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, where suburban tranquility meets vibrant community life. Known for its picturesque landscapes, Winter Springs boasts an array of lush parks, scenic trails, and beautiful lakes, making it a haven for outdoor enthusiasts and families alike. With its warm climate and friendly atmosphere, this city offers a delightful blend of small-town charm and modern conveniences, ensuring residents enjoy a high quality of life.

One of the most appealing aspects of Winter Springs is its diverse real estate market, particularly for homebuyers seeking properties under $500,000. Here, you'll find a variety of homes that cater to different lifestyles and budgets. From cozy single-family residences to spacious townhomes, the options are plentiful. Many of these homes come equipped with modern amenities, updated interiors, and beautiful outdoor spaces, perfect for entertaining or simply enjoying the Florida sunshine.

Winter Springs is also conveniently located near major highways, providing easy access to the bustling cities of Orlando and Sanford, where you can indulge in shopping, dining, and entertainment. The city is known for its excellent schools and family-friendly atmosphere, making it an ideal place to raise children or enjoy a peaceful retirement.

With its inviting community spirit and a range of affordable housing options, Winter Springs is more than just a place to live; it’s a place to thrive. Discover your dream home in this enchanting city and experience all the beauty and warmth that Winter Springs has to offer!

Newest Winter Springs Homes under $500,000

122 Burgos Road, Winter Springs
$259,000
3 Beds ⋅ 2 Baths ⋅ North Orlando 2nd Add SubDv. ⋅ 32708 Zip Code
Winter Springs Fixer-Upper with Great Potential! Welcome to 122 Burgos Road, a 3-bedroom, 2-bath home nestled in a quiet Winter Springs neighborhood with plenty of potential to make it your own. This handyman special is a great opportunity for a buyer looking for a project, an investor, or someone ready to transform a home into something truly their own. The property features a fenced-in yard with space to enjoy the outdoors, while the existing garage space has been converted into an additional room. With the right vision, this space could potentially be converted back into a garage to suit your needs. Located in a desirable Winter Springs area surrounded by established neighborhoods, nearby schools, beautiful natural scenery, wildlife, walking and biking trails, and outdoor recreation. You'll also enjoy convenient access to the many attractions and amenities in Central Florida including Orlando, Disney, and Florida's beautiful beaches. This home is ready for its next chapter!

122 Burgos Road, Winter Springs
1481 Casa Park Circle, Winter Springs
$234,000
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 2 SubDv. ⋅ 32708 Zip Code
Move-in condition in the prestigious Tuscawilla country club golf community area! Top-rated schools! New paint, baseboards, water heater, toilet, lighting, granite, tile backsplash, carpet and laminate! All Stainless Steel kitchen appliances and washer/dryer (included) closet next to the kitchen. Nest thermostat. This unit has 2 Primary bedroom suites with full bathrooms. One has a tub/shower combo and the other has a new, tiled shower. New bathroom flooring, vanities and faucets. Recently updated Trotwood Park is across the street and includes basketball, tennis and pickleball courts, playground, splash pad, picnic pavilions with BBQ, boardwalk over Lake Maria, and ample parking! Community Pool! Close to Winter Springs Town Center, Cross Seminole Trail, UCF, and 417. There is also a paved path to the elementary school to keep the children off the main roads!

1481 Casa Park Circle, Winter Springs
1354 Casa Park Circle, Winter Springs
$245,000
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully remodeled, move-in-ready townhome in the desirable Casa Park Villas community of Winter Springs! Perfectly situated directly across from Trotwood Park and conveniently located near highly regarded Seminole County schools, this charming 2-bedroom, 2.5-bath home offers the perfect combination of modern elegance, comfort, and convenience! Step inside and fall in love with the beautifully updated interior, featuring a remodeled kitchen with stylish finishes and newer appliances (2025), perfect for everyday living and entertaining. The entire first floor showcases beautiful tile flooring, while the second floor features gorgeous luxury vinyl plank flooring installed in 2025, creating a seamless blend of style and functionality. Both upstairs bathrooms were beautifully remodeled in 2025 with modern finishes, offering a fresh and contemporary feel. Additional improvements include four new front windows (2025), a new sliding glass door (2025), a water heater (2023), and a newly installed backyard fence (2025), creating a private outdoor space perfect for relaxing or entertaining. Enjoy the benefits of living in Casa Park Villas, where the HOA covers pool maintenance and lawn maintenance, allowing you to spend less time on upkeep and more time enjoying your home! Community amenities include a pool, spa, and sauna. Outdoor enthusiasts will love having Trotwood Park just across the street, offering wonderful opportunities for recreation and relaxation. Ideally located near Winter Springs Town Center, SR-417, UCF, shopping, restaurants, and entertainment, this home provides convenient access to everything Central Florida has to offer. Beautifully remodeled, thoughtfully updated, and ready for its next owner! Why spend time and money renovating when you can move right into a home where the work has already been done? Schedule your private showing today and discover the beauty, convenience, and low-maintenance lifestyle of Casa Park Villas!

1354 Casa Park Circle, Winter Springs
604 Casa Park Court G, Winter Springs
$235,000
2 Beds ⋅ 2 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Move-In Ready 2-Bedroom Townhouse in Winter Springs! This beautifully refreshed 2-bedroom, 1.5-bath townhouse features fresh interior paint, new baseboards, new laminate flooring upstairs, and refreshed tile grout downstairs. The kitchen has been refreshed with freshly painted cabinets, a new countertop, faucet, and oven. Additional improvements include new ceiling fans, a new bedroom light fixture, new blinds throughout, and a new smoke detector. The bathroom features a brand-new bathtub, new toilet seats, and updated fixtures. The unit also includes two assigned parking spaces and access to a community pool. Just nearby, enjoy a community park with tennis courts, barbecue pavilions, and a playground. Available for immediate occupancy. Don’t miss this opportunity to enjoy a freshly refreshed home in a convenient Winter Springs location!

604 Casa Park Court G, Winter Springs
432 Tradition Lane, Winter Springs
$279,999
2 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to 432 Tradition Ln, a charming townhouse located in the desirable Winter Springs, FL. This residence accords a comfortable and efficient living space with 1,275 square feet, designed to accommodate a variety of lifestyles. Inside, you'll find two generously sized bedrooms. The property is set on a manageable lot of 0.039 acres, making maintenance simpler while still offering outdoor possibilities. This townhouse presents a fantastic opportunity to enjoy the benefits of living in a vibrant community, with the convenience of nearby amenities and attractions. Whether you're looking for a primary residence or an investment opportunity, this property holds great potential.

432 Tradition Lane, Winter Springs
846 Benchwood Court, Winter Springs
$385,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
PRICED TO SELL! Opportunity awaits at 846 Benchwood Ct in Winter Springs! This fixer-upper is ready for its next chapter and offers plenty of potential for buyers looking to renovate, customize, or invest. Notable features include a private fenced backyard and a screened-in pool, providing a great starting point for creating an inviting outdoor living space. Conveniently located in Winter Springs with access to shopping, dining, parks, and major roadways. Bring your vision and explore the possibilities this property has to offer. Priced to reflect its current condition and the improvements needed. Sold as-is.

846 Benchwood Court, Winter Springs
226 Bennett Street, Winter Springs
$310,000
3 Beds ⋅ 2 Baths ⋅ North Orlando Townsite 4th Add Rep SubDv. ⋅ 32708 Zip Code
NO HOA. NO RULES. NO MONTHLY FEES. JUST YOUR HOME, YOUR WAY. Imagine owning a home in Winter Springs where nobody tells you what color to paint your door, where to park your truck, or what you can build in your backyard. That freedom is rare, and it’s right here. This 3-bedroom, 2-bathroom home sits on a quiet, established street and gives you something most new communities can’t: real ownership without the HOA bill every month. A 1-car garage keeps your vehicle protected and gives you extra storage space, while the yard is ready for weekend cookouts, a garden, or your next big idea. And the location? Minutes from SR 434 and SR 417, Winter Springs Town Center, shopping, dining, parks, and Orlando Sanford International Airport. Layer Elementary is just around the corner. Whether you’re a first-time buyer tired of renting or an investor looking for a smart Winter Springs buy, this one checks the boxes. No HOA homes at this price point don’t last. Schedule your showing before someone else does!

226 Bennett Street, Winter Springs
1000 Troon Trace, Winter Springs
$412,000
3 Beds ⋅ 3 Baths ⋅ Greenbriar Sub Ph 1 SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to Greenbriar in Winter Springs! Situated on a corner lot, this 3-bedroom, 2.5-bath home offers 1,703 square feet of living space with a two-story layout and an inviting combination of indoor and outdoor spaces. The living and dining area features vaulted ceilings, luxury vinyl plank flooring, and a wood-burning fireplace, while French doors lead to a spacious screened rear patio. The kitchen offers quartz countertops, white shaker-style cabinetry, a tile backsplash, and a separate dining nook. Conveniently located on the main floor, the primary suite features a spacious closet, private bathroom with dual vanities, and sliding doors leading to the screened patio. Upstairs, two additional bedrooms provide flexible space for guests, hobbies, or a home office. Additional highlights include a two-car garage, tile roof, fenced backyard, and a community pool. Location-wise, you will enjoy immediate access to Tuscawilla Country Club, Trotwood Park, Bear Creek Nature Trail, Sam Smith Memorial Park, and the Oviedo Mall. Located in the established Greenbriar community, this home offers convenient access to shopping, dining, medical services, entertainment options, recreation activities, and everyday essentials. Schedule your private showing today and experience everything that this property has to offer.

1000 Troon Trace, Winter Springs
270 Moree Loop Unit 4, Winter Springs
$225,000
3 Beds ⋅ 3 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 3-bedroom, 2.5-bath townhome in desirable Winter Springs! This spacious, move-in-ready home features a recently remodeled kitchen, bathrooms, and flooring throughout! The updated kitchen boasts sleek countertops, dark wood cabinetry, and stainless steel appliances. Enjoy the Florida lifestyle with covered, screened-in front and rear porches, perfect for relaxing or entertaining. The HOA maintains the building exteriors, roofs, and common areas, with basic cable included. Residents can also enjoy the community pool and a convenient location near parks, shopping, and dining. Low-maintenance living in a great location?don't miss this opportunity!

270 Moree Loop Unit 4, Winter Springs
1354 Tarflower Drive, Winter Springs
$445,000
4 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to Hickory Grove, where modern living meets everyday convenience in the heart of Winter Springs! Built in 2024, this beautifully designed two-story townhome offers 4 bedrooms, 2.5 bathrooms, an open-concept living and dining area, and a spacious kitchen featuring stainless steel appliances, solid-surface countertops, a breakfast island, and a spacious pantry. The thoughtfully designed floor plan provides a comfortable balance of gathering space and private retreats, with the primary suite and additional bedrooms conveniently located upstairs. An attached two-car garage adds everyday functionality, while the covered front porch offers a welcoming place to unwind. Residents of Hickory Grove can enjoy community amenities including a swimming pool, playground, and dog park. Conveniently situated near Winter Springs Town Center, this location offers easy access to grocery stores, shopping, dining, coffee shops, parks, and major roadways for commuting throughout Central Florida. Enjoy the convenience of a connected location while having a comfortable place to call home. Whether you are looking for your next home or an opportunity to own in an established Central Florida market, this townhome offers a wonderful combination of modern design, low-maintenance living, and accessibility. Schedule your private showing and discover all that Hickory Grove and Winter Springs have to offer!

1354 Tarflower Drive, Winter Springs
878 Benchwood Drive, Winter Springs
$449,900
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
Welcome to this freshly updated, single-story block home in the established Oak Forest neighborhood of Winter Springs! Inside, new luxury vinyl plank flooring, plush new carpet, and fresh two-tone paint create a bright, modern atmosphere. The sunken living room features a refreshed fireplace with a sleek black finish and new recessed lighting, creating a stylish and inviting focal point. The kitchen has been enhanced with updated matte black hardware and modern lighting, while new interior doors and coach-style exterior lighting add a fresh, contemporary touch. A screened-in rear porch provides the perfect spot to relax and enjoy the outdoors. Conveniently located near SR-434 and SR-417, this home offers easy access to Winter Springs Town Center, Trotwood Park, Central Winds Park, and the Cross Seminole Trail. With its thoughtful updates, inviting spaces, and convenient location, this move-in-ready home is a wonderful opportunity to enjoy all that Winter Springs has to offer!

878 Benchwood Drive, Winter Springs
955 Wedgewood Drive, Winter Springs
$440,000
2 Beds ⋅ 2 Baths ⋅ Wedgewood Unit 2 SubDv. ⋅ 32708 Zip Code
Welcome to 955 Wedgewood Dr, a beautifully renovated home in Winter Springs, FL, with the big-ticket items already taken care of: a brand-new HVAC system (2026), a new water heater (2026), and a roof replaced in 2019. Every inch of the interior has been thoughtfully updated with high-end finishes, including new flooring throughout, new appliances, designer showers, custom cabinetry, upgraded hardware, and stylish vanities. This inviting residence has 1,640 square feet of comfortable living space, providing ample room for a variety of lifestyle needs. Situated on a 0.127-acre lot, the property features a manageable outdoor area great for enjoying the Florida sunshine. Inside, the home features two bedrooms, offering plenty of space for rest and relaxation. The layout is designed to maximize functionality and comfort, making it a welcoming place to call home. With its convenient location in Winter Springs, residents can enjoy the benefits of a vibrant community with easy access to nearby amenities.

955 Wedgewood Drive, Winter Springs
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