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105 Forest Street, Windermere
$900,000
Windermere Town SubDv. ⋅ 34786 Zip Code
Build Your Dream Home in the Heart of Downtown Windermere! An incredible opportunity awaits on this desirable 0.38-acre corner lot with NO HOA, perfectly situated in the charming heart of Downtown Windermere! This exceptional vacant homesite offers a fantastic head start toward building your dream home, with approved building plans included in the sale, along with completed septic and well permits. Enjoy the perfect combination of small-town charm, outdoor recreation, and everyday convenience in one of Central Florida's most sought-after communities. Embrace the wonderful Windermere lifestyle with access to several resident-only parks featuring playgrounds, picnic and barbecue areas, beach volleyball, tennis, and frisbee golf. For those who love being on the water, launch your boat onto Lake Bessie, Lake Butler, or the renowned Butler Chain of Lakes and enjoy endless opportunities for boating, fishing, and soaking up the Florida sunshine. Just a leisurely stroll away, picturesque Downtown Windermere offers charming boutique shops, a variety of dining options, and a welcoming community atmosphere. Enjoy local favorites such as the weekly Farmers Market, Food Truck Nights, and seasonal events that bring the community together throughout the year. For additional shopping, dining, and entertainment, The Grove Orlando and Winter Garden Village at Fowler Groves are just a short drive away, featuring an impressive selection of popular retailers and restaurants. Rarely does an opportunity like this come along! With its prime downtown location, generous corner lot, no HOA, and the added convenience of approved building plans and completed septic and well permits, this property provides an exceptional opportunity to bring your vision to life. Build the home you've always dreamed of and experience the very best of the Windermere lifestyle!

105 Forest Street, Windermere

12422 Park Avenue, Windermere
$8,695,000
Chaine Du Lac SubDv. ⋅ 34786 Zip Code
WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities over 2 parcels with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of Lake Butler among the famed Butler Chain of Lakes, within one of Windermere’s most desirable communities - Chaine Du Lac – this exclusive homesite truly has it all. The gates within the gates that this property offers ensure that the estate that is built here will boast both privacy and security. With over 200 feet of lake frontage and amazing water views you will get to enjoy all of the beauty, nature and wildlife that Florida lake living has to offer. There is a Brazilian hardwood boat dock that leads out over the lake and includes a 2000SF observation deck, boat and jet ski hoist. The property also features private launch access for your personal watercraft and a 3’ concrete seawall. The opportunities to build your dreams into reality are limitless. Schedule your showing today!

12422 Park Avenue, Windermere

11544 Willow Gardens Drive, Windermere
$1,000,000
Willows At Lake Rhea Ph 03 SubDv. ⋅ 34786 Zip Code
Rare Waterfront Estate Opportunity in Windermere. Discover an exceptional opportunity to build your dream home on over 2.72 acres in the Willows at Lake Rhea community. This remarkable homesite offers approximately 150 feet of lake frontage and breathtaking water views from every angle. Enjoy the serenity of Lake Rhea in your backyard and a private pond in the front, creating a truly unique and picturesque setting. The property is enhanced by a 25-foot conservation buffer to the south, providing added privacy, while substantial brick privacy walls along the north and west boundaries further contribute to the estate-like atmosphere. Opportunities like this are seldom available—experience the setting in person to fully appreciate its beauty, privacy, and potential.

11544 Willow Gardens Drive, Windermere

1661 Roberts Landing Road, Windermere
$549,900
Roberts Landing SubDv. ⋅ 34786 Zip Code
Location, Location, Location!! Windermere Lot: 2.62 acres, with 1 acre buildable, for an incredible luxury designer estate with partial water views of Lake Olivia and a stream. NO HOA REQUIRED! Bring your custom builder. When you see this land, you will admire the beauty of nature. Gorgeous conservation views and spacious areas between the homes in the community. Nestled in the heart of Central Florida, the city of Windermere, FL, is a charming lakeside town boasting a rich history, luxurious real estate, and an exceptional quality of life. With easy access to Orlando's world-famous attractions, Windermere, Florida, offers the perfect balance between serene lakeside living and vibrant city life. Top-rated schools, fine dining, shopping, world-class golf, theme parks, and quick access to major expressways. Roberts Landing in Windermere, FL, is located on the east shore of Lake Olivia. The main entrance is on Westover Roberts Road across from Westover Club and Westover Reserve, two other Windermere, FL, communities. The streets here are winding and well-shaded, like most mature Windermere communities. Lake Olivia in north Windermere, FL, is a private lake. This rare lot in Windermere is an incredible opportunity. Build the luxury estate of your dreams.

1661 Roberts Landing Road, Windermere

13125 Filly Court, Windermere
$825,000
Farms SubDv. ⋅ 34786 Zip Code
A Once In A Lifetime Opportunity to build your dream home in the heart of Windermere within a Private, Equestrian-Friendly Community * The Farms in Windermere consists of 14 larger than 1 Acre Homesites * Flanked by nearly 11 acres of Fully Fenced and Manicured Pasture and Riding Field, Stables, 2 Spring Fed Ponds and Towering Oaks providing shade for the Lucky Horses that make The Farms their Home * This homesite is over 199 feet wide and 243 feet deep offering plenty of room to create a 1 story home that will meet every family’s wants & desires * If you have a Multi-Generational Family then you will find there is plenty of room for a large Inlaw Suite or ADU (Accessory Dwelling Unit) * If you are a Car Collector there is plenty of room for a Large Garage or RV Building * Having The Stables & Pasture directly next door offers a rare opportunity to have a “Farm” without the expensive maintenance or driving miles to a boarding facility * Bring Your Own Builder to Create Your Dream Home or Use The HOA Approved & Fully Engineered Plans the Owners have available saving precious time and expense * A unique chance to craft a one-of-a-kind estate in one of Windermere’s most desirable communities.

13125 Filly Court, Windermere

10948 Down Park Lane, Windermere
$1,499,000
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

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

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

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

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