,000 square feet of space including an expansive 20,333 square-foot Georgian-style Plantation mansion that is a showplace residence with generous luxurious spaces, classic elegance, and the ultimate in security and serenity. 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 provide 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. The vast and open water location offers an ideal space for seaplane arrivals and departures. 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 Southern grandeur, lakefront serenity, and equestrian potential—without any interference of an HOA. Truly a legacy compound crafted for those who demand the extraordinary.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: Under contract-accepting backup offers. Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and 5 baths, lives large at 3751 sq ft (4936 total), and is ideally situated on pristine shoreline frontage with some of the lake’s most expansive water views. Showcasing fine craftsmanship and opulent elegance in every detail, Chalet du Lac serves up a host of amenities ideal for Florida lakeside living. At the entry, the handcrafted metal and glass doors open to a stunning foyer, capturing sensational pool and lake views from the formal living room. A distinctive formal dining area and generous study greet, then to the large great room overlooking the pool oasis and lake. The kitchen features new appliances, a gas cooktop, a luxurious ogee edged stone island with farmhouse sink plus a huge walk-in pantry. A built-in Miele espresso machine as well as a beverage cooler and even more cabinet space. The primary suite features his and her walk-in custom closets, luxurious spa tub, spacious walk-in shower, oversized double vanities, and an inviting bedroom lounge that opens to the pool area. Poolside, enjoy the elevated patio over the lake, along with Lakeside, the boathouse includes an electric boat lift, with the entire dock made of composite decking, accessed by the walkway dressed with a nautical balustrade. Evenings are enjoyed at the poolside outdoor kitchen and patio, complete with a fireplace to sit by while taking in the moonlight. Verdant, lush landscaping fosters relaxation and inspires reflection and rejuvenation. Lake Sawyer is both a water sports paradise and a prime opportunity for pristine Florida lakefront living. Lake Sawyer features a certified competition water ski slalom course for those who love to ski and is even home to a float plane on the lake. At the north end, Lake Sawyer connects to Little Lake Sawyer, availing more beautiful water to explore. Chalet du Lac is ideally situated with immediate proximity to Windermere Prep and Windermere High School, and only minutes from downtown Windermere, downtown Winter Garden, Walt Disney World and the world-famous attractions of Orlando.

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Drew Ross (407-383-6497)

Remarks: Welcome to 13936 Eden Isle Blvd, where comfort, space, and modern updates come together in one of Windermere’s desirable and sought after gated communities - Eden Isle. Step into a fresh chapter of elevated living with this beautifully updated 4-bedroom, bonus room, 3.5-bathroom residence offering approximately 2,675 square feet of thoughtfully designed living space. The open and functional floor plan creates the perfect balance for both everyday living and effortless entertaining. The first floor features a seamless flow between the kitchen, dining, and living areas, all enhanced by a blend of vinyl and tile flooring. The sleek kitchen showcases stainless-steel appliances, generous counter space, and brand-new cabinetry with elegant granite countertops, creating a stylish and functional centerpiece of the home. Upstairs, three well-proportioned bedrooms, including a secondary suite, offer comfort, privacy, and a versatile layout ideal for family or guests. The upper level provides a bright and functional living arrangement designed for everyday convenience. The spacious primary suite is located on the main level and features dual vanities, a separate shower, and generous closet space, creating a relaxing private retreat. A versatile bonus room located near the entry adds exceptional flexibility—ideal as a home office, media room, playroom, or additional lounge space. A first-floor laundry room adds everyday convenience, while the attached two-car garage and extended driveway provide ample parking. Recent upgrades include a new roof (2021), downstairs A/C unit replacement (2021), new water heater (2024), new exterior paint (April – May 2026), new carpet fully replaced upstairs and in the downstairs primary suite creating a fresh and cohesive interior feel (April – May 2026), and full kitchen and bathroom cabinetry upgrades with granite countertops (April – May 2026), delivering both style and long-term peace of mind. Outdoor living is just as inviting, with front and back porches perfect for morning coffee or evening relaxation, all set within a well-maintained community environment. Perfectly positioned in Windermere, known for its A-rated schools. The residents from Eden Isle Community enjoy gated security, a private boat dock with canal access to Lake Speer, and a prime location just outside the Summerport shopping plaza and Publix. You’re also minutes from Winter Garden Village, top-rated schools, grocery stores, dining, and major conveniences. This move-in-ready Windermere home delivers the ideal combination of location, upgrades, and lifestyle—an opportunity not to be missed. Schedule your showing today.

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.

Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)

Listing Agent: Bruce Higgins (407-883-2728)

Remarks: Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is offering up to a $25,000 closing cost credit, providing added flexibility and value for buyers. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.

Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)

Listing Agent: Frank Smith (401-644-4762)