Homes for Sale Under 300K in Winter Park FL
73 results
Showcase - 7 days on Zillow
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- 2302 BARBADOS DRIVE, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,544 sqft
KELLER WILLIAMS REALTY AT THE PARKSOpen: Sun 12-3pm (10/18)
- 4882 TANGERINE AVENUE #4882, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,281 sqft
SIMPLYSOLD REAL ESTATE PREMIERLovely courtyard view
- 2463 GRAND TETON CIRCLE #2463, WINTER PARK, FL 32792
- 3 bds
- 3 ba
- 1,720 sqft
MAINFRAME REAL ESTATEDedicated office space
- 7348 GRAND AVENUE, WINTER PARK, FL 32792
- 3 bds
- 2 ba
- 1,509 sqft
BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTYThree-bedroom two-bathroom home
- 2918 ANTIQUE OAKS CIRCLE #25, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,018 sqft
PREMIER MANAGEMENT GROUP INCTree lined streets
- 311 E MORSE BOULEVARD #7-11, WINTER PARK, FL 32789
- 1 bd
- 1 ba
- 570 sqft
FANNIE HILLMAN & ASSOCIATESCorner studio
- 7488 WHISPERWOOD DRIVE #28, WINTER PARK, FL 32792
- 2 bds
- 3 ba
- 1,578 sqft
PARKVIEW REAL ESTATETownhome-style layout
- 5108 LAZY OAKS DRIVE #5108, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,008 sqft
BEYCOME OF FLORIDA LLCPrice cut: $14,000 (10/9)
- Fresh interior paint
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- 5143 LAZY OAKS DRIVE #5143, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,008 sqft
KELLER WILLIAMS REALTY AT THE PARKSAttached garage
- Garden space
- Granite countertops
- 2450 GRAND TETON CIRCLE #2450, WINTER PARK, FL 32792
- 3 bds
- 2 ba
- 1,311 sqft
CHARLES RUTENBERG REALTY ORLANDOTennis courts
- Swimming pool
3D Tour 
- 7453 DANIEL WEBSTER DRIVE #A5, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,063 sqft
LA ROSA REALTY PREMIER LLCConvenient outdoor space
- Start survey
Help others discover what makes this area unique.
Fill out a short survey to help others know what it's like to live here. - Stylish lighting fixtures
- 1250 S DENNING DR #Unit 233, WINTER PARK, FL 32789
- 2 bds
- 2 ba
- 913 sqft
STOCKWORTH REALTY GROUPPrice cut: $2,500 (10/12)
Showcase 
- 1250 S DENNING DRIVE #127, WINTER PARK, FL 32789
- 2 bds
- 2 ba
- 908 sqft
PREMIER SOTHEBY'S INTL. REALTY3D Tour 
- Price cut: $5,000 (9/25)
3D Tour 
- 7300 DANIEL WEBSTER DRIVE #M7, WINTER PARK, FL 32792
- 2 bds
- 3 ba
- 1,108 sqft
STIRLING INTERNATIONAL REAL ESStunningly updated two-story condo
- 66 days on Zillow
- 3302 ROYAL STREET, WINTER PARK, FL 32792
- 3 bds
- 2 ba
- 1,197 sqft
SAND DOLLAR REALTY GROUP INCPrice cut: $5,000 (9/30)
- 7476 WOODBURN COURT #38, WINTER PARK, FL 32792
- 2 bds
- 3 ba
- 1,031 sqft
COLDWELL BANKER REALTYTwo spacious bedrooms
- 623 GRENADINE COURT #623, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,037 sqft
COLDWELL BANKER REALTYPrice cut: $5,000 (9/15)
- 1500 GAY ROAD #3C, WINTER PARK, FL 32789
- 2 bds
- 2 ba
- 1,026 sqft
FANNIE HILLMAN & ASSOCIATESCommunity deck
- 2712 TORTOISE CV, WINTER PARK, FL 32792
- 2 bds
- 1 ba
- 924 sqft
CHARLES RUTENBERG REALTY ORLANDOPrice cut: $5,000 (10/2)
3D Tour 
- 2383 SUN VALLEY CIRCLE #2383, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 1,295 sqft
RE/MAX PRIME PROPERTIESGranite counters
- 3027 AARON BURR AVENUE #L1, WINTER PARK, FL 32792
- 2 bds
- 3 ba
- 1,090 sqft
STIRLING INTERNATIONAL REAL ESModern upgrades
- End-unit home
- 3651 N GOLDENROD ROAD #C109, WINTER PARK, FL 32792
- 2 bds
- 2 ba
- 840 sqft
REAL ESTATE PROFESSIONALS SE35 days on Zillow
- 1000 S SEMORAN BOULEVARD #302, WINTER PARK, FL 32792
- 1 bd
- 1 ba
- 796 sqft
KELLER WILLIAMS ADVANTAGE IIIPrice cut: $5,000 (9/26)
- 7340 Daniel Webster Dr, Winter Park, FL 32792
- 3 bds
- 2 ba
- -- sqft
RE/MAX - CITY CENTRE REALTY349 days on Zillow
- 1250 S DENNING DRIVE #119, WINTER PARK, FL 32789
- 2 bds
- 2 ba
- 908 sqft
FANNIE HILLMAN & ASSOCIATES3D Tour 
- 7450 WYNNEWOOD SQUARE #189, WINTER PARK, FL 32792
- 2 bds
- 3 ba
- 1,031 sqft
REAL ESTATE PROFESSIONALS SEPrice cut: $15,000 (9/23)
- Tennis courts
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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of GAMLS. All real estate listings are marked with the GAMLS Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Copyright 2026 GAMLS. All rights reserved.
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.
