Winter Springs Homes under $500,000

Winter Springs Homes under $500,000

Welcome to Winter Springs, Florida—a hidden gem nestled in the heart of Seminole County! Known for its charming neighborhoods, lush parks, and vibrant community spirit, Winter Springs offers an inviting atmosphere that appeals to families, retirees, and everyone in between. With its convenient location just north of Orlando, residents enjoy easy access to the excitement of theme parks, shopping, and dining, while still relishing the tranquility of suburban living.

One of the standout features of Winter Springs is its commitment to preserving nature. The city boasts an extensive network of trails, parks, and recreational facilities, making it a haven for outdoor enthusiasts. Whether you’re strolling through the scenic Central Winds Park or enjoying a weekend picnic at the picturesque Lake Jesup, you’ll find ample opportunities to connect with nature and unwind.

For homebuyers seeking affordability without compromising on quality, Winter Springs has a delightful selection of homes priced under $500,000. From charming single-family homes to modern townhouses, the real estate market here caters to a variety of tastes and lifestyles. Many of these homes feature spacious layouts, updated amenities, and beautifully landscaped yards—perfect for creating lasting memories with loved ones.

In Winter Springs, you’ll find a welcoming community that values education, with top-rated schools and family-oriented events throughout the year. With its perfect blend of suburban charm, outdoor adventure, and affordable housing options, Winter Springs is not just a place to live; it’s a place to thrive. Come discover your dream home in this enchanting city today!

Newest Winter Springs Homes under $500,000

624 Huntly Lane, Winter Springs
$245,000
2 Beds ⋅ 2 Baths ⋅ O6454234 MLS
Auction Property. Auction Property being sold, occupied. No Interior Access. Welcome to The Highlands, an established community in the heart of Winter Springs! Discover the possibilities of this 2-bedroom, 2-bath residence offering 1,156 square feet of living space with a convenient single-story layout. Whether you're looking to add your personal touch or create a space that suits your lifestyle, this home offers an opportunity to bring your ideas to life. Situated on a 0.12-acre lot, the property features an attached two-car garage and a spacious driveway for additional parking. Enjoy the convenience of being near SR-434 and US-17, providing access to shopping, dining, parks, indoor and outdoor recreation activities, and everyday essentials. With its established neighborhood setting and appealing nearby amenities, this property is ready for its next chapter.

624 Huntly Lane, Winter Springs
585 Green Spring Circle, Winter Springs
$230,000
2 Beds ⋅ 2 Baths ⋅ O6455300 MLS ⋅ 585 BLDG.
Move-in ready 2-bedroom, 1.5-bath townhome in the established Mount Greenwood community of Winter Springs. This two-story home offers 1,136 square feet with a combined living and dining area, an eat-in kitchen, tile flooring downstairs, and two bedrooms upstairs. A screened rear porch provides additional space to relax, and two assigned parking spaces add convenience. Residents enjoy a community pool, with community grounds maintenance included in the HOA fees. Convenient to shopping, restaurants, and everyday services along SR 434, with access to US 17-92 and SR 417. Central Winds Park and the Cross Seminole Trail offer recreation options in the surrounding area. Zoned for Winter Springs Elementary, Indian Trails Middle, and Winter Springs High School. A practical home with room to add your own personal touches.

585 Green Spring Circle, Winter Springs
732 Woodhaven Drive, Winter Springs
$300,000
3 Beds ⋅ 2 Baths ⋅ O6455677 MLS
732 Woodhaven Dr is a single-story Winter Springs home with three bedrooms, two bathrooms and over 1,300 square feet of living space. Sliding doors connect an additional living room to the rear patio, while the main living and dining areas share an open layout. The galley kitchen has counters and cabinets on both sides, a window above the sink and a separate laundry room at one end. The primary bedroom includes a wide closet and an attached bathroom with a tub-shower combination. Two secondary bedrooms sit near the hall bathroom, and an attached one-car garage provides covered parking. Included 100-Day Home Warranty

732 Woodhaven Drive, Winter Springs
122 Burgos Road, Winter Springs
$259,000
3 Beds ⋅ 2 Baths ⋅ G5119422 MLS
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
428 Blue Bayou Lane, Winter Springs
$321,000
2 Beds ⋅ 2 Baths ⋅ O6454612 MLS ⋅ 428 BLDG.
Welcome to effortless living in the heart of Winter Springs. This stunning end-unit townhome in the highly sought-after Jesups Reserve community offers a perfect blend of style and convenience. The thoughtful layout features a private first-floor bedroom complete with an en-suite bath, offering a versatile space for guests or a home office. Head upstairs to the main living area, where an open concept layout connects the living and dining rooms to a beautiful kitchen. Home chefs will love the granite countertops, 42" cabinetry, stainless steel appliances, and custom backsplash, all complemented by easy-to-maintain tile flooring. Storage is never an issue with the rear facing two car garage, providing plenty of room for vehicles and gear. Located just steps away from the community pool, and super close to convenient shopping and dining options at the Winter Springs Town Center. Great location near SR-434, Tuskawilla Road, and the 417! Roof replaced by the community HOA in 2023, water heater replaced in 2023, washer/dryer unit does convey and was replaced in 2024, Don't let this one slip away—schedule your showing today and see why this is the perfect place to call home.

428 Blue Bayou Lane, Winter Springs
1481 Casa Park Circle, Winter Springs
$234,000
2 Beds ⋅ 3 Baths ⋅ O6453524 MLS ⋅ 1481 BLDG.
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 ⋅ O6454132 MLS ⋅ 1354 BLDG.
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 ⋅ O6453699 MLS ⋅ 604 BLDG.
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 ⋅ O6453934 MLS ⋅ 432 Tradition Ln BLDG.
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 ⋅ O6453509 MLS
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 ⋅ O6453326 MLS
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 ⋅ O6440283 MLS
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
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