Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie.
Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere. Imagine waking up to shimmering water views, paddle-boarding before breakfast, and ending each day with sunsets that paint the sky—this is everyday life at 311 E 8th Avenue.
Tucked within one of Central Florida’s most desirable communities, this home offers unmatched privacy, no HOA, and timeless design with modern updates. A screened front porch sets a relaxed tone, leading into an open floor plan that blends comfort and sophistication. The chef’s kitchen with stainless steel appliances, natural gas range, and custom cabinetry opens to sunlit gathering spaces that overlook the lake, creating an effortless flow for entertaining.
A cozy fireplace anchors the dining area, framed by windows with views of the koi pond and rock waterfall. Two main-floor ensuite bedrooms provide convenience for family or guests, while the upstairs primary suite feels like a private sanctuary with panoramic views of Lake Bessie and Isleworth Golf Course, a spa-inspired bath, and a spacious walk-in closet.
Outside, life slows down. Start your mornings lakeside with coffee and birdsong, spend afternoons fishing or paddle-boarding from your own shoreline, and wind down by the firepit under the stars. Recent updates—50-year architectural roof, Carrier AC units, new flooring, water softener, updated drain field, and fresh paint inside and out—offer peace of mind for years to come.
Here, every day feels like a getaway. Windermere’s golf cart-friendly lifestyle puts you steps from weekly farmers markets, local cafés, food truck Fridays, and the Butler Chain of Lakes. Zoned for top-rated schools and only minutes from Winter Garden, Dr. Phillips, and Disney, this rare property blends luxury, lifestyle, and lakefront living in one unforgettable home.
Your lakefront story begins here. Schedule your private tour today. One or more pictures are virtually staged.
Discover exceptional value and refined Florida living in this updated Longwood home located in the sought-after Highland Hills community with no HOA. Thoughtfully maintained and improved, this residence offers a compelling blend of modern upgrades, open living spaces, and an expansive fenced backyard ideal for today’s buyers seeking comfort, flexibility, and long-term value in Seminole County.
Inside, vaulted ceilings and abundant natural light enhance the home’s open layout, creating a bright and welcoming atmosphere for everyday living and entertaining. The spacious living room features a wood-burning fireplace, built-in shelving, and sliding glass doors that open to a screened patio overlooking the oversized backyard perfect for pets, gardening, outdoor dining, or planning a future pool.
Recent major system upgrades provide peace of mind, including a NEW HVAC system and ductwork, NEW water heater, and NEW privacy fencing, reflecting the home’s strong condition and ongoing care. The split floor plan offers versatility with a comfortable primary suite and two additional bedrooms well suited for guests, a home office, or hobby space. Enjoy the freedom of no HOA restrictions and a central Longwood location with convenient access to SR-434, I-4, Orlando, parks, trails, shopping, and dining. Zoned for highly rated Seminole County schools, this property presents a standout opportunity for buyers seeking an updated home in a prime, established neighborhood.
If you’ve been searching for a Longwood home that combines meaningful upgrades, generous outdoor space, and lifestyle convenience, this Highland Hills property is ready for its next owner. Schedule your private showing today.
Luxury Orlando Condo for Sale – Prime Location Near Universal Studios!
Discover this beautifully renovated 2-bedroom, 2 and one-half-bathroom luxury condo in one of Central Orlando’s most sought-after communities! This spacious, light-filled home features dual ensuite bedrooms, a private balcony with serene creek views, and a screened-in patio overlooking lush tropical landscaping—perfect for relaxing or entertaining.
Enjoy modern upgrades throughout, including fresh interior paint, newer HVAC system, energy-efficient water heater, and updated electrical panel (2021). The building also boasts a new roof and siding (2024) for added peace of mind. In-unit washer and dryer included for your convenience!
Experience low maintenance living with an HOA that covers water, sewer, trash, exterior maintenance, pest control, pool service, and high-speed internet. Indulge in resort-style amenities such as two sparkling swimming pools, tennis courts, and a clubhouse ideal for social gatherings.
Located just minutes from Universal Studios Orlando, Mall at Millenia, I-4, and top-rated restaurants, this condo offers unbeatable access to Orlando’s best attractions, shopping, and dining. Whether you're a first-time buyer, investor, or looking for a vacation home, this property delivers the perfect blend of comfort, convenience, and lifestyle.
Schedule your private showing today and make this stunning Orlando condo your new home!
One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental | Downtown Windermere | Lake Bessie.
Now offered at an exceptional value, this rare luxury lakefront rental in Downtown Windermere delivers the ultimate Florida lifestyle for relocating executives and discerning families. Set on the shores of Lake Bessie, this beautifully renovated residence blends refined comfort, privacy, and unmatched walkability in one of Central Florida’s most sought-after communities.
Wake up to panoramic lake and golf course views, unwind on the screened porch, or enjoy evenings by the fireplace and dedicated fire-pit area. The landscaped backyard oasis features a tranquil koi pond and access to lake activities including paddle-boarding and kayaking a true retreat rarely available as a rental.
Inside, the open-concept layout showcases a chef’s kitchen with gas range, custom cabinetry, and premium finishes ideal for entertaining or everyday living. Two first-floor ensuite bedrooms provide flexible options for guests or home offices, while the second-floor primary suite offers a private sanctuary with sweeping lake views.
Located in Windermere’s golf-cart-friendly downtown, residents enjoy weekly farmers markets, food truck nights, top-rated schools, and charming tree-lined streets, all just minutes from Orlando’s business districts and world-class Disney and Universal attractions.
Highlights Include: Prime Downtown Windermere location, Renovated luxury interiors, Exceptional outdoor living and entertaining spaces, Ideal executive and relocation rental. This is more than a rental it’s a lifestyle opportunity. Schedule your private showing today and experience why Windermere continues to attract executives seeking luxury, convenience, and community.
STELLAR / Coldwell Banker Realty / Karen O'Neil
Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere. Imagine waking up to shimmering water views, paddle-boarding before breakfast, and ending each day with sunsets that paint the sky—this is everyday life at 311 E 8th Avenue.
Tucked within one of Central Florida’s most desirable communities, this home offers unmatched privacy, no HOA, and timeless design with modern updates. A screened front porch sets a relaxed tone, leading into an open floor plan that blends comfort and sophistication. The chef’s kitchen with stainless steel appliances, natural gas range, and custom cabinetry opens to sunlit gathering spaces that overlook the lake, creating an effortless flow for entertaining.
A cozy fireplace anchors the dining area, framed by windows with views of the koi pond and rock waterfall. Two main-floor ensuite bedrooms provide convenience for family or guests, while the upstairs primary suite feels like a private sanctuary with panoramic views of Lake Bessie and Isleworth Golf Course, a spa-inspired bath, and a spacious walk-in closet.
Outside, life slows down. Start your mornings lakeside with coffee and birdsong, spend afternoons fishing or paddle-boarding from your own shoreline, and wind down by the firepit under the stars. Recent updates—50-year architectural roof, Carrier AC units, new flooring, water softener, updated drain field, and fresh paint inside and out—offer peace of mind for years to come.
Here, every day feels like a getaway. Windermere’s golf cart-friendly lifestyle puts you steps from weekly farmers markets, local cafés, food truck Fridays, and the Butler Chain of Lakes. Zoned for top-rated schools and only minutes from Winter Garden, Dr. Phillips, and Disney, this rare property blends luxury, lifestyle, and lakefront living in one unforgettable home.
Your lakefront story begins here. Schedule your private tour today. One or more pictures are virtually staged.