Windermere Homes for Sale

Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities.Every detail has been considered—NEW ROOF, NEW A/C, NEW

Robert Larkan EXECUTIVE PROPERTIES

Welcome to luxury on Lake Butler Blvd with stunning Wauseon Bay views. This estate spans nearly an acre of landscaped grounds, ideal for relaxation and entertainment. The property features a secondary oversized, air-conditioned garage that could be converted into a guest suite. The main home is a custom-built residence with high ceilings, new wood flooring and expansive lake-view windows. The

Toni Marie Cafferty COMPASS FLORIDA LLC

Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina and Launch Ramp for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the

Darrell Nunnelley VINTAGE REALTY GROUP LLC

Welcome to your dream home in the heart of Windermere! This beautifully updated 4-bedroom, 4.5-bathroom residence is an entertainer’s paradise and tech-lover’s haven, offering a thoughtful blend of modern convenience and timeless charm. Step inside to discover spacious living areas, a dedicated office, and a versatile bonus room perfect for a gym, playroom, or guest suite. The expanded master

Christie Tannler COLDWELL BANKER REALTY

PRICE IMPROVEMENT *** Up to $25,000 in Buyer Closing Cost CREDIT Available with Preferred Lender! *** Inquire for further information *** Awake to awe-inspiring sunrises from this unparalleled lakefront estate on LAKE DOWN, nestled within the renowned BUTLER CHAIN of LAKES. Experience the tranquility and exclusivity of Sunset Bay without the burden of HOA fees. Upon entry, be captivated by

Ashley Boyd BHHS FLORIDA REALTY

Surrounded by glistening lakes and shaded by towering oaks, Windermere offers an unbeatable blend of natural beauty and small-town charm. Friendly neighbors, golf cart-friendly streets, and walkability to cafes, shops, parks, and a local brewery make everyday living feel like a getaway. Enjoy sandy beaches, tennis and pickleball courts, and easy access to kayaking, fishing, and boating on the

Amanda Black UPSIDE REAL ESTATE INC

One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.43-acre double lot with over 200 feet of prime shoreline on Lake Down, this

Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

Never Lived In Since Completely Remodeled and Expanded - Total of 6 Bedrooms - 5 Full Baths - 1 Pool or Guest Bath - Primary Suite & Guest Suite on 1st Floor - 4 More Bedrooms & 3 Bathrooms on 2nd Floor - Huge Bonus Room / Theatre / Game Room with Full Bathroom Over Garage - Separate Office on 1st Floor - 12 Foot Wide Folding Glass Doors Overlooking The Screened Pool & Lake Bessie - Newly

Darrell Nunnelley VINTAGE REALTY GROUP LLC

RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of downtown Windermere. Pull up into your drive of Italian laced pavers and enter into your new home through custom French doors. You will be met by 2 story open floor plan where the oversized family room overlooks an outdoor oasis. A modernized chefs kitchen where no detail has

Jay Martin CORCORAN PREMIER REALTY

Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space. From the moment you step inside, you're enveloped in elevated elegance, soaring ceilings, rich custom millwork,

Christopher Christensen COMPASS FLORIDA LLC

Absolutely stunning, crisp and clean pool home with tall ceilings and lots of land surrounding you in an amazing location! Nestled among majestic mature oaks on a private .74-acre conservation lot in quiet, highly desirable Windermere Reserve with access to the Butler Chain of Lakes. Enjoy serene views from most rooms in this rarely available community. As you enter through a canopy of trees,

Sarah Bosch THE BOSCH GROUP

Great Open Floorplan - 1 Story Ranch - Large Covered Rear Screened Porch - 4 bedrooms - 2 baths - Vaulted Ceilings - Large Fenced Lot - Located on the East side of Main Street and 1 House South of Conroy makes this home easy to get to - New Roof - Recently updated Kitchen - Tile Floors - Spacious Bedrooms - County Water - Natural Gas - Covered Parking in Backyard for Boat or RV - No HOA - Town of

Darrell Nunnelley VINTAGE REALTY GROUP LLC

Stunning Remodeled Executive Home in The Willows at Lake Rhea.Welcome to 11401 Willow Stowe Lane, a beautifully renovated 4-bedroom, 3-bath executive home located in the prestigious Windermere community of The Willows at Lake Rhea. This move-in-ready residence seamlessly blends luxury, energy efficiency, and modern upgrades—perfectly positioned in one of Central Florida’s most desirable

David Fraser KELLER WILLIAMS ADVANTAGE III

Fully renovated modern residence on a spacious 1-acre lot, featuring a brand-new contemporary kitchen with custom cabinetry, quartz countertops, and high-end appliances. This 4-bedroom home offers 4 full bathrooms, expansive living areas with soaring ceilings, and oversized porcelain tile flooring throughout.All windows and sliding doors have been replaced, bringing in natural light and

Eduardo Pavone ON ME REALTY

BUTLER CHAIN OF LAKES. Tucked away on the charming, tree-lined Oakdale Street, one of the most cherished streets in the Town of Windermere, this unique property offers a rare opportunity to enjoy lake views and quick access to Lake Down, part of the prestigious Butler Chain of Lakes, which consists of 13 interconnected, spring-fed lakes known for their clarity, beauty, and recreational lifestyle.

Tiffany Pantozzi ALIGN REAL ESTATE LLC

Prime Windermere Location! Fully Renovated and Move-In Ready!Don’t miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms—perfect for comfortable family living and entertaining.Recent Upgrades Include: Fresh interior and

Sammy Nakhleh SUNDIAL REAL ESTATE LLC

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

Michael Julian JULIAN PROPERTIES, INC.

Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a serene 1.2-acre cul-de-sac lot in the esteemed Lake Butler Estates of Windermere, Florida. This expansive 5-bedroom, 3-bathroom residence offers 2,918 square feet of thoughtfully designed living space, combining modern updates with timeless charm.The home boasts a formal living room featuring a whitewashed

Michael Julian JULIAN PROPERTIES, INC.

Gorgeous Private Lakefront Custom Brick Estate over 10,000 sq ft under roof, just under 7,000 sq ft under HVAC. First Time Ever on Market! Step thru the Gorgeous Leaded Glass Doors into this Magnificent Estate the Entry made for Royalty Custom Magnolia Curved Staircase with custom Italian Marble Flooring installed 2024. Updated Massive Chandler with Sconces lighting grace the Staircase. To the

Carolyn Cook DALTON WADE INC

Now is your chance to live "Among the Lakes"! This canal-front home includes a private boat dock with DIRECT ACCESS to the famous Butler Chain-of-Lakes! This 3BR/1.5BA home sits on an impressive .39 acre lot and is located on one of the very few paved streets in the Town of Windermere. Property features include No HOA, enormous in-ground pool (30 x 16), partially-finished 2nd floor, county water

Bill Martini BHHS FLORIDA REALTY

Welcome to Your Private Retreat in Windermere!Nestled on a tranquil 1-acre lot in an exclusive enclave of just nine homes, this beautifully upgraded residence offers the perfect blend of comfort, style and convenience yet just minutes from downtown Windermere.Step inside to discover a thoughtfully designed 4-bedroom, 3 bath home featuring a versatile bonus room ideal for a home office,

Holly Pham ZARIA REALTY GROUP LLC

LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWNUnveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakes—a residence that redefines lakefront luxury in the exclusive town of Windermere. Custom-built in 2019, this Mediterranean-inspired estate is a sanctuary of sophistication, offering unparalleled waterfront living with direct frontage

George Doulamis COMPASS FLORIDA LLC

Experience the epitome of lakefront living on the Butler Chain of Lakes with this exceptional Windermere estate. On one of the area’s desirable streets, this home offers over $350,000 of recent luxurious upgrades, including a new kitchen and fireplace, new windows and doors, landscape lighting, new landscaping, a newly painted exterior and roof. The home also boasts a newly added $85,000 dock,

Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all

Julie Bettosini STOCKWORTH REALTY GROUP

This custom built estate home in a gated private cul de sac is walking distance to Windermere Elementary. The home is nestled in the exclusive subdivision of Lake Crescent Reserve. This expansive estate, spanning over one acre, is located in the highly sought-after Town of Windermere and offers access to multiple lakes, including the prestigious Butler Chain of Lakes. This stunning 4,018 square

John Cunningham KELLER WILLIAMS CLASSIC

In one of the most desirable Windermere neighborhoods for bikers, joggers, and boaters, you will find this tastefully updated home with DEEDED PRIVATE ACCESS to the Butler Chain of Lakes! The oversized lot suitable for boat parking is incredibly private with mature oak trees, lush bamboo and solid board fencing encompassing the entire perimeter! This 4/2 features a classic layout with family

Brady Kanan KANAN REALTY LLC

Welcome to this beautiful, unique and modern home, built less than 3 years ago. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much more!!! This luxury property also has a HOA 1/24th private deeded land with lake access, dock and

Stella Freeman QUATTRO R E SOLUTIONS LLC

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,

Frank Del Toro REVEL REALTY LLC

Detached Guest Suite overlooking Pool with Fireplace has Private Entrance in Courtyard - Courtyard Pool with Waterfall from the Heated Spa has the feel of an Olde World European Resort - Formal Living Room with Fireplace - Formal Dining Room with Fireplace - Family Room with Fireplace - Large Kitchen with Wine Cellar and Pantry in the Heart of the Home has incredible views of the Pool & Lake -

Darrell Nunnelley VINTAGE REALTY GROUP LLC

Under Construction. Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor

Gustavo Bettin TALENT REALTY SOLUTIONS