Windermere Homes under $350,000

Windermere Homes under $350,000

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County that perfectly blends small-town charm with modern conveniences. Known for its stunning lakes and lush landscapes, Windermere is a tranquil haven that offers a serene lifestyle just a stone's throw away from the bustling attractions of Orlando. This vibrant community is characterized by its friendly neighborhoods, top-rated schools, and a plethora of outdoor activities, making it an ideal place for families, retirees, and everyone in between.

One of the most appealing aspects of Windermere is the availability of homes under $350,000. Yes, you read that right! Despite its reputation for luxury properties, Windermere offers a variety of affordable options for first-time homebuyers or those looking to downsize without compromising on quality of life. You can find charming single-family homes, cozy townhouses, and well-maintained condos that provide both comfort and style. Many of these properties are situated in family-friendly communities that boast amenities such as playgrounds, walking trails, and community pools.

Living in Windermere means enjoying the best of both worlds—peaceful suburban living with easy access to urban amenities. With nearby shopping, dining, and recreational opportunities, you’ll never run out of things to do. Whether you’re taking a leisurely stroll around the scenic Lake Bessie or enjoying a sunset at the Windermere Town Square, this community invites you to experience a lifestyle where nature and community thrive together. Discover your dream home in Windermere today and embrace the enchanting lifestyle that awaits!

Newest Windermere Homes under $350,000

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
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
14030 Sparkling Cove Lane Unit 603, Windermere
$324,900
2 Beds ⋅ 3 Baths ⋅ Oasis Cove I/Lakeside Village Ph 01 SubDv. ⋅ 34786 Zip Code
BRAND NEW ROOF & BRAND NEW HVAC SYSTEM!! — Two of the biggest investments already made for you. This beautifully maintained 2-bedroom, 2.5-bath townhome-style condominium tucked inside the gated community of Oasis Cove at Lakeside Village, in the heart of Windermere. This move-in-ready home delivers comfort, style, and convenience in equal measure. An open-concept floor plan floods the interior with natural light, creating an inviting space for everyday living and entertaining alike. Oasis Cove residents enjoy resort-style living behind a secure gated entrance — a community pool, fitness center, playground, clubhouse, and beautifully maintained grounds set the tone. Even better, HOA fees cover water, internet, cable, ground maintenance, and exterior maintenance, taking the guesswork out of monthly budgeting. The location puts everything Central Florida has to offer within easy reach — Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools all just minutes away. Whether you're searching for a primary residence, a second home, or an investment property, this one checks every box. Schedule your private showing today — with a new roof and new HVAC already in place, this Windermere gem won't last. Ideally located just minutes from Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools, this home grants easy access to everything Central Florida has to give. Whether you're looking for your primary residence, a second home, or an investment opportunity, this exceptional property checks all the boxes. Don't miss your chance to own a beautiful home in one of Windermere's most desirable communities—schedule your private showing today!

14030 Sparkling Cove Lane Unit 603, Windermere
8180 Boat Hook Loop Unit 102, Windermere
$295,000
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
***Seller offering $5,891.88 to cover the first year of HOA fees.*** Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Welcome to effortless Florida living in this move-in ready, light-filled first-floor condo located in the heart of Windermere. Perfectly positioned, this beautifully maintained residence offers the ideal combination of comfort, convenience, and resort-style amenities just minutes from Disney, Winter Garden Village, & directly across from Lakeside Village Center with shopping, dining, and everyday conveniences. Designed with a desirable split-bedroom floor plan, this spacious home features an inviting open-concept layout that seamlessly connects the kitchen, dining, and living areas, creating the perfect space for both entertaining and everyday living. Crown molding adds an elegant touch throughout, while abundant natural light enhances the warm, welcoming atmosphere. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private en-suite bath. Two additional bedrooms offer flexibility for family, guests, or the perfect home office. Step outside to your private screened and covered patio, an ideal place to enjoy morning coffee or relax after a long day. Located within a beautifully maintained gated community, residents enjoy an exceptional collection of resort-style amenities, including a sparkling swimming pool, clubhouse, fitness center, playground, volleyball court, BBQ and picnic areas, scenic walking trails, plus water and valet trash service for added convenience. One reserved parking space is included. Adding even more value, the community has recently completed significant exterior improvements, including new roofs, freshly resurfaced and striped parking areas, and exterior building repainting, enhancing both curb appeal and long-term investment potential. Fiber optic internet is also available, providing high-speed connectivity for remote work, gaming, and streaming. Whether you’re searching for a primary residence, vacation home, or investment opportunity, this exceptional Windermere condo offers low-maintenance living, outstanding amenities, and an unbeatable location close to top-rated schools, major highways, world-class attractions, shopping, dining, and everything Central Florida has to offer.

8180 Boat Hook Loop Unit 102, Windermere
12930 Vennetta Way, Windermere
$350,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 3 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2.5-bathroom townhouse in Berkshire Park, a highly desirable community in the heart of Windermere, Florida. With 1,644 sq ft of meticulously maintained living space, this move-in ready home is perfect for anyone seeking comfort, style, and convenience—just minutes from Walt Disney World, top-rated schools, and all that Central Florida has to offer. Step inside and feel the care of the original owners, with brand-new carpet, fresh interior paint, new blinds, and professionally cleaned tile and grout throughout. The kitchen features modern appliances—including a refrigerator, dishwasher, and microwave—all less than two years old—plus a new faucet, garbage disposal, and updated fixtures for added convenience. The downstairs bathroom has been completely refreshed with a new vanity, toilet, and faucet, while the upstairs bathrooms feature new fixtures and faucets, and the primary bathroom includes newly upgraded exhaust fans for added comfort. The laundry room is upgraded for efficiency, with a high-performance exhaust fan, updated faucets, LED lighting, and thoughtful details that simplify daily routines. The garage is a standout feature, offering a new subpanel and GFCI-protected breakers, additional outlets, LED lighting, ceiling fan, and its very own AC unit—perfect for a home gym, workshop, or extra storage. Smart home touches include a Ring doorbell, Govee under-cabinet LED lighting, and an Aladdin smart garage door opener with keypad. Downstairs features sleek LED wafer lighting and dual ceiling fans in the living room for a stylish and energy-efficient vibe. Enjoy quiet evenings in your rear-facing backyard with peaceful conservation views, and hear the nightly Disney fireworks, and the nostalgic sounds of the Disney World Railroad —all from the comfort of home. Berkshire Park is part of an “A”-rated school district and known for its scenic walking trails, community pool, and proximity to everything—theme parks, shopping, dining, and major highways. This home is a rare find in one of Central Florida’s most coveted neighborhoods. Some images have been virtually staged using digital/AI technology to illustrate the potential use of the space. Furnishings, décor, and other digitally added items shown are not included with the property.

12930 Vennetta Way, Windermere
Start Your Search