Windermere Homes with Two Story Property Description

Windermere Homes with Two Story Property Description

Welcome to Windermere, Florida – a picturesque town nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and a close-knit community, Windermere offers a serene escape from the hustle and bustle of city life while still providing easy access to the vibrant attractions of Central Florida. With its charming streets lined with moss-draped oaks and a variety of recreational opportunities, Windermere is the perfect place to call home.

One of the standout features of Windermere is its diverse selection of homes, particularly the exquisite two-story properties that grace this idyllic town. These homes are designed to impress, offering spacious layouts that seamlessly blend comfort and elegance. With multiple bedrooms and ample living space, two-story homes in Windermere are perfect for families, providing room to grow and thrive.

Imagine waking up to breathtaking views from your second-story balcony, sipping coffee while soaking in the morning sun. The open-concept floor plans allow for easy entertaining, whether you’re hosting a family gathering or a cozy get-together with friends. Many of these homes also feature modern amenities, gourmet kitchens, and luxurious master suites, ensuring that your living experience is nothing short of exceptional.

Windermere’s strong sense of community is reflected in its top-rated schools, charming local shops, and vibrant parks. With a wealth of outdoor activities, including boating and fishing on the nearby lakes, residents enjoy a lifestyle that embraces both relaxation and adventure.

Discover your dream home in Windermere today, where two-story elegance meets a welcoming community!

Newest Windermere Homes with Two Story Property Description

3 Beds ⋅ 3 Baths ⋅ Whickham Park SubDv. ⋅ 34786 Zip Code

This beautiful 3 bedroom, 2.5 bath townhome is in the heart of Windermere. The home features a spacious, open kitchen complete with stainless steel appliances. Step outside to access a private courtyard that connects directly to a two car garage, providing both convenience and privacy. Upstairs you’ll find three comfortable bedrooms and two full bathrooms. With its low maintenance exterior, the HOA takes care of lawn and shrub maintenance, ensuring hassle free living. The Wickham Park community also offers fantastic amenities, including a pool, clubhouse, and scenic walking trails. Just minutes away from Disney, Winter Garden Village, and top rated schools. This home offers an unbeatable location for easy access to everything.

7752 Rigby Street, Windermere

4 Beds ⋅ 3 Baths ⋅ Windermere Trls Ph 1c SubDv. ⋅ 34786 Zip Code

Move-In Ready! Beautifully Updated Home in the Highly Desirable Windermere Area! Welcome to this beautifully refreshed 4-bedroom, 2.5-bath home located in the sought-after Windermere Trails community. Built in 2014, this two-story residence includes approximately 2,074 square feet of living space with an open-concept layout, abundant natural light, and tasteful updates throughout. The kitchen features granite countertops, stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. The spacious primary suite includes a walk-in closet and an ensuite bath with dual vanities, a soaking tub, and a separate shower. Additional highlights include updated flooring, fresh interior finishes, a covered lanai, and a fenced backyard. Conveniently located near shopping, dining, major highways, Disney, and top-rated schools.

11938 Silverlake Park Drive, Windermere

6 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code

This exceptional, fully renovated residence offers the perfect blend of contemporary design, luxury finishes, smart technology, and resort-style living. Every detail has been thoughtfully curated, featuring large-format porcelain tile throughout the main level and luxury vinyl flooring throughout the second floor, complemented by custom millwork, imported Italian wallpaper, designer lighting, and premium finishes that create a timeless modern aesthetic. The professionally designed gourmet kitchen showcases bespoke cabinetry, a dramatic waterfall island, premium stone countertops and full-height backsplash, along with a complete Samsung appliance package. Smart home features include Alexa-integrated custom blinds and window treatments, motion-activated LED staircase lighting, and advanced home automation for effortless everyday living. The functional floor plan offers 6 spacious bedrooms and 4 beautifully appointed bathrooms, including a first-floor primary suite. Every bedroom features custom walk-in closets with built-in cabinetry, while the bathrooms include custom vanities, large-format tile, frameless glass showers, rainfall showerheads, body jets, and modern fixtures. A dramatic two-story foyer with glass railings and a contemporary statement chandelier creates a memorable first impression. The home also features a custom-designed wine bar complete with built-in cabinetry, wine display racks, and a temperature-controlled wine refrigerator, making it ideal for entertaining family and guests. The outdoor living area has been designed to provide a true resort-style experience, featuring a heated swimming pool, a custom mini putting green, and low-maintenance landscaping. Enjoy beautiful lake views and the rare opportunity to watch Disney’s spectacular nightly fireworks from the comfort of your own backyard, creating an unforgettable setting for relaxation and entertaining. Ideally located in the highly desirable Town of Windermere, this home offers convenient access to shopping, dining, major highways, golf courses, and Walt Disney World. The property is zoned for highly rated public schools and is just minutes from Windermere Preparatory School. Move-in ready, this exceptional residence combines outstanding craftsmanship, contemporary design, smart home technology, beautiful lake views, nightly Disney fireworks, and an excellent location, offering a rare opportunity to own one of Windermere’s most remarkable homes.

12676 Salomon Cove Drive, Windermere

5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with modern design and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zerio appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office with custom built-ins offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. A covered lanai and fully equipped summer kitchen overlook the custom swimming pool and spa, creating the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living.

5577 Lemon Orchard Bend, Windermere

4 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 1 SubDv. ⋅ 34786 Zip Code

Virtually Staged. 13228 Roskin Ln is a two-story Windermere home with a two-story foyer and hardwood flooring through the main level. The kitchen features granite countertops, stainless steel appliances, wood cabinetry, and a center island that opens to the great room for connected living. A separate living area provides space for larger gatherings, with sliding doors leading to the screened lanai. The primary bathroom offers a soaking tub, a separate glass shower, and a dual-sink vanity, complemented by a spacious walk-in closet for organized storage. Additional bedrooms and full bathrooms provide flexible space throughout. A three-car garage completes this well-maintained residence with practical amenities throughout.. Included 100-Day Home Warranty with buyer activation

13228 Roskin Lane, Windermere

3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twnh SubDv. ⋅ 34786 Zip Code

Located in one of Windermere’s most desirable communities, this beautifully updated 3-bedroom, 2.5-bath townhouse offers the perfect blend of style, comfort, and convenience. Just minutes from Disney, Horizon West, premier shopping, dining, and major highways Step inside to discover a bright, open-concept floor plan filled with natural light and designed for both everyday living and effortless entertaining. The modern kitchen features elegant quartz countertops, stainless steel appliances, ample cabinetry, and overlooks the spacious living and dining areas, creating the perfect gathering space for family and friends. One of the home’s standout features is the private fenced courtyard—an inviting outdoor retreat ideal for relaxing, grilling, entertaining, or simply enjoying Florida’s beautiful weather. The detached two-car garage provides added convenience and extra storage. Upstairs, the spacious primary suite offers a walk-in closet and private en-suite bathroom, while two additional bedrooms and a full bath provide flexibility for family, guests, or a home office. Residents enjoy a low HOA along with outstanding community amenities, including a resort-style swimming pool, playground, sidewalks, and scenic surroundings that make this neighborhood one of Windermere’s most sought-after communities. Zoned for highly desirable schools and located in the heart of the thriving Windermere/Horizon West area, this exceptional home combines modern updates, an unbeatable location, and outstanding value. Don’t miss this incredible opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12744 Langstaff Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code

Welcome to Berkshire Park, a highly sought-after community where timeless style, everyday comfort, and low-maintenance living come together in the heart of Windermere. This impeccably maintained 3-bedroom, 2.5-bath townhome offers 1,644 square feet of beautifully designed living space, combining tasteful finishes with exceptional functionality. The beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area provides the perfect setting for everything from casual breakfasts to holiday gatherings, while a walk-in pantry with ample storage keeps the space organized and functional. French doors lead from the kitchen to a private, fenced patio, creating an inviting outdoor retreat for dining al fresco, entertaining guests, or simply relaxing in the Florida sunshine. Backing to conservation land with picturesque views of mature trees, the backyard offers a peaceful and private setting rarely found in townhome living. Seamlessly connected to the kitchen, the spacious living room offers a warm and welcoming atmosphere, highlighted by an electric fireplace, which is included with the sale of the home. A detached two-car garage completes the property, providing additional storage and everyday convenience. Upstairs, the spacious primary suite serves as a private retreat, complete with a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a full bathroom, offering comfortable accommodations for family, guests, or a dedicated home office. Residents of Berkshire Park enjoy an exceptional lifestyle with amenities designed for both recreation and relaxation, including a community pool, tennis courts, basketball courts, and scenic walking trails winding around tranquil ponds beneath a canopy of mature trees. The HOA further enhances the ease of homeownership by providing landscaping, structural exterior maintenance, and pest control, allowing you to spend more time enjoying everything this beautiful community has to offer. Ideally located just minutes from Walt Disney World, Winter Garden Village, Hamlin Town Center, premier shopping and dining, major roadways, and top-rated schools, this move-in-ready residence offers the perfect balance of location, lifestyle, and convenience. Whether you're searching for your primary residence, a seasonal retreat, or an investment opportunity, 12914 Vennetta Way presents an exceptional opportunity to own a beautifully maintained home in a highly sought-after Windermere community.

12914 Vennetta Way, Windermere

6 Beds ⋅ 5 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. Under Construction. SWEETWATER H - Our beautiful huge 2 story home, located on a conservation lot, with 6 Bedrooms and 4.5 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. The living area has an extension to the room, 9' hidden sliding glass doors and a huge lanai that runs the width of the home. Downstairs flex room works well as an office or study. Upstairs, find 5 large bedrooms most with walk in closets, 3 full baths, and a second laundry room,(that's right! 1 upstairs, and 1 downstairs). Common areas upstairs include a spacious bonus room with wet bar, and a second flex room that works well as a theatre room. SAMPLE IMAGES

14213 Crest Palm Avenue, Windermere

5 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of the most peaceful cul-de-sacs in the Keene's Pointe community. Perfectly positioned on a stunning water-view homesite with an expansive backyard and exceptional privacy, this home offers an incredibly flexible floor plan rarely found in today's market. The thoughtfully designed layout places the main living areas, private office, and spacious primary suite all on the first floor, creating the perfect setup for everyday living. Upstairs, three generously sized bedrooms and a large bonus room are tucked away, providing an ideal retreat for family or guests. Adding even more versatility, a completely separate detached in-law suite features a spacious bedroom and full bath, making it perfect for extended family, guests, a private home office, or live-in accommodations. Major updates provide peace of mind for years to come, including a brand-new roof, new glass sliders and windows, new septic system and drain field, A/C in 2024, and 2021 water heater. Keene's Pointe is one of Central Florida's premier 24-hour guard-gated communities, set along the pristine Butler Chain of Lakes. Residents enjoy beautifully maintained parks, playgrounds, walking trails, private boat launch access to Lake Burden, fishing piers, and a vibrant community atmosphere. Optional membership to the renowned Golden Bear Club provides access to a Jack Nicklaus Signature golf course, tennis and pickleball courts, a resort-style swimming pool, fitness center, and more. Families will also appreciate the community's proximity to top-rated schools, upscale shopping, fine dining, world-famous attractions, and Orlando International Airport.

9904 Brentford Court, Windermere

4 Beds ⋅ 7 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code

Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious guard-gated community of Keene’s Pointe in Windermere. Completely reimagined with exceptional attention to detail, this residence seamlessly blends timeless architecture with sophisticated contemporary design. From the moment you enter, soaring ceilings accented by exposed wood beams, expansive porcelain flooring, designer lighting, custom millwork, and walls of glass create an atmosphere of understated elegance and warmth. Designed for both everyday living and grand-scale entertaining, the impressive great room is anchored by a striking floor-to-ceiling porcelain fireplace with custom illuminated built-ins. The gourmet kitchen is beautifully appointed with premium Viking appliances, custom European-style cabinetry, quartz countertops, an oversized center island, and a separate catering kitchen that makes hosting effortless. The luxurious primary suite offers a peaceful private retreat featuring custom-designed walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, a walk-in shower, and exceptional designer finishes throughout. Spacious guest suites provide comfort and privacy for family and visitors alike. One of the home’s most remarkable features is the expansive climate-controlled lanai, thoughtfully designed as a true extension of the interior living space. Complete with a fully equipped summer kitchen, multiple gathering areas, and panoramic golf course views, it offers the perfect setting for year-round indoor-outdoor living and unforgettable entertaining. One of the very few homes on Valhalla Drive to feature a four-car garage, this residence provides exceptional space for automobiles, golf carts, and additional storage. The pool and spa overlook the beautifully manicured fairways, creating a tranquil backdrop that captures the beauty and serenity of one of Central Florida’s premier private golf communities. Located in one of Windermere’s most sought-after addresses, Keene’s Pointe offers 24-hour guarded security, picturesque tree-lined streets, and an exceptional lifestyle centered around the renowned Golden Bear Club. Residents enjoy convenient access to top-rated schools, upscale shopping, fine dining, world-class attractions, and Orlando International Airport. This is more than a luxury home. It is an exceptional opportunity to own a beautifully renovated residence in one of Windermere’s most distinguished private golf communities.

6719 Valhalla Way, Windermere

5 Beds ⋅ 5 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code

Welcome to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulously maintained 5-bedroom, 4.5-bathroom residence offers 3,036 square feet of elegant living space designed for comfort, functionality, and entertaining. A long private driveway and charming front courtyard create a grand first impression. Inside, you'll discover spacious living and entertaining areas filled with natural light, soaring ceilings, and an inviting floor plan that flows effortlessly from room to room. Whether hosting holiday gatherings or enjoying quiet evenings at home, every space has been thoughtfully designed for comfortable living. The gourmet kitchen serves as the heart of the home and features abundant cabinetry, generous counter space, and premium appliances. Included with the sale are the kitchen refrigerator, stove/range, built-in wine refrigerator, built-in espresso machine, washer, and dryer, allowing the next owner to move in with ease. One of this home's most distinctive features is its private detached suite, located separately from the main residence with its own private entrance and full bathroom. This versatile space is ideal as an in-law suite, private guest quarters, executive home office, fitness studio, creative workspace, or media room, offering endless possibilities while maintaining privacy from the main living areas. The second story offers generously sized bedrooms and comfortable accommodations for family and guests. The staircase and upstairs bedroom carpeting were replaced approximately 1.5 years ago, while one upstairs bedroom showcases beautiful hardwood flooring, adding warmth and character. Step outside into your own private backyard retreat. The fully fenced backyard provides both privacy and security while creating the perfect setting for outdoor entertaining, pets, or simply relaxing in your own personal oasis. The sparkling swimming pool offers exceptional flexibility, as it can be operated as either a traditional chlorine pool or converted to saltwater, depending on the owner's preference. Recent upgrades include a new pool motor and complete pool filter assembly installed in 2025, and all existing pool equipment is included with the sale. The existing wicker patio furniture also conveys, allowing the next owner to begin enjoying the outdoor living space immediately. The property has been meticulously maintained, with all HVAC units receiving regular service, one HVAC unit replaced, and the tile roof professionally maintained annually, including semiannual soft washing, tile replacement, and recementing as needed to preserve both appearance and longevity. The garage features epoxy flooring, an insulated garage door, its own air-conditioning unit, built-in shelving, and a workbench, while a backyard storage shed provides additional storage. Conveniently located just minutes from top-rated schools, championship golf courses, world-class dining, upscale shopping, Disney, and the Butler Chain of Lakes, this exceptional home offers the perfect blend of luxury, flexibility, and everyday convenience. Whether you're looking for multigenerational living, a private home office, or simply an impeccably maintained luxury residence, this Windermere gem is truly move-in ready.

11434 Rapallo Lane, Windermere

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