Refine Search
Sort by
12418 Park Avenue, 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

713 Main Street, Windermere
$1,999,000
6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
SIGNIFICANT PRICE IMPROVEMENT! Come 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. Pool Possibility! The accompanying video has been digitally altered to illustrate what the property could look like with a pool added. The property currently does not include a pool; however, there is potential to add one....

713 Main Street, Windermere

4226 Downeast Lane, Windermere
$9,250,000
34786 Zip Code
NEW 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

4415 Blue Major Drive, Windermere
$779,900
5 Beds ⋅ 3 Baths ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code
This beautiful move-in-ready two-story home in the highly desirable Summerport community of Windermere offers an exceptional combination of renovated interiors, versatile living spaces, and resort-style amenities. The renovated kitchen features brand-new gray travertine countertops, a natural gas range, stainless-steel appliances, a coffee and wine station, and a large center island with breakfast bar. Both upstairs bathrooms have also been renovated with Galaxy stone from floor to ceiling, and one includes a high-tech self-flushing toilet. Fresh neutral paint, added recessed lighting downstairs, luxury vinyl flooring in the main living areas, recently replaced upstairs flooring, and abundant natural light enhance the home’s modern appeal. The upstairs theater is designed for memorable movie nights and entertaining, with four cinema chairs and an oversized 9-foot projection screen. Sliding glass doors open to a screened lanai and gazebo, while the beautifully maintained lawn, landscaping, and private backyard create an inviting setting for outdoor dining, entertaining, and relaxation. The open floor plan includes a dramatic cathedral ceiling, spacious family room, kitchen, and dinette area. Four bedrooms and two full bathrooms are located upstairs. The fifth bedroom is downstairs and has direct access to the third full bathroom, making it ideal for guests, multigenerational living, or a home office. The primary suite includes an enormous walk-in closet and en-suite bathroom with a double-bowl vanity, private water closet, soaking tub, and separate shower. The garage includes a new independent ductless mini-split air-conditioning system and is currently configured as a music studio and recording/TV production space. It can easily be adapted for storage, a gym, workshop, recreation area, or additional creative space. Two newer air-conditioning units were installed in 2021 and June 2022. The roof was replaced in September 2023 and includes a lifetime warranty. The water heater was replaced on October 18, 2026, and remains under warranty. The seller is a medical professional relocating due to a hospital transfer. Summerport amenities include a clubhouse, oversized pool, tennis and pickleball courts, basketball courts, fitness room, and walking and jogging paths. The home is conveniently located near top-rated schools, shopping, dining, Disney attractions, Downtown Orlando, and Orlando International Airport.

4415 Blue Major Drive, Windermere

1361 Whitney Isles Drive, Windermere
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Whitney Isles/Belmere Ph 02 SubDv. ⋅ 34786 Zip Code
Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated, this home features new flooring, a kitchen, bathrooms, and both interior and exterior paint, perfectly combining technology, comfort, and sophistication. The integrated sound system extends throughout the house, while the gourmet kitchen impresses with a ceramic range, built-in refrigerator, quartz countertops, and LED lighting. Motorized cabinets, a built-in oven and microwave, a large pantry, and a sink with a glass washer complete this space designed for culinary enthusiasts. Also, a state-of-the-art whole-house water filtration system is installed at the main water line, treating all the water that enters the house. A newly constructed deck is ready for the installation of an oversized jacuzzi, with all plumbing already in place. Additional features such as touch-activated LED stair lighting and vitrified epoxy-coated garage flooring further elevate the living experience. The home offers spacious, bright, and contemporary living areas. The family room, filled with natural light, opens directly to the outdoor area, creating a seamless connection between indoor and garden spaces. The expansive and elegant kitchen serves as the heart of the home, ideal for family gatherings around the central island. The master suite is a true private retreat, offering serene garden views and a luxurious bathroom featuring a soaking tub, the perfect spot to unwind after a long day. The outdoor area provides a tranquil and inviting setting, ideal for family gatherings or moments of peace surrounded by nature. The outdoor kitchen also provides a 6-burner gas stove, gas grill, sink, and a mini refrigerator.

1361 Whitney Isles Drive, Windermere

8724 Peachtree Park Court, Windermere
$800,000
4 Beds ⋅ 4 Baths ⋅ Peachtree Park SubDv. ⋅ 34786 Zip Code
Recent price adjustment creates a compelling opportunity in Peachtree Park, a boutique Windermere community of just 28 homes located across from Walt Disney World. This Ashton Woods Bimini model offers 4 bedrooms, 3.5 baths, a private office, formal dining room, upstairs loft, and thoughtfully designed living spaces throughout. Highlights include wood flooring on the first level, a gourmet kitchen with quartz countertops, butler’s pantry with wine cooler, custom breakfast-nook seating, and a spacious primary suite with a custom walk-in closet. Outdoor living is a standout feature, with more than 1,000 sq. ft. of decking under screen enclosure, overlooking a peaceful pond and wooded backdrop. A rare combination of privacy, space, upgrades, and location in one of Windermere’s most distinctive communities. Schedule your private showing today.

8724 Peachtree Park Court, Windermere

1516 Hempel Avenue, Windermere
$595,000
Gotha Town SubDv. ⋅ 34786 Zip Code
Vacant Land – ½ Acre in Windermere - Property is zoned R-CE with Variance to allow construction of single family! Build your dream home or secure a smart investment in one of Central Florida’s most highly desired communities—Windermere! Spacious ½ acre lot with endless possibilities Prime location in the heart of Windermere Surrounded by A+ rated schools Easy access to shopping, dining, and major highways Rare opportunity in a highly desirable area Development plans available with owner approval. Small structure in back. Whether you’re ready to design your forever home, invest for future growth, or simply hold in a market with limited inventory, this property delivers unmatched potential in a location that buyers seek out year after year.

1516 Hempel Avenue, Windermere

Usa, Windermere
$900,000
34786 Zip Code
VALUE-ADDED Rare Opportunity to Own a Thriving, Well-Established Business! This is your chance to step into a business with an incredible 42-year legacy, serving Florida’s theme parks, luxury hotels, financial institutions, major corporations, and affluent residents both locally and beyond. With 51 years of combined service to Disney and Universal, this custom art framing company has built a reputation as a trusted leader in the industry. The business specializes in custom art framing, offering services such as shadow boxing, mirroring, linen and fabric matting, French matting, textile arts, document and archival framing, and sports memorabilia. It excels in handling unique shapes and oversized framing projects, with over 1,000 frame options available on-site and access to hundreds more. Located in an upscale area of Southwest Orange County, Florida, this business is perfectly positioned to attract a high-end clientele. No prior experience is necessary, as comprehensive training is available for the new owner. The sale includes all essential equipment and some inventory, making it a turnkey operation. Both 110 and 220 amp service in the workshop. This is also an excellent opportunity for EB-5 or E-1 visa applicants, offering a solid foundation for long-term success. Whether you’re an entrepreneur looking for a profitable venture or an investor seeking a business with untapped growth potential, this is a rare opportunity to own a well-established and highly respected company. Don’t miss out on this exceptional chance—contact us today to learn more!

Usa, Windermere

11923 Lake Butler Boulevard, Windermere
$1,630,000
3 Beds ⋅ 2 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code
Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!

11923 Lake Butler Boulevard, Windermere

How much is your home worth?

Get instant property value now!