Winter Park Real Estate

Homes for Sale in Winter Park, FL Between $400,000 to $500,000

Welcome to your dedicated resource for Homes for Sale Between $400,000 to $500,000 in Winter Park, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Park, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $400,000 to $500,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Park, FL Homes for Sale Between $400,000 to $500,000

4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.

2054 Eastbrook Boulevard, Winter Park

4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code

Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a renovated, generously sized kitchen—ideal for everyday living and entertaining. Recent improvements include a 2020 roof, 2021 HVAC system, plus new windows, doors, and added insulation. The dining room features French doors opening to a newly poured concrete patio and charming backyard offering loads of potential for gardening, play, pets, or creating your own private outdoor retreat. Previously utilized as an investment rental, this property presents an excellent opportunity for an owner-occupant or investor seeking a desirable Winter Park location with strong rental appeal. Enjoy close proximity to AdventHealth’s world-class Orlando campus, as well as the shopping, dining, and lifestyle destinations of Winter Park, Park Avenue, Mills 50, and downtown Orlando. A wonderful opportunity to own a character-filled home in one of the area’s most desirable central neighborhoods.

1652 Berkshire Avenue, Winter Park

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

2231 Nairn Drive, Winter Park

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

230 Strathy Lane, Winter Park

3 Beds ⋅ 2 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code

Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

2231 Nairn Drive, Winter Park

2 Beds ⋅ 1 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code

Completely Remodeled Winter Park Home – Prime Location Beautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing. Ideally situated directly across from Advent Health Winter Park Hospital, this property provides exceptional convenience while remaining tucked into an established residential neighborhood. The functional floor plan offers comfortable living spaces filled with natural light, along with modern finishes throughout. Zoned for Winter Park’s highly regarded public schools, this home is well-suited for a primary residence or long-term investment. Easy access to major roadways, shopping, dining, and downtown Winter Park amenities. Move-in ready and centrally located — a rare opportunity in one of Orange County’s most desirable areas. Owner owns the house next door as well. Both properties for sale.

230 Strathy Lane, Winter Park

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code

Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park

2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

981 Aragon Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.

2715 Prince John Road, Winter Park

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location and a home that is ready to be enjoyed from day one while maintaining long term upside.

525 Ololu Drive, Winter Park

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