36$129,900
2 bd · 2 ba · 828 sqft
6066 SE Southern Oaks Dr, Winter Haven, FL
Ryan Odenweller, LLC · RE/MAX HERITAGE PROFESSIONALS
Homes Under $300K in Winter Haven, FL
Hide MapHomes Under $300K in Winter Haven, FL
24 of 464 Listings
36$129,900
2 bd · 2 ba · 828 sqft
6066 SE Southern Oaks Dr, Winter Haven, FL
Ryan Odenweller, LLC · RE/MAX HERITAGE PROFESSIONALS
New10$54,900
2 bd · 1 ba · 672 sqft
213 Lakeside Ranch Cir, Winter Haven, FL
Nadia Aguilar · EXIT REALTY 4CORNERS
New10$270,000
3 bd · 2 ba · 1,820 sqft
1358 Buckeye Trace Blvd, Winter Haven, FL
Don Jerue · KELLER WILLIAMS REALTY SMART 1
New38$295,000
4 bd · 2 ba · 1,876 sqft
4956 Jackson St, Winter Haven, FL
Anthony Medina · KELLER WILLIAMS REALTY SMART 1
New24$170,000
2 bd · 2 ba · 1,093 sqft
395 San Jose Dr, Winter Haven, FL
Chrissi Jasso · ASSOCIATE REALTY
New7$275,000
4 bd · 2 ba · 1,607 sqft
3944 Giorgio Dr, Winter Haven, FL
Bryan Sumner · MERITAGE HOMES OF FL REALTY
New25$269,900
3 bd · 2 ba · 1,372 sqft
503 William Ave, Winter Haven, FL
Miriam Adame · OAKSTRAND REALTY
44$134,990
1 bd · 1 ba · 481 sqft
7060 Fairview Village Cir, Winter Haven, FL
AJ Alvarez · LPT REALTY, LLC
21$295,000
3 bd · 2 ba · 1,292 sqft
1354 Haines Dr, Winter Haven, FL
Aizat Tuleeva · LPT REALTY, LLC
New27$211,000
2 bd · 2 ba · 1,017 sqft
306 Eagle Pond Drive #306, Winter Haven, FL
Amy Sullivan · FLORIDA HOME REALTY GROUP, LLC
New42$285,000
3 bd · 2 ba · 1,432 sqft
668 Reggie Rd, Winter Haven, FL
Kenny Medina · LPT REALTY, LLC
New71$165,500
2 bd · 2 ba · 1,224 sqft
6733 Kensington Dr NE, Winter Haven, FL
Cynthia Cole · FLORIDA REALTY MARKETPLACE
New34$299,999
4 bd · 3 ba · 1,933 sqft
997 Harold Pass, Winter Haven, FL
Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL
NewOpen house Sat, Oct 17 · 9:00 AM22$300,000
3 bd · 3 ba · 1,867 sqft
222 Cloverdale Rd, Winter Haven, FL
Karen Albright · OPENDOOR BROKERAGE LLC
New33$225,000
3 bd · 2 ba · 1,245 sqft
125 Whittier Ln, Winter Haven, FL
Lori Roberts · GOLD HEART REALTY LLC
New64$249,900
3 bd · 2 ba · 1,140 sqft
240 Westwood Ave, Winter Haven, FL
Nicole Silva · RE/MAX COLLECTIVE
15$294,990
5 bd · 3 ba · 2,112 sqft
6245 Botticella Blvd, Winter Haven, FL
Ben Goldstein · LENNAR REALTY
21$278,000
4 bd · 2 ba · 1,830 sqft
703 Avenue L SE, Winter Haven, FL
Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC
42$279,900
3 bd · 2 ba · 1,556 sqft
420 Hillcrest Dr SE, Winter Haven, FL
Raymond Thomas · STAR BAY REALTY CORP.
21$130,000
3 bd · 2 ba · 1,678 sqft
1406 Meadow Dr NE, Winter Haven, FL
Cesar Estrada, PA · EXP REALTY LLC
1$296,990
4 bd · 2 ba · 1,574 sqft
2771 Adeline Ave, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
27$269,999
2 bd · 2 ba · 1,826 sqft
86 Lake Daisy Blvd, Winter Haven, FL
Steven Torres · DALTON WADE INC
1$298,990
4 bd · 2 ba · 1,574 sqft
2767 Adeline Ave, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
23$224,900
3 bd · 2 ba · 1,430 sqft
609 Maggie Cir, Winter Haven, FL
Lynne Powers · POWERS REAL ESTATE SOLUTIONS LLC
Homes Under $300K in Winter Haven, FL: 464 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Single Family Residence | 293 | 63.1% |
| Condominium | 62 | 13.4% |
| Manufactured Home | 61 | 13.1% |
| Townhouse | 22 | 4.7% |
| Mobile Home | 5 | 1.1% |
























Stellar MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 99.9% of asking price
Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026