Winter Haven, FL homes for sale & real estate

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NEW 20 HRS AGO

ABOUT THIS HOME
Winter Haven, FL Homes for Sale
Spacious and move-in ready 4-bedroom, 2.5-bath, two-story pool home in the gated Overlook Estates community of Winter Haven. Boasting 2,850 sq. ft. , this home features multiple living areas including a formal living room with a wood-burning fireplace, a cozy family room with a second wood-burning fireplace, and an open kitchen perfect for entertaining. The wrap-around porch and fenced backyard overlook a sparkling saltwater pool and hot tub, with solar lighting that creates a magical evening ambiance. The primary suite offers a sitting vanity area, walk-in closet, and a walk-in shower. Practical touches include a workshop/pool house with electricity, a 2-car oversized garage, utility room

$462,900

4 beds2.5 baths2,850 sq ft

240 Santa Rosa Dr, Winter Haven, FL 33884

Saltwater pool • Wrap-around porch • Fenced backyard

ABOUT THIS HOME
Winter Haven, FL Homes for Sale
* * * WELL CARED FOR WITH MANY RECENT UPDATES IN THIS SOLID BLOCK 3 BED 1 BATH HOME * * * NEW ROOF, FRESH PAINT INSIDE & OUT, ALL NEW FLOORING, NEW KITCHEN WITH APPLIANCE PACKAGE & MUCH MORE * * * WALK INTO THIS HOME AND YOU'LL SEE OPEN LIVING AREA WITH VAULTED CEILINGS AND WOOD BEAMS, TONS OF NATURAL LIGHT AND NICE SIZED BEDROOMS * * * COME CHECK THIS OUT TODAY * * *

$189,900

3 beds1 bath1,118 sq ft

2334 Avenue E NW, Winter Haven, FL 33880

New kitchen • Fresh paint • Wood beams

ABOUT THIS HOME
Winter Haven, FL Homes for Sale
Located in desirable Southeast Winter Haven, this property offers a solid footprint with strong upside for the right investor or handy buyer. With some TLC, this home provides an excellent foundation to add value! The layout features both a formal living room and a separate family room, offering flexibility for future tenants or resale appeal. One of the key value-add opportunities is the 10x10 utility room, which currently includes the half bath and offers great potential to be reconfigured into a full private primary en-suite, significantly enhancing functionality and long-term value. Split bedroom plan with the other two bedrooms and full bath on the other side of the formal living room.

$190,000

3 beds1.5 baths1,435 sq ft

137 Lowell Rd, Winter Haven, FL 33884

Formal living room • Split bedroom plan • 10x10 utility room

NEW 29 HRS AGO

ABOUT THIS HOME
Winter Haven, FL Homes for Sale
Cute Bungalow with 2 bedrooms/1 bath. Ceramic tile throughout with new fixtures and lighting. Kitchen features quartz counters and a breakfast bar. Bat has been updated with new shower tile and pedestal sink. Roof 2023. Convenient to the many lakes and parks in the area.

$130,000

2 beds1 bath600 sq ft

713 Sears Ave NE, Winter Haven, FL 33881

Quartz counters • Roof 2023 • Ceramic tile

ABOUT THIS HOME
Winter Haven, FL Homes for Sale
PRICED TO SELL!! MOTIVATED SELLER! WELL-MAINTAINED 4 BEDROOM 2 BATH HOME BUILT IN 2021 IN THE GATED COMMUNITY OF BUCKEYE TRACE! This open floor plan boasts 4 bedrooms, perfect for a growing family! The primary suite is designed with a split bedroom plan, en-suite bath and walk-in closet. The spacious kitchen is at the heart of the home, complete with upgraded, full extension cabinets, breakfast bar and large pantry. You'll love the beautiful luxury vinyl flooring throughout, fresh paint, and large screened lanai. The private, PVC fenced backyard is large enough to add a POOL! Upgrades also include a whole-house generator, hurricane shutters, water softener and gutters. Conveniently located

$299,900

4 beds2 baths1,814 sq ft

1434 Grey Eagle Ln, Winter Haven, FL 33881

Gated community • Open floor plan • Large pantry

Property at 276 18th St NE, Winter Haven, FL 33881, 3 beds, 2 baths

$144,900

3 beds2 baths1,218 sq ft

276 18th St NE, Winter Haven, FL 33881

Property at 119 Doll Dr, Winter Haven, FL 33884, 3 beds, 1.5 baths

$298,000

3 beds1.5 baths1,852 sq ft

119 Doll Dr, Winter Haven, FL 33884

Property at 112 Longfellow Rd, Winter Haven, FL 33884, 2 beds, 2 baths

$139,900

2 beds2 baths1,218 sq ft

112 Longfellow Rd, Winter Haven, FL 33884

Property at 4156 Limerick Dr, Lake Wales, FL 33859, 2 beds, 2 baths

$350,000

2 beds2 baths1,326 sq ft

4156 Limerick Dr, Lake Wales, FL 33859

Property at 301 26th St SW, Winter Haven, FL 33880, 3 beds, 1 bath

$169,900

3 beds1 bath950 sq ft

301 26th St SW, Winter Haven, FL 33880

Property at 1729 Teagan Ln, Winter Haven, FL 33884, 3 beds, 2 baths

$250,000

3 beds2 baths1,300 sq ft

1729 Teagan Ln, Winter Haven, FL 33884

Property at 2727 Rutledge Ct, Winter Haven, FL 33884, 3 beds, 2 baths

$239,900

3 beds2 baths1,536 sq ft

2727 Rutledge Ct, Winter Haven, FL 33884

Property at 241 Paine Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$279,000

3 beds2 baths1,730 sq ft

241 Paine Dr, Winter Haven, FL 33884

Property at 258 Terranova Blvd, Winter Haven, FL 33884, 4 beds, 3 baths

$419,000

4 beds3 baths2,639 sq ft

258 Terranova Blvd, Winter Haven, FL 33884

Property at 3622 Plymouth Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$299,000

2 beds2 baths1,935 sq ft

3622 Plymouth Dr, Winter Haven, FL 33884

Property at 2925 Dayton Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$310,000

3 beds2 baths2,109 sq ft

2925 Dayton Dr, Winter Haven, FL 33884

Property at 4072 Stone Creek Loop, Lake Wales, FL 33859, 3 beds, 2 baths

$355,000

3 beds2 baths1,820 sq ft

4072 Stone Creek Loop, Lake Wales, FL 33859

Property at 214 Green Meadow Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$95,000

2 beds2 baths1,456 sq ft

214 Green Meadow Dr, Winter Haven, FL 33884

Property at 2735 Gladiola Rd, Winter Haven, FL 33884, 3 beds, 2.5 baths

$265,490

3 beds2.5 baths1,758 sq ft

2735 Gladiola Rd, Winter Haven, FL 33884

Property at 6394 Lolly Bay Loop NE, Winter Haven, FL 33881, 2 beds, 2 baths

$200,000

2 beds2 baths1,620 sq ft

6394 Lolly Bay Loop NE, Winter Haven, FL 33881

Property at 2519 Avenue E SW, Winter Haven, FL 33880, 3 beds, 2 baths

$330,000

3 beds2 baths1,675 sq ft

2519 Avenue E SW, Winter Haven, FL 33880

Property at 2186 Lasso Loop, Eagle Lake, FL 33839, 3 beds, 2 baths

$270,490

3 beds2 baths1,429 sq ft

2186 Lasso Loop, Eagle Lake, FL 33839

Property at 3807 Pomelo Dr, Winter Haven, FL 33880, 3 beds, 2 baths

$321,490

3 beds2 baths1,672 sq ft

3807 Pomelo Dr, Winter Haven, FL 33880

Property at 1600 Hummingbird Rd, Winter Haven, FL 33884, 4 beds, 2 baths

$293,990

4 beds2 baths1,720 sq ft

1600 Hummingbird Rd, Winter Haven, FL 33884

Property at 154 Eloise Oaks Dr, Winter Haven, FL 33884, 4 beds, 2 baths

$329,999

4 beds2 baths1,707 sq ft

154 Eloise Oaks Dr, Winter Haven, FL 33884

Property at 2194 Lasso Loop, Eagle Lake, FL 33839, 4 beds, 3 baths

$307,740

4 beds3 baths2,174 sq ft

2194 Lasso Loop, Eagle Lake, FL 33839

Property at 4463 Rapallo Ave, Winter Haven, FL 33884, 3 beds, 2 baths

$302,900

3 beds2 baths1,744 sq ft

4463 Rapallo Ave, Winter Haven, FL 33884

Property at 6428 Domizio Dr, Winter Haven, FL 33884, 5 beds, 2.5 baths

$304,990

5 beds2.5 baths2,112 sq ft

6428 Domizio Dr, Winter Haven, FL 33884

Property at 2218 Avenue B SW, Winter Haven, FL 33880, 3 beds, 2 baths

$300,000

3 beds2 baths1,852 sq ft

2218 Avenue B SW, Winter Haven, FL 33880

Property at 1592 Hummingbird Rd, Winter Haven, FL 33884, 4 beds, 2 baths

$293,990

4 beds2 baths1,720 sq ft

1592 Hummingbird Rd, Winter Haven, FL 33884

Property at 6024 Navona Way, Winter Haven, FL 33884, 4 beds, 2.5 baths

$338,590

4 beds2.5 baths2,039 sq ft

6024 Navona Way, Winter Haven, FL 33884

Property at 2799 Adeline Ave, Winter Haven, FL 33881, 3 beds, 2 baths

$311,990

3 beds2 baths1,328 sq ft

2799 Adeline Ave, Winter Haven, FL 33881

Property at 5860 Heaven Rd, Haines City, FL 33844, 5 beds, 3.5 baths

$467,475

5 beds3.5 baths3,182 sq ft

5860 Heaven Rd, Haines City, FL 33844

Property at 1604 Hummingbird Rd, Winter Haven, FL 33884, 4 beds, 2.5 baths

$330,990

4 beds2.5 baths2,308 sq ft

1604 Hummingbird Rd, Winter Haven, FL 33884

Property at 5425 San Pietro Dr, Winter Haven, FL 33884, 4 beds, 2 baths

$340,981

4 beds2 baths1,850 sq ft

5425 San Pietro Dr, Winter Haven, FL 33884

Property at 6436 Domizio Dr, Winter Haven, FL 33884, 5 beds, 2.5 baths

$314,990

5 beds2.5 baths2,326 sq ft

6436 Domizio Dr, Winter Haven, FL 33884

Property at 2783 Adeline Ave, Winter Haven, FL 33881, 5 beds, 2 baths

$333,990

5 beds2 baths1,708 sq ft

2783 Adeline Ave, Winter Haven, FL 33881

Property at 203 Summer View Dr, Winter Haven, FL 33880, 3 beds, 1 bath

$215,000

3 beds1 bath1,195 sq ft

203 Summer View Dr, Winter Haven, FL 33880

Property at 220 ST Georges Cir, Eagle Lake, FL 33839, 3 beds, 2 baths

$264,000

3 beds2 baths1,479 sq ft

220 ST Georges Cir, Eagle Lake, FL 33839

Property at 2500 21st St NW #58, Winter Haven, FL 33881, 3 beds, 2.5 baths

$179,000

3 beds2.5 baths1,334 sq ft

2500 21st St NW #58, Winter Haven, FL 33881

Property at 800 Avenue L SE, Winter Haven, FL 33880, 4 beds, 2 baths

$295,000

4 beds2 baths1,728 sq ft

800 Avenue L SE, Winter Haven, FL 33880

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Based on information submitted to the MLS GRID as of Thu Dec 25 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Winter Haven, FL

Cities

Neighborhoods
Zip Codes

Rock Springs Ridge homes for sale
$594,950
Downtown Dundee homes for sale
$295,000
Eloise Woods homes for sale
$264,500
Caribe Cove homes for sale
$220,000
Garden Grove homes for sale
$129,895
Traditions homes for sale
$299,000
Orchid Springs homes for sale
$205,000
Lake Ashton homes for sale
$430,450
Downtown Winter Haven homes for sale
$249,000
Lake Ashton Golf Club homes for sale
$372,450

Winter Haven, FL real estate trends

All Home Types trends in Winter Haven, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$310,690

+6.8% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Winter Haven, FL

$310,690

+6.8%

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