Winter Park Homes under $400,000

Winter Park Homes under $400,000

Welcome to Winter Park, Florida—a picturesque city that beautifully blends charm, culture, and community spirit. Nestled just north of Orlando, Winter Park is known for its lush landscapes, stunning lakes, and vibrant arts scene. With its tree-lined streets and historic architecture, this city offers a unique blend of small-town warmth and urban convenience.

One of the most appealing aspects of Winter Park is its commitment to preserving its natural beauty and fostering a sense of community. The city is home to an array of parks, including the renowned Central Park, where residents can enjoy leisurely strolls, outdoor concerts, and seasonal festivals. The Winter Park Chain of Lakes provides ample opportunities for boating, fishing, and enjoying the great Florida outdoors.

For those considering a move to this enchanting city, there are fantastic housing options available, particularly for first-time buyers and families looking for homes under $400,000. Winter Park offers a variety of charming single-family homes, townhouses, and condos that cater to diverse lifestyles and budgets. These properties often feature modern amenities, inviting outdoor spaces, and proximity to local schools and shopping centers.

In addition to its beautiful homes, Winter Park boasts a thriving downtown area filled with boutique shops, art galleries, and delectable dining options. The city is also home to the prestigious Rollins College, which adds to its vibrant cultural tapestry.

Whether you’re looking to settle down in a welcoming community or invest in a property with immense charm, Winter Park is the perfect place to call home. Discover the magic of Winter Park and find your dream home today!

Newest Winter Park Homes under $400,000

4832 Tangerine Avenue Unit 4832, Winter Park
$188,800
2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Welcome to comfortable living in desirable East Winter Park. This beautifully maintianed condominium offers a spacious and inviting floor plan in a quiet,establised community with convienent location. The resdience features generous room sizes, and a functional layout designed for comfortable everday living. The open lving room and dining areas provide a welcoming space for relaxing or entertaing, while the private screened porch offers a peaceful outdoor retreat to ejoy Florida's year-round lifestyle. Additional storage on the porch adds convienence. Community ammenities include sparkling swimming pool,clubhouse beautifully maintained grounds,and ample parking.HOA services and amentities may include exterior maintiance, landscaping,water,trash service,and roof maintenance. Buyers are encoruaged to verify all fees,services,inclusions,and commnity restrictions with the association.

4832 Tangerine Avenue Unit 4832, Winter Park
4786 Tangerine Avenue Unit 4786, Winter Park
$220,000
2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 square feet of living space with a spacious, functional layout designed for everyday living and entertaining. Step inside to find ceramic tile flooring, an inviting living and dining area, and a beautifully appointed kitchen featuring granite countertops, attractive cabinetry, a stylish backsplash, and stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, including a primary bedroom with a walk-in closet. Enjoy your morning coffee or unwind in the evening on the private screened-in porch overlooking a peaceful green space, complete with an additional storage closet. Interior laundry adds everyday convenience. Located in the established Wrenwood condominium community, residents enjoy access to a community swimming pool and clubhouse. The property also offers two assigned parking spaces and convenient access to major roads, shopping, restaurants, and entertainment. LOCATION, LOCATION, LOCATION! Just minutes from Full Sail University, UCF, Rollins College, Downtown Winter Park, and the popular Park Avenue shopping and dining district. Whether you're searching for your primary residence or an investment opportunity, this property offers an appealing combination of location, space, and convenience. Don't miss this opportunity to own a condominium in desirable Winter Park! Schedule your private showing today!

4786 Tangerine Avenue Unit 4786, Winter Park
5468 Bracken Court, Winter Park
$299,000
3 Beds ⋅ 3 Baths ⋅ Fernbrook Trails SubDv. ⋅ 32792 Zip Code
Welcome to this spacious end unit townhome in Winter Park’s Fernbrook Trails community! Featuring 3 bedrooms and 2.5 bathrooms, this home offers a convenient main floor primary bedroom and two additional bedrooms upstairs. The kitchen’s breakfast bar overlooks the family room, while a separate living and dining area provides flexible space for everyday living and entertaining. Inside laundry, a covered front porch, and a private fenced backyard complete the home. Seller willing to make upgrades. Schedule your showing today!

5468 Bracken Court, Winter Park
2640 Beverly Avenue, Winter Park
$305,000
3 Beds ⋅ 1 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A clean shell for a fix-and-flip or a hold-and-rent strategy, with detached ADU potential under Orange County rules. 3 bed, 1 bath, approx. 1,216 sq ft of living area on approx. 0.17 acre, FEMA Zone X (minimal flood hazard). Straightforward single-story footprint with room to improve, not expanded. Out back, a canopy of mature trees creates a shaded, private backyard sanctuary. Already handled: brand-new roof (October 2026) and a replaced water heater. Kitchen cabinets are in very good shape; if you choose to update the countertops, keep the cabinets and simply resurface and repaint. The deck is in good condition today (plan on rebuilding down the road). Still to do: central HVAC is not operational (home is cooled by window units), the shower needs a light spruce-up, and a cosmetic refresh throughout. Strong bones and a good shell for a focused remodel. Location: Lake Killarney, a 234-acre spring-fed lake, is just blocks away, where seaplanes drop in for lunch at Hillstone. Centrally located to I-4 at Fairbanks Avenue, with downtown Orlando about 15 minutes away. Less than 2 miles to the newly renovated Winter Park Village with its Regal cinema, restaurants, boutiques and patio dining, and minutes to Park Avenue, Rollins College, the Morse Museum, the Saturday Farmers Market, Trader Joe's, Whole Foods, AdventHealth Winter Park and the Winter Park SunRail station. ADU snapshot: under Orange County R-1A (Sec. 38-1426), a detached one-story ADU is typically limited to 50 percent of the primary living area or 1,000 sq ft, whichever is less, about 608 sq ft here. The lot appears to meet the 7,500 sq ft minimum. Homestead and owner-occupancy rules apply. Buyer to verify all zoning, setback, ADU eligibility, homestead and permitting items directly with Orange County Zoning. Figures are informational only and not a guarantee of approval. Renovate the primary and add a rental ADU for a two-income setup, or flip it. New roof and water heater done, interior ready for a focused remodel.

2640 Beverly Avenue, Winter Park
1740 Puritan Avenue, Winter Park
$314,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code
WINTER PARK POOL HOME PRICE IMPROVEMENT Looking for a pool home you can truly make your own? Welcome to 1740 Puritan Ave in Winter Park! This property offers an exciting opportunity for the right buyer with the vision to unlock its full potential. Imagine relaxing by your private pool, entertaining family and friends, and creating your own backyard retreat! Whether you're searching for your next home or an investment opportunity, this property is full of possibilities. This home needs some TLC, but with the right care, creativity, and personal touches, it could become something truly special. Bring your imagination and make this pool home your own! Don't miss this opportunity to create the home you've been dreaming of in Winter Park. Schedule your private showing today!

1740 Puritan Avenue, Winter Park
148 Oak Grove Rd, Winter Park
$320,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Oaks SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 water heater, and updated plumbing. That means your weekends are for enjoying life where you call home. Fresh paint inside and out sets the tone the moment you pull up. Step inside to a bright, open floor plan where the kitchen, dining, and living spaces flow together for easy weeknight dinners and lazy Saturday mornings. The kitchen and bathrooms have been updated with a clean, modern feel, so all that’s left is to unpack. Out back, a fully fenced vinyl yard gives you privacy and room to play, garden, or host the cookout. A one-car garage adds plenty of storage. And the location? It’s hard to beat. You’re minutes from everything Winter Park has to offer, tucked right behind the new LifeTime fitness club, with exciting new development planned for the area. Homes this updated in this location don’t come around often. Schedule your showing today!

148 Oak Grove Rd, Winter Park
216 Lewfield Cir Unit 216, Winter Park
$230,000
3 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condominium SubDv. ⋅ 32792 Zip Code
Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of the sparkling community pools. Balcony features additional outside storage room. Dining/Breakfast Nook adjacent to Living Room & Kitchen. Kitchen features refrigerator, electric range, dishwasher, microwave, garbage disposal, pantry, and laundry closet with stackable washer/dryer. Nice sized bedrooms, see attached floor plan. Primary Suite features walk in closet, walk in shower and tile flooring. Guest Bath features tub & shower and tile flooring. Unit conveniently located at back of community by both community pools and tennis courts. Lovely shady, treed community with sidewalks, Clubhouse, two (2) Pools, BBQ areas, and Tennis Court. HOA Fees Cover: trash removal, water, internet only, amenities maintenance, landscaping, and roof. Community Docs and 2026 Budget available for review. Conveniently located to shopping, parks, restaurants, and major transportation routes. Property sold "AS IS", it won't last long!

216 Lewfield Cir Unit 216, 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
3032 Antique Oaks Circle Unit 145, Winter Park
$134,999
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
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