Cheap Homes For Sale in Winter Park, FL

329 homes

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3D VIEW
$485,000
3 Beds
2 Baths
2,028 sqft
3207 Lowndes Dr,
Winter Park, FL 32792
MILLER GRANT AND COMPANY
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3D VIEW
$490,000
3 Beds
2.5 Baths
1,808 sqft
1593 Lawndale Cir,
Winter Park, FL 32792
EXP REALTY LLC
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$495,000
3 Beds
2 Baths
1,710 sqft
2707 Tierra Cir,
Winter Park, FL 32792
RE/MAX 200 REALTY
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$495,000
2 Beds
2.5 Baths
1,428 sqft
630 Killarney Bay Ct #3,
Winter Park, FL 32789
FLORIDA ONE REAL ESTATE LLC
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0.25 ACRES
$499,000
4 Beds
3 Baths
1,526 sqft
731 Bongart Rd,
Winter Park, FL 32792
FANNIE HILLMAN & ASSOCIATES
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$499,000
2 Beds
1 Bath
920 sqft
230 Strathy Ln,
Winter Park, FL 32792
PARK TOWN REAL ESTATE LLC
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$499,000
3 Beds
2 Baths
1,088 sqft
2231 Nairn Dr,
Winter Park, FL 32792
PARK TOWN REAL ESTATE LLC
$500,000
3 Beds
2 Baths
1,413 sqft
512 N Lakemont Ave,
Winter Park, FL 32792
COLDWELL BANKER REALTY
$510,000
4 Beds
3 Baths
1,805 sqft
2627 Ambergate Rd,
Winter Park, FL 32792
COLDWELL BANKER REALTY
3D VIEW
$510,000
2 Beds
1 Bath
1,073 sqft
1036 Aragon Ave,
Winter Park, FL 32789
WATSON REALTY CORP
$515,000
3 Beds
3 Baths
1,786 sqft
525 Ololu Dr,
Winter Park, FL 32789
CAISSA REALTY INVESTMENT INC
FOR SALE BY OWNER
$519,000
3 Beds
1.5 Baths
1,200 sqft
781 W Webster Ave,
Winter Park, FL 32789
0.53 ACRES
$524,900
4 Beds
2.5 Baths
2,058 sqft
4190 Bear Gully Rd,
Winter Park, FL 32792
ADVANCE REALTY & MANAGEMENT LLC
$525,000
3 Beds
2 Baths
1,627 sqft
1438 Tierra Cir,
Winter Park, FL 32792
COLDWELL BANKER REALTY
$539,000
3 Beds
2.5 Baths
1,660 sqft
1261 Indiana Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
$549,000
3 Beds
3 Baths
1,920 sqft
423 Ololu Dr,
Winter Park, FL 32789
KELLER WILLIAMS WINTER PARK
3D VIEW
$549,000
3 Beds
2.5 Baths
1,818 sqft
1809 Hammerlin Ave,
Winter Park, FL 32789
NICOLE-HUDSON REALTY CORP
$550,000
3 Beds
2.5 Baths
1,818 sqft
1807 Hammerlin Ave #G,
Winter Park, FL 32789
ALL REAL ESTATE & INVESTMENTS
3D VIEW
$554,900
3 Beds
2 Baths
1,570 sqft
330 Elkhorn Ct,
Winter Park, FL 32792
LA ROSA REALTY CW PROPERTIES L
0.29 ACRES
$560,000
3 Beds
3 Baths
1,602 sqft
7641 Village Green Drive,
Winter Park, FL 32792
Compass Florida, LLC
NEW CONSTRUCTION
BUILDABLE PLAN
$562,500+
3 Beds
2.5 Baths
2,250 sqft
West New Hampshire - Build On Your Lot Plan in Mitchell Mckee Sales Center,
Winter Park, FL 32789
$579,000
4 Beds
2 Baths
1,821 sqft
2829 Aloma Ave,
Winter Park, FL 32792
LPT REALTY, LLC
3D VIEW
$589,900
3 Beds
2 Baths
1,269 sqft
1354 Indiana Ave,
Winter Park, FL 32789
CHARLES RUTENBERG REALTY ORLANDO
$595,000
3 Beds
2 Baths
1,396 sqft
616 Fitzwalter Dr,
Winter Park, FL 32792
EXP REALTY LLC
$595,000
3 Beds
2 Baths
1,434 sqft
1741 Westchester Ave,
Winter Park, FL 32789
PREMIER SOTHEBY'S INTL. REALTY
$595,000
3 Beds
2 Baths
1,126 sqft
1319 Bessmor Rd,
Winter Park, FL 32789
GALLOWAY REAL ESTATE
$595,000
3 Beds
3.5 Baths
2,083 sqft
1134 Washington Ave #13,
Winter Park, FL 32789
KELLY PRICE & COMPANY LLC
3D VIEW
$624,000
3 Beds
3 Baths
1,620 sqft
1822 Yorkshire Dr,
Winter Park, FL 32792
PREMIER SOTHEBY'S INTL. REALTY
3D VIEW
$624,000
4 Beds
2 Baths
1,920 sqft
2087 Laurelwood Way,
Winter Park, FL 32792
COMPASS FLORIDA LLC
$624,500
3 Beds
2 Baths
1,785 sqft
2708 Lion Heart Rd,
Winter Park, FL 32792
EQUITYPRO LLC
$625,000
3 Beds
2 Baths
1,610 sqft
1760 Greenwich Ave,
Winter Park, FL 32789
FANNIE HILLMAN & ASSOCIATES
3D VIEW
$625,000
3 Beds
2 Baths
1,812 sqft
2756 Sheriff Way,
Winter Park, FL 32792
PALM CIRCLE REALTY
3D VIEW
$625,000
3 Beds
2.5 Baths
1,770 sqft
1174 Wildmeadow Run,
Winter Park, FL 32792
COLDWELL BANKER REALTY
0.28 ACRES
$630,000
6 Beds
3 Baths
3,145 sqft
2600 Euston Rd,
Winter Park, FL 32789
AROD PARTNERS REALTY
3D VIEW
$630,000
5 Beds
3 Baths
2,472 sqft
2612 Roxbury Rd,
Winter Park, FL 32789
EXP REALTY LLC
3D VIEW
$639,900
3 Beds
2 Baths
1,469 sqft
1926 Natalen Rd,
Winter Park, FL 32792
JAMIESON PROPERTIES, INC.
$649,800
3 Beds
2 Baths
1,287 sqft
1830 Edwin Blvd,
Winter Park, FL 32789
ZEN LIVING HOMES LLC
0.27 ACRES
$649,900
4 Beds
2.5 Baths
2,636 sqft
2220 Fairglenn Way,
Winter Park, FL 32792
ELLIS GROUP REALTY, LLC
$659,000
3 Beds
2 Baths
1,761 sqft
3018 Northwood Blvd,
Winter Park, FL 32789
ROCK SPRINGS REALTY, LLC
NEW CONSTRUCTION
BUILDABLE PLAN
$672,900+
3 Beds
2.5 Baths
2,243 sqft
Hammerlin - Build On Your Lot Plan in Mitchell Mckee Sales Center,
Winter Park, FL 32789

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All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright 2026 Beaches Multiple Listing Service, Inc. Information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Cheap Homes For Sale in Winter Park, FL

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