Winter Park Homes under $500,000

Winter Park Homes under $500,000

Welcome to Winter Park, Florida—a picturesque city that seamlessly blends small-town charm with vibrant cultural experiences. Nestled just north of Orlando, Winter Park is renowned for its stunning tree-lined streets, historic architecture, and a lively arts scene. With beautiful parks, serene lakes, and a plethora of outdoor activities, it’s no wonder that residents enjoy a lifestyle that embraces both relaxation and adventure.

One of the most appealing aspects of Winter Park is its diverse real estate market, particularly for those seeking homes under $500,000. Here, you’ll find a variety of options that cater to different tastes and lifestyles. From charming bungalows to modern townhomes, there’s something for everyone in this affordable price range. Many of these homes feature beautiful landscaping, spacious yards, and easy access to the city’s many amenities.

Living in Winter Park means you’ll be close to a thriving downtown area filled with boutique shops, gourmet restaurants, and art galleries. The city is also home to the renowned Rollins College, which adds a vibrant energy and a wealth of cultural events to the community. With an excellent school system, family-friendly parks, and a strong sense of community, Winter Park is an ideal place to call home.

Whether you’re a first-time buyer or looking to downsize, exploring the homes under $500,000 in Winter Park opens up a world of possibilities. Discover your dream home in this enchanting city where the charm of Florida living awaits you!

Newest Winter Park Homes under $500,000

1320 Buckingham Road, Winter Park
$449,000
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
LOCATION, LOCATION, LOCATION! Don't miss this opportunity to own a property in the highly desirable Winter Park area! Ideally situated near the shopping, dining, parks, and cultural attractions that make Winter Park one of Central Florida's most sought-after places to live, this property offers an excellent opportunity for homeowners and investors alike. Major updates include a brand-new roof, along with HVAC and electrical systems updated in 2015, providing added peace of mind. Enjoy convenient access to major roadways, everyday amenities, and the vibrant shopping and dining destinations of Park Avenue and the surrounding Winter Park community. Whether you're looking for a place to call home or an investment in a desirable location, this property offers plenty of potential. Don't miss your chance to take advantage of this fantastic location!

1320 Buckingham Road, Winter Park
1407 Broad Wing Lane, Winter Park
$491,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 baths, and 2,308 sqft of modern, open-concept living. The main level flows from the foyer into a bright living/dining area and an island kitchen with granite-look counters, subway tile backsplash, and a full stainless appliance suite. Wood-look vinyl plank flooring throughout the living areas; carpeted bedrooms upstairs including a primary suite with tray ceiling, dual vanity, and glass-door walk-in shower with large-format tile. A versatile loft adds flexible living space. Step out to the covered lanai with ceiling fan overlooking a wooded view. 2-car garage plus a laundry room with sink and cabinetry. Enjoy resort-style community amenities — clubhouse, pool, playground, and park — minutes from Winter Park shopping and dining. HOA $333/mo. Call and schedule your showing today!

1407 Broad Wing Lane, Winter Park
1462 Siciliano Point, Winter Park
$325,000
3 Beds ⋅ 3 Baths ⋅ Vistas At Lake Howell SubDv. ⋅ 32792 Zip Code
Location! Situated in the Vistas at Lake Howell community in Winter Park, this three-bedroom end-unit townhome offers approximately 1,628 square feet of heated living space across two levels. The combined living and dining area opens through sliding glass doors to a screened rear porch. The kitchen includes a refrigerator, range, microwave, and dishwasher. Tile and vinyl flooring, a laundry closet, and an attached one-car garage complete the home. The location provides convenient access to Howell Branch Road and SR 436 for connections throughout Central Florida. Schedule a private showing today. Some photos have been virtually staged to illustrate potential furniture placement and use of space.

1462 Siciliano Point, Winter Park
4882 Tangerine Avenue Unit 4882, Winter Park
$185,000
2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Charming 2BD/1.5BA Wrenwood Condo in Winter Park! Adorable & affordable townhome-style condo with immaculate flooring, well maintained kitchen and appliances, brand-new water heater, and a recently replaced roof and AC unit ! You will also enjoy a lovely courtyard view. Enjoy 1,281 sq ft of comfortable living in a peaceful and highly sought-after location. Just steps away from the community pool and just a short drive to local shoppes and restaurants. Perfect starter home or investment opportunity- pets welcome! Call today to schedule your private showing!

4882 Tangerine Avenue Unit 4882, Winter Park
700 Melrose Avenue Unit M23, Winter Park
$354,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park
1500 Gay Road Unit 26-C, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park
3307 Amber Wood Way Unit 106, Winter Park
$169,000
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 06 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Whether you are looking for a home for yourself, or a great investment, don’t miss this opportunity close to Full Sail, UCF, and Valencia all while being zoned for Winter Park High! The property features 2 bedrooms with en-suite upstairs and a guest half bath downstairs. The unit comes nicely finished with laminate flooring throughout (no carpet!), granite countertops in the kitchen and a private gated back patio with storage! The community features a pool and the HOA covers all exterior maintenance along with the roof!

3307 Amber Wood Way Unit 106, Winter Park
2020 Leanne Court, Winter Park
$479,900
4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 14 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome home to 2020 Leanne Ct, a spacious pool residence offering versatile living and classic Florida charm in Winter Park! According to updated Seminole County tax and public records, this property features 4 bedrooms, 3 full bathrooms, and 2,088 square feet of functional interior living space set on an expansive 0.31-acre lot (13,504 sq ft). Inside, bright common areas feature formal living and dining spaces alongside a open central kitchen with breakfast bar overlooking a cozy family room. The desirable split-bedroom floor plan includes four well-proportioned bedrooms and three full baths, ideal for family accommodations, a primary suite, or dedicated home workspace options. Outside, enjoy a private backyard setting complete with a sparkling swimming pool and garden space—perfect for outdoor entertaining. Conveniently located near top-rated local schools, parks, shopping, and major routes

2020 Leanne Court, Winter Park
3032 Antique Oaks Circle Unit 145, Winter Park
$139,999
1 Beds ⋅ 1 Baths ⋅ Parkview Village Condominium SubDv. ⋅ 32792 Zip Code
Investment opportunity in the heart of Winter Park! This tenant-occupied 1-bedroom, 1-bath condo in Parkview Village offers 749 square feet of comfortable living space with an open living and dining area, functional kitchen, in-unit washer and dryer, and sliding glass doors leading to a private screened patio. The community features a pool and clubhouse, while the convenient location provides easy access to Full Sail University, UCF, SR-436, SR-417, shopping, dining, and everyday conveniences. With a tenant already in place, this property offers an excellent opportunity for an investor looking to add an income-producing Winter Park condo to their portfolio.

3032 Antique Oaks Circle Unit 145, Winter Park
310 Granada Drive, Winter Park
$350,000
3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code
Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview Heights community, this 3-bedroom, 2-bath concrete-block home offers 1,344 square feet of living space with a functional single-story floor plan and plenty of potential for a buyer looking to make a home their own. Inside, the home features tile flooring throughout the main living and dining areas, vaulted ceilings, ceiling fans, and a split-bedroom layout that provides added separation and flexibility. The kitchen is equipped with a convection oven, dishwasher, microwave, and refrigerator, while indoor washer and dryer hookups add everyday convenience. Step outside through the covered rear entry to a brick-paver patio overlooking the fully fenced backyard. Mature trees provide natural shade, while the outdoor space offers plenty of room for entertaining, gardening, pets, or simply enjoying the Florida lifestyle. A one-car carport provides covered parking, and the property is connected to public water and sewer. One of the property's biggest advantages is its Winter Park location. Enjoy convenient access to shopping, restaurants, parks, major roadways, downtown Winter Park, Park Avenue, College Park, and surrounding Orlando destinations while still coming home to an established residential neighborhood. With NO HOA, solid concrete-block construction, a fenced yard, and a sought-after 32789 address, 310 Granada Drive presents an exciting opportunity for an owner-occupant, investor, or buyer looking to renovate and add their personal style. Schedule your private showing and discover the possibilities this Winter Park property has to offer!

310 Granada Drive, Winter Park
302 Lewfield Circle Unit 302, Winter Park
$140,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
ENJOY THE WINTER PARK LIFESTYLE from this charming one-bedroom, one-bath condo offering low maintenance living in a convenient Central Florida location. Step inside to a bright and comfortable floor plan with a private second floor balcony that extends the living space outdoors, perfect for sipping coffee, reading a book, or enjoying the Florida weather. The community offers a refreshing pool and clubhouse, providing additional spaces to relax and enjoy. Located just minutes from the shops and restaurants of Park Avenue, Rollins College, local parks, and everyday conveniences, you’ll have easy access to everything that makes Winter Park such a desirable place to call home. A great opportunity for a full-time residence, seasonal getaway, or anyone looking to enjoy a simplified lifestyle in Winter Park! Listing photos have been virtually staged for visualization and illustrative purposes only. The property is currently vacant and move-in ready.

302 Lewfield Circle Unit 302, Winter Park
200 Saint Andrews Boulevard Unit 3408, Winter Park
$170,000
1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
Great opportunity to own or invest in a 1 bedroom, 1 bath, second floor condo in the highly sought after Four Seasons community of Winter Park. The entire unit has just been newly painted, includes stackable washer and dryer and a newly painted screened porch with a storage closet facing the lushly landscaped courtyard. The community offers three community pools, tennis courts, car wash area and multiple laundry facilities. Conveniently located to restaurants, Winter Park Hospital and grocery stores. Easy access to Park Avenue and close proximity to Rollins, Full Sail and UCF.

200 Saint Andrews Boulevard Unit 3408, Winter Park
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