Homes for sale under $400k in Winter Park, FL

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ABOUT THIS HOME
Homes for sale under $400k in Winter Park, FL
This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, and stylish modern finishes that create a light and inviting atmosphere. The open and spacious common areas flow seamlessly, offering the perfect setting for gatherings and entertaining. The kitchen is equipped with stainless steel appliances, while both bathrooms have been fully remodeled with sleek, contemporary details. Enjoy Florida living outdoors with your private screened pool area, per

$399,900

3 beds2 baths1,401 sq ft

1670 Clematis Ln, Winter Park, FL 32792

Spacious deck • Screened-in pool • 8,250 sq ft lot

3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $400k in Winter Park, FL
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome home to 5422 Albert Drive this beautifully remodeled 3-bedroom, 2-bathroom home is located in the heart of Winter Park. Situated on a generous 0.21-acre lot with no HOA, this home offers the perfect blend of modern upgrades and everyday comfort in a highly sought-after location. Inside, you'll find brand-new wood-look tile flooring throughout—no carpet—offering both durability and style. The fully remodeled kitchen is a standout feature, showcasing a brand-new stainless steel appliance package, sleek finishes, and a functional layout that’s ideal for both entertaining an

$399,900

3 beds2.5 baths1,689 sq ft

5422 Albert Dr, Winter Park, FL 32792

Remodeled kitchen • Fully repiped • New ac system

ABOUT THIS HOME
Homes for sale under $400k in Winter Park, FL
Welcome to this unique 4-bedroom ranch-style home in the heart of Winter Park! This residence offers flexibility and comfort for today’s lifestyle. The converted two-car garage has been transformed into an additional bedroom with separate entrance, perfect for guests or an in-law suite. Inside, the kitchen flows seamlessly into the bright family room. Entertain with ease in the large dining and living room combination, or step outside to enjoy the expansive screened and covered patio overlooking the fully fenced backyard. Additional highlights include energy-efficient Low-E double-pane windows, a gas water heater, and tiled living areas. Two guest bedrooms, along with the original pri

$399,000

4 beds3 baths2,179 sq ft

1362 Tierra Cir, Winter Park, FL 32792

Separate entrance • Gas water heater • 9,020 sq ft lot

ABOUT THIS HOME
Homes for sale under $400k in Winter Park, FL
Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining! This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy a BRAND NEW WATER HEATER, vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring throughout. The open-concept kitchen is a showstopper, featuring quartz countertops and stainless steel appliances. Upstairs, you'll find two oversized bedrooms—each with their own walk-in closet and en-suite bathroom. Additional highlights include a private second-floor balcony, inside

$399,000

2 beds2.5 baths1,536 sq ft

240 Killarney Bay Ct #4, Winter Park, FL 32789

Quartz countertops • Open concept kitchen • Modern upgrades

3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $400k in Winter Park, FL
One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $399,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation was extensive and included new electrical re-wiring and plumbing. The scope of the renovation extended to creating new conditioned space, currently being used as the dining room from old patio space. The kitchen and bathroom updates were numerous. A few highlights are new cabinets, stainless steel appliances, quartz countertops, a farmhous

$399,000

1 bed1 bath900 sq ft

311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

Quartz countertops • Community pool • Expansive windows

Property at 801 Ellendale Dr, Winter Park, FL 32792, 3 beds, 2 baths

$395,000

3 beds2 baths1,516 sq ft

801 Ellendale Dr, Winter Park, FL 32792

Property at 1229 Park Green Pl, Winter Park, FL 32789, 2 beds, 2 baths

$395,000

2 beds2 baths1,495 sq ft

1229 Park Green Pl, Winter Park, FL 32789

Property at 7728 Glenmoor Ln, Winter Park, FL 32792, 3 beds, 2 baths

$389,900

3 beds2 baths1,676 sq ft

7728 Glenmoor Ln, Winter Park, FL 32792

Property at 5110 N Woodcrest Dr, Winter Park, FL 32792, 3 beds, 2 baths

$365,500

3 beds2 baths1,220 sq ft

5110 N Woodcrest Dr, Winter Park, FL 32792

Property at 7580 Aloma Pines Ct, Winter Park, FL 32792, 3 beds, 3.5 baths

$359,500

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Property at 311 E Morse Blvd Unit 7-5, Winter Park, FL 32789, 1 bed, 1 bath

$359,000

1 bed1 bath482 sq ft

311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

Property at 150 Killarney Bay Ct #5, Winter Park, FL 32789, 2 beds, 2 baths

$355,000

2 beds2 baths1,140 sq ft

150 Killarney Bay Ct #5, Winter Park, FL 32789

Property at 1033 Hamlet Dr, Maitland, FL 32751, 3 beds, 2 baths

$350,000

3 beds2 baths1,146 sq ft

1033 Hamlet Dr, Maitland, FL 32751

Property at 5047 Ferncrest Dr, Winter Park, FL 32792, 4 beds, 2 baths

$349,000

4 beds2 baths1,242 sq ft

5047 Ferncrest Dr, Winter Park, FL 32792

Property at 5117 Cypress Ct, Winter Park, FL 32792, 3 beds, 2 baths

$340,000

3 beds2 baths1,534 sq ft

5117 Cypress Ct, Winter Park, FL 32792

Property at 1605 Puritan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$340,000

3 beds2 baths1,285 sq ft

1605 Puritan Ave, Winter Park, FL 32792

Property at 3204 Netherwood, Winter Park, FL 32792, 2 beds, 1.5 baths

$339,000

2 beds1.5 baths1,056 sq ft

3204 Netherwood, Winter Park, FL 32792

Property at 520 Killarney Bay Ct #2, Winter Park, FL 32789, 2 beds, 2 baths

$339,000

2 beds2 baths1,160 sq ft

520 Killarney Bay Ct #2, Winter Park, FL 32789

Property at 121 Stefanik Rd, Winter Park, FL 32792, 3 beds, 2 baths

$337,500

3 beds2 baths1,392 sq ft

121 Stefanik Rd, Winter Park, FL 32792

Property at Undisclosed address, Winter Park, FL 32792, 3 beds, 2 baths

$335,000

3 beds2 baths1,104 sq ft

Undisclosed address, Winter Park, FL 32792

Property at 2417 Passamonte Dr Unit 1E, Winter Park, FL 32792, 3 beds, 2.5 baths

$329,999

3 beds2.5 baths1,837 sq ft

2417 Passamonte Dr Unit 1E, Winter Park, FL 32792

Property at 311 E Morse Blvd Unit 7-11, Winter Park, FL 32789, 1 bed, 1 bath

$329,900

1 bed1 bath570 sq ft

311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

Property at 311 E Morse Blvd Unit 6-3, Winter Park, FL 32789, 1 bed, 1 bath

$329,000

1 bed1 bath570 sq ft

311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

Property at 615 Warrenton Rd, Winter Park, FL 32792, 2 beds, 2 baths

$320,000

2 beds2 baths1,221 sq ft

615 Warrenton Rd, Winter Park, FL 32792

Property at 1920 Carrigan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$315,000

3 beds2 baths1,242 sq ft

1920 Carrigan Ave, Winter Park, FL 32792

Property at 2458 Grand Teton Cir #2458, Winter Park, FL 32792, 2 beds, 2 baths

$310,000

2 beds2 baths1,457 sq ft

2458 Grand Teton Cir #2458, Winter Park, FL 32792

Property at 184 Sandlewood Trl #2, Winter Park, FL 32789, 2 beds, 2.5 baths

$309,000

2 beds2.5 baths1,133 sq ft

184 Sandlewood Trl #2, Winter Park, FL 32789

Property at 1074 Hamlet Dr, Maitland, FL 32751, 3 beds, 2 baths

$308,000

3 beds2 baths1,076 sq ft

1074 Hamlet Dr, Maitland, FL 32751

Property at 151 N Orlando Ave #118, Winter Park, FL 32789, 2 beds, 1 bath

$299,999

2 beds1 bath710 sq ft

151 N Orlando Ave #118, Winter Park, FL 32789

Property at 1618 Gulfview Dr #417, Maitland, FL 32751, 3 beds, 3 baths

$299,000

3 beds3 baths1,328 sq ft

1618 Gulfview Dr #417, Maitland, FL 32751

Property at 2384 Sun Valley Cir, Winter Park, FL 32792, 3 beds, 2 baths

$298,500

3 beds2 baths1,311 sq ft

2384 Sun Valley Cir, Winter Park, FL 32792

Property at 609 Gallery Dr Unit B204, Winter Park, FL 32792, 2 beds, 2 baths

$298,000

2 beds2 baths893 sq ft

609 Gallery Dr Unit B204, Winter Park, FL 32792

Property at 2336 Sun Valley Cir Bldg 20, Winter Park, FL 32792, 2 beds, 2 baths

$295,000

2 beds2 baths1,669 sq ft

2336 Sun Valley Cir Bldg 20, Winter Park, FL 32792

Property at 1250 S Denning Dr #213, Winter Park, FL 32789, 2 beds, 2 baths

$275,000

2 beds2 baths908 sq ft

1250 S Denning Dr #213, Winter Park, FL 32789

Property at 1500 Gay Rd Unit 24B, Winter Park, FL 32789, 2 beds, 2 baths

$275,000

2 beds2 baths1,026 sq ft

1500 Gay Rd Unit 24B, Winter Park, FL 32789

Property at 2489 Tahoe Cir, Winter Park, FL 32792, 3 beds, 2 baths

$272,900

3 beds2 baths1,311 sq ft

2489 Tahoe Cir, Winter Park, FL 32792

Property at 2009 Cornell Ave, Winter Park, FL 32789, 2 beds, 1 bath

$269,000

2 beds1 bath762 sq ft

2009 Cornell Ave, Winter Park, FL 32789

Property at 151 N Orlando Ave #101, Winter Park, FL 32789, 2 beds, 1 bath

$260,000

2 beds1 bath804 sq ft

151 N Orlando Ave #101, Winter Park, FL 32789

Property at 1601 Grove St #552, Maitland, FL 32751, 2 beds, 2 baths

$260,000

2 beds2 baths1,087 sq ft

1601 Grove St #552, Maitland, FL 32751

Property at 7707 Country Pl #4, Winter Park, FL 32792, 2 beds, 2 baths

$259,900

2 beds2 baths1,068 sq ft

7707 Country Pl #4, Winter Park, FL 32792

Property at 1996 Indiana Ave, Winter Park, FL 32789, 2 beds, 1 bath

$250,000

2 beds1 bath818 sq ft

1996 Indiana Ave, Winter Park, FL 32789

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes for sale under $400k in Winter Park

There are currently 100 homes for sale under $400k in Winter Park. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park stay on the market for 94 days and receive 5 offers. Popular neighborhoods include Audubon Park, College Park, Winter Park Pines, Baldwin Park, and Downtown Maitland. This map is refreshed with the newest listings in Winter Park every 15 minutes.

In the past month, 51 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 66 condos, 16 townhouses, and 2 multi-family units for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Homes for sale under $400k in Winter Park, FL

Homes for sale under $400k in Winter Park

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