Winter Park Homes under $750,000

Winter Park Homes under $750,000

Welcome to Winter Park, Florida – a charming city that perfectly blends small-town warmth with vibrant cultural offerings. Nestled just north of Orlando, Winter Park is renowned for its picturesque lakes, lush parks, and stunning tree-lined streets. This delightful community is home to an array of boutiques, art galleries, and gourmet restaurants, making it a haven for those who appreciate a lifestyle rich in arts and culture.

One of Winter Park's standout features is its commitment to preserving its historic charm while embracing modern living. The city boasts a variety of architectural styles, from Mediterranean Revival to Craftsman homes, each telling a story of its own. For homebuyers seeking a slice of this enchanting locale, there are fantastic options available under $750,000.

Imagine waking up in a cozy bungalow or a contemporary townhouse, all while being just moments away from the serene beauty of Lake Virginia or the vibrant activities of Park Avenue. With a thriving community atmosphere, Winter Park offers excellent schools, beautiful parks, and a calendar full of events, from outdoor concerts to seasonal festivals.

Whether you’re a first-time homebuyer or looking to downsize, Winter Park's real estate market presents an array of opportunities that cater to diverse lifestyles. Embrace the charm of Winter Park and discover your dream home in this idyllic Florida city, where every day feels like a vacation. Don’t miss out on the chance to be part of this vibrant community!

Newest Winter Park Homes under $750,000

2322 Woodcrest Drive, Winter Park
$675,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, 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
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
1409 Aster Court, Winter Park
$589,900
4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to 1409 Aster Court, a fully refreshed single-story home in Garden Lake Estates, where Winter Park’s address meets the quiet of Seminole County. No HOA. No monthly dues. Just a private, fenced backyard, a screened pool, and the kind of established street where the loudest thing most evenings is the breeze through the palms. From the concrete pavers walkway, fieldstone columns and a James Hardie board and batten gable frame a modern entry and a two-car garage. Inside, the renovation is the story. Light luxury vinyl runs through an open living area that flows straight to the kitchen: shaker cabinets, matte hardware, speckled quartz counters, and stainless appliances, including a French-door refrigerator. A warm wood-slat accent wall gives the great room a finished, designer feel without making the space feel small. The primary suite is set up for real everyday living, with a wood vanity, dual sinks, a backlit mirror, and a marble-look walk-in shower. A second bath carries the same updated finishes, glass enclosure, and rainfall shower. Bedrooms are light and flexible, one with a barn door and a wood-blade fan, another in a soft sage that already feels move-in ready. Out back, the screened pool cage opens to a generous yard — room for morning coffee, weekend swims, and the kind of privacy that is hard to find this close to everything. Garden Lake Estates is a settled, low-key pocket of larger lots and mature trees, with the community lake nearby and none of the restrictions that come with a managed association. Seminole County schools are a major draw here; buyers should confirm the exact zone for this address. Winter Park dining, Park Avenue, and the chain of lakes are a short drive. Oviedo, Casselberry, and the 417 and 434 corridors keep commuting practical. If you have been looking for an updated pool home, a quiet street, and the freedom of no HOA in a strong Seminole County school area, this is the one to walk through.

1409 Aster Court, 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
Start Your Search