Winter Springs Homes under $500,000

Winter Springs Homes under $500,000

Welcome to Winter Springs, Florida – a charming city nestled in the heart of Seminole County, known for its welcoming atmosphere, lush landscapes, and family-friendly community. Just a stone's throw from the bustling city of Orlando, Winter Springs offers a perfect blend of suburban tranquility and urban convenience. With its picturesque parks, scenic trails, and vibrant local culture, it’s no wonder that families and professionals alike are drawn to this delightful city.

Winter Springs boasts a variety of homes that cater to diverse lifestyles, and one of the most appealing aspects is the availability of beautiful properties under $500,000. Whether you're a first-time homebuyer, looking to downsize, or seeking an investment opportunity, Winter Springs has something for everyone. You can find charming single-family homes with spacious yards, modern townhouses, and cozy villas that offer both comfort and style.

The community is rich with amenities, including top-rated schools, shopping centers, and recreational facilities, making it an ideal place for families. Enjoy weekend outings at the nearby parks, take a stroll along the scenic trails, or indulge in the local dining scene that showcases a variety of culinary delights.

With its affordable housing options and vibrant community spirit, Winter Springs is not just a place to live; it's a place to thrive. Discover your dream home in this enchanting city and experience the perfect balance of relaxation and excitement that Winter Springs has to offer!

Newest Winter Springs Homes under $500,000

1361 San Diego Court, Winter Springs

1361 San Diego Court, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Sunrise Village Unit 1 SubDv. ⋅ 32708 Zip Code

Welcome home to this freshly updated 3-bedroom, 2-bath single-story block home in the Sunrise Village neighborhood of Winter Springs. Featuring a two-car garage, this home has been refreshed throughout with new luxury vinyl plank flooring in the main living areas and bathrooms, new carpet in all three bedrooms, fresh two-tone interior paint, and modern black hardware, lighting, and ceiling fans. The updated kitchen features new Carrara quartz countertops, an undermount sink with a pull-down faucet, and new stainless steel appliances, including a range and dishwasher. The living room features a cozy fireplace and sliding glass doors leading to the rear porch, creating a welcoming space to relax or entertain. With convenient access to Red Bug Lake Road, SR-417, and nearby shopping and dining, this move-in-ready home offers comfort and convenience in Winter Springs.

1361 San Diego Court, Winter Springs

154 Wooded Vine Drive, Winter Springs

154 Wooded Vine Drive, Winter Springs

3 Beds ⋅ 3 Baths ⋅ Tuskawilla Crossings 34'S SubDv. ⋅ 32708 Zip Code

Welcome to Tuskawilla Crossings! Discover the perfect blend of comfort, style, and convenience in the heart of Winter Springs. Built by Lennar Homes in 2019, this beautifully maintained home offers modern finishes, thoughtful upgrades, and an exceptional location within the desirable Tuskawilla Crossings community. Step inside to a bright, welcoming interior featuring luxury vinyl plank flooring throughout and an open-concept main living area designed for both everyday living and entertaining. The spacious living and dining areas flow seamlessly into the modern kitchen, complete with a large quartz island, upgraded cabinetry, and plenty of workspace for cooking and gathering. A convenient guest half-bath completes the first floor. Upstairs, a spacious hallway leads to a generously sized primary suite featuring a walk-in closet, along with two additional well-appointed bedrooms and a convenient laundry room. Natural light fills the home, enhanced by custom retractable window shades that provide both style and privacy. Step outside and enjoy one of the home's standout features—a private backyard with no rear neighbors! The fully fenced yard offers plenty of room for outdoor entertaining and relaxation, while the covered patio creates the perfect space for enjoying your morning coffee or hosting friends and family. A covered walkway leads directly to the oversized rear-entry garage, adding both convenience and functionality. Life at Tuskawilla Crossings offers an impressive array of community amenities, including a community pool, dog park, playground, clubhouse, and covered pavilions with cookout areas. Nature lovers will appreciate being within walking distance of the nearby nature trail, making it easy to enjoy the outdoors right from home. And the location is hard to beat! With quick and convenient access to the 417, you'll have an easy commute and be just minutes from an abundance of shopping, dining, entertainment, and everyday conveniences—many within a 10-minute drive. Beautifully maintained, move-in ready, private, and ideally located—this Tuskawilla Crossings home offers the lifestyle you've been looking for. Come see it for yourself!

154 Wooded Vine Drive, Winter Springs

499 Club Drive, Winter Springs

499 Club Drive, Winter Springs

2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code

Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!

499 Club Drive, Winter Springs

3600 Biscayne Drive, Winter Springs

3600 Biscayne Drive, Winter Springs

4 Beds ⋅ 2 Baths ⋅ Hollowbrook Ph 2 SubDv. ⋅ 32708 Zip Code

Welcome to 3600 Biscayne Drive in the delightful Hollowbrook neighborhood of Winter Springs. This roomy corner-lot home offers 4 bedrooms, 2 full baths, a versatile den/flex space, and an enclosed Florida room. The kitchen opens to the living room, perfect for entertaining, with extra bar seating for guests. The spacious living room features a cozy fireplace for chilly evenings. The primary bedroom has direct access to the Florida room, and the renovated primary bathroom adds a touch of elegance with a large walk-in closet. The den/flex space is ideal for working from home, while the fenced backyard off the Florida room provides privacy. The roof was installed in 2013. Zoned for Lake Howell High—Go Silver Hawks!

3600 Biscayne Drive, Winter Springs

140 Bombay Avenue, Winter Springs

140 Bombay Avenue, Winter Springs

3 Beds ⋅ 2 Baths ⋅ North Orlando 5th Add SubDv. ⋅ 32708 Zip Code

Virtually Staged. Welcome to this renovated 3 bed 2 bath home featuring a converted garage that provides a large fourth bedroom or perfect for guest room, home office, or additional living space. Enjoy outdoor living on the aluminum-covered, screened-in patio--an inviting spot for morning coffee or relaxing evenings. The large yard offers plenty of room for family barbecues, celebrations, and relaxing weekends outdoors, while the driveway provides convenient off-street parking. With versatile space inside and room to entertain outside, this home is ready to move in. 2026 Roof and newer HVAC. Schedule your showing today.

140 Bombay Avenue, Winter Springs

113 Lido Road, Winter Springs

113 Lido Road, Winter Springs

4 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 09 SubDv. ⋅ 32708 Zip Code

Virtually Staged. MOVE-IN READY WITH MODERN UPDATES + NEW A/C (2025) + RENOVATED KITCHEN! Discover the perfect blend of comfort, style, and convenience in this beautifully refreshed 4-bedroom, 2-bath home nestled in the heart of Winter Springs. Featuring a bright, spacious layout, thoughtfully updated interiors, and an oversized backyard, this home offers inviting spaces for everyday living and entertaining, with many of the major improvements already completed! From the moment you enter, you'll appreciate the fresh, welcoming feel created by NEW LVP FLOORING THROUGHOUT, FRESH INTERIOR PAINT, and abundant natural light. The beautifully RENOVATED KITCHEN features NEW WOOD CABINETRY, GRANITE COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES, and generous storage. An adjoining eat-in dining area features charming FRENCH DOORS opening to the backyard, creating an effortless connection between indoor and outdoor living. The comfortable PRIMARY SUITE features an updated en-suite bathroom with NEW CABINETRY, GRANITE COUNTERTOPS, and a tub/shower combination. Three additional bedrooms offer flexibility for guests, a HOME OFFICE, or hobbies, while the guest bathroom has also been refreshed with NEW CABINETRY AND GRANITE COUNTERTOPS. Beyond the interior improvements, major updates include a NEW A/C SYSTEM (2025), ROOF REPLACED IN 2018, and WHOLE-HOUSE REPIPE, providing added value and peace of mind. Outside, find the OVERSIZED BACKYARD, offering plenty of space for entertaining, gardening, outdoor activities, or creating your own private retreat. Conveniently located in WINTER SPRINGS, with easy access to shopping, dining, parks, major roadways, and surrounding Central Florida destinations, this home offers the perfect combination of an established neighborhood and modern comfort. Schedule your private showing today!

113 Lido Road, Winter Springs

627 Clearn Court, Winter Springs

627 Clearn Court, Winter Springs

5 Beds ⋅ 4 Baths ⋅ The Highlands Sec Four Tracts A & B Rep SubDv. ⋅ 32708 Zip Code

Welcome to this beautifully updated home, with it's own IN-LAW SUITE, tucked away on a quiet cul-de-sac in Winter Springs! The first floor offers plenty of room to spread out, featuring a sunken living room, cozy fireplace, and formal dining area. This living space opens to the large fully fenced backyard. The kitchen has been updated with bright & light cabinets, countertops, stainless steel appliances, and right off the kitchen is a screened covered porch with access to the backyard. Through the laundry room, is the garage which has been thoughtfully converted into a private 1 bedroom, 1 bathroom in-law suite with its OWN ENTRANCE. This space has been beautifully done and features its own kitchen with a stove, microwave, and refrigerator, and it's own AC unit. You can access the in-law suite from inside or outside the home, depending on how you'd like to use the space. Whether used as an in-law setup, guest space, home office, or additional flex space, it gives the home versatility that is hard to find. Upstairs, is the primary suite with an en-suite bathroom and generous closet. Off the primary suite is a spacious balcony, just in time for Florida's great fall weather! Three additional bedrooms and a full guest bathroom provide plenty of space for family, guests, or working from home. Conveniently located in Seminole County with easy access to Winter Springs Town Center, Longwood, Lake Mary, Altamonte Springs, SR 434, US 17-92, and I-4, making getting around Central Florida easy. If you've been looking for a home with extra space and possibilities beyond the traditional floor plan, this one deserves a look! The Highlands neighborhood features a great community pool and tennis courts/pickleball courts, as well as beautiful nature trails and stately historic trees.

627 Clearn Court, Winter Springs

1013 Walnut Creek Cove, Winter Springs

1013 Walnut Creek Cove, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Parkstone Unit 4 SubDv. ⋅ 32708 Zip Code

Beautiful 4-bedroom POOL home with awesome pond front in the exclusive gated community of Parkstone! Formal Living, Dining, and Family rooms. Spacious eat-in kitchen with stainless steel appliances. Large owner's suite with huge closet and elegant garden tub and separate shower. High ceilings and tile flooring throughout house. One story home. New AC. Laundry room. Covered screened-in back porch with POOL and stunning view of the pond. 2 car garage. Roof about 5 years old. HOA mows yard. House is on a CUL-DE-ac so very quiet. Enjoy the community pool, splash pad, tennis courts, playground, and fishing pier. Near the Seminole Trail for biking and walking as well as Central Winds Park/dog park. Good schools. Great location. Must See!

1013 Walnut Creek Cove, Winter Springs

408 Lancers Drive, Winter Springs

408 Lancers Drive, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Mount Greenwood Unit 5 Of SubDv. ⋅ 32708 Zip Code

Virtually Staged. Welcome to this charming home in the Mount Greenwood community of desirable Winter Springs! Offering comfortable one-story living, this home combines a versatile layout with a fantastic Seminole County location surrounded by established neighborhoods, parks and recreation. Vaulted ceilings give the main living spaces an open, airy feel, while the split bedroom plan provides separation between the primary suite and secondary bedrooms. The living and dining area features French doors opening directly to the fenced backyard. The kitchen features a closet pantry and pendant lighting, with an adjacent dining area that keeps meals and gatherings conveniently close. Just off the kitchen, an indoor laundry room leads to a flex area that can be used as a breakfast nook, home office or sitting area. Prefer your breakfast nook toward the front of the home? The area to the left of the front door provides another option, leaving the flex space available for whatever best suits your needs. The primary suite includes a generously sized walk-in closet and its own bathroom with a tub and shower combination. The secondary bathroom also offers a tub and shower combination, and the additional bedrooms provide space for guests, a home office or hobbies. The Winter Springs location is another major plus, offering access to Seminole County public schools and plenty of ways to enjoy the outdoors. Spend time at Central Winds Park, explore the Cross Seminole Trail on foot or by bike, or enjoy the shopping and dining options throughout Winter Springs and neighboring communities. Access to State Road 434 and the 417 makes it convenient to connect with the greater Orlando area while enjoying an established residential setting. A two-car garage provides parking and storage, and the fenced backyard offers room to create your own outdoor gathering space, add a garden or simply relax at the end of the day. With flexible living spaces and so much to enjoy in the surrounding area, this home is ready for your personal touch. Come check out your future home today!!

408 Lancers Drive, Winter Springs

1436 Winter Wharf Lane, Winter Springs

1436 Winter Wharf Lane, Winter Springs

3 Beds ⋅ 4 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code

Virtually Staged. Welcome to easy, stylish living in Jesup’s Landing, one of Winter Springs’ most desirable communities. This spacious 3 Bedroom, 3 1/2 Bath Townhome features a versatile split-level design that creates a comfortable sense of separation between living areas while still offering plenty of room to gather and entertain. The beautifully appointed kitchen features 42-inch cherry cabinetry, granite countertops, and a spacious prep island, creating an inviting and functional space for cooking, baking, and entertaining. Upstairs, the primary suite offers a generous bedroom, a spacious walk-in closet, and a well-designed primary bath with a double-sink vanity, separate shower, and soaking tub. A second upstairs bedroom also features its own en-suite bath with a walk-in shower and a large walk-in closet, providing added privacy and convenience. The lower level includes an additional secondary bedroom with its own en-suite shower bath, along with access to the two-car garage and extra storage space. New Carpet in the Bedrooms and Stairways was just installed for a MOVE-IN READY transition for the new Owner. The exterior has also been refreshed with New Paint, New Screen on Balcony and the home features a New Roof for added value and peace of mind. The location offers exceptional convenience with Central Winds Park, shopping, dining, SR 417, Orlando Sanford International Airport, UCF, and Seminole State College all within easy reach. Jesup’s Landing residents enjoy a variety of community amenities, including a clubhouse, fitness center, and inviting swimming pool. With its spacious floor plan, recent updates, convenient location, and low-maintenance lifestyle, this home offers a wonderful opportunity to enjoy all that Winter Springs has to offer. ROOF - 2026, A/C and Water Heater - 2014.

1436 Winter Wharf Lane, Winter Springs

711 Thistle Place, Winter Springs

711 Thistle Place, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code

Welcome to Wildwood! This three-bedroom, two-bath home features ceramic tile flooring throughout, newer windows, siding and water heater, roof replaced in 2016. Enjoy the private, fenced backyard and spacious screened porch—perfect for relaxing or entertaining. This move-in-ready home offers plenty of potential to add your personal touches. The centrally located close to shopping and schools. The community features a pool, playground, tennis courts, and park. Call today for more details or to schedule your private showing.

711 Thistle Place, Winter Springs

725 Adidas Road, Winter Springs

725 Adidas Road, Winter Springs

2 Beds ⋅ 2 Baths ⋅ Wedgewood Tennis Villas SubDv. ⋅ 32708 Zip Code

Enjoy peaceful pond views from this 2-bedroom, 2-bath Winter Springs home that blends thoughtful updates with genuine character. Exposed wood beams and a fireplace anchor the living room, while the kitchen was renovated in 2021 with butcher block counters and new wood cabinetry. New exterior paint in September 2026! The home was fully repiped in 2024, and the primary bath features an updated shower. The enclosed porch, cooled by its own mini-split AC, adds flexible space for a home office, reading nook, or entertaining. Step outside to a 14' x 14' brick paver patio overlooking the pond. Conveniently located near Trotwood Park, Seminole County schools, and SR 417, making it easy to get anywhere in Central Florida. Schedule your showing today!

725 Adidas Road, Winter Springs

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