Winter Park Homes under $500,000

Winter Park Homes under $500,000

Welcome to Winter Park, Florida—a picturesque city that perfectly blends charm, culture, and community. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush landscapes, and vibrant downtown area filled with boutique shops, delightful cafes, and art galleries. With its tree-lined streets and historic architecture, this enchanting city offers a serene suburban lifestyle while being just a stone's throw away from the excitement of Orlando.

For those seeking an affordable entry into this idyllic community, Winter Park offers a variety of homes under $500,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, there’s something for everyone in this price range. From charming bungalows to modern townhomes, these properties provide the perfect foundation for your dream lifestyle. Imagine waking up in a cozy home with access to beautiful parks, top-rated schools, and a friendly neighborhood atmosphere.

Additionally, Winter Park is known for its exceptional quality of life, featuring a wealth of recreational opportunities. Enjoy leisurely strolls along the scenic shores of Lake Osceola, explore the beautiful gardens at the Charles Hosmer Morse Museum of American Art, or indulge in the vibrant local dining scene.

With its unique blend of natural beauty, cultural richness, and affordability, Winter Park is not just a place to live—it's a place to thrive. Discover your perfect home here today and become part of this thriving community!

Newest Winter Park Homes under $500,000

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
170 Balfour Drive Unit 1, Winter Park
$299,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pointe 01 SubDv. ⋅ 32792 Zip Code
RARELY AVAILABLE CORNER VILLA IN A PRIVATE, SERENE SETTING! Welcome to this beautifully remodeled Winter Park villa, tucked away on a private drive and offering the exceptional privacy and charm of a coveted corner location. From the moment you arrive, the inviting front courtyard sets the tone for a home that feels both elegant and effortlessly comfortable. This residence offers a fresh, elegant feel throughout, including a beautifully updated kitchen, bedrooms, lighting, plumbing, appliances, and more. The home has been remodeled with attention to both style and everyday living. A recently renovated Mediterranean-style tile roof, completed in March 2026, adds timeless architectural character while providing peace of mind for years to come. The indoor-outdoor living experience is equally appealing, with a lovely private rear patio creating the perfect setting for entertaining or simply unwinding at the end of the day. A spacious attached two-car garage provides exceptional convenience and plenty of storage space. And for everyday ease, you even have your own private mailbox attached directly to the home. One of the things that makes this villa especially appealing is the peace of mind that comes with the HOA. If you’re looking for a true lock-and-go lifestyle, the HOA takes care of the exterior maintenance, beautiful landscaping, pest control, and more, so you can simply come home, relax, and enjoy it without worrying about the upkeep. Ideally situated near all that makes Winter Park so desirable, this home places you just minutes from the charm of Park Avenue, where boutique shopping, celebrated dining, cafés, arts, culture, and leisurely strolls come together in one of Central Florida’s most beloved destinations. This is a rare opportunity to enjoy a turnkey villa with character, comfort, privacy, and an enviable location—a home that lets you spend more time enjoying where you live and less time taking care of it. Call for your private showing today!

170 Balfour Drive Unit 1, Winter Park
3150 Shady Pine Avenue, Winter Park
$439,900
4 Beds ⋅ 2 Baths ⋅ Bel Aire SubDv. ⋅ 32792 Zip Code
MOVE-IN READY with a spectacular LAP POOL! Nestled in the desirable Bel Aire Pines community of Winter Park, this beautifully maintained 4-bedroom, 2-bath home offers an exceptional combination of comfortable living, valuable updates, and fantastic outdoor space—all with NO HOA! Step inside to a bright and inviting floor plan featuring formal living and dining rooms, along with a spacious kitchen appointed with granite countertops, upgraded cabinetry, and a charming dinette area for casual meals. The spacious primary suite offers a private ensuite bath with a walk-in shower and built-in seating, granite counter, mirrored medicine cabinets, and beautiful cabinetry. Three additional bedrooms provide plenty of space for family, guests, a home office, or hobby room. The elegant upgraded hall bath features granite counter, spacious mirrored medicine cabinets, and a tub/shower combination with neutral tile and Listello accent. Step outside to discover one of this home's standout features—a fabulous 17' x 50' lap pool, perfect for swimming and exercise, cooling off on warm Florida days, or hosting fun gatherings with family and friends! A screened rear patio provides additional space to relax and entertain while overlooking the pool and private backyard framed by attractive white vinyl fencing. The home has been thoughtfully maintained with important improvements including replumbing (2024), water heater (2026), electrical panel (2023), HVAC system (2023), Energy Star Qualified windows (2023), garage door (2022), and roof (2017)—valuable updates that add comfort and peace of mind. Additional features include carpet, tile and bamboo flooring, water softener, attic fan, and a washer and dryer in the garage. ALL APPLIANCES, INCLUDING THE WASHER AND DRYER, ARE INCLUDED! Ideally situated in Winter Park with convenient access to shopping, dining, Full Sail University, UCF, schools, major roadways, and everyday conveniences, this move-in-ready home offers the space, updates, location, and incredible pool you've been looking for. Schedule your private showing today!

3150 Shady Pine Avenue, Winter Park
2500 Lee Road Unit 123, Winter Park
$169,900
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-bath condo offers 645 SF of move-in-ready living in desirable Lakeside Manor on beautiful Lake Killarney. Enjoy easy first-floor access, peaceful park-like grounds, a sparkling lakefront pool, clubhouse, community boat access and docks—all just steps from your door. The location is exceptional—minutes from Winter Park Village, Park Avenue, Rollins College, shopping, dining and entertainment, with quick access to I-4 and Downtown Orlando. Perfect as a primary residence, second home or low-maintenance getaway. UPDATED. GROUND FLOOR. LAKEFRONT COMMUNITY. PRIME WINTER PARK LOCATION. Come see why Lakeside Manor remains one of Winter Park’s best-kept secrets!

2500 Lee Road Unit 123, Winter Park
188 Sandlewood Unit 1, Winter Park
$290,000
2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code
Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park
712 Baffie Avenue, Winter Park
$448,000
3 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern improvements, featuring beautiful hardwood floors, crown molding, a fireplace, and plenty of natural light throughout. The bright enclosed Florida room provides flexible space for a home office, sitting area, playroom, or additional entertaining space. The updated kitchen offers dark cabinetry, stone countertops, stainless steel appliances, and contemporary finishes. Major improvements include a brand-new roof installed in 2026, along with updated electrical, plumbing, and HVAC systems completed in 2025. These recent improvements provide added value and peace of mind for the next owner. The interior laundry room adds everyday convenience, while the covered rear porch creates a comfortable place to relax and enjoy the outdoors. The fenced backyard offers room for entertaining, gardening, pets, or creating a private outdoor retreat. Enjoy a prime location near A-rated schools, Dubsdread Golf Course, College Park, downtown Winter Park, AdventHealth, shopping, dining, and major roadways. With no HOA and easy access to some of Central Florida’s most popular neighborhoods, this home delivers the character, location, and major updates that make it stand out.

712 Baffie Avenue, Winter Park
200 Saint Andrews Boulevard Unit 704, Winter Park
$159,000
1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
LOCATION, LIFESTYLE & OPPORTUNITY IN THE HEART OF WINTER PARK! Welcome to 200 Saint Andrews Boulevard #704, a charming top-floor, 1-bedroom, 1-bath condominium in the established Four Seasons Condominiums of Winter Park. Whether you’re searching for a primary residence, low-maintenance Winter Park retreat, or investment property, this condo offers an incredible opportunity just minutes from Rollins College, Park Avenue, and Downtown Winter Park. Located on the second and top floor, the residence offers a comfortable and functional layout with beautiful wood flooring throughout the living room and bedroom. The spacious living area flows into the dining space and kitchen, while the primary bedroom features a generous walk-in closet. Two separate entrances add convenience, and the oversized screened-in balcony provides the perfect place to enjoy morning coffee, unwind at the end of the day, or enjoy Florida’s year-round outdoor lifestyle. A private storage closet on the balcony provides additional space, and abundant community parking makes everyday living easy. Four Seasons is an established approximately 20-acre condominium community located within the City of Winter Park. Residents enjoy three community swimming pools, tennis courts, shuffleboard, a clubhouse with library, community laundry facilities, and more. COA INCLUDES WATER, TRASH, SEWER, PEST CONTROL, EXTERIOR AND GROUNDS MAINTENANCE. For buyers who value LOCATION, this one is hard to beat. Rollins College, iconic Park Avenue, and Downtown Winter Park are just minutes away, providing easy access to some of Central Florida’s best restaurants, boutiques, coffee shops, museums, community events, and entertainment. Enjoy nearby outdoor recreation at Cady Way Trail, Ward Park, Showalter Field, and the YMCA, plus convenient access to AdventHealth Winter Park, Baldwin Park, Winter Park Village, Downtown Orlando, I-4, and major Central Florida roadways. For investors, the combination of a Winter Park address, proximity to Rollins College and major employment, healthcare, shopping, dining, and recreation destinations makes this property an option worth considering for a long-term real estate investment. For an owner-occupant, it offers the opportunity to enjoy the Winter Park lifestyle in a low-maintenance condominium setting. Enjoy the convenience of being close to everything while coming home to an established community in one of Central Florida’s most recognized locations. Schedule your private showing and discover the possibilities at Four Seasons Winter Park!

200 Saint Andrews Boulevard Unit 704, Winter Park
5405 Justine Way, Winter Park
$399,900
3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 4th Add SubDv. ⋅ 32792 Zip Code
Welcome to 5405 Justine Way, a charming 3-bedroom, 2-bathroom single-family home in the desirable Winter Park area. This well-located residence offers approximately 1,247 square feet of living space, a private pool, and a garage, providing a great combination of comfort and functionality. Situated on a spacious lot in a residential neighborhood, this property offers an excellent opportunity for a primary residence or investment. Conveniently located near shopping, dining, schools, major roads, and the many attractions of Central Florida. NO HOA. Schedule your showing today and discover the possibilities this home has to offer. *PLEASE CONTACT DIRECTLY CINDY SOTO*

5405 Justine Way, Winter Park
7498 Aloma Pines Court, Winter Park
$364,900
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly maintained. With an open and spacious floor plan is great for family activities and entertaining. NEW A/C AND NEW WATER HEATER. kitchen features all stainless steel appliances, large island great for prep with seating for "4" or more on the oposite side. The large slider leads out to your 5' X 11" private lani, allows natural light to fill the entire space. There is a first floor powder room for convenience for you and your guest. Second floor laundry closet for your convenience. Your oversize primary bedroom features a spacious walk-in closet and ensuite with large vanity and double sinks. There are "2" additional guest bedrooms. The home has a one car garage with an extended pad for a second car. the NEW water heater is located in the garage. The A/C is also NEW. Aloma Trails is convenient to shopping directly accross the street from the complex. minutes from Aloma (426), 417, UCF, Full Sail, Rollins, a Park Ave., Airport and Beaches.

7498 Aloma Pines Court, Winter Park
7786 Fox Knoll Place, Winter Park
$410,500
4 Beds ⋅ 2 Baths ⋅ Bridgewater SubDv. ⋅ 32792 Zip Code
PHENOMENAL DEAL, newer updates INCLUDE: beautifully renovated 4-bedroom, 2-bathroom, two car garage home that perfectly blends modern design with everyday comfort. From the moment you step inside, you’ll appreciate the open-concept floor plan, thoughtfully designed to create a bright, spacious atmosphere that’s perfect for both entertaining and daily living. This move-in-ready home features custom finishes throughout, including stylish fixtures, updated flooring, and a beautifully remodeled kitchen and living space. The expansive primary suite offers a private retreat with a generous bedroom and a stunning ensuite bathroom designed with comfort and luxury in mind. Additional updates include newer roof, AC, water heater, Updated kitchen and bathrooms, The Kitchen is Large with all major appliances: Fridge, Stove, and Dishwasher. You don't want to miss this opportunity to make this house your home!

7786 Fox Knoll Place, Winter Park
1695 Lee Road Unit C206, Winter Park
$140,000
2 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
Welcome to this bright and beautifully updated second-floor condo located in one of Winter Park's most desirable communities! This 2-bedroom, 1-bathroom residence offers the perfect blend of comfort, modern upgrades, and an unbeatable location. Updated Kitchen: Features dark wood cabinetry, light quartz counter tops, black and stainless-steel appliances, a modern commercial-style faucet, and an in-unit washer/dryer set. Spacious Living & Bedroom Areas: Enjoy durable luxury vinyl plank flooring throughout the main areas, bright natural light, and modern finishes. Renovated Bathroom: Outfitted with a updated vanity, chic black hardware, and stylish lighting fixtures. Private Balcony: Relax outdoors on your private covered balcony with peaceful views of the lush green courtyard and community grounds. Resort-style sparkling swimming pool with expansive sun deck. Well-maintained grounds with mature landscaping and tropical palm trees. Quiet, well-kept building entrance and grounds. Situated right off Lee Road, you are just minutes away from top dining, shopping, and entertainment spots. Enjoy close proximity to Park Avenue in Downtown Winter Park, Rollins College, I-4 access for an easy commute to Downtown Orlando or major attractions. Local parks, lakes, and grocery stores. Whether you are looking for a primary residence or a strong investment opportunity in the booming Central Florida market, this move-in-ready condo is a must-see! Schedule your private tour today!

1695 Lee Road Unit C206, Winter Park
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