Windermere Homes under $400,000

Windermere Homes under $400,000

Welcome to Windermere, Florida—a picturesque town that perfectly blends small-town charm with modern conveniences. Nestled in Orange County, just a stone's throw from the bustling city of Orlando, Windermere is renowned for its stunning lakes, lush landscapes, and a vibrant community spirit. This idyllic locale is not just a place to live; it’s a lifestyle choice that offers a tranquil escape from the hustle and bustle of city life.

For those looking to invest in their dream home without breaking the bank, Windermere presents an exciting opportunity with homes available for under $400,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, there’s something for everyone in this charming community. Imagine waking up to serene lake views, enjoying leisurely strolls along tree-lined streets, and having access to top-rated schools and recreational parks—all within your budget.

Windermere’s real estate market is diverse, featuring a mix of single-family homes, townhouses, and condos, all designed to cater to various lifestyles and preferences. Many of these homes boast modern amenities, spacious layouts, and beautiful outdoor spaces, perfect for entertaining or enjoying a quiet evening under the stars.

With its friendly atmosphere, excellent dining options, and a plethora of outdoor activities—from boating to biking—Windermere is not just a place to live; it’s a community to thrive in. Explore the possibility of making Windermere your home today, and discover the perfect blend of affordability and quality living in this enchanting Florida gem!

Newest Windermere Homes under $400,000

8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
8179 Maritime Flag Street Unit 206, Windermere
$350,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Enjoy easy Florida living in this beautifully maintained first-floor, 3-bedroom, 2-bathroom condo in Windermere. The split floor plan offers privacy, while premium upgrades and 18-inch tile throughout the common areas make this move-in-ready home both comfortable and practical. Spend your weekends enjoying the community pool, fitness center, clubhouse, volleyball court, and grilling and picnic areas. Tennis courts and a playground are also available through the master association. HOA fees include water, sewer, garbage collection, and exterior maintenance, giving you more time to enjoy your surroundings. Conveniently located near Publix, Starbucks, shopping, and dining, this Windermere condo puts Walt Disney World, Disney Springs, Horizon West, and Winter Garden within easy reach. Whether you’re looking for a primary residence or a seasonal retreat, this home offers comfort, convenience, and more time for the Florida lifestyle you love.

8179 Maritime Flag Street Unit 206, Windermere
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
11446 Jasper Kay Terrace Unit 202, Windermere
$295,000
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to easy Florida living in the desirable Lakeside community of Windermere! This beautifully maintained 2-bedroom, 2-bathroom condo offers a comfortable open-concept layout with plenty of natural light and a warm, inviting feel throughout. The spacious living and dining areas create an ideal setting for both everyday living and entertaining, while the well-appointed kitchen offers modern appliances, generous counter space, and plenty of room. The primary suite features a private en-suite bath and ample closet space, while the second bedroom offers flexibility for guests, a home office, or additional living needs. Step outside to your private balcony and enjoy your morning coffee or unwind at the end of the day while taking in the peaceful community surroundings. Residents of Lakeside enjoy a variety of amenities designed for an active and relaxed lifestyle, including a community pool, fitness center, and walking trails. Conveniently located near shopping, dining, entertainment, and highly sought-after Windermere-area schools, this home offers the perfect combination of comfort, convenience, and community. Whether you're looking for a low-maintenance primary residence, a place to settle into the Windermere lifestyle, or a smart addition to your real estate portfolio, this condo is ready to welcome you home.

11446 Jasper Kay Terrace Unit 202, Windermere
12934 Vennetta Way, Windermere
$369,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the added privacy of an end-unit location, a peaceful conservation backdrop, and a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. Freshly painted throughout with brand-new carpet, the home feels bright, clean, and move-in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy everyday life. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual-sink vanity, and upgraded frameless-glass walk-in shower. Step outside to your private courtyard—a versatile outdoor space perfect for morning coffee, weekend gatherings, or unwinding at the end of the day. Beyond the courtyard, the rear of the home overlooks a conservation area, creating a peaceful natural setting with no immediate rear neighbors. It’s a rare combination of privacy and convenience. And there’s more to look forward to—a new roof is coming soon, adding another layer of value and peace of mind for the next owner. Ideally located near A-rated schools, parks, shopping, dining, and everyday conveniences, this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

12934 Vennetta Way, Windermere
8608 Brookvale Drive, Windermere
$379,900
3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Lake Reams Twnh SubDv. ⋅ 34786 Zip Code
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 !!!

8608 Brookvale Drive, Windermere
12417 Cruxbury Drive, Windermere
$359,000
2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twhm SubDv. ⋅ 34786 Zip Code
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!

12417 Cruxbury Drive, Windermere
8168 Boat Hook Loop Unit 303, Windermere
$320,000
3 Beds ⋅ 2 Baths ⋅ Lakeside At Lakes Of Windermere SubDv. ⋅ 34786 Zip Code
Welcome to 8168 Boat Hook Loop, Unit 303, a beautifully maintained condominium offering comfortable, low-maintenance living in a desirable community. This move-in ready residence features a spacious three-bedroom, two-bathroom floor plan designed for both everyday living and entertaining. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting atmosphere. The kitchen features 42-inch upper cabinets, stone countertops, and a functional layout with ample storage and preparation space. Updates include a replaced HVAC system and hot water heater, providing added comfort and peace of mind. The spacious primary suite offers a comfortable retreat with a private en-suite bathroom and generous closet space. Two additional bedrooms provide flexibility for guests, a home office, or other lifestyle needs. Enjoy the convenience of condominium living with access to community amenities and a location close to shopping, dining, entertainment, and major roadways.

8168 Boat Hook Loop Unit 303, Windermere
7430 Bentonshire Avenue, Windermere
$354,900
2 Beds ⋅ 3 Baths ⋅ Wickham Park 04 05 06 09 10 11 12 01 SubDv. ⋅ 34786 Zip Code
Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community of Windermere! This desirable END UNIT 2-bedroom, 2.5-bath townhome offers CAREFREE, LOW-MAINTENANCE LIVING with the added benefit of its end-unit location and an outstanding setting directly across the street from expansive OPEN GREEN SPACE and an ORANGE COUNTY COMMUNITY PARK. Designed for easy Florida living, the home features a recently painted interior and a comfortable, functional floor plan with two bedrooms, each offering its own private full bath. Step outside to the PRIVATE COURTYARD connecting the home to a DETACHED TWO-CAR GARAGE—creating an inviting outdoor space with added privacy and versatility. Major improvements have already been completed, making this home truly MOVE-IN READY: HVAC replaced in 2021, NEW ROOF in 2023, exterior painted in 2024, recently painted interior, and all toilets replaced in 2026. Wickham Park residents enjoy desirable COMMUNITY AMENITIES, including a COMMUNITY POOL and CLUBHOUSE, along with a sought-after Windermere location convenient to Walt Disney World, Orlando theme parks and attractions, shopping, dining, entertainment, schools, and major Central Florida roadways. Enjoy the best of the FLORIDA LIFESTYLE with the convenience and ease of low-maintenance townhome living. Whether you're searching for a PRIMARY RESIDENCE, SECOND HOME, or simply a low-maintenance Windermere home close to Disney and Orlando's world-famous attractions, this END-UNIT townhome delivers LOCATION, CONVENIENCE, OUTDOOR SPACE, and CAREFREE LIVING. With the big-ticket updates already completed, all that's left to do is move in and enjoy. Schedule your private showing today!

7430 Bentonshire Avenue, Windermere
8860 Herencia Alley, Windermere
$398,000
3 Beds ⋅ 3 Baths ⋅ Legado 95/47 Lot 99 SubDv. ⋅ 34786 Zip Code
Priced to sell! Great location and highly desired community! This beautifully maintained two-level townhome in the charming Legado community of Windermere offers 1,578 sq. ft. of modern living space, featuring 3 bedrooms and 2.5 bathrooms. This home combines modern construction, energy efficiency, comfort, and convenience in one of Windermere’s sought-after locations. The kitchen features upgraded granite countertops, backsplash, 42" cabinets, stainless steel appliances, and an oversized island. The open-concept living area is perfect for entertaining and gathering with family and friends. The attached two-car garage provides additional convenience. Upstairs, you’ll find three comfortable bedrooms, including a spacious primary suite with a large private balcony offering beautiful views of the Magic Kingdom fireworks. The primary bedroom also features a spacious walk-in closet and an ensuite bathroom with dual sinks. The washer and dryer are conveniently located on the second floor. Ceiling fans with remote controls are installed in all bedrooms and the main living area. The highly desirable Legado community offers a peaceful setting surrounded by conservation areas and a relaxing pond, while providing excellent amenities including a community pool and playground. The property is currently tenant-occupied, with the lease having started in December 2024. This makes it an excellent opportunity for investors seeking an income-producing property in a highly desirable area. The location is unbeatable in Windermere, close to top-rated schools, shopping, dining, outdoor activities, and the Walt Disney World resorts and theme parks. Convenient access to 535, I-4, the Florida Turnpike, and 429, as well as nearby hospitals and major attractions. School zoning: Windermere High School, Horizon West Middle School, and Castleview Elementary School. Priced to sell! Don’t miss this opportunity to own a beautifully maintained townhome in one of Central Florida’s most desirable communities. Schedule your showing today!

8860 Herencia Alley, Windermere
7752 Rigby Street, Windermere
$395,000
3 Beds ⋅ 3 Baths ⋅ Whickham Park SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome home to this beautiful 3 bedroom, 2.5 bath townhome in one of Windermere’s most sought after communities. Offering a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. The home feels bright, clean, and is move in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy day to day living. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual sink vanity, and upgraded frameless glass walk-in shower. The home features a spacious kitchen complete with stainless steel appliances. As you step outside to access the private courtyard you will notice that it connects directly to a two car garage, providing both convenience and privacy. With its low maintenance exterior, the HOA takes care of lawn and shrub maintenance, ensuring hassle free living. Ideally located near A-rated schools, like Sunset Park Elementary and Horizon West Middle School. Your have access to the Wickham Park community offering fantastic amenities including a pool, clubhouse, and scenic walking trails. You are also close to Disney, great shopping and dining like in the Winter Garden Village. You are near several parks and everyday conveniences, so this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

7752 Rigby Street, Windermere
12744 Langstaff Drive, Windermere
$394,900
3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twnh SubDv. ⋅ 34786 Zip Code
Price Improvement! Recently reduced.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
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