Windermere Homes with Olympia High High school

Windermere Homes with Olympia High High school

Welcome to Windermere, Florida – a charming town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its serene lakes, lush greenery, and stunning sunsets, Windermere offers a tranquil escape from the hustle and bustle of city life while still being conveniently located near the excitement of Orlando.

The town is renowned for its exceptional quality of life, making it an ideal place for families and professionals alike. One of the standout features of Windermere is its proximity to Olympia High School, a top-rated educational institution that prides itself on academic excellence and a wide range of extracurricular activities. Parents can rest easy knowing their children have access to a supportive learning environment just a stone's throw away from home.

Real estate in Windermere boasts a variety of options, from charming single-family homes to luxurious estates, catering to diverse tastes and budgets. Many properties are situated in family-friendly neighborhoods, complete with parks, walking trails, and community amenities that foster connection and outdoor enjoyment.

Living in Windermere means embracing a lifestyle filled with outdoor adventures, from boating on the pristine lakes to exploring the scenic trails. The town’s quaint downtown area features delightful shops, cozy cafes, and restaurants that serve up delicious cuisine, creating a warm, inviting atmosphere for residents and visitors alike.

Discover the magic of Windermere, where beautiful homes, excellent schools, and a close-knit community come together to create the perfect place to call home. Come experience the charm of Windermere, where every day feels like a vacation!

Newest Windermere Homes with Olympia High High school

6 Beds ⋅ 9 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe Drive, Windermere

1 Beds ⋅ 1 Baths ⋅ Marsh Sub SubDv. ⋅ 34786 Zip Code

Pro pics coming soon * Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Mature Oak Trees * The covered porches on the front and rear offer additional spaces to entertain, watch nature or read your favorite book while you slow down and truly experience the "Old Windermere" lifestyle * Home has been lovingly maintained and will impress even the most finicky Buyer * Don't miss this rare opportunity * Must see inside to really appreciate the home

628 Forest Street, Windermere

3 Beds ⋅ 2 Baths ⋅ Marsh Sub SubDv. ⋅ 34786 Zip Code

Professional Pics Coming Soon - They say Good Things Come in Small Packages & This Proves It * Must see this Gem to really appreciate the craftsmanship and attention to detail throughout * Completely renovated in 2020 & 2023, this exceptional Windermere property seamlessly blends timeless character with modern luxury, offering thoughtfully designed spaces, quality finishes, and an impressive level of care in every detail. From the beautifully appointed kitchen featuring Kitchenaid Fridge, Miele Dishwasher, Kitchenaid Gas Range, to the versatile in-law apartment with Sub Zero Double Drawer Fridge, every aspect of this home has been designed for comfort, functionality, and effortless Florida living * Everything was improved, the Roof, AO Smith Water Heater, Septic, A/C, Hardwood Flooring, Tile * Fireplace * Natural Gas * 1 Block from the Boat Ramp to Lake Butler and the Chain of Lakes * Downtown Windermere offers many fun events and the New Frescos Italian Restaurant, Dixie Cafe' and the Windermere Brewery are just a few places you can walk to get a great meal * Mature Landscaping and Oak Trees * 2 Covered Carports for Boat or Auto * Storage Shed with Electric provides ample room for a workshop * Book your Private Tour Now

611 Butler Street, Windermere

Windermere Town Rep SubDv. ⋅ 34786 Zip Code

A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone. Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas and county water already available. With no HOA, you have the freedom to design and build exactly the home you envision. Just a short walk to downtown shops, restaurants, and community events, this homesite combines small-town charm with unbeatable convenience. Opportunities like this don't last long — bring your builder and make it yours! Lots approx. 100' x 167'. Lots 19-22: $650,000 each | Lot 18: $700,000 | Lot 29: $750,000 | Lot 30: $800,000. Multiple offers on lots 29 & 30. Highest and best by Friday, 9/18 at 5:00 pm.

618 Ridgewood Drive, Windermere

5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere

5 Beds ⋅ 4 Baths ⋅ Down Point Sub SubDv. ⋅ 34786 Zip Code

Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.

4301 Down Point Lane, Windermere

4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 158 feet wide and one of four being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. LOT 4 IS ALSO AVAILABLE AT THIS SAME PRICE. OTHER PRICING FOR LOTS 2 and 3 AVAILABLE BY REQUEST. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

2 Beds ⋅ 1 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code

Opportunity awaits at 9764 Gotha Road! This 2-bedroom, 1-bathroom home offers 1,216 square feet of living space, a private fenced yard, and NO HOA. Whether you're searching for a place to call home or looking to add another property to your investment portfolio, this home offers plenty of flexibility and potential. Inside, you'll find tile throughout the main living areas and hardwood flooring in both bedrooms. The converted garage provides additional flex space that can be utilized as a home office, game room, workout area, hobby space, or bonus room, with the laundry conveniently located within the space. Enjoy the outdoors from the screened front patio or take advantage of the wood privacy-fenced yard with room to entertain, garden, or create your own outdoor retreat. The property is serviced by a private well and septic system, features a gas water heater, and best of all-no HOA restrictions or monthly HOA fees. Located in the established Gotha area with convenient access to shopping, dining, major roadways, and surrounding Central Florida communities, this property presents an opportunity for homeowners and investors alike. Bring your vision and see the possibilities 9764 Gotha Road has to offer. Schedule your private showing today!

9764 Gotha Road, Windermere

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 215 feet wide and one of three being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 175 feet wide and one of three being carved out of a larger compound to create an extraordinary and private home site being offered for the first time. No time frame to build, no HOA approval, and a convenient location in East Windermere, bypassing downtown Windermere traffic. A rare find indeed. *Seller unified parcels after purchase. Parcel ID reflects entire estate but only the lot noted by solid white lines is being offered for this price.

Windy Ridge Road, Windermere

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

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