Homes for Sale in Winter Haven, FL

820 homes are for sale in Winter Haven, FL as of 2026-09-06, with 128 more under contract. The median list price is $284,990 ($168/sq ft), most homes list between $156K to $435K, and the median listing has been on the market 51 days. 195 homes came on the market this week.

Newest homes for sale in Winter Haven

The most recently listed homes in Winter Haven, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.

$515,000 New

4 bd · 3 ba · 3,024 sq ft

230 BROAD STREET

Winter Haven

Listing courtesy of DALTON WADE INC

$395,000 New

4 bd · 3 ba · 2,468 sq ft

1380 S LAKE ROY DR DRIVE

Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1

$335,900 New

4 bd · 3.5 ba · 2,227 sq ft

2820 SAN MARCO WAY

Winter Haven

Listing courtesy of CAMBRIDGE REALTY OF CENTRAL FL

$299,000 New

3 bd · 2 ba · 1,540 sq ft

1104 TYLER LOOP

Winter Haven

Listing courtesy of RE/MAX PRIME PROPERTIES

$299,000 New

3 bd · 2 ba · 1,833 sq ft

7158 SUMMIT PLACE

Winter Haven

Listing courtesy of FLORIDA HOME CHOICE REALTY

$289,900 New

4 bd · 2 ba · 1,560 sq ft

2128 BRETTON RIDGE BOULEVARD

Winter Haven

Listing courtesy of KISHROY REALTY GROUP LLC

$274,999 New

3 bd · 2 ba · 1,632 sq ft

3947 WARBLER DRIVE

Winter Haven

Listing courtesy of FLORIDA REALTY INVESTMENTS

$260,000 New

3 bd · 2 ba · 1,444 sq ft

307 STERLING DRIVE

Winter Haven

Listing courtesy of KELLER WILLIAMS ADVANTAGE III

$255,000 New

4 bd · 2 ba · 1,532 sq ft

1024 31ST STREET

Winter Haven

Listing courtesy of GOYAL & DECOSTER REALTY

$184,900 New

2 bd · 2 ba · 1,436 sq ft

2215 STARBOARD DRIVE #29

Winter Haven

Listing courtesy of KLINE REAL ESTATE SERVICES

$152,000 New

2 bd · 2 ba · 1,073 sq ft

350 WINTER RIDGE BOULEVARD #350

Winter Haven

Listing courtesy of RP INVESTMENT REALTY LLC

$145,000 New

3 bd · 2 ba · 1,226 sq ft

333 LAKE HOWARD DRIVE #204D

Winter Haven

Listing courtesy of UNITED REAL ESTATE PREFERRED

$95,000 New

1 bd · 1 ba · 1,078 sq ft

1100 MARTINIQUE DRIVE #117

Winter Haven

Listing courtesy of LA ROSA REALTY LLC

$54,900 New

2 bd · 1 ba · 672 sq ft

213 LAKESIDE RANCH CIRCLE

Winter Haven

Listing courtesy of EXIT REALTY 4CORNERS

$44,900 New

3 bd · 2 ba · 988 sq ft

1116 40TH STREET

Winter Haven

Listing courtesy of MILLSHIRE REALTY

$760,000 New

5 bd · 3.5 ba · 3,694 sq ft

1016 S LAKE MARIAM DRIVE

Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY SMART 1

$750,000 New

4 bd · 3 ba · 2,056 sq ft

7 LAKE ARROWHEAD DRIVE

Winter Haven

Listing courtesy of CENTURY 21 WATSON & MYERS REALTY

$699,000 New

4 bd · 3 ba · 2,511 sq ft

644 HART LAKE DRIVE

Winter Haven

Listing courtesy of THE STONES REAL ESTATE FIRM

$649,900 New

3 bd · 3.5 ba · 3,020 sq ft · built 1990

2241 WINTERSET ROAD, 33884

Lake Winterset Acres

Listing courtesy of KLINE REAL ESTATE SERVICES

$510,000 New

6 bd · 4 ba · 2,820 sq ft

302 AVENUE P NW

Winter Haven

Listing courtesy of LOKATION

$495,000 New

2 bd · 2.5 ba · 1,640 sq ft · built 2015

154 2ND STREET #Unit 7, 33880

RainGarden

Listing courtesy of POLK REALTY ADVISORS LLC

$450,000 New

4 bd · 2.5 ba · 2,829 sq ft

2734 ROCHELLE DRIVE

Winter Haven

Listing courtesy of GATAP REALTY

$435,000 New

3 bd · 2 ba · 2,702 sq ft

1755 BETH LANE

Winter Haven

Listing courtesy of COLDWELL BANKER REALTY

$429,500 New

4 bd · 3.5 ba · 2,766 sq ft · built 1994

139 WODEN WAY, 33884

Valhalla

Listing courtesy of FLORIDA HOME CHOICE REALTY

Winter Haven homes for sale by price

Every active listing in Winter Haven grouped by price, with the newest listings in each band. The median is $284,990; the busiest band is $200K – $300K.

Under $200K: 163 homes

• $44,900 · 3 bd / 2 ba / 988 sq ft · 1116 40TH STREET
• $54,900 · 2 bd / 1 ba / 672 sq ft · 213 LAKESIDE RANCH CIRCLE
• $95,000 · 1 bd / 1 ba / 1,078 sq ft · 1100 MARTINIQUE DRIVE #117
• $145,000 · 3 bd / 2 ba / 1,226 sq ft · 333 LAKE HOWARD DRIVE #204D

$200K – $300K: 310 homes

• $255,000 · 4 bd / 2 ba / 1,532 sq ft · 1024 31ST STREET
• $260,000 · 3 bd / 2 ba / 1,444 sq ft · 307 STERLING DRIVE
• $274,999 · 3 bd / 2 ba / 1,632 sq ft · 3947 WARBLER DRIVE
• $289,900 · 4 bd / 2 ba / 1,560 sq ft · 2128 BRETTON RIDGE BOULEVARD

$300K – $400K: 236 homes

• $335,900 · 4 bd / 3.5 ba / 2,227 sq ft · 2820 SAN MARCO WAY
• $395,000 · 4 bd / 3 ba / 2,468 sq ft · 1380 S LAKE ROY DR DRIVE
• $305,000 · 3 bd / 2 ba / 1,535 sq ft · 2579 SAGE VALLEY WAY
• $305,000 · 4 bd / 2.5 ba / 1,879 sq ft · 981 HAROLD PASS

$400K – $500K: 54 homes

• $405,000 · 4 bd / 2 ba / 2,000 sq ft · 2011 RECKER HIGHWAY
• $410,000 · 3 bd / 2 ba / 2,350 sq ft · 5016 RIVER LAKE ROAD
• $420,000 · 3 bd / 2 ba / 2,117 sq ft · 204 LAKE MARIAM COURT
• $425,000 · 4 bd / 2.5 ba / 2,434 sq ft · 5009 STRADA DRIVE

$500K – $750K: 40 homes

• $515,000 · 4 bd / 3 ba / 3,024 sq ft · 230 BROAD STREET
• $510,000 · 6 bd / 4 ba / 2,820 sq ft · 302 AVENUE P NW
• $649,900 · 3 bd / 3.5 ba / 3,020 sq ft · 2241 WINTERSET ROAD (Lake Winterset Acres)
• $699,000 · 4 bd / 3 ba / 2,511 sq ft · 644 HART LAKE DRIVE

$750K – $1M: 13 homes

• $750,000 · 4 bd / 3 ba / 2,056 sq ft · 7 LAKE ARROWHEAD DRIVE
• $760,000 · 5 bd / 3.5 ba / 3,694 sq ft · 1016 S LAKE MARIAM DRIVE
• $865,000 · 5 bd / 3 ba / 3,482 sq ft · 2510 CYPRESS GARDENS BOULEVARD
• $849,900 · 5 bd / 3.5 ba / 4,108 sq ft · 25 LAKEWOOD CAUSEWAY

$1M and up: 4 homes

• $1.40M · 4 bd / 3 ba / 3,309 sq ft · 3640 CRUMP ROAD
• $1.20M · 5 bd / 5.5 ba / 3,235 sq ft · 250 BRIGHAM ROAD
• $1.80M · 4 bd / 4 ba / 4,708 sq ft · 13 BOGEY DRIVE
• $1.15M · 6 bd / 5.5 ba / 6,100 sq ft · 1200 W LAKE OTIS DRIVE

Homes for sale in Winter Haven by ZIP code

Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.

Winter Haven communities with the most homes for sale

The Winter Haven neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.

What is for sale in Winter Haven: property types

• Single-family homes: 656
• Condos: 68
• Manufactured homes: 54
• Townhouses: 23
• Villas: 19

Another 3 listings in Winter Haven are land, commercial or other non-residential property and are not counted above.

Browse by type: Condos for sale in Winter Haven (68) · Townhomes for sale in Winter Haven (23) · Manufactured and Mobile Homes for sale in Winter Haven (54).

What a home in Winter Haven costs to own

Take the median $284,990 listing with 20% down at today’s 6.71% 30-year rate: principal and interest run about $1,473/month. Polk County’s typical millage of 16.19 puts property tax near $3,804/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Polk County is about $1,931/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $1,951/month plus any HOA or CDD assessment.

Explore Winter Haven

• All homes for sale in Polk County, FL
• Winter Haven market intelligence: prices, supply and trends
• Moving to Winter Haven: the data guide
• Cost of living in Winter Haven
• Best neighborhoods in Winter Haven
• Polk County property tax guide
• Search every Winter Haven community
• All Florida cities and counties

Homes for sale near Winter Haven

• Homes for sale in Davenport, FL — 1714 listings
• Homes for sale in Lakeland, FL — 1222 listings
• Homes for sale in Haines City, FL — 538 listings
• Homes for sale in Lake Wales, FL — 357 listings
• Homes for sale in Auburndale, FL — 258 listings
• Homes for sale in Poinciana, FL — 162 listings
• Homes for sale in Bartow, FL — 152 listings
• Homes for sale in Lake Alfred, FL — 127 listings
• Homes for sale in Polk City, FL — 98 listings
• Homes for sale in Mulberry, FL — 96 listings
• Homes for sale in Eagle Lake, FL — 77 listings
• Homes for sale in Dundee, FL — 72 listings

Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Haven as of 2026-09-06 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.