Florida, Winter Park Condos/Co-ops For Sale — from $119K | Broker One

Condos/Co-ops For Sale in Florida, Winter Park

Search Condos/Co-ops and apartments For Sale in Florida, Winter Park with floor plans, photos, building amenities, and HOA details. Filter by price, size, floor level, waterfront access, and building features to find the right unit.

Condo market in Florida, Winter Park

The condo market in Florida, Winter Park includes high-rise luxury towers, boutique mid-rises, and affordable garden-style complexes. Key factors — monthly HOA fees, special assessments, reserve fund health, and building insurance costs — all of which affect your true cost of ownership beyond the purchase price.

Due diligence for condo buyers

Request the HOA financials, recent inspection reports (milestone inspections are now required in Florida), and any pending special assessments before making an offer. Buildings with deferred maintenance or underfunded reserves may face significant costs. Review our buyer guide for a full checklist.

2423 BRANCH WAY UNIT 105 placeholder 2423 BRANCH WAY UNIT 105
6 days
For Sale
Condo/Co-op
$138,900
3 bds 2 ba 1,428 sqft
2423 BRANCH WAY UNIT 105
2525 CAPER LANE UNIT 205 placeholder 2525 CAPER LANE UNIT 205
8 days
For Sale
Condo/Co-op
$119,000
1 bds 1 ba 550 sqft
2525 CAPER LANE UNIT 205
 placeholder
9 days
For Sale
Condo/Co-op
$257,000
2 bds 2 ba 959 sqft
1500 GAY ROAD UNIT 8D placeholder 1500 GAY ROAD UNIT 8D
10 days
For Sale
Condo/Co-op
$267,000
2 bds 2 ba 1,026 sqft
1500 GAY ROAD UNIT 8D
2401 SUN VALLEY CIRCLE UNIT 2401 placeholder 2401 SUN VALLEY CIRCLE UNIT 2401
11 days
For Sale
Condo/Co-op
$285,000
2 bds 2 ba 1,495 sqft
2401 SUN VALLEY CIRCLE UNIT 2401
1140 S ORLANDO AVENUE UNIT F8 placeholder 1140 S ORLANDO AVENUE UNIT F8
11 days
For Sale
Condo/Co-op
$479,900
2 bds 2 ba 816 sqft
1140 S ORLANDO AVENUE UNIT F8
101 S NEW YORK AVENUE UNIT 302 placeholder 101 S NEW YORK AVENUE UNIT 302
11 days
For Sale
Condo/Co-op
$1,630,000
3 bds 3 ba 3,174 sqft
101 S NEW YORK AVENUE UNIT 302
1100 S ORLANDO AVENUE UNIT 306 placeholder 1100 S ORLANDO AVENUE UNIT 306
15 days
For Sale
Condo/Co-op
$649,000
2 bds 2 ba 1,125 sqft
1100 S ORLANDO AVENUE UNIT 306
1000 S ORLANDO AVENUE UNIT B25 placeholder 1000 S ORLANDO AVENUE UNIT B25
17 days
For Sale
Condo/Co-op
$335,000
2 bds 2 ba 952 sqft
1000 S ORLANDO AVENUE UNIT B25
300 CAROLINA AVENUE UNIT 207 placeholder 300 CAROLINA AVENUE UNIT 207
-$55K (2026/03/23)
For Sale
Condo/Co-op
$495,000
1 bds 2 ba 1,149 sqft
300 CAROLINA AVENUE UNIT 207
538 W PAR STREET UNIT 538 placeholder 538 W PAR STREET UNIT 538
18 days
For Sale
Condo/Co-op
$349,000
2 bds 2 ba 1,200 sqft
538 W PAR STREET UNIT 538
200 SAINT ANDREWS BOULEVARD UNIT 312 placeholder 200 SAINT ANDREWS BOULEVARD UNIT 312
+$3K (2026/03/20)
For Sale
Condo/Co-op
$170,000
1 bds 1 ba 793 sqft
200 SAINT ANDREWS BOULEVARD UNIT 312
1807 HAMMERLIN AVENUE UNIT G placeholder 1807 HAMMERLIN AVENUE UNIT G
19 days
For Sale
Condo/Co-op
$580,000
3 bds 2 ba 1,818 sqft
1807 HAMMERLIN AVENUE UNIT G
144 LEWFIELD CIRCLE UNIT 144 placeholder 144 LEWFIELD CIRCLE UNIT 144
-$5K (2026/03/23)
For Sale
Condo/Co-op
$144,000
1 bds 1 ba 678 sqft
144 LEWFIELD CIRCLE UNIT 144
2918 ANTIQUE OAKS CIRCLE UNIT 25 placeholder 2918 ANTIQUE OAKS CIRCLE UNIT 25
25 days
For Sale
Condo/Co-op
$189,000
2 bds 2 ba 1,018 sqft
2918 ANTIQUE OAKS CIRCLE UNIT 25
4392 WARDELL PLACE UNIT 102 placeholder 4392 WARDELL PLACE UNIT 102
25 days
For Sale
Condo/Co-op
$615,000
3 bds 2 ba 1,410 sqft
4392 WARDELL PLACE UNIT 102
259 E CANTON AVENUE UNIT 259 placeholder 259 E CANTON AVENUE UNIT 259
-$20K (2026/03/25)
For Sale
Condo/Co-op
$629,000
2 bds 2 ba 1,040 sqft
259 E CANTON AVENUE UNIT 259
1140 S ORLANDO AVENUE UNIT H-13 placeholder 1140 S ORLANDO AVENUE UNIT H-13
-$26K (2026/03/25)
For Sale
Condo/Co-op
$449,000
2 bds 1 ba 816 sqft
1140 S ORLANDO AVENUE UNIT H-13
1140 S ORLANDO AVENUE UNIT F11 placeholder 1140 S ORLANDO AVENUE UNIT F11
30 days
For Sale
Condo/Co-op
$349,000
2 bds 1 ba 816 sqft
1140 S ORLANDO AVENUE UNIT F11
188 LEWFIELD CIRCLE UNIT 188 placeholder 188 LEWFIELD CIRCLE UNIT 188
-$1K (2026/03/26)
For Sale
Condo/Co-op
$139,000
1 bds 1 ba 678 sqft
188 LEWFIELD CIRCLE UNIT 188