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Windermere Homes For Sale, Condos For Sale Over $1,000,000 & Orlando Real Estate

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10014 Park Ridge Gotha Rd Windermere, FL 34786

$2,200,000 - 5Br/6Ba -  for Sale in Windermere Rural Neighborhood, Windermere
Open House
$2,200,000
5 Beds
5.5 Baths
8,114 SqFt
Status Active
MLS # O5708749
Property Type Single Family Residence
One of the prettiest property settings in Windermere, this privately gated estate home rests on nearly five acres surrounded by a canopy of gorgeous oaks. Enjoy the privacy and serenity of this amazing location with equestrian amenities of fenced pastures, paddocks, tack room and 7 stall stable. Greeted by the stone exterior, wrapped porches and stately columns, this home has an abundance of custom features that showcase elegance and warmth that will make you feel at home. From the grand staircase with wrought iron rail and designer light fixtures, stone fireplace and stone kitchen hearth, herringbone ceilings and wood beams, dual laundry rooms and plentiful closets, this home is a blend of perfection. A remarkable chefs kitchen awaits with 48” natural gas range, full size refrigerator and freezer, warming drawer, custom cabinetry, walk in pantry, island and wine storage. Journey into the master suite featuring a tray ceiling, walnut floors and a beautifully finished bathroom. Continue to enjoy the high quality of living as you walk through this spacious home with of 8114SF that has just been painted inside and out. The heart of this home is the open floor plan of the family room, breakfast nook and kitchen where everyone is sure to gather. The breezeway provides access to even more living space that is limitless and overlooks the pool and spa. Whether you have horses or not, this property is picturesque and relaxing with its ideal location. Listing is for 2 parcels-1.69 and 3.04 total of 4.73 acres

316 Palm St Windermere, FL 34786

$1,339,000
2 Beds
2 Baths
1,022 SqFt
Status Active
MLS # O5705714
Property Type Single Family Residence
Wouldn't you like to have this view from your home in the heart of Historic Olde Windermere? This western exposure offers the most spectacular views and sunsets that the entire family can enjoy! Located on The Butler Chain, Florida's Outstanding Waterways which consist of 11 interconnecting pristine lakes ideal for all water sports, fishing, skiing and swimming! This location is only a short walk to downtown Windermere, a small town with lots of charm, offering year-round activities and a weekly Farmer's Market! Parks, tennis courts and playgrounds are also a part of this charming town. Put your roots down in this very special community as you will not want to leave! Located among 2500 residents and easy access to major roadways, schools, golf courses, fine dining and shopping, along with Disney and other area attractions! Don't let this pass you by because this is only one of approximately three remaining on this Chain of Lakes.

12202 Park Ave Windermere, FL 34786

$5,200,000
3 Beds
4 Baths
5,162 SqFt
Status Active
MLS # O5702966
Property Type Single Family Residence
Extraordinary and private Lake Butler estate with 3.24 acres of manicured grounds, 314 ft lake shoreline (226 ft across), a sprawling custom single story residence on double lot with detached 4-car garage, separate pool house and mammoth 50x19ft swimming pool, sandy beach and landing area plus concrete seawall, and grandfathered double boat house with garage doors featuring an enclosed sitting room with docking pier that cannot be duplicated. Welcome to “Architectural Digest’s House of the Year 1987”. Set behind its own private gates inside the gated Chaine Du Lac neighborhood in Windermere, this spectacular residence offers the luxury of a secured community without being subject to HOA restrictions. A brick paver drive winds beneath the towering grandfather oaks and past manicured grounds with lush landscaping to reveal an expansive Mid-century modern home built with brick and an abundance of glass, featuring large open gathering spaces within its 5,162 sq feet. A massive great room is perfect for family gatherings or large events. The sprawling enclosed screened patio with summer kitchen will be a favorite spot for entertaining. This is one of the largest parcels on Windermere’s signature Lake Butler. And because of zoning changes, this enclosed boathouse with 3-boat garage lifts with motorized doors, separate sitting room, docking or fishing pier, and jet ski lift space cannot be replicated. Whole-home generator. Opportunities like this are rare indeed. A private retreat with so many possibilities.

31 Pine St Windermere, FL 34786

$1,049,900
3 Beds
3 Baths
2,460 SqFt
Status Active
MLS # O5571132
Property Type Single Family Residence
Beautifully finished and updated this lakefront home is located on Wassean Bay of the famed Butler Chain of Lakes. The welcoming entry and foyer extend to the formal living and dining areas boasting wood flooring and stunning lakefront vistas. The large windows bring natural light and elegance to the family areas. A private study/office just off the entry allows for quiet pursuits. In the gourmet kitchen paneled cabinetry and solid surface countertops contribute to the thoroughly modern feel, featuring stainless steel appliances, custom built cabinetry, stone flooring, and granite countertops. The kitchen opens naturally to the spacious family living areas. The outdoor covered lanai is extends to the huge rear yard, perfect for entertaining family and friends. Views of the pool, with the backdrop of gorgeous water views and beautiful oak trees, can be seen from all the family areas. Paved roads directly from 2nd Avenue directly to your home.

4207 Isabella Cir Windermere, FL 34786

$1,545,000
5 Beds
7 Baths
5,355 SqFt
Status Active
MLS # O5568007
Property Type Single Family Residence
Stunning Toll Brothers Villa Milano floor plan home located in the gated community of Casabella at Windermere. Set on a 1/2 acre home site with water view, this luxury home features a grand two-story foyer leading into the formal living room with an expansive curved window wall and coffered 23' ceilings. The open gourmet kitchen with a large center island, Sub-Zero and Wolf appliances, and granite countertops adjoins the expanded family room and breakfast area that is great for entertaining. An elegant master suite with dual walk in closets, and exercise area and spa style bath reside on the first floor. Completing the first floor is a 2-story formal dining room, study, and en-suite guest room. Upstairs features a second master suite with a covered balcony, a loft overlooking the living room and two additional en-suite bedrooms. Casabella at Windermere is zoned for A rated schools and is conveniently located minutes from Winter Garden Village and major roadways.

533 Ridgewood Dr Windermere, FL 34786

$1,998,000
3 Beds
3.5 Baths
3,162 SqFt
Status Active
MLS # O5563788
Property Type Single Family Residence
We proudly present this ONE-OF-A-KIND custom-built home by Wyatt Anderson, a primo local builder. The gourmet cook had a special kitchen package designed, which includes a pass-through pantry just for the kitchen. All rooms are large for comfort, and ease of entertainment, plus three fireplaces FLR, FDR and in the superb and large master suite. Popular hardwood floors throughout and a metal roof the smart trend in today’s roofs, plus more upgrades. The sloping lot is over-sized and leads down to pristine Lake Down of the famed Butler Chain of Lakes. The boathouse is huge for all of the water toys. A full list of upgrades and other is included in attachments.

92 Pine St Windermere, FL 34786

$1,299,000
5 Beds
4.5 Baths
4,684 SqFt
Status Active
MLS # S4856525
Property Type Single Family Residence
Private tranquil and peaceful lake front property, A beautiful family home, situated on almost 3/4 s of an acre and located in the heart of olde windermere, in one of the most picturesque of settings on one of the most desirable paved streets in the olde town, with almost 150 feet on the water on a private secluded cove, almost like having your own private marina on the butler chain , mature trees,lots of space, fenced & gated, with a boat dock & a double floating jet sk iplatform . Enjoy taking walks to the local park that is only a couple of hundred yards from the property or the boutique shops & cafes located in the Olde town of windermere, For reference, All of the bedrooms in the house are upstairs.

1111 Oakdale St Windermere, FL 34786

$2,195,000
4 Beds
4.5 Baths
5,018 SqFt
Status Active
MLS # O5562328
Property Type Single Family Residence
Start living the Windermere lakefront lifestyle you've always dreamed of... An entertainer's dream, this open and airy custom-built home is in immaculate, like new condition. Save the expense of renovating or time of building new! Enjoy sweeping lake views from virtually every room. Painting has been refreshed with transitional tones, new air conditioning, pool pump and spa heater. Lake Bessie's private 170 acres offers endless hours of skiing and fishing fun. Rarely available is an oversized fenced backyard. Featuring generously sized living and family areas, a master bedroom and additional ensuite bedroom downstairs and two ensuite bedrooms upstairs, the home’s functionality will not disappoint. Upstairs is a large office with custom built ins, theater game room with wet bar and access to balcony. Exquisite custom finishes -- travertine and hardwood floors, top of the line kitchen; spa like master bath experience; oversized sliding glass walls emphasize this special location's beauty and make for a truly memorable Florida outdoor experience. Outdoor amenities include lanai, pool and spa with privacy wall, outdoor fireplace and summer kitchen. Whole home sound system, lightening and surge protection systems. You will love the convenience, charm, low taxes and no HOA fees that Downtown Windermere offers. Welcome yourself home to enjoy this exceptional lifestyle with A rated schools. View virtual tour for more photos!

1319 Estancia Woods Loop Windermere, FL 34786

$1,024,000
5 Beds
6.5 Baths
5,603 SqFt
Status Active
MLS # O5561989
Property Type Single Family Residence
UNDER CONSTRUCTION. The Treviso is a spacious home with exquisite features and options. It gracefully blends formal areas such as a separate dining room and dramatic two-story living room with casual spaces including an open plan kitchen with island and walk-in pantry, eating nook and inviting family room. The master retreat has its own wing downstairs for ultimate privacy. Upstairs are secondary bedrooms, open lofts and a game room. Popular options include a second owner’s suite with extended covered balcony, outdoor kitchen and media room. Builder warranty! (Disclaimer: some or all photos are stock photos or rendering of home.)

4326 Isabella Cir Windermere, FL 34786

$2,495,000
5 Beds
7 Baths
5,441 SqFt
Status Active
MLS # O5560515
Property Type Single Family Residence
AVAILABLE - THE VILLA MILANO AT CASABELLA AT WINDERMERE - TOLL BROTHERS LUXURY GATED COMMUNITY IN UPSCALE WINDERMERE. Offering only 79 single family homes on half-acre home sites. Conveniently located to first class golf courses, world famous attractions, and the Butler Chain of Lakes. The award-winning Villa Milano Mediterranean model has impressed our home buyers and visitors and is now ready to welcome home its new owner, after a short term lease back, to the half-acre corner waterfront home site with clear views of the water and fountain, with designer appointed features in 5441 sq. ft. of gracious living space. Many beautiful custom embellishments, a dramatic 2 story entry foyer, living room with curved glass wall and custom window treatments, gourmet kitchen with built-in Sub Zero and Wolf stainless steel appliances, luxurious stone and wood floors, custom designed coffered ceilings and built-ins. A spacious family room with casual dining leads to the covered lanai and an exciting outdoor living area complete with summer kitchen, gas fireplace, TV and separate fire pit. The resort style pool has a lazy river feel with palm tree island and spa overlooking the pond and water fountain. Luxuriate in the master suite overlooking the sparkling pool, then retreat to the private spa style bath with separate water closets, an inviting garden tub and separate shower. So many beautiful appointments to behold.

9575 Westover Roberts Rd Windermere, FL 34786

$2,750,000
8 Beds
8 Baths
8,464 SqFt
Status Active
MLS # O5552133
Property Type Single Family Residence
Bella Olivia... Majestic Mediterranean Windermere Lakefront Masterpiece. This home will please all of your home needs. 8,464 sq ft, 8 Beds, 8 baths, 2 master suites, 2 Guest Apartments, 6 car garage, pool and spa, summer kitchen, lake front with a Boat Dock on over 5 Acres without an HOA!! As you approach this private estate you will be welcomed by your own private gates, a gorgeous water fountain and elegant driveway. As you enter the wrought iron 10 ft. doors giving you a true sense of arrival. The granite and travertine floors are sure to “wow” the pickiest of buyers. As you enter into the family living area you will pass the under stair wine storage. The Coffered ceilings and beautiful natural wood beams and stone wrapped gas fireplace in the family room give you a true sense of quality finishes to be expected on your tour. The kitchen has been finished with custom cabinetry and top of the line stainless steel appliances. The master suite has hardwood floors with beautifully finished tray ceiling with 7 ¼ in triple crown molding. The master bath has been finished with the finest travertine and granite throughout. This home is truly built for entertaining with a game room, theatre, huge lanai, pool and spa, summer kitchen you can expect to create many memories here. Welcome to “Bella Olivia”. Please see virtual tours for pictures, too many details to list.

235 Magnolia St Windermere, FL 34786

$1,180,000
4 Beds
2 Baths
2,461 SqFt
Status Active
MLS # O5544005
Property Type Single Family Residence
Rare opportunity to own on the Butler Chain of Lakes! Designated as a Florida Outstanding Waterway, the Butler Chain of Lakes is comprised of 13 interconnecting lakes and 32 navigable canals that make up over 5,000 acres of surface water! This fabulous piece of property features magnificent expansive views of Lake Down to enjoy eagles, osprey, and otters in their natural habitat or enjoy the lake life boating from the dock and grandfathered boathouse! This unique mid century mediterranean style home has fantastic architectural features and is a blank canvas to make it your own! The double arched entry way with iron gates welcome you to the breezeway leading to the beautiful wood double doors. The home features 4 bedrooms and 2 baths with a huge living room/great room, dining room and oversized entry foyer featuring slate flooring. Be sure to not miss the push button light switches! The views from the kitchen/family room are breathtaking and invite you to sit and stay awhile! If you can pull yourself away from the gorgeous views, take a stroll through the dirt streets of downtown Windermere and enjoy the Farmer's Market, monthly Food Truck Friday, visit the coffee shop, cafe, wine shop, and ice cream parlor just to name a few! Located minutes from major roads, theme parks, and restaurant row, Windermere is the perfect place to call home!
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