Immaculate move-in ready
Homes for Sale Under $500K in Winter Park FL
143 results
- Price cut: $25,000 (3/20)
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- 10 hours ago
- 518 Shoreview Ave, Winter Park, FL 32789
- 2 bds
- 2 ba
- 1,609 sqft
UNITED REAL ESTATE PREFERRED10 hours ago
- 2126 N Hampton Cir, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,745 sqft
KELLER WILLIAMS WINTER PARKScreened-in pool
3D Tour 
- Beautifully renovated pool home
3D Tour 
- 3651 N Goldenrod Rd APT D101, Winter Park, FL 32792
- 2 bds
- 2 ba
- 840 sqft
ANNE ROGERS REALTY GROUP INC3D Tour 
- 3027 Aaron Burr Ave Unit L-1, Winter Park, FL 32792
- 2 bds
- 3 ba
- 1,090 sqft
STIRLING INTERNATIONAL REAL ESModern upgrades
- Price cut: $11,000 (2/25)
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- 7300 Daniel Webster Dr #M7, Winter Park, FL 32792
- 2 bds
- 3 ba
- 1,108 sqft
STIRLING INTERNATIONAL REAL ESStunningly updated two-story condo - 3463 Arnel Dr, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,770 sqft
KELLER WILLIAMS ADVANTAGE 2 REALTY3D Tour - 7716 Wicklow Cir, Orlando, FL 32817
- 3 bds
- 2 ba
- 1,611 sqft
CHARLES RUTENBERG REALTY ORLANDO3D Tour - 13 hours ago
- Kitchen island
- 1617 Chilean Ln, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,359 sqft
CHARLES RUTENBERG REALTY ORLANDOFresh paint - Price cut: $5,000 (2/26)
- 7796 Fernbrook Way, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,332 sqft
PREMIER SOTHEBY'S INTL. REALTYGenerously sized bedrooms - Oversized corner lot
Showcase - Fresh interior paint
- 240 Orange Terrace Dr, Winter Park, FL 32789
- 4 bds
- 2 ba
- 1,718 sqft
A+ REALTY PROFESSIONALS, INCPrice cut: $4,900 (3/20) - 1000 S Semoran Blvd APT 805, Winter Park, FL 32792
- 2 bds
- 2 ba
- 1,003 sqft
SHAWFIELD REALTY GROUPBeautifully renovated kitchen 3D Tour - 300 Carolina Ave APT 207, Winter Park, FL 32789
- 1 bd
- 2 ba
- 1,149 sqft
FANNIE HILLMAN & ASSOCIATESPrice cut: $55,000 (3/23) - Price cut: $39,001 (3/16)
- 5473 Bracken Ct, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,178 sqft
KELLER WILLIAMS ADVANTAGE IIIPrice cut: $10,000 (3/12) 3D Tour - 3312 Heartwood Ave, Winter Park, FL 32792
- 4 bds
- 3 ba
- 2,878 sqft
MID-STATE PROPERTIES PSL LLCStorage shed - 3642 Periwinkle Dr, Winter Park, FL 32792
- 5 bds
- 3 ba
- 1,945 sqft
HONEST REAL ESTATE COMPANYGenerous storage - 630 Killarney Bay Ct #3, Winter Park, FL 32789
- 2 bds
- 3 ba
- 1,428 sqft
FLORIDA ONE REAL ESTATE LLCPrice cut: $54,900 (3/11) - 2519 Windward Way, Winter Park, FL 32792
- 2 bds
- 2 ba
- 1,105 sqft
NONA LEGACY POWERED BY LA ROSALarge private enclosed patio 3D Tour - 1280 Gladiolas Dr, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,624 sqft
FLORIDA PRESTIGIOUS HOMES INCScreened-in pool - 2401 Antilles Dr, Winter Park, FL 32792
- 3 bds
- 2 ba
- 1,719 sqft
KELLER WILLIAMS REALTY AT THE PARKSOpen: Sun 12-3pm (3/29) 3D Tour - Open: Wed 9am-7pm (3/25)
- Beautiful pool
- Price cut: $25,000 (3/24)
- Price cut: $2,500 (3/19)
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website. Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
- For Sale
- Florida
- Orange County
- Winter Park
Find a Home You'll Love
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Disclaimer: School attendance zone boundaries are supplied by Pitney Bowes and are subject to change. Check with the applicable school district prior to making a decision based on these boundaries.
About the ratings: GreatSchools ratings are based on a comparison of test results for all schools in the state. It is designed to be a starting point to help parents make baseline comparisons, not the only factor in selecting the right school for your family. Learn more
