Windermere FL Real Estate & Homes for Sale

218 Properties Found

Sort Results:
51–75 of 218 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 of 9    Prev | Next
Beds:
4
Baths:
5.00
Sq.Ft.:
4,739
Status:
Active
MLS#:
O6382040
Type:
Single Family
Subdivision:
Isleworth
Lot size:
1.01 Acres
Year built:
1990
A broker reciprocity listing Courtesy: FLORIDA REALTY INVESTMENTS 407-207-2220
View additional info

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Presenting a newly remodeled luxury estate ideally positioned along Isleworth’s renowned championship golf course, showcasing stunning views of the signature 3rd hole. This exceptional residence offers approximately 4739 square feet of refined living space with 4 bedrooms and 4 1/2 bathrooms, soaring ceilings, elegant formal living and dining rooms, a private office, and a spacious owner’s retreat. Designed for elevated living and effortless entertaining, the home features marble and luxury vinyl flooring throughout, as well as a beautifully upgraded chef's kitchen with a casual dining area. Enclosed sunroom provides additional flex space and is not included in the official living square footage. The fully reimagined front and rear grounds create a true estate setting, highlighted by a grand front fountain entrance, a resort-style pool, an expansive lanai, a pavilion, and a summer kitchen. The upper-level balcony offers breathtaking golf course vistas, while the fully fenced private grounds include an extended driveway and an impressive circular motor court. A rare opportunity to own a move-in-ready luxury residence in one of Isleworth’s, golf-front locations.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,044
Status:
Active
MLS#:
O6377273
Type:
Single Family
Subdivision:
Glenmuir 48 39
Lot size:
0.47 Acres
Year built:
2002
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
View additional info

ADDITIONAL INFORMATION

New Price Gated Windermere Community Spacious .47 Acre Lot Single-Story Home A standout value in Windermere, this open and bright single-story home is located within the gated community of Glenmuir. Vaulted ceilings in the formal living and dining rooms, and a kitchen with stainless steel appliances, that opens to the family room. Situated on a .47-acre fenced lot, one of the largest lots in the neighborhood, the backyard offers space to create your own outdoor retreat. The Dawson floor plan offers 4 bedrooms, 2 full bathrooms, and 2,044 square feet of living space, the home features a barrel tile roof, two-car garage, and interior laundry room. The AC was replaced in 2022. Glenmuir is a gated community with a neighborhood park and playground, basketball courts, soccer field, pavilion, and picnic areas. Conveniently located near Winter Garden Village, Lakeside Village, Walt Disney World, and zoned for top-rated Orange County schools, less than one mile from Windermere Preparatory School.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,269
Status:
Active
MLS#:
O6382243
Type:
Single Family
Subdivision:
Roberts Landing
Lot size:
1.01 Acres
Year built:
1984
A broker reciprocity listing Courtesy: VINTAGE REALTY GROUP LLC 407-217-5458
View additional info

ADDITIONAL INFORMATION

Your Private Windermere Oasis Awaits * Step into a lifestyle of space, serenity, and sophisticated upgrades with this stunning 4-bedroom family estate nestled on over an acre of pristine land. Perfectly positioned to blend modern comfort with the beauty of nature, this property is a rare find for those who refuse to compromise on size or scenery. Highlights of the Estate: Breathtaking Vistas: Wake up to calming lake views from the comfort of your home, or step into the backyard for an even more expansive panorama of the water. Ultimate Move-In Readiness: Enjoy peace of mind with a brand-new roof and extensive high-end upgrades throughout, meticulously curated by the current owner. The Ultimate Entertaining Terrace: Discover an outdoor patio so grand it was originally designed to host a wedding. This space virtually doubles your living area, featuring a built-in outdoor kitchen and built-in propane firepit and a cozy integrated seating area for unforgettable evenings under the stars. A Haven for Pets: Your four-legged family members will be in heaven with a dedicated dog run and a custom dog door integrated into the screen enclosure, ensuring they enjoy the patio as much as you do. Endless Potential: With over an acre of usable land, the possibilities are limited only by your imagination. There is ample room to add an in-law suite, a professional-grade shop building, or even a private soccer field. Special Opportunity To make this dream home even more accessible - Inquire about the generous buyer’s credit being offered at closing!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,332
Status:
Active
MLS#:
O6382035
Type:
Condo
Subdivision:
Lakeside/lks/windermere
Lot size:
0.31 Acres
Year built:
2007
A broker reciprocity listing Courtesy: REALTY ONE GROUP MVP 800-896-8790
View additional info

ADDITIONAL INFORMATION

Beautifully maintained condo located in the highly desirable Lakeside Lakes of Windermere community. Situated on the third floor with elevator access, this residence features a spacious split floor plan offering both privacy and functionality. The open concept living and dining area flows seamlessly to a private balcony perfect for enjoying your morning coffee or relaxing evenings. The generous primary suite includes a walk in closet and an en suite bath with dual sinks. Wood flooring runs throughout the main living areas, with ceramic tile in wet areas for added durability. Residents enjoy an array of resort style amenities including a community pool, fitness center, outdoor grilling areas, sand volleyball courts, and more. Conveniently located near Disney, Winter Garden Village, shopping, dining, and zoned for top rated schools, this property is ideal for first time buyers, investors, or as a second home. Schedule your private showing today.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,119
Status:
Active
MLS#:
O6382068
Type:
Single Family
Subdivision:
Windermere Trls Ph 1a
Lot size:
0.17 Acres
Year built:
2012
A broker reciprocity listing Courtesy: BB GROUP REALTY CORP 407-624-7625
View additional info

ADDITIONAL INFORMATION

Windermere Trails Award Winning Model - Voted #1 Model by HBA 2013 It's surrounded by The Butler Chain of Lakes, with fabulous shopping and dining just minutes away. These are just a few of the celebrated qualities you'll love about Windermere Trails. Located in Windermere, FL, Windermere Trails is a community of new, incredibly energy-efficient homes, ranging 2,260 - 4,400 sq. ft. just south-east of downtown Orlando and is only a short drive to the SR 429 giving you access to the Florida Turnpike, SR 408 and I4; so you're close to all of Orlando's most popular area attractions. If golfing, boating, shopping and great schools are on your list of must-haves, you'll absolutely cherish living at Windermere Trails with Butler Chain of Lakes, several area golf courses and excellent schools, such as Windermere Prep nearby. Every home we build showcases our commitment to providing incredibly energy-efficient homes that let you spend your money on better things than utility bills. After all, we believe in building new homes and communities the way they can, and should be, built. That's why every Meritage home at Windermere Trails is built standard with the following energy- and money-saving features: - Spray-Foam Insulation - ENERGY STAR Appliances - ENERGY STAR Programmable Thermostat - Low-E2 Double pane/tinted Vinyl Windows - Variable SEER 15 HVAC - CFL Lighting and Fixtures - Weather-Sensing Irrigation - Water-Efficient Fixtures - Dual-Flush Toilets - Low VOC Carpets, Paints and Finishes

Beds:
6
Baths:
7.00
Sq.Ft.:
7,349
Status:
Active
MLS#:
O6385276
Type:
Single Family
Subdivision:
Sunset Bay
Lot size:
2.64 Acres
Year built:
1998
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
View additional info

ADDITIONAL INFORMATION

Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless entertaining, the residence offers six bedrooms, six full baths, and a powder bath — including a fully equipped private guest apartment ideal for extended family or long-term visitors. From the moment you arrive, the home’s striking architectural presence is undeniable. A dramatic entry with soaring ceilings and intricate iron detailing introduces expansive living spaces crafted with both grandeur and comfort in mind. Walls of glass and retractable doors blur the line between indoors and out, inviting natural light and panoramic lake vistas into nearly every room. The main level showcases elegant formal spaces, a richly appointed study, and a music room, along with a stunning lakefront family room and game room complete with a stylish wet bar. At the heart of the home, the gourmet kitchen features premium finishes, abundant workspace, and seamless flow for hosting gatherings large or intimate. The primary suite and an additional guest suite are thoughtfully positioned on the first floor for privacy and convenience. Upstairs, guests are treated to elevated lake views from a spacious lounge with kitchenette, multiple bedroom suites, a private theater with adjoining sitting area, and a spectacular balcony overlooking the water. Outdoor living is simply extraordinary. A heated saltwater pool and spa anchor the expansive terrace, complemented by a summer kitchen, bar seating, and a fireplace — the perfect setting for sunset evenings on the water. A private boathouse offers direct access for boating, paddleboarding, or fishing along one of Central Florida’s most coveted waterways. Despite its serene setting, the home is just minutes from upscale shopping, dining, and world-class attractions, including Walt Disney World, and approximately 20 minutes to Orlando International Airport. With the owners preparing for their next chapter, this extraordinary waterfront retreat presents a rare opportunity to own on the Butler Chain at a compelling value. A lifestyle of privacy, beauty, and convenience awaits.

Open House:

Saturday, 3/7 11:00-2:00PM

More Open House Info >

Beds:
6
Baths:
5.00
Sq.Ft.:
4,625
Status:
Active
MLS#:
O6377789
Type:
Single Family
Subdivision:
Windermere Isle
Lot size:
0.19 Acres
Year built:
2018
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-696-8000
View additional info

ADDITIONAL INFORMATION

Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,910
Status:
Active
MLS#:
O6381662
Type:
Townhouse
Subdivision:
Lake Burden South Ph 2
Lot size:
0.06 Acres
Year built:
2014
A broker reciprocity listing Courtesy: METROPOLITAN R.E SOLUTIONS INC 407-953-6501
View additional info

ADDITIONAL INFORMATION

Beautiful lake view townhome in the highly sought-after Lake Burden community! Discover the perfect blend of comfort, style, and convenience in this spacious 3-bedroom, 2.5-bath townhome. A private brick-paver courtyard welcomes you home and provides a charming outdoor retreat ideal for relaxing or entertaining. Inside, the beautifully appointed kitchen features 42” cabinets, granite countertops, and stainless steel appliances — perfect for everyday living and hosting guests. The primary bedroom is conveniently located on the first floor, offering ease and privacy. Upstairs, you'll find a versatile loft space along with two generously sized bedrooms, ideal for guests, family, or a home office. A washer and dryer are included for added convenience. The detached 2-car garage offers ample parking and storage space. Ideally located with quick access to SR-535, shopping, dining, and everyday conveniences, this home offers low-maintenance living in a prime location. Don't miss the opportunity to buy this exceptional property!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,360
Status:
Active
MLS#:
O6381542
Type:
Single Family
Subdivision:
Summerport Ph 03
Lot size:
0.24 Acres
Year built:
2005
A broker reciprocity listing Courtesy: WRA BUSINESS & REAL ESTATE 407-512-1008
View additional info

ADDITIONAL INFORMATION

Welcome to this stunning and spacious single-family home located in the heart of Windermere, offering breathtaking lake views from both the front and rear of the property. With 3,360 sqft heated living space, this beautifully maintained residence features a thoughtfully designed floor plan ideal for comfort and functionality. The first floor includes a private primary suite with its own balcony, providing a serene retreat, as well as a dedicated home office perfect for remote work or study. Generous living areas are filled with natural light and create a seamless connection between indoor and outdoor living. Step outside to enjoy the covered patio and expansive backyard, offering ample space for entertaining, relaxing, or future customization. The property sits on a well-sized lot and is part of a community that features amenities such as a pool, park, playground, and sidewalks. Conveniently located near top-rated schools, shopping, dining, and major roadways, this home delivers an exceptional combination of location, space, and lifestyle. A rare opportunity to own a lake-view property in one of Windermere’s most desirable areas. Schedule your private showing today.

Beds:
5
Baths:
7.00
Sq.Ft.:
5,071
Status:
Active
MLS#:
O6380812
Type:
Single Family
Subdivision:
Keenes Pointe
Lot size:
0.51 Acres
Year built:
2014
A broker reciprocity listing Courtesy: DOUGLAS ELLIMAN 561-655-8600
View additional info

ADDITIONAL INFORMATION

Welcome to an extraordinary custom residence located within the prestigious guard-gated golf community of Keene’s Pointe, one of Windermere’s most sought-after luxury enclaves. Built in 2014 and set on an expansive 0.51-acre, this estate offers over 5,000 square feet of refined living space, thoughtfully designed to balance elegance, comfort, and modern functionality. The property enjoys a rare premium setting with serene pond views wrapping both the rear and side of the home, creating a private, picturesque backdrop rarely found within the community. The residence features 5 bedroom suites, including a luxurious primary suite on the main level along with an additional first-floor guest suite, ideal for multigenerational living or extended visitors. Three spacious ensuite bedrooms are located upstairs, each offering comfort and privacy. At the heart of the home, the chef’s kitchen is a true showpiece, appointed with top-of-the-line appliances, custom cabinetry, an oversized island, and seamless flow into the main living and entertaining areas. Expansive windows and sliding glass doors flood the interiors with natural light while framing tranquil water views. Outdoor living is equally impressive, highlighted by a beautiful pool and spa, an extended brick-paver lanai, and a fully equipped summer kitchen, all designed for year-round Florida entertaining. The oversized yard, enhanced by the half-acre lot and pond frontage, provides both privacy and space rarely available in Keene’s Pointe. Additional highlights include: • 3-car garage • High ceilings & architectural detailing • Hidden pantry • Office on the 1st floor • Gas fireplace in the family room and outdoors • Modern transitional finishes throughout Residents enjoy 24-hour guard-gated security, lush landscaping, private roads, and optional membership to the Golden Bear Club, featuring golf, dining, fitness, tennis, and social amenities. Ideally located near top-rated Windermere schools, fine dining, shopping, and major roadways, this exceptional estate represents the pinnacle of luxury living in one of Central Florida’s premier golf communities.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,997
Status:
Active
MLS#:
S5143431
Type:
Townhouse
Subdivision:
Vineyards/horizons West Ph 4
Lot size:
0.07 Acres
Year built:
2019
A broker reciprocity listing Courtesy: AGENT TRUST REALTY CORPORATION 407-251-0669
View additional info

ADDITIONAL INFORMATION

Location!!! Great price!!! Top-rated school district!!! and a Renovated!!! Property ready for you to move in or invest. High rental demand and low inventory, ideal for investors or families. Fresh paint inside and out, new carpets, new indoor A/C with warranty, rear entry 2-car garage with epoxy flooring, and a spacious driveway. Kitchen island, granite counters, breakfast bar, stainless appliances large porch with relaxing views, a patio ideal for barbecues or outdoor breakfasts, surrounded by beautiful landscaping. Upstairs: 3 spacious bedrooms, plus a flexible loft. Primary Suite with walk-in closet and bath with dual sinks, second bedroom with walk -in closet, third bedroom with a reach-in closet, shared bathroom with dual sinks. Vineyard at Horizon West community amenities include: 2 clubhouses, swimming pools, park, community mailbox, sidewalks and recreational areas. Windermere High School (0.6 mi) Independence Elementary (1,3 mi) Bridgewater Middle School (1,7 mi). Just minutes from Winter Garden Village, hospitals, Disney Springs, Walt Disney World, Universal Studios, and Orange County National Golf Center and lodge. Approx 3,5 miles to FL-429 exit 19. With our preferred lender, you'll receive an additional benefit. Contact me today and don't let this opportunity pass you by!

Beds:
5
Baths:
5.00
Sq.Ft.:
3,619
Status:
Active
MLS#:
S5143447
Type:
Single Family
Subdivision:
Windermere Trls Ph 4b
Lot size:
0.17 Acres
Year built:
2017
A broker reciprocity listing Courtesy: PRIMUS CRE GROUP 305-988-7978
View additional info

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Stunning 5-Bedroom, 4.5-Bathroom Home in the Highly Desirable Windermere Trails Community This luxurious and spacious residence is located in one of Windermere’s most privileged and sought-after areas. It features open-concept living spaces, a gourmet kitchen with premium finishes, and a beautiful and cozy primary suite with a spa-style bathroom and a large walk-in closet. Step outside to a beautifully landscaped backyard, perfect for family gatherings and weekend BBQs—offering both comfort and style. The Windermere Trails community offers exceptional amenities, including walking trails, dog parks, and playgrounds—designed for an active, family-friendly lifestyle. Enjoy the convenience of being just minutes from top-rated schools, fine dining, shopping centers, and Orlando’s world-class attractions. Luxury, comfort, and a prime location—all in one place. Move-in ready and waiting for you!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,424
Status:
Active
MLS#:
O6380701
Type:
Single Family
Subdivision:
Lake Sawyer South Ph 1
Lot size:
0.21 Acres
Year built:
2011
A broker reciprocity listing Courtesy: RATIO REAL ESTATE, LLC 407-674-0460
View additional info

ADDITIONAL INFORMATION

Welcome to this impeccably maintained former model home in Windermere, beautifully positioned on a premium corner lot in a quiet, highly desirable community and zoned for top-rated schools. Offering over 3,400 square feet with 4 bedrooms and 3.5 bathrooms, this home stands out for its smart use of space, generous room sizes, and the refined “model home” presentation that feels clean, polished, and truly move-in ready. From the moment you arrive, the corner-lot setting provides a more open feel and excellent curb appeal, complemented by mature landscaping and a wide driveway. The exterior was fully repainted in 2025, adding a fresh, updated look. Inside, you’ll appreciate a bright, well-planned layout with spacious living and dining areas and clear separation of rooms that keeps daily life organized while still feeling connected. Multiple gathering spaces allow you to host comfortably, work from home, and enjoy everyday living without wasted square footage. A major highlight is the first-floor primary suite, offering privacy and convenience, along with a dedicated first-floor study/office that works perfectly as a home office, library, homework room, or flex space. A convenient half bath on the main level is ideal for guests. The home lives comfortably with practical flow and strong functionality, and the bedroom and bathroom count makes routines smoother for busy households and visiting guests alike. At the center of the home, the kitchen is designed for both function and gatherings. It features granite countertops, stainless steel appliances, a center island, breakfast bar, pantry, and abundant wood cabinetry, all positioned to stay open to the main living area so the cook is never separated from the conversation. Recent updates include a new kitchen hood, new refrigerator, and a new kitchen faucet, giving the space a refreshed, turnkey feel. Upstairs, you’ll find three additional bedrooms and two full bathrooms, plus a bonus/media room that easily becomes a second living area, movie room, playroom, fitness space, or guest retreat. The upstairs layout is thoughtfully arranged for privacy and flexibility, making the space ideal for family living and guests. Step outside to enjoy a backyard designed for easy outdoor living and low-stress entertaining, offering a private outdoor area and an outdoor kitchen/BBQ setup that creates a natural gathering spot for weekend cookouts and casual dinners. The corner-lot placement adds extra breathing room and a more spacious feel outdoors. The home also features major improvements already completed, including a NEW roof (2024), two AC units replaced (2025), new solid hardwood flooring (2024), and plumbing updates completed in 2021. A spacious 3-car garage with upgraded finished flooring and ample driveway parking completes the package. Ideally located in a top-rated Windermere school zone with excellent public and private options, the community features a pool, playground, walking trails, and year-round neighborhood events. Enjoy the added backdrop of nearby conservation areas and community amenities, with Disney fireworks often visible in the distance. Just minutes to Disney, major highways, Publix, Lakeside Village, shopping, dining, and everyday conveniences, this home combines a peaceful setting with exceptional convenience throughout Central Florida.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,044
Status:
Active
MLS#:
O6380782
Type:
Single Family
Subdivision:
Ashlin Park Ph 1
Lot size:
0.14 Acres
Year built:
2015
A broker reciprocity listing Courtesy: RE/MAX PRIME PROPERTIES 407-347-4512
View additional info

ADDITIONAL INFORMATION

Beautifully updated 4-bedroom, 3.5-bath two-story home located on a quiet cul-de-sac in the highly sought-after Ashlin Park community of Windermere. This spacious residence offers a functional layout with generous living and dining areas, perfect for both everyday living and entertaining. The kitchen and main living spaces flow seamlessly toward the backyard, where you’ll enjoy the privacy of no rear neighbors. The oversized garage provides excellent storage and parking options, ideal for busy households or hobby enthusiasts. A newer roof (2023) adds peace of mind, while the community pool and amenities are just a short distance away. Zoned for A-rated schools and conveniently located near shopping, dining, and major roadways, this move-in-ready home delivers the best of Windermere living.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,937
Status:
Active
MLS#:
O6380732
Type:
Single Family
Subdivision:
Keenes Pointe
Lot size:
0.26 Acres
Year built:
2004
A broker reciprocity listing Courtesy: SOUTHERN REALTY GROUP LLC 407-217-6480
View additional info

ADDITIONAL INFORMATION

Completely renovated and thoughtfully reconfigured in 2023, this stunning 4-bedroom, 3-bath home is located in the highly sought-after, 24-hour gated and guarded community of Keene’s Pointe. Designed for modern living, the home features an open and refreshed layout with new flooring throughout and elegant paneling details that elevate the interior design. The expansive primary suite has been completely reimagined, showcasing a beautifully reconfigured spa-like bathroom and an oversized custom primary closet. The kitchen is equipped with premium appliances including a Thermador panel-ready refrigerator, KitchenAid gas stove, KitchenAid oven/microwave combo, and panel-ready dishwasher — all new in 2023. A new washer and dryer were also added for convenience. Major system upgrades provide peace of mind, including a new roof (2023), new HVAC units (2022 & 2023), and a new hot water heater (2023). The exterior was freshly painted in 2024. An impressive accordion-style glass door seamlessly connects indoor and outdoor living spaces, opening to a spacious, fenced backyard with no rear neighbors — offering both privacy and room to entertain. Keene’s Pointe is home to the Golden Bear Country Club, featuring an 18-hole Jack Nicklaus-designed golf course, restaurant, and tennis facilities, delivering an exceptional lifestyle in one of the area’s premier communities. Conveniently located near shopping, dining, major expressways, and world-renowned tourist attractions, as well as top-rated public and private schools, this turnkey home blends luxury updates, privacy, and prime location — a rare opportunity in Keene’s Pointe.

Open House:

Sunday, 3/8 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
2,002
Status:
Active
MLS#:
O6379257
Type:
Townhouse
Subdivision:
Vineyards/horizons West Ph 4
Lot size:
0.07 Acres
Year built:
2019
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY 407-965-1155
View additional info

ADDITIONAL INFORMATION

Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a playground area. The Vineyards of Horizon West community offers easy access to SR-429, SR-535, and US-192 and area employers, including Walt Disney World®, Orange County National Golf Center and Lodge, and Universal Orlando® Resort. The community is also close to several excellent dining and shopping options, including Winter Garden Village and downtown Windermere.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,151
Status:
Active
MLS#:
O6378820
Type:
Single Family
Subdivision:
Lakes/windermere Ph 02a
Lot size:
0.15 Acres
Year built:
2005
A broker reciprocity listing Courtesy: MY REALTY GROUP, LLC. 786-847-7421
View additional info

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends the living space outdoors. Situated within a well-established community with a low HOA fee of $230 quarterly and no CDD, this property offers long-term cost efficiency compared to many newer developments. The Windermere location provides convenient access to major roadways, shopping, dining, retail centers, and entertainment throughout Central Florida. Some images have been virtually staged for illustrative purposes only.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,875
Status:
Active
MLS#:
O6370886
Type:
Single Family
Subdivision:
Lake Butler Park Pt Rep
Lot size:
0.58 Acres
Year built:
1953
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
View additional info

ADDITIONAL INFORMATION

Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless indoor-outdoor lifestyle. Over 4800sq 5 bedrooms, 4 full bathrooms, Recently enhanced by renovations completed in 2020, the residence now features a newly added owner’s retreat with spa-inspired bathroom, thoughtfully designed to maximize comfort, privacy, and sweeping lake views. Additional updated interior in 2022 showcases refined craftsmanship and high-end finishes, including Provenza engineered hardwood flooring, vaulted tongue-and-groove ceilings, cedar beams, updated bathrooms, custom drapery, and plantation shutters. The large open kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, two oversized kitchen islands, a GE Profile refrigerator, and an Advantium double oven, all seamlessly connected to the main living areas. The great room opens effortlessly to the outdoor living spaces through fully retractable sliding doors, creating an ideal setting for gatherings of any size. Outdoor amenities rival those of a private resort, featuring a saltwater pool with pebble-tech finish and shallow lounging shelf, summer kitchen with natural gas Artisan grill, motorized patio screens, indoor/outdoor surround sound, and a luxury boat dock with electric cradle and Trex decking—perfect for enjoying the Butler Chain lifestyle year-round. Additional highlights include interior and exterior security systems, natural gas, city water, roof 2020, and a newer septic tank. Located just steps from downtown Windermere, residents enjoy a charming small-town atmosphere with farmers markets, cafés, local shops, and dining, while remaining only minutes from Restaurant Row and Orlando’s premier amenities. A rare opportunity to own a fully updated lakefront retreat in one of Central Florida’s most coveted communities.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,724
Status:
Active
MLS#:
O6379681
Type:
Single Family
Subdivision:
Windermere Trls Ph 1c
Lot size:
0.15 Acres
Year built:
2014
A broker reciprocity listing Courtesy: KARDOSH REALTY 407-499-4466
View additional info

ADDITIONAL INFORMATION

The Melville floor plan features a functional and well-designed layout with formal living and dining areas, a spacious primary suite, an open-concept family room and a versatile flex space that can be used as a game room or adapted to suit a variety of lifestyle needs. Located in the desirable Windermere Trails community, the property offers convenient access to area lakes, daily essentials, highly rated schools, outdoor recreation, as well as nearby shopping, dining, and local attractions. Designed with energy-efficient features, the home provides comfort, reduced noise levels, and improved overall energy performance. Schedule your private showing today.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,847
Status:
Active
MLS#:
S5142930
Type:
Single Family
Subdivision:
Preston Square
Lot size:
0.18 Acres
Year built:
2009
A broker reciprocity listing Courtesy: IAD FLORIDA LLC 407-720-0020
View additional info

ADDITIONAL INFORMATION

Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago — an exceptional offering in a premier Windermere community. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.

Open House:

Saturday, 3/7 2:00-5:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
4,437
Status:
Active
MLS#:
G5107723
Type:
Single Family
Subdivision:
Lake Cawood Estates
Lot size:
0.99 Acres
Year built:
2006
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
View additional info

ADDITIONAL INFORMATION

Don’t miss out on this one !!! Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a three-car garage and exceptional privacy. A long driveway and inviting covered front porch create a warm welcome, while soaring ceilings and tranquil pool views greet you the moment you step inside. The open floor plan is ideal for entertaining and everyday living, featuring a grand living room with gas fireplace, formal dining room with wet bar, expansive family room, and a versatile game or bonus room perfect for a media space, home office, or guest retreat. The gourmet kitchen opens seamlessly to the breakfast nook and family room and is beautifully appointed with granite countertops, stainless steel appliances, built-in double ovens, and a large center island. The luxurious primary suite offers tray ceilings, a private fireplace, sitting area, and abundant natural light, along with a spa-inspired ensuite featuring dual vanities, a jacuzzi tub and two spacious walk-in closets. Three additional bedrooms are generously sized with large closets and a convenient cabana bath provides direct access to the outdoor living area. Step outside to your private resort-style retreat featuring a screened heated pool and spa, expansive paver patio, and a fully equipped summer kitchen designed for year-round Florida living and entertaining. Large sliding doors provide seamless indoor-outdoor flow, enhancing the home’s open and airy feel. Built in 2004 and extensively upgraded for modern comfort and peace of mind, this move-in-ready home features a brand-new roof (2024), new A/C system (2024), new well system (2025), new water filtration system, new saltwater pool system (2025), fresh interior paint (2025), updated lighting and fans (2024), and new kitchen and laundry appliances including a GE Café refrigerator and dishwasher and Samsung washer and dryer. The property operates on well and septic, providing efficiency and long-term value. Ideally located near top-rated dining, shopping, and everyday conveniences, this exceptional home is approximately 15 minutes from Walt Disney World and less than 30 minutes from Orlando International Airport. This rare opportunity combines luxury, space, and major system upgrades in one of Central Florida’s most desirable communities. Schedule your private showing today and experience the lifestyle you’ve been dreaming of.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,139
Status:
Active
MLS#:
O6379533
Type:
Single Family
Subdivision:
Windermere Landings Ph 2
Lot size:
0.09 Acres
Year built:
2012
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY 407-965-1155
View additional info

ADDITIONAL INFORMATION

Ideally situated within WINDERMERE LANDINGS and in close proximity to highly rated schools, convenience stores, restaurants, golf courses & other amenities, this IMMACULATELY presented 3 bedroom and 2.5 bath property with 2 car garage and private driveway is a true GEM with its stunning curb appeal and TURNKEY presentation! On approach the front porch feels inviting with its welcoming entryway and foyer area that leads into a versatile living room with contemporary FIREPLACE. At the heart of the home is the expansive OPEN PLAN CONCEPT kitchen and family room with plenty of natural light which flows into an informal sunlit breakfast/dining nook. Enjoy cooking and entertaining in the GOURMET KITCHEN which is a chef’s dream with its ample cabinetry, central island, granite countertops, stainless steel appliances, tile backsplash, high-top countertop seating and recently upgraded fixtures including a touchless faucet. The first floor has a separate guest powder half bath serving the living room areas. All bedrooms, loft and laundry room are located on the second level. Upstairs the spacious LOFT is a FLEX SPACE which can be retained as a study or games area or indeed can be converted into a 4th bedroom. The primary bedroom is a well-appointed, true retreat with views of the nightly Disney fireworks and boasts UPGRADED walk-in closet and ensuite bathroom consisting of separate vanities and walk-in shower with new fittings. Each of the other two bedrooms are well-proportioned with generous & recently upgraded closet spaces and adjacent to a full bathroom. A conveniently located laundry room with digital combo washer and dryer completes the second floor. Home has NO CARPETS and features designer light fixtures, plenty of storage closets on both floors, windows adorned with drapes & blinds and new water heater. A further highlight is an an in-built surround sound system to create ambiance in both the home and the patio area! Seamlessly blending the outdoor with the indoor, enjoy Florida lifestyle living either lounging under the shade of the covered patio area or out on the fully enclosed/fenced in PAVED COURTYARD with focal point PERGOLA. An added benefit with this property is the ULTRA-LOW MAINTENANCE LANDSCAPING ! Windermere Landings has a community pool, cabana house, playground, dog park and a green space kick ball area. Easy access to major highways/roads, local shopping malls and entertainment as well as the theme parks and Orlando International Airport. All furniture is available but separately negotiated. Don’t miss out, book your private showing today!

Beds:
4
Baths:
5.00
Sq.Ft.:
5,130
Status:
Active
MLS#:
O6377087
Type:
Single Family
Subdivision:
Harbor Isle
Lot size:
1 Acres
Year built:
2002
A broker reciprocity listing Courtesy: STOCKWORTH REALTY GROUP 407-909-5900
View additional info

ADDITIONAL INFORMATION

Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of amenities, right at home. Through the grand entrance, the formal living room is bright and chic, with ceiling niche lighting and picturesque windows to enhance the details of this beautifully-crafted estate. Formal living, wine bar, and fabulous chef’s kitchen with breakfast nook with built-ins, plus generously-sized family room enhance your largest gatherings and everyday living. The chef’s kitchen with island and preparation sink feature gas cooktop with hood, stainless appliances, and double ovens. The vast owner’s retreat spans the entire south wing of the house and includes a lovely sitting area, French doors to the patio, large walk-in closets, and a spa-like bath with double vanities, jetted tub, and large shower. Two additional bedrooms are located on the opposite side of the house on the first floor with a Jack and Jill bath and a secondary bed and bath are upstairs off a large game room. The resort-style pool and spa with mammoth paver patio decking and summer kitchen offers a private outdoor retreat under a large screen enclosure. New carpeting and new Plantation shutters just installed. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,693
Status:
Active
MLS#:
O6371471
Type:
Single Family
Subdivision:
Lake Down Estates
Lot size:
0.59 Acres
Year built:
1999
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
View additional info

ADDITIONAL INFORMATION

Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,455
Status:
Active
MLS#:
O6378432
Type:
Condo
Subdivision:
Lakeside/lks/windermere
Lot size:
0.37 Acres
Year built:
2006
A broker reciprocity listing Courtesy: BHHS FLORIDA REALTY 407-876-2090
View additional info

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Step into this beautifully maintained second -floor unit in the sought-after Lakeside at Lakes of Windermere community. Ideally located Directly across from the community pool and clubhouse. Offering 1,455 square feet, this 3-bedroom, 2-bathroom home is designed for effortless Florida living—with timeless details and upscale finishes throughout. The spacious kitchen features granite countertops, ample cabinetry, and a custom walk-in pantry, while the open-concept layout seamlessly connects the living and dining areas. Relax on your screened-in balcony, overlooking the sparkling community pool. Your primary suite offers a private retreat with dual vanities, separate shower, and a custom walk-in closet. Two additional bedrooms are filled with natural light, ideal for guests or a home office. Includes appliances, new Laundry Machines (2026), new AC Condenser (2026), New Range (2026) 2 parking spaces (1 assigned + guest), and valet trash. HOA covers water, sewer, security, and amenities. Convenient Windermere location near Disney and Winter Garden Village.

Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 of 9    Prev | Next
51–75 of 218 properties displayed
Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.



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

    $800,000
    29.6%
    change since last quarter
  • # Active listings

    229
    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