Windermere FL Real Estate & Homes for Sale

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Beds:
4
Baths:
4.00
Sq.Ft.:
2,628
Status:
NEW LISTING
MLS#:
O6443170
Type:
Single Family
Subdivision:
Lake Sawyer South Ph 02
Lot size:
0.14 Acres
Year built:
2009
A broker reciprocity listing Courtesy: BUYER REBATES REALTY 407-629-2300
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ADDITIONAL INFORMATION

Welcome to this 4-bedroom, 3.5-bath home in Windermere, zoned for top-rated schools including Windermere High School and Horizon West Middle School. Located near Horizon West shopping, dining, parks, and major roadways, this Windermere pool home combines a desirable location, functional layout, and the indoor-outdoor lifestyle that buyers are searching for in Central Florida.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,264
Status:
NEW LISTING
MLS#:
G5117935
Type:
Single Family
Subdivision:
Windermere Trails
Lot size:
0.23 Acres
Year built:
2014
A broker reciprocity listing Courtesy: PREMIER SOTHEBYS INT'L REALTY 407-581-7888
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ADDITIONAL INFORMATION

Located in desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate 4 bedroom 3 1/2 bath pool home offers an exceptional combination of style, comfort and Central Florida convenience. Unwind beside your own heated saltwater pool and spa while enjoying views of the Disney fireworks. Inside, tile flooring extends throughout the home, creating a clean and cohesive look that is both attractive and easy to maintain. Fresh interior paint in 2026 enhances the bright, welcoming atmosphere. The formal dining room makes a beautiful first impression with its gorgeous coffered ceiling, providing an elegant setting for holiday dinners, celebrations and evenings w/friends. The kitchen is designed for anyone who appreciates generous workspace and exceptional storage. A substantial amount of cabinetry is complemented by expansive granite countertops, a tiled backsplash and an oversized walk-in pantry. Pendant lighting highlights the breakfast bar, creating a natural place for casual meals and conversation. Built-in stainless steel appliances and a Bosch Dacor refrigerator installed in 2022 complete this impressive space. A drinking water filtration system and a whole-house water softener add everyday convenience. The kitchen opens naturally to the spacious family room, where a stacked stone accent wall adds warmth, texture and architectural interest. Views of the pool create a beautiful backdrop and keep the indoor living areas connected to the outdoor setting. Whether hosting a crowd or enjoying a quiet evening at home, the open arrangement allows everyone to remain part of the conversation. Step outside to the heated saltwater pool and spa. With the propane heater, the pool can be enjoyed well beyond the traditional swimming season, while the space offers plenty of room for lounging, dining and entertaining. The pool filtration equipment was replaced in 2024. The thoughtfully planned 4 bedroom 3 1/2 bath layout provides flexibility for family, guests or a home office. The washer and dryer (2022) are also included. A complete Bosch HVAC system, including interior and exterior equipment, was installed in spring 2024 and carries a 10-year parts/labor warranty w/required annual maintenance. The water heater is 2019, and the exterior and tile roof were professionally power washed in 2024. An interior ADT security system and exterior CCTV camera system provide additional peace of mind. A separate 2 car (with epoxy floor in 2023 and 1 car garage epoxy 2026) provide 3 total spaces for vehicles, storage or hobbies. Just inside one of the garages, a convenient drop station features areas for phone charging, along with space for packages, bags and daily essentials. Windermere Trails offers a resort-style community pool, walking trails, playgrounds, pavilions, a dog park and fitness areas. Surrounded by the natural beauty of the Butler Chain of Lakes, the community is close to highly regarded A rated schools, Lakeside Village, Hamlin Town Center, Winter Garden Village, Horizon West and the renowned dining of Dr. Phillips. Nearby SR 429 provides convenient connections to the Turnpike, SR 408 and I-4, while Walt Disney World, Disney Springs, shopping, golf, boating, restaurants and medical services are all nearby. Beautifully maintained and ready now, this home brings together inviting interior spaces, a private pool retreat, valuable recent improvements and a location that places the best of Central Florida at your doorstep.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,557
Status:
NEW LISTING
MLS#:
O6442835
Type:
Single Family
Subdivision:
Reserve At Lake Butler Sound
Lot size:
0.34 Acres
Year built:
2004
A broker reciprocity listing Courtesy: ACME REAL ESTATE FLORIDA LLC 407-601-4958
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ADDITIONAL INFORMATION

Auction Property. A Windermere address. A 24-hour guard-gated community. A home with the scale to make a statement. Tucked along a quiet cul-de-sac in the Reserve at Lake Butler Sound, this estate offers the chance to create something exceptional in a coveted setting. Soaring ceilings, architectural columns and expansive gathering spaces give the home a sense of occasion from the moment you enter. French doors open to a screened pool retreat, setting the scene for sunlit afternoons, dinner with friends and evenings under the Florida sky. Enjoy the privacy of an established luxury neighborhood with Windermere’s dining and shopping, the Butler Chain of Lakes and Orlando’s attractions within easy reach. The setting is here. The possibilities are yours.

Beds:
6
Baths:
10.00
Sq.Ft.:
13,494
Status:
NEW LISTING
MLS#:
O6441344
Type:
Single Family
Subdivision:
Isleworth Amd 03
Lot size:
2.27 Acres
Year built:
2006
A broker reciprocity listing Courtesy: IRWIN REALTY GROUP LLC 407-739-8772
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ADDITIONAL INFORMATION

Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,681
Status:
NEW LISTING
MLS#:
O6442555
Type:
Single Family
Subdivision:
Wickham Park
Lot size:
0.14 Acres
Year built:
2012
A broker reciprocity listing Courtesy: NEWKEY REAL ESTATE LLC 321-490-3001
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ADDITIONAL INFORMATION

Welcome to this beautifully located single-story home in the highly desirable Windermere area! This 3-bedroom, 2-bath home offers 1,681 sq ft of comfortable living space with an open floor plan, stone countertops, walk-in closet, spacious living and dining areas, and an attached 2-car garage. Enjoy Florida living with a covered and screened patio, plus access to community amenities including a resort-style pool, clubhouse, playground, and sidewalks. Location is a major highlight! The home is zoned for highly rated schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School, while offering convenient access to shopping, dining, entertainment, major roadways, and everything the Windermere and Horizon West areas have to offer. Offered at $520,000, this is an excellent opportunity to own a home in one of Central Florida’s most desirable locations. Schedule your private showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,214
Status:
NEW LISTING
MLS#:
O6438323
Type:
Single Family
Subdivision:
Ashlin Park Ph 2
Lot size:
0.14 Acres
Year built:
2017
A broker reciprocity listing Courtesy: REALSOURCE PROPERTY MANGNT LLC 407-298-9777
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ADDITIONAL INFORMATION

This spacious Single-Family Home is located at the Windermere Ashlin Park, 4 bedrooms 3 full bathrooms. ?Large kitchen, bar kitchen island with basin, equipped with stainless steel appliances, closet pantry, open to breakfast nook. Family/Great room with sliding door overlooking covered patio and fenced backyard. Large laundry room with electric washer and dryer with storage cabinet. Security system installed, cable/internet distribution box . Double garage with 2 separate electric door openers. Community Pool and Club. The property is conveniently located with easy access to S.R. 535 and toll road 419. Schools, shopping areas and nearby Disney and tourist attractions.

Beds:
7
Baths:
10.00
Sq.Ft.:
8,362
Status:
NEW LISTING
MLS#:
O6443379
Type:
Single Family
Subdivision:
Keenes Pointe Unit 03 46/104
Lot size:
1.54 Acres
Year built:
2004
A broker reciprocity listing Courtesy: NOVA REAL ESTATE SERVICES INC 407-592-1744
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ADDITIONAL INFORMATION

Located directly on Lake Tibet within the guard-gated community of Keene’s Pointe, this extensively updated Stonebridge custom residence blends Mediterranean-inspired architecture with transitional interiors. A long brick-paver driveway leads to a circular motor court, porte cochère, tile roof, stone accents, and arched windows. Oversized glass entry doors frame immediate lake views and open to two-story formal living spaces featuring newly installed wood flooring, detailed ceilings, clerestory windows, and abundant natural light. The kitchen includes an oversized island, quartz countertops, glazed custom cabinetry, double ovens, premium appliances, and a walk-in pantry. Open gathering areas and expansive windows provide continuous views of Lake Tibet. Additional interior features include a game room, dedicated home theater, and a private primary suite with an oversized walk-in closet and updated bathroom. Each secondary bedroom includes an ensuite bathroom. The bathrooms have been updated, the interior has been freshly painted, and the carpeting has been replaced. A detached guest house offers additional flexible living space. Added in 2019, the covered outdoor kitchen and dining pavilion features a wood-paneled ceiling, large dining and preparation island, built-in grill, pizza oven, wine cooler, and oversized refrigerator. The outdoor area also includes a resort-style pool, heated spa, expansive lawn, sand volleyball court, and soccer area overlooking the lake. A private dock with boat lift provides direct access to Lake Tibet and the Butler Chain of Lakes.

Open House:

Saturday, 9/26 2:00-6:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
1,480
Status:
NEW LISTING
MLS#:
S5157627
Type:
Townhouse
Subdivision:
Lakes/windermere Lake Reams Twnh
Lot size:
0.06 Acres
Year built:
2013
A broker reciprocity listing Courtesy: AGENT TRUST REALTY CORPORATION 407-251-0669
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ADDITIONAL INFORMATION

LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic of Walt Disney World and located in a highly rated school zone! This beautiful 3-bedroom, 2.5-bath townhouse offers the perfect combination of location, comfort, and lifestyle, featuring a spacious and functional layout plus a private fenced backyard, ideal for relaxing, entertaining, and enjoying the Florida lifestyle. Experience a beautiful community surrounded by nature and exceptional amenities, including a community pool, playground, walking trails, scenic lakes, and lush green spaces. Conveniently located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions. Whether you’re looking for your next home or an investment opportunity in one of the Orlando area’s most sought-after locations, this is an opportunity you don’t want to miss!. LIVE IT. INVEST IN IT. LOVE WINDERMERE !!!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,750
Status:
NEW LISTING
MLS#:
O6442193
Type:
Single Family
Subdivision:
Lake Sawyer South Ph 01
Lot size:
0.21 Acres
Year built:
2007
A broker reciprocity listing Courtesy: THE SIMON SIMAAN GROUP 407-558-1396
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ADDITIONAL INFORMATION

Welcome to your beautiful corner lot home in the sought after Berkshire Park community of Windermere! Don’t miss the opportunity to own this thoughtfully designed 4 bedroom, 3.5-bath home with a bonus room and 3-car garage, offering an ideal blend of space, comfort, and functionality. Major updates include a new roof installed in 2022 and a new AC system installed in 2025, providing added peace of mind for the next owner. A brick-paver driveway and charming walkway welcome you to the inviting front porch, perfectly positioned along a quiet, tree-lined street. Step inside to a spacious foyer featuring soaring ceilings and an open, airy feel that continues throughout the main living areas. The formal dining room flows seamlessly into the open concept kitchen and family room, creating an ideal space for both everyday living and entertaining. The kitchen features a large center island, granite counters, stainless steel appliances, ample cabinetry, and a dedicated eat-in area, while the family room opens to a screened in patio overlooking the generously sized backyard making a wonderful setting for morning coffee, outdoor dining, or relaxing with family and friends. The main level owner’s suite offers convenience and privacy with dual vanities, tub, shower, and walk in closet. Your well appointed laundry room provides direct access to the spacious three-car garage. Upstairs, a versatile bonus room serves as the perfect media room, playroom, home office, or additional gathering space. Three generously sized bedrooms and two full bathrooms complete the second floor, providing plenty of room for family and guests. Residents of Berkshire Park enjoy community amenities including a beautiful neighborhood pool and playground, all within the highly desirable Windermere area. The close proximity to Disney World, shopping, restaurants, and "A" rated schools make this an unbeatable location. With its spacious floor plan, prime Windermere location, 3-car garage, newer roof, newer AC, and inviting outdoor living space makes this a home you won’t want to miss. Be sure to click on the virtual tours.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,006
Status:
NEW LISTING
MLS#:
S5157579
Type:
Single Family
Subdivision:
Vineyards Of Horizons West Phase 1b
Lot size:
0.14 Acres
Year built:
2014
A broker reciprocity listing Courtesy: MY REALTY GROUP, LLC. 786-847-7421
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ADDITIONAL INFORMATION

The best family living location! Welcome home to this fabulous 5 bedrooms, 3 full baths, 2 car garage located in the peaceful community of Vineyards in Windermere Florida. Gorgeous subdivision convenient to major roadways, A+ Rated Schools, Shopping, entertainment and so much more. Just minutes away from Walt Disney World. Spacious Master ensuite with walk-in closet. Modern Kitchen with stainless steel appliances with a gas range, granite counter tops and dark wood cabinets! Screened patio with beautiful spacious view of the large yard and conservation. Community comes with a Park/playground and community pool. Do not miss this awesome opportunity!!!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,852
Status:
NEW LISTING
MLS#:
O6435895
Type:
Single Family
Subdivision:
Belmere Village G2 48 65
Lot size:
0.15 Acres
Year built:
2003
A broker reciprocity listing Courtesy: MAINSTAY BROKERAGE LLC 800-583-2914
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ADDITIONAL INFORMATION

Virtually Staged. Welcome to this spacious 3-bedroom, 2-bathroom single-story home in the gated Belmere community of Windermere. The open floor plan provides a comfortable flow between the living spaces, with a formal living room and dining room offering flexibility for entertaining, gatherings, or everyday use. The family room features high ceilings and opens to the kitchen and breakfast area, creating a central space for relaxing and spending time together. The primary suite offers a private retreat with a walk-in closet and an ensuite bathroom featuring a garden tub, separate shower, and dual vanities. Two additional bedrooms provide comfortable space for family, guests, a home office, or other needs. A screened-in patio extends the living space outdoors and overlooks the landscaped backyard. The home also includes an attached 2-car garage and convenient interior laundry area. Belmere offers residents access to community amenities including a pool, clubhouse, fitness center, tennis courts, basketball court, and playground. Conveniently located near shopping, dining, major roadways, and Orlando-area attractions, this home offers a practical layout in a desirable Windermere community.

Beds:
1
Baths:
1.00
Sq.Ft.:
750
Status:
NEW LISTING
MLS#:
O6441329
Type:
Single Family
Subdivision:
Marsh Sub
Lot size:
0.19 Acres
Year built:
1945
A broker reciprocity listing Courtesy: VINTAGE REALTY GROUP LLC 407-217-5458
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ADDITIONAL INFORMATION

Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Whole House Natural Gas Generator keeps the lights and hot water on during all storms * 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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,774
Status:
Active
MLS#:
O6441248
Type:
Single Family
Subdivision:
Marsh Sub
Lot size:
0.19 Acres
Year built:
1940
A broker reciprocity listing Courtesy: VINTAGE REALTY GROUP LLC 407-217-5458
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ADDITIONAL INFORMATION

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

Beds:
6
Baths:
9.00
Sq.Ft.:
15,337
Status:
Active
MLS#:
O6441249
Type:
Single Family
Subdivision:
Isleworth
Lot size:
0.69 Acres
A broker reciprocity listing Courtesy: ISLEWORTH REALTY LLC 407-909-9000
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,919
Status:
Active
MLS#:
O6441184
Type:
Townhouse
Subdivision:
Carrington
Lot size:
0.06 Acres
Year built:
2014
A broker reciprocity listing Courtesy: KARDOSH REALTY 407-499-4466
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ADDITIONAL INFORMATION

Welcome to 12333 Via Derna Pl, a beautifully updated townhome located in the highly desirable Carrington community of Windermere. Offering 1,919 sq. ft. of living space, this spacious 3-bedroom, 2.5-bath home features a bright open-concept floor plan designed for both comfortable everyday living and entertaining. Recent updates to the family room, kitchen, and shared bathroom give the home a fresh, modern feel, while abundant natural light creates a warm and inviting atmosphere throughout. The property is also EV-ready, with infrastructure already in place for an electric vehicle charger. Ideally located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions, this move-in-ready home offers an excellent combination of location, space, and modern convenience. The Tesla charger and window curtains are not included in the listing price but may be negotiated separately. Schedule your private showing and discover everything this Windermere home has to offer!

Beds:
5
Baths:
7.00
Sq.Ft.:
5,747
Status:
Active
MLS#:
O6439814
Type:
Single Family
Subdivision:
Keenes Pointe
Lot size:
0.4 Acres
Year built:
2003
A broker reciprocity listing Courtesy: STOCKWORTH REALTY GROUP 407-909-5900
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ADDITIONAL INFORMATION

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

Beds:
5
Baths:
7.00
Sq.Ft.:
5,667
Status:
Active
MLS#:
O6440385
Type:
Single Family
Subdivision:
Bellaria
Lot size:
0.76 Acres
Year built:
2014
A broker reciprocity listing Courtesy: MAXLIFE REALTY LLC 321-373-3536
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ADDITIONAL INFORMATION

BELLARIA ESTATE. Toll Brothers-built Spanish/Mediterranean estate on a 0.76-acre homesite in Bellaria, Windermere's 64-home, 24-hour guard-gated enclave off Lake Butler Road. Built in 2014 and offering 5 bedrooms, 6 baths, 1 office, and 5,667 sq ft across two stories, with block-and-stucco construction, a tile roof, and mature, tree-lined landscaping framing a paver drive and 3-car garage. LIVING SPACES. The plan is designed around everyday living and entertaining alike, with generous formal and casual gathering areas, an open kitchen at the heart of the home, and a first-floor primary suite. Upstairs, the secondary bedrooms and bonus space give family and guests room of their own. OUTDOOR LIVING. Out back, the covered lanai opens to a heated pool and spa with a full summer kitchen, all set against the privacy of the oversized lot, a true year-round Florida outdoor room. LOCATION. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and minutes to Winter Garden Village, Downtown Windermere, Disney, and the 429 for a quick run to the airport or downtown Orlando. Quarterly HOA covers the manned gate, and community park. SHOWINGS. Private showings by appointment. Pre-approval or proof of funds requested prior to scheduling.

Beds:
5
Baths:
6.00
Sq.Ft.:
7,675
Status:
Active
MLS#:
O6439156
Type:
Single Family
Subdivision:
ISLEWORTH
Lot size:
0.52 Acres
Year built:
1988
A broker reciprocity listing Courtesy: STOCKWORTH REALTY GROUP 407-909-5900
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
7.00
Sq.Ft.:
5,502
Status:
Active
MLS#:
O6439995
Type:
Single Family
Subdivision:
Casabella
Lot size:
0.71 Acres
Year built:
2015
A broker reciprocity listing Courtesy: JOHN SILVA REALTY & ASSOCIATES 407-420-7908
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ADDITIONAL INFORMATION

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida’s sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

Beds:
5
Baths:
4.00
Sq.Ft.:
10,041
Status:
Active
MLS#:
O6439832
Type:
Single Family
Subdivision:
DOWN POINT SUB
Lot size:
0.72 Acres
Year built:
1983
A broker reciprocity listing Courtesy: MARIANI REALTY GROUP 407-257-3610
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,455
Status:
Active
MLS#:
O6439822
Type:
Condo
Subdivision:
Lakeside/lks/windermere
Lot size:
1.48 Acres
Year built:
2006
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
View additional info

ADDITIONAL INFORMATION

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Windermere community. Offering a perfect blend of comfort, style, and convenience, this move-in-ready home is an exceptional opportunity in one of Central Florida’s most sought-after areas. Step inside to discover a thoughtfully designed interior featuring no carpet throughout, making everyday living and maintenance a breeze. The well-appointed kitchen showcases stainless steel appliances, stone countertops, a stylish backsplash, and abundant cabinet space. Ceiling fans throughout the home, including on the private balcony, add an extra level of comfort and convenience. A washer and dryer are also included. Residents of Lakeside at Lakes of Windermere enjoy an array of resort-style amenities, including a sparkling community pool, spacious fitness center, and beautifully maintained grounds—creating a welcoming environment to relax, entertain, and enjoy the Florida lifestyle. The location is truly hard to beat! Lakeside Village Center is directly across the street, putting everyday conveniences just steps from your front door. Just minutes from Walt Disney World, major highways, highly regarded schools, shopping, dining, and the charming community of Windermere, this condo offers an incredible combination of lifestyle and location. Whether you're searching for a primary residence, vacation home, or investment property, this exceptional condo checks all the boxes. Come see why this Lakeside at Lakes of Windermere gem deserves to be at the top of your list!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,818
Status:
Active
MLS#:
O6439656
Type:
Townhouse
Subdivision:
LAKES/WINDERMERE-LK REAMS TWHM
Lot size:
0.06 Acres
Year built:
2006
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
View additional info

ADDITIONAL INFORMATION

Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out front and a tranquil conservation area in the back. The affordable HOA provides added peace of mind by covering exterior and roof maintenance, landscaping, and access to the sparkling community pool. This 2-bedroom, 2.5-bath townhome with a 2-car garage offers a flexible floor plan filled with inviting living spaces. A tiled entry foyer welcomes you into the first floor. Crown molding throughout adds an elegant finishing touch to the home’s inviting interior. The open kitchen features granite countertops, white subway tile backsplash, an undermount sink with a beautiful view, 42" wood-grain cabinetry, closet pantry and stainless steel appliances. The adjoining breakfast nook provides plenty of space for casual dining. Just off the kitchen is a separate dining room with beautiful wood flooring that could easily serve as a home office, den or flex space. The wood flooring continues into the bright and comfortable living room overlooking the private courtyard. Step outside to your fenced courtyard, complete with grass, pavers and a concrete patio area ready to accommodate your outdoor living needs. The courtyard also provides convenient access to the detached 2-car garage. Upstairs the beautiful wood flooring continues. The spacious primary suite is a true retreat. A modern barn door opens to the ensuite bath featuring dual undermount sinks, a walk-in closet, linen closet and an oversized soaking tub and shower combination. The second bedroom also offers a walk-in closet and its own private ensuite bathroom—ideal for guests, family or a roommate arrangement. An upstairs laundry area adds everyday convenience. Enjoy easy access out front to the bike/walking path that leads just over 1 mile to Lakeside Village Center, home to Publix, Starbucks, cafés, banks, recreation areas, and other everyday conveniences. The Lakes of Windermere is highly sought after for its desirable location, convenient access to high rated schools, shopping, dining, and all of the Walt Disney World parks. And with the Magic Kingdom nearby, you can even enjoy the magic of nightly fireworks right from your front door. With its flexible floor plan, private outdoor space, conservation setting, 2-car garage, and exceptional location, this townhome has so much to offer. Now is your opportunity to own a beautiful home in one of Windermere’s most convenient communities!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,516
Status:
Active
MLS#:
O6439730
Type:
Single Family
Subdivision:
Providence Ph 01 50 03
Lot size:
0.19 Acres
Year built:
2004
A broker reciprocity listing Courtesy: BEYCOME OF FLORIDA LLC 804-656-5007
View additional info

ADDITIONAL INFORMATION

Welcome to this spacious pond-front home in Providence, featuring a private screened pool and peaceful water views. Major updates include the roof, A/C system, and water heater, all replaced in 2021. Inside, the home features plantation shutters on most windows, hardwood and tile flooring with no carpet, high ceilings, and 8-foot doors throughout. The spacious primary suite overlooks the pond and provides direct access to the oversized covered lanai and pool. The updated primary bath features dual sinks, a large walk-in tiled shower with built-in bench and niches, and a spacious walk-in closet. Generously sized secondary bedrooms provide plenty of space, while the bright family room features large windows and sliding doors overlooking the pool and pond. The updated kitchen features modern cabinetry, stainless steel appliances, contemporary lighting, generous counter space, and bar seating. Step outside to enjoy the expansive covered lanai, private screened pool, mature landscaping, and tranquil pond backdrop-an inviting setting for relaxing or entertaining. Providence includes a community pool and playground. Conveniently located near shopping, dining, Winter Garden Village, major roadways, and area attractions.

Beds:
4
Baths:
6.00
Sq.Ft.:
3,966
Status:
Active
MLS#:
O6439554
Type:
Single Family
Subdivision:
Windermere Town
Lot size:
0.66 Acres
Year built:
2000
A broker reciprocity listing Courtesy: VINTAGE REALTY GROUP LLC 407-217-5458
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
5.00
Sq.Ft.:
4,843
Status:
Active
MLS#:
O6438618
Type:
Single Family
Subdivision:
ISLEWORTH
Lot size:
0.52 Acres
Year built:
1987
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
View additional info

ADDITIONAL INFORMATION

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.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Windermere Real Estate

Windermere is located in Florida. Windermere, Florida has a population of 3,046. Windermere is more family-centric than the surrounding county with 31.63% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Windermere, Florida is $131,392. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Windermere is 52.9 years.

Windermere Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 48.8 degrees. The average rainfall is approximately 51.5 inches per year, with 0 inches of snow per year.

Windermere Map

Windermere Real Estate Market Conditions

  • Median sales price

    $830,000
    29.6%
    change since last quarter
  • # Active listings

    307
    30-day change

Windermere Schools and Demographics

Education near Windermere, FL

City County
High School Graduates 97.9 89.47
College Degree - 2 year 5.91 11.45
College Degree - 4 year 68.16 35.7
Graduate Degree 17.43 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Windermere, FL

Grades Students P/T Ratio ZIP
Bay Meadows Elementary School PK - 05 578 15.6 32836
Dillard Street Elementary School PK - 05 742 15.5 34787
FLVS Full Time K-8 KG - 08 3,868 30.2 32835
Keenes Crossing Elementary School PK - 05 1,191 15.3 34786
Kids Community College Charter KG - 05 141 14.1 34734
Lake Whitney Elementary School PK - 05 598 14.9 34787
Metrowest Elementary School PK - 05 1,515 16.5 32835
Montessori of Winter Garden Charter KG - 08 205 15.8 34787
Oak Hill Elementary School PK - 05 485 13.9 32835
Orlo Vista Elementary School PK - 05 604 15.9 32835
Sand Lake Elementary School PK - 05 559 14 32836
Sunridge Elementary PK - 05 720 15.7 34787
Sunset Park Elementary School PK - 05 1,242 15 34786
Tildenville Elementary School PK - 05 540 14.6 34787
Whispering Oak Elementary School PK - 05 812 16.2 34787
William Frangus Elementary PK - 05 619 14.1 32835
William S Maxey Elementary PK - 05 271 12.9 34787
Windermere Elementary School PK - 05 753 15.7 34786
Windy Ridge K-8 PK - 08 1,144 14.3 32835

Middle Schools near Windermere, FL

Grades Students P/T Ratio ZIP
Bridgewater Middle School 06 - 08 1,373 19.1 34787
Chain of Lakes Middle School 06 - 08 1,285 17.4 32835
FLVS Part Time 6-8 06 - 08 0 32835
Gotha Middle School 06 - 08 1,272 19 34786
Lakeview Middle School 06 - 08 1,032 16.6 34787
Sunridge Middle 06 - 08 1,260 19.7 34787

High Schools near Windermere, FL

Grades Students P/T Ratio ZIP
FLVS Full-Time 9-12 09 - 12 2,240 32835
FLVS Part Time 9-12 09 - 12 0 32835
Olympia High School 09 - 12 2,990 22.3 32835
West Orange High School 09 - 12 3,835 21.5 34787

Ungraded Schools near Windermere, FL

Grades Students P/T Ratio ZIP
* Sunshine High Charter 09 - 12 608 43.4 32835
FLVS Part Time K-5 UG - UG 0 32835

Demographics near Windermere, FL

City County
Neighborhood Type
Population 3,046 1,409,949
Population Density 1,591 1,562
Median Age 52.9 35.7
People per Household 2.5 2.9
Median Household Income 131,392 65,784
Average Income per Capita 88,316 33,498

Real estate near Windermere