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$2,175,000
4 Beds ⋅ 5 Baths ⋅ Diamondhead SubDv. ⋅ 34786 Zip Code
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.

606 E 6th Avenue, Windermere
$2,249,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
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 with walkability to town, and a bike ride to Windermere Elementary. 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 shops and dining on the 500 Block. Inside, the home is both comfortable and thoughtfully updated, with travertine flooring in the main living areas and new luxury vinyl plank in two bedrooms —no carpet. The kitchen features a gas cooktop with vented exhaust, a new Dacor refrigerator and a newer all-in-one convection oven, microwave, and air fryer. The large dining room provides a pleasurable dining experience with lake views. The 4th bedroom/theater room is a flexible space that can be used as a guest bedroom, theatre room, workout room or a game room. It can also work as a large office, playroom, or just a place to sit and relax with views of the lake. 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—with no HOA.

325 Magnolia Street, Windermere
$1,545,000
Lake Down Estates SubDv. ⋅ 34786 Zip Code
LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Windermere. This exceptional vacant homesite offers over 2.12 acres and is the largest buildable lot within this private gated enclave of only four estate properties, providing exceptional privacy and generous spacing between homes. The property sits along a picturesque pond with two fountains, creating a beautiful and peaceful setting for future indoor and outdoor living. With the Butler Chain of Lakes just moments away, there is potential for views of Lake Down, which is located incredibly close by. Accessed from a private gated street, this boutique community offers a unique blend of exclusivity and convenience. Located just minutes from Downtown Windermere, residents enjoy easy access to popular restaurants, cafes, shopping, hospitals, parks, farmers markets, playgrounds, and community events. This prime location is also close to top rated schools, Disney World, Universal Studios, and major highways, making it easy to access everything Central Florida has to offer. Opportunities like this are incredibly rare in Windermere. Come experience the privacy, space, and charm that this unique homesite has to offer.

10948 Down Park Lane, Windermere
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Windermere Rep SubDv. ⋅ 34786 Zip Code
CHARMING LAKEVIEW HOME IN THE HEART OF WINDERMERE! Enjoy unobstructed views of Lake Down from this beautifully located 3-bedroom, 2-bath home in the Town of Windermere. A stunning 44-foot-wide front porch provides the perfect place to relax and take in the peaceful lake scenery, morning sunrises, and evening breezes. Inside, the home offers comfortable living spaces designed for everyday living and entertaining. The backyard provides privacy and mature landscaping perfect for entertaining and family recreational activities! The property also features an impressive 33’ x 23’ oversized garage, providing abundant space for vehicles, storage, a workshop, or recreational gear. Located in the charming and highly sought-after Town of Windermere, residents enjoy a true small-town atmosphere with exceptional local amenities. Stroll or bike to nearby shopping, cozy coffee shops, wine boutiques, and the popular Windermere Brewery. The town also offers a public library, Town Hall, Windermere Police Department, multiple playgrounds, and recreation parks.Windermere is known for its strong sense of community, highlighted by the beloved weekly farmers market and a variety of town-sponsored events held throughout the year.This is a rare opportunity to enjoy lake views, generous space, and the lifestyle that makes Windermere one of Central Florida’s most desirable communities.

414 E 5th Avenue, Windermere
$910,000
3 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Fully Renovated Windermere Home. Move-In Ready! Discover 735 Oakdale St, a beautifully updated 3-bedroom, 2.5-bathroom home in the heart of Windermere Town. Over the past four years, no detail has been overlooked: new roof, new gutters, marble flooring, resurfaced pool, new fence and shed, windows, two independent HVAC systems, water filtration system, water heater, well pump, renovated bathrooms, and a striking new façade with marble ledger panel. The backyard features new concrete slabs, perfect for entertaining or relaxing. Inside, the home is filled with natural light thanks to beautiful skylights, creating a warm, inviting atmosphere. Enjoy a functional kitchen, dedicated dining room, living room with cozy fireplace and a den, along with a spacious and versatile bonus room ready to become a music room, home office, playroom, media room, or craft studio, with and additional room for extra storage. The master bedroom is conveniently located downstairs, while the other two spacious bedrooms are upstairs, one featuring a private balcony overlooking the pool and backyard, perfect for morning coffee or morning sunrises. Nestled among sparkling lakes, this home offers a serene, private feel while keeping you close to convenience: just minutes to Restaurant Row, Winter Garden Village, boat ramps, tennis courts, farmers markets, food truck nights, and Orlando’s top theme parks. Enjoy the perfect balance of calm and accessibility in a lively, welcoming community. This isn’t just a house, it’s a place to create memories, pursue a charming lifestyle, and live fully. 735 Oakdale St is ready to welcome you home.

735 Oakdale Street, Windermere
$812,000
4 Beds ⋅ 2 Baths ⋅ 34786 Zip Code
Welcome to this beautifully renovated home in highly desirable Windermere, where modern upgrades meet timeless comfort on a rare one-acre lot with NO HOA. Completely remodeled this home has been thoughtfully updated from top to bottom. Renovations include new flooring throughout, fresh interior paint, a fully redesigned kitchen, updated bathrooms, new windows, new interior doors and custom blinds. Every detail was carefully selected to create a cohesive, move-in-ready space. The kitchen shines with contemporary finishes and flows seamlessly into the main living areas — perfect for both everyday living and entertaining. Bathrooms have been stylishly updated, and custom master and coat closet provide elevated organization and storage. Enjoy true peace of mind with major system upgrades, including: • Whole-house water treatment system (2020), softener equipment updated in (2025) • Septic drain field in (2025) • Trane A/C installed (2026) • Well pump (2024) • Insulation (2021) • Balcony deck and railing (2025) Step outside to your private backyard retreat featuring a saltwater pool with electric heater, ideal for year-round enjoyment. The expansive one-acre property offers space, privacy, and endless possibilities — bring your boat, RV, or build your dream outdoor oasis. This home has been remodeled with tremendous care, offering confidence that the work has been done and done right. A rare opportunity in Windermere combining luxury updates, land, and freedom from HOA restrictions. Move-in ready. Fully upgraded. Peace of mind included.

2641 Hempel Avenue, Windermere
$2,500,000
5 Beds ⋅ 4 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees or restrictions, you have the freedom to design and build your dream home exactly as you envision it or use the plans already available and variances approved — saving you time and expense. Offering approximately 5,516 SF of impeccably appointed living space and over 8,316 SF under roof, every detail has been curated to the highest standard of elegance and sophistication. Dramatic sightlines from the grand entry sweep through sun-drenched principal rooms to the resort-caliber outdoor living spaces beyond. The showstopping gourmet kitchen dazzles with extra-thick natural quartzite countertops, an oversized center island, pot filler, a fully integrated refrigerator and dishwasher with bespoke wood-panel cabinetry, and an oversized walk-in pantry — a culinary stage worthy of the most discerning chef. A soaring great room with designer tray ceilings and an elegant formal dining room set the scene for unforgettable entertaining, complemented by a private study and home office. The first-floor primary suite is a true sanctuary — a sumptuous walk-in closet, sculptural freestanding soaking tub, and a spa-inspired shower enclosure deliver five-star hotel indulgence at home. Upstairs, a second master suite, a spectacular lake-view recreation room with oversized balcony, three additional bedrooms, a chic loft with front balcony, and a second laundry suite elevate every aspect of daily life. Outside, a breathtaking covered lanai unfolds into a private lakeside paradise — summer kitchen, outdoor fireplace, alfresco dining, and a heated pool and spa framed by elegant paver decking and the glittering expanse of Lake Sawyer. A 4-car garage with EV charging, dual laundry rooms, impact-rated windows and doors, and bespoke designer finishes complete this extraordinary offering. Minutes from Windermere Prep School, shopping, dining and within minutes of Walt Disney World. *Images have been taken from a similar model home*

6606 Sawyer Shores Lane, Windermere
$900,000
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.

4 Chase Road, Windermere
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Windermere Rep SubDv. ⋅ 34786 Zip Code
Don’t let the 1962 build date keep you from considering this 4 Bedroom 3 Bath home that received a major renovation to the Electrical, Water Heater & Bath Updates in 2016 * New HVAC 2017 and a New Roof in 2018 made obtaining low cost Tower Hill property insurance easy * in 2025 the luxurious Kitchen was updated with a Thermador Natural Gas Range & top of the line Stainless Appliances with Waterfall Porcelain Tops and all Travertine Stone Backsplash with Marble Inlay Deco Panel – This impressive Craftsman 1 story solid block home offers a very spacious and well laid out floorplan with the Primary Suite overlooking the Pool with a Private Covered Porch – The main house also has a covered porch providing 2 entertaining and BBQ options – The huge 32 x 21 Garage is the perfect setup for family vehicles, golf cart and water toys – The separate 22 x 12 pool cabana provides an inviting space for relaxation and gatherings this ultimate Man Cave or She Shed is limited to your imagination and family’s needs * This very large totally fenced private shaded lot with mature landscaping enjoys the convenience of being within walking distance or just a short golf cart ride to Charming Downtown Windermere, offering Boutique Shopping, Dining, Community Events, Award Winning Schools, Weekly Farmers Market & the Monthly Food Truck Friday Night * No HOA or dues * Oversized windows bring in Natural Light and views to the Landscaped Yard * A Public Dock and Beach on Lake Down are a short walk away, offering opportunities for Fishing, Picnics, Sunset Views, and Water Activities on the Lake Butler Chain of Lakes - a defining feature of Windermere living * With close proximity to Winter Garden Village, Restaurant Row, and all of the Area Attractions you are truly in the Heart of it All.

316 E 5th Avenue, Windermere
$8,500,000
6 Beds ⋅ 9 Baths ⋅ Down Point Sub SubDv. ⋅ 34786 Zip Code
Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudriet. The grand entry sets the tone, with a majestic staircase, a 25+ft hand-painted rotunda ceiling, and a stunning 10-ft Waterford chandelier. Every inch of this residence exudes sophistication, from the marble floors and corbels to the intricately carved fireplace mantels or even the ornate door hinges. Boasting 5 spacious bedroom suites, four with outdoor walk-outs, in the main home, complemented by a separate guest/staff apartment, this estate offers flexibility and privacy. A resort-style pool, cabana, along with a boathouse, dock and paver paths meandering through the property, create an outdoor haven for entertaining and relaxation. The guest quarters or a private office that takes in views from 3 sides. Architectural marvels abound, with handcrafted coffered ceilings, exposed wood beams, and a gourmet kitchen featuring a red brick barreled ceiling and appliances by Wolf and Sub-Zero. Hosting events is effortless with a separate full caterer's kitchen. The primary suite offers serene panoramic water views, complemented by an extraordinary dressing room and bathroom. For wine connoisseurs, a climate-controlled 3,000+ bottle wine cellar awaits. Verandas and terraces afford fresco dining, bar area and sweeping views, enhancing the outdoor experience. Work in the masterful office with birds’ eye 180-degree water views or step into the game room for a game of pool or a sunset view off the balcony. A large travertine parking area for events and a 4-car garage adds practicality to this extraordinary property. This masterpiece transcends the ordinary, offering a lifestyle of unparalleled luxury and sophistication. Seize the opportunity to make this stunning estate your own.

4200 Down Point Lane, Windermere
$725,000
Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
CANAL FRONT on LAKE SAWYER! Rare opportunity to own a cleared and ready-to-build .39-acre lot with canal frontage on Lake Sawyer (150-acre spring-fed, skiable lake in desirable Windermere). This beautiful parcel offers the perfect canvas for your dream home with direct access to one of Central Florida's most sought after recreational lakes. The property has already been cleared, with soil samples performed and variances approved for future construction. Enjoy peace of mind with a sea wall, fenced perimeter, a locked iron gate for added privacy, and front hedges that enhance the secluded feel of the lot. For boating enthusiasts, the property includes a private boat ramp, allowing for easy access to the lake. Whether you enjoy water skiing, fishing, or simply relaxing by the water, this lot provides the ultimate lakeside lifestyle. Don’t miss this rare opportunity to own prime canal-front property with lake access in one of Windermere’s most coveted areas. Easy access to 1-4, 429, Winter Garden Village, Shopping, Dining and 10 minutes to Walt Disney World. Schedule your showing today to learn more about this exceptional property!

6518 Sawyer Shores Lane, Windermere
$305,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. Step into this beautifully maintained second -floor unit in the sought-after Lakeside at Lakes of Windermere community. Ideally located Directly across from the community pool and clubhouse. Offering 1,455 square feet, this 3-bedroom, 2-bathroom home is designed for effortless Florida living—with timeless details and upscale finishes throughout. The spacious kitchen features granite countertops, ample cabinetry, and a custom walk-in pantry, while the open-concept layout seamlessly connects the living and dining areas. Relax on your screened-in balcony, overlooking the sparkling community pool. Your primary suite offers a private retreat with dual vanities, separate shower, and a custom walk-in closet. Two additional bedrooms are filled with natural light, ideal for guests or a home office. Includes appliances, new Laundry Machines (2026), new AC Condenser (2026), New Range (2026) 2 parking spaces (1 assigned + guest), and valet trash. HOA covers water, sewer, security, and amenities. Convenient Windermere location near Disney and Winter Garden Village.

8168 Boat Hook Loop Unit 207/714, Windermere
$2,895,000
4 Beds ⋅ 5 Baths ⋅ Lake Down Estates SubDv. ⋅ 34786 Zip Code
Under contract-accepting backup offers. Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.

10870 Bayshore Drive, Windermere
$710,000
3 Beds ⋅ 2 Baths ⋅ Windermere Rep SubDv. ⋅ 34786 Zip Code
Here is an opportunity to truly make this exceptional 3-bedroom, 2-bath pool home your own in the heart of Windermere. Offering 1,784 sq ft of fully renovated living space, this residence features a refined open-concept layout with high-end vinyl flooring throughout, a statement kitchen with an oversized waterfall-edge island, and a private attached office framed by custom barn doors. Set on a spacious lot, the outdoor living experience feels like a private resort with a saltwater pool, fully enclosed screened area, and an outdoor hot shower, ideal for entertaining or everyday enjoyment. Thoughtful upgrades include a brand-new roof (2025), HVAC replacement, and updated plumbing completed during renovation. The property also offers space to accommodate a boat or small RV along the side of the home with access to the Butler Chain of Lakes, and is ideally located minutes from shopping, dining, everyday conveniences, and zoned for highly rated schools within a highly desirable community.

415 E 6th Avenue, Windermere
$1,082,946
5 Beds ⋅ 4 Baths ⋅ Palms/Windermere SubDv. ⋅ 34786 Zip Code
Beautiful brand-new home at Palms at Windermere.

14342 Crest Palm Avenue, Windermere
$315,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere Ph 3 SubDv. ⋅ 34786 Zip Code
Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.

8180 Boat Hook Loop Unit 108/301, Windermere
$1,750,000
4 Beds ⋅ 6 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
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.

84 Oakdale St, Windermere
$4,395,000
Chaine Du Lac SubDv. ⋅ 34786 Zip Code
WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of gates within the gates, the property ensures exceptional privacy and security for the custom estate envisioned here. With 100 feet of direct lake frontage, the setting delivers stunning water views and front-row access to the natural beauty, wildlife, and lifestyle that define Florida lakefront living. Property offers a 3' block seawall and NO HOA. All of the benefits of a secure gated community but the freedom to build your dream without restrictions. This is a truly rare canvas to bring your vision to life in one of Central Florida’s most prestigious waterfront communities. The possibilities are as expansive as the views. Schedule your private showing today. Adjacent 1 acre lot with dock also available for sale with purchase. Additional information and pricing available upon request.

12418 Park Avenue, Windermere
$2,170,000
6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom-built, this one-owner Transitional Craftsman residence blends timeless architecture with exceptional livability, just steps from downtown's quaint lifestyle, multiple parks, weekly farmers market, tennis courts, playgrounds, and resident-only access to the Butler Chain of Lakes. From the moment you arrive, handcrafted timber details, natural stone accents, and inviting front porch creates a sense of warmth rarely found in newer construction. Inside, soaring wood ceilings, exposed pecky cypress beams, custom built-ins, and a dramatic floor-to-ceiling stone fireplace make this house both elegant and welcoming. Designed for everyday living as much as entertaining, the chef's kitchen features premium JennAir appliances, a striking stone cooking alcove, ceiling-height cabinetry, expansive island, generous walk-in pantry, and seamless connection to the dining and family rooms. The flexible floor plan offers six bedrooms and six baths, including two private owner's suites on the main level, making the home ideal for multi-generational living, long-term guests or one of many private spaces. Upstairs, 4 spacious secondary bedrooms and a large over-garage flex room provide endless possibilities as a home fitness studio, media room, hobby space, or home office. Outdoor living is equally impressive with a large covered porch, a wood-burning fireplace, outdoor kitchen, cabana bath, Tiki hut, circular fire pit, designed for year-round enjoyment. The backyard offers ample room to design the custom pool, allowing the next owner to create a backyard tailored to their lifestyle rather than inheriting someone else's design. Additional highlights include a newer roof (2024), commercial grade fire suppression, an oversized three-car garage with exceptional storage and workspace, and the opportunity to add a front gate for enhanced privacy off Main St. Storm hardy with underground electrical utility lines and public water. This is a home has been meticulously maintained and for buyers who appreciate exceptional craftsmanship, enduring quality, and the unique lifestyle that only Historic Windermere offers. Take a short stroll to the Downtown Redevelopment Project and shop at Victoria Jewelers, Ace Hardware, Solvino Wine Bar and Fresco's, one of Dr. Phillips' favorite Italian restaurants, adding even more charm and convenience to this incredible location.

713 Main Street, Windermere
$9,750,000
34786 Zip Code
DRAMATIC PRICE IMPROVEMENT on this exceptional 5+ acre Lake Down development opportunity, offering 300 feet of pristine shoreline on the coveted BUTLER CHAIN of Lakes and positioned on the best side of WINDERMERE with unmatched convenience to SR-408 and downtown Orlando. This rare parcel, zoned R-CE, allows for the creation of up to THREE luxury lakefront homes or a single premier estate compound, all while enjoying the prestige of a Windermere address with immediate access to Isleworth, Bay Hill, and downtown Windermere. The property includes an existing 5,000 sq ft home with five bedrooms, 3.1 baths, and an oversized four-car garage—ideal as a temporary residence or teardown for redevelopment. Beyond its development potential, the land itself is a natural sanctuary: mature trees and lush landscaping create a haven for native birds, passion flower vines attract vibrant butterflies, and natural Florida water plants along the shoreline provide a thriving nursery habitat for breeding wildlife and small fish. This is a rare chance for developers, CUSTOM BUILDERS or investors to deliver exceptional lakefront homes in one of Central Florida’s most desirable luxury corridors. Also listed as Residential MLS #O6355233.

4226 Downeast Lane, Windermere
$300,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Amazing apartment in an Excellent area, Luxury Condo in community of LAKESIDE at LAKES OF WINDERMERE. Gorgeous 3 bedroom / 2 bathroom on third floor over looking pond and clubhouse. Granite Counter Tops, 42" Kitchen Cabinets. Specious living room with sliding doors that lead to a beautiful screened balcony/patio area overlooking the pond and clubhouse. Large Master bedroom with a walk in closet. Corner unit with lot of light . Very convenient location, shopping, dinning and entertainment. The community offers lot of amenities, Walking trails, fitness center, pool, volleyball, Tennis and Basketball Courts. Besides the amazing schools that you have in this area, you also have a great location inside the neighborhood. This beautiful apartment has a great Elevator too. Wonderful price and Location, Location, Location

8180 Boat Hook Loop Unit 321, Windermere
$752,500
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
STOP --DON'T HESITATE! APPRAISED NOVEMBER 2025 FOR $750,000! This charming traditional cottage on one of Windermere’s signature sandy streets offers the perfect blend of nostalgia and convenience. Enjoy the timeless feel of this tranquil location just steps to the Farmers Market, Town Hall, Windermere Library, new Ace Hardware shopping plaza and family events hosted by the Town of Windermere. Set on a .38-acre lot beneath beautiful mature trees, this 3-bedroom, 2-bath home features a Brand-New Roof & Skylights (11/2025). Step inside to a vaulted-ceiling great room/kitchen with newly refinished REAL wood floors, exposed beams, and abundant natural light. A cozy adjacent living room includes built-in shelving and a double closet. The quaint kitchen offers tile and wood countertops, vintage-style paneled appliances and a nearby laundry. A separate dining room with REAL wood floors accommodates seating for eight and leads, through French doors, to a freshly updated screened rear porch with new carpeting—an ideal place to unwind. From here, new wood steps invite you into the expansive fully fenced backyard, framed by lush landscaping. The bedroom wing includes two secondary bedrooms with a shared hall bath, while the primary suite offers its own en-suite bath and French doors to a private open-air porch. Major updates support peace of mind: HVAC (May 2024), Natural Gas Water Heater (Oct 2021), Stackable Washer/Dryer (Sept 2022), Dishwasher (Aug 2019), Septic Pumped (June 2025), Exterior Paint (Jan 2024), Tree Trimming (Sept 2025), and gutters in place. A transferable termite bond is active through April 2026 and the home was re-sealed with the new roof installation. An oversized carport with a large enclosed storage/workshop room completes this picture-perfect Windermere opportunity. IF YOU BLINK THIS WILL BE GONE!

825 Oakdale Street, Windermere
$292,500
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Location, Location! Price Adjustment on this 3 bedroom 2 bathroom condo situated in highly desirable Windermere is designed for easy Florida living. Spacious open concept with a seamless flow from the living room and dinning area to your large kitchen featuring an abundance of wood cabinets, granite counters tops, pantry and stainless appliances. Master en-suite with dual vanities,bath and walk in closet. Two additional bedrooms provide plenty of additional space for guests, office,play or hobby room. Your private screened balcony is the perfect spot for morning coffee or relaxing with a book. Washer and Dryer are included and the unit is tiled throughout for easy upkeep. Property is gated with a Community pool, fitness center, playground, elevators, bike racks, beach volleyball. One assigned and one parking pass spot, water, sewer,trash,ground upkeep,amenties and 24/7 security all included in your HOA fee. Perfect property for first time buyers, snow birds, investment or anybody wishing to live a care free low maintaince Florida lifestyle. Excellent location for Disney, Winter Garden Village, Hospitals, Shopping. This unit is priced to sell, book your showing today.

11562 Amidship Lane Unit 207, Windermere
$925,000
3 Beds ⋅ 2 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Freshly remodeled and full of charm, this one-story home lives light, bright, and effortlessly easy. White oak floors flow from room to room like a warm welcome, setting the stage for airy spaces and sun-drenched corners. At the heart of the home, the family room opens wide with vaulted ceilings, a cozy fireplace, and windows that pull the outdoors in. The kitchen feels like the place everyone wants to gather, with a wraparound breakfast bar, quartz countertops, a wine fridge, and a cheerful breakfast nook that soaks in the morning light. Just beyond, a spacious dining room offers the ideal spot for long dinners, holiday celebrations, or spreading out homework and craft projects. A bonus room with plantation shutters adds an extra dash of flexibility — office, playroom, studio, you choose. The magic continues outside. French doors from the primary suite open straight to the pool, giving the whole space a resort-like feel. The oversized, solar-heated pool sits amid a lush, fenced backyard. A covered lanai waits for afternoon lounging, weekend barbecues, or quiet mornings with coffee and birdsong. Practical touches shine just as brightly, including an abundance of windows, a sunny laundry room near the primary suite, a functional open layout, and a 2-car garage offering storage and everyday convenience. Walk or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience. Move-in ready and filled with character, this home delivers a blend of comfort, beauty, and easy Florida living.

1209 Main Street, Windermere
$1,160,000
3 Beds ⋅ 2 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
CANAL FRONTAGE ON 2 SIDES! Extremely RARE in the TOWN OF WINDERMERE, a single story 3/2 in a CUL-DE-SAC, on a PAVED STREET with a DOCK and CANALS ON 2 SIDES giving DIRECT ACCESS to LAKE DOWN AND WASEON BAY and the ENTIRE BUTLER CHAIN BEYOND. This lovingly maintained home is move-in ready, ready for your personal touches, or the ideal lot for your waterfront dream home. Extensive landscaping with abundant flowering plants and a covered front porch provide a warm welcome to this spacious ranch home. A foyer divides the kitchen and living spaces from the bedroom wing. The kitchen features solid surface countertops, wood cabinets and a breakfast nook with views of Lake Down. A large formal dining room and living room offer ample space for hosting holidays and entertaining family and friends. An absolutely enormous family room with wood plantation shutters is anchored by a beautiful wood burning fireplace and views of the canals. The spacious bedrooms feature vaulted ceilings and California closet organizers. The primary suite has an en-suite bathroom and sliding doors to a large, covered patio in the rear. The primary bath and hall bath have been beautifully updated. The large rear and side yards are also heavily landscaped with wood paths, mature cypress trees and unparalleled views of the canals. There is a COVERED DOCK in the rear. This is a NATURAL GAS home with hookups for the GRILL, DRYER and TANKLESS WATER HEATER. One of the 2 car garage bays currently houses a SAUNA. ROOF REPLACED in 2019, A/C in 2016. This is what Windermere living is all about - a large cul-de-sac waterfront lot on the Butler Chain of Lakes and a short distance to the shops and events in downtown Windermere.

2 Oakdale Street, Windermere
$820,000
2 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Back on the Market. Buyer unable to secure financing. Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated. The family room feels like a cozy tale come to life with its high ceilings, original wood floors, beadboard ceiling, and brick fireplace—the kind of spot that begs for gatherings, laughter, and quiet evenings by the fire. Sunlight pours through an abundance of windows, making every corner feel warm and cheerful. A sunny dinette awaits weekend breakfasts, while the formal living room offers a refined space for hosting or unwinding. The spacious laundry room and pantry off the kitchen brings a surprising sense of ease and practicality. Outdoors, the magic continues. This charming cottage backs up to a leafy park, with no homes behind or across the street, offering a rare pocket of privacy and peaceful views. There’s room to grow — add an addition, dream up a pool, or simply enjoy the open space as it is. A detached carport and one-car garage add to the home’s quaint, functional appeal. New A/C and septic within the past 3 years. Just a short stroll down the lane, the lake awaits with glorious sunrises that feel straight out of a painting or spectacular night rocket launches. Walk or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience. A home with a heart, a history, and a touch of whimsy — ready for its next chapter.

416 Magnolia Street, Windermere
$2,200,000
5 Beds ⋅ 5 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code
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.

81 Oakdale Street, Windermere
$4,850,000
7 Beds ⋅ 8 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code
Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5.4 acres and no HOA. This private palace with brand new roof impresses with large circular paver drive, 3-tiered fountain, 10-foot iron front doors, 35-foot high ceilings, custom iron railings, and marble and travertine flooring – plus, coffered ceilings and elegant details throughout. Home has been extensively updated and lovingly cared for to highlight classic style and luxury to compliment today’s sophisticated lifestyle. The main kitchen features beautiful marble counters, three islands, two preparation sinks, custom cabinetry, and stainless appliances including two dishwashers, two microwaves, double ovens, and a Viking gas stove. The first-floor primary retreat is dressed with hardwood flooring, tray ceiling, and triple crown molding, and an exceptional bathroom with tiled shower, jetted tub, dual vanities, and expansive double closets. The main living spaces are abundant and stately with two first-floor family rooms, billiards room, living room, dining room, theater, and guest suite – upstairs is a third family room, secondary master suite, and three additional guest suites, plus a large balcony with screens. A separate entrance off the kitchen provides access to a private guest apartment with a kitchenette, family room, and bedroom. Plus, a second private apartment (978 sq feet, not included in the listed 8,931 sq feet) is accessible from the outside and is located over the 4-car garage and features family room, sink, and bedroom. Functional outdoor living space is extended to the mammoth screened enclosure to encompass a sitting area off the master and an additional family room with fireplace, tv, and full summer kitchen across the pool deck that can be separated by an electric additional privacy screen. The showstopping infinity edge pool is colossal in size and includes a sun shelf for shallow water relaxing and an infinity hot tub. Both sides of the house have all been paved with a new drainage system and ramps for easy access for boats and watercraft to Lake Olivia. The 150 ft refreshed covered dock has two cradles: currently set for a boat and two jet skis. There’s also a sitting area for lounging lakeside. Experience the best of Windermere with this lakefront retreat built for privacy, luxury, and lifestyle.

9575 Westover Roberts Road, Windermere
$862,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot for morning coffee, outdoor dining, or unwinding beneath the shade of mature trees. The island kitchen features granite countertops and generous workspace for cooking and entertaining. The first floor includes a full bedroom and bath, perfect for guests or a home office. Upstairs, the spacious primary suite offers a peaceful retreat, joined by two additional bedrooms and the convenience of a second-floor laundry room. New Septic and drain field 2020, A/C 2024, Well re-sleaved and new pump 2024. A partially air-conditioned, three-car garage provides excellent storage and space for vehicles, golf carts, or weekend adventure gear. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.

299 W 4th Avenue, Windermere
$520,000
Windermere SubDv. ⋅ 34786 Zip Code
Almost half an acre located on Main Street in the Town of Windermere

2 Chase Road, Windermere