Winter Haven, FL Homes

$409,635

New Construction Pending
- 4 Beds
- 3 Baths
- 2,551 Sq Ft
1739 Upland Ln, Winter Haven, FL 33884

The Sandalwood single-family home sets the standard for main level luxury. A convenient family entry welcomes you inside to unmatched space and style. A full bath sits between 2 bedrooms, while a guest suite with full bath is found off the 3-car garage. Use the versatile flex space as a home office. The gourmet kitchen includes a large island overlooking dining space and the family room, ideal

William Maltbie

MALTBIE REALTY GROUP

1739 Upland Ln, Winter Haven, FL 33884
/16
$1,650 Per Month
- 3 Beds
- 2 Baths
- 1,310 Sq Ft
- House for Rent
3740 Imperial Dr, Winter Haven, FL 33880

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Rent this home by September 30, 2026 and receive $500 Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart

3740 Imperial Dr, Winter Haven, FL 33880
/12
$334,499

Sold Feb 10, 2026

6044 Navona Way, Winter Haven, FL 33884
- 5 Beds
- 3 Baths
- 2,471 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $135/SF
- 40 Days On Market
Current Estimated Value $333,821

Casa Fresca Homes Villa Mar

6044 Navona Way, Winter Haven, FL 33884

/2
Not Listed For Sale

6471 Peppertree Path NE, Winter Haven, FL 33881
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
- Built 1985
6471 Peppertree Path NE, Winter Haven, FL 33881

Last Sold Summary
- 181 Days On Market
Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

/24
$310,000

$100K PRICE DROP Pending
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
4612 Reynosa Dr SW, Winter Haven, FL 33880

Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from

Trent Shackelford

LPT REALTY LLC

4612 Reynosa Dr SW, Winter Haven, FL 33880
/17
$1,795 Per Month
- 3 Beds
- 2 Baths
- 1,541 Sq Ft
- House for Rent
417 Kensington View Dr, Winter Haven, FL 33880

** MOVE IN SPECIAL! Get 2 Weeks FREE off 1st Full Month with Deposit Paid by 9/19/2026**This 3-bedroom, 2-bath home offers 1,541 square feet of thoughtfully designed, single-story living space. The open floor plan keeps the main living areas feeling connected, while the kitchen features granite countertops and stainless-steel appliances for a polished, modern look.The spacious

417 Kensington View Dr, Winter Haven, FL 33880
/2
$284,000

Sold Dec 30, 2025

232 Spirit Landing Cir, Winter Haven, FL 33880
- 3 Beds
- 2 Baths
- 1,546 Sq Ft
- Built 2024
Last Sold Summary
- 2% Below List Price
- $184/SF
- 21 Days On Market
Current Estimated Value $283,432

Last Listing Agent Samuel Eckerson KELLER WILLIAMS ADVANTAGE REALTY

232 Spirit Landing Cir, Winter Haven, FL 33880

/25
Est $283,438

Not Listed For Sale

842 Terranova Rd, Winter Haven, FL 33884
- 3 Beds
- 2.5 Baths
- 1,320 Sq Ft
- Built 2012
842 Terranova Rd, Winter Haven, FL 33884

Last Sold Summary
- 84 Days On Market
Last Listing Agent Javier Paredes PROPERTIES IN TOWN

/20
$195,000

$54K PRICE DROP Under Contract
- 3 Beds
- 2 Baths
- 1,238 Sq Ft
1109 5th St SW, Winter Haven, FL 33880

Under contract-accepting backup offers. Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the

Carlos DeJesus

EXIT REALTY 4CORNERS

1109 5th St SW, Winter Haven, FL 33880
/17
$995 Per Month
- 2 Beds
- 1 Bath
- 761 Sq Ft
- Condo for Rent
3058 St Paul Dr, Jan Phyl Village, FL 33880

Apply now for free! Don’t miss out on this incredible deal—reach out today to learn more and schedule a tour! Enjoy a comfortable living space with 2 bedrooms and 1 bathroom. Perfect for those seeking convenience and style. - Includes appliances: Refrigerator and Electric Range - Cooling and heating: Central, Heat Pump - Off-street parking available - Flooring: Tile and

3058 St Paul Dr, Jan Phyl Village, FL 33880
/46
$30,000

Sold May 21, 2026

802 Bunker Cir, Winter Haven, FL 33881
- 2 Beds
- 1.5 Baths
- 686 Sq Ft
- Built 1988
Last Sold Summary
- 23% Below List Price
- $44/SF
- 32 Days On Market
Last Listing Agent Patti Alvin Sunset Home Sales

802 Bunker Cir, Winter Haven, FL 33881

/2
Est $81,597

Not Listed For Sale

1100 Martinique Dr Unit 109, Winter Haven, FL 33884
- 1 Bed
- 1 Bath
- 826 Sq Ft
- Built 1974
1100 Martinique Dr Unit 109, Winter Haven, FL 33884

Last Sold Summary
- 11 Days On Market
Last Listing Agent Dwight Head ALLSTATE REALTY SERVICES

/33
$259,000
- 4 Beds
- 2 Baths
- 1,746 Sq Ft
1429 Lucerne Loop Rd NE, Winter Haven, FL 33881

4 BEDROOM, 2 BATH HOME BUILT IN 2019 WITH LOW HOA AND NO CDD. The Brick-paver drive leads to a two-car garage and a bright open floor plan. Kitchen has a large island, plenty of cabinets, and all appliances included. Living and dining rooms flow together for easy daily living. Split-bedroom layout puts three bedrooms on one side and the primary suite (ensuite bath with private toilet room +

Brad Martin

BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

1429 Lucerne Loop Rd NE, Winter Haven, FL 33881
/12
$2,000 Per Month
- 4 Beds
- 2 Baths
- 1,850 Sq Ft
- House for Rent
1336 Axel Cir, Winter Haven, FL 33880

Property Id: 836169 4 bedroom 2 Bathroom Single Family Home Easy commute to either Tampa or Orlando. Large kitchen granite countertops, large pantry, stainless steel appliances, Washer and Dryer included, vaulted ceiling, 2-car garage. Security deposit due at signing. $2000 1st and Last and security due at move in. Well qualified applicants may be

1336 Axel Cir, Winter Haven, FL 33880
/29
$274,900

Sold Aug 05, 2026

5561 Taverna Loop, Winter Haven, FL 33884
- 3 Beds
- 2 Baths
- 1,504 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $183/SF
- 21 Days On Market
Current Estimated Value $272,671

D.R. Horton VillaMar

5561 Taverna Loop, Winter Haven, FL 33884

/2
Est $319,293

Not Listed For Sale

491 Majestic Gardens Blvd, Winter Haven, FL 33880
- 5 Beds
- 2 Baths
- 2,018 Sq Ft
- Built 2012
491 Majestic Gardens Blvd, Winter Haven, FL 33880

Last Sold Summary
- 22 Days On Market
Last Listing Agent Vicky Torres Rodriguez RE/MAX HERITAGE PROFESSIONALS

/9
$95,000

$50K PRICE DROP Pending
- 3 Beds
- 1 Bath
- 1,080 Sq Ft
108 9th Eloise St, Winter Haven, FL 33880

Investor special with endless potential! **SELLER MOTIVATED** This 3-bedroom, 1-bath home is a fantastic opportunity for investors, flippers, or buyers looking to renovate and make it their own. The property features a durable metal roof, a fully fenced yard offering privacy and space for pets, play, or gardening, and is conveniently located near John Snively Elementary School, shopping, dining,

Samantha Whitmore

WHITMORE PROPERTIES

108 9th Eloise St, Winter Haven, FL 33880
/17
$1,850 Per Month
- 3 Beds
- 2 Baths
- 1,393 Sq Ft
- House for Rent
4651 Magnolia Ave, Winter Haven, FL 33880

Property Id: 2816201 AVAILABLE NOW - Beautiful 3-Bedroom, 2-Bath Home with 2-Car Garage Welcome home to this beautiful and well-maintained 3-bedroom, 2-bath single-family home in Winter Haven offering 1,393 sq. ft. of comfortable living space. Enjoy beautiful flooring throughout with no carpet, a bright and open living/dining area, and a desirable split-bedroom floor plan for added

4651 Magnolia Ave, Winter Haven, FL 33880
/2
$305,046

Sold Mar 20, 2026

2319 Brassie Ct, Winter Haven, FL 33884
- 4 Beds
- 2.5 Baths
- 2,202 Sq Ft
- Built 2025
Last Sold Summary
- 10% Below List Price
- $139/SF
- 124 Days On Market
Current Estimated Value $306,861

Last Listing Agent Claudia Gutierrez ADAMS HOMES REALTY

2319 Brassie Ct, Winter Haven, FL 33884

/44
Est $414,062

Not Listed For Sale

849 Terranova Rd, Winter Haven, FL 33884
- 4 Beds
- 3 Baths
- 2,483 Sq Ft
- Built 2012
849 Terranova Rd, Winter Haven, FL 33884

Last Sold Summary
- 2 Days On Market
Last Listing Agent Jonathon Gattuso LOMBARDO TEAM REAL ESTATE LLC

/10
$179,000
- Land
- 8,712 Sq Ft
- $895,000 per Acre
702 Avenue A E, Winter Haven, FL 33880

Rare development opportunity in the heart of Winter Haven's Urban Core. This corner parcel is zoned R-4 and designated Primary Mixed Use Hub (PMUH), placing it within one of the city's most flexible and growth-oriented future land use districts. According to the City of Winter Haven zoning and future land use maps, the property allows for a variety of residential development opportunities

Veronica Bard

LA ROSA REALTY PRESTIGE

702 Avenue A E, Winter Haven, FL 33880
/20
$1,800 Per Month
- 4 Beds
- 2 Baths
- House for Rent
1108 Carefree Cove Dr, Winter Haven, FL 33881

Property Id: 1524046 Large House for a family with fenced in large yard, tiles floors, updated kitchen and bathrooms with lots of extras. Available July 2025. Please call both contact numbers to get more information on property and terms of rental.

1108 Carefree Cove Dr, Winter Haven, FL 33881
/42
$305,112

Sold Apr 22, 2026

5032 Abigail Dr, Winter Haven, FL 33859
- 4 Beds
- 2 Baths
- 2,110 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $145/SF
- 137 Days On Market
Current Estimated Value $310,742

Dream Finders Homes Annabelle Estates

5032 Abigail Dr, Winter Haven, FL 33859

/21
Not Listed For Sale

5722 E Lake Fox Dr, Winter Haven, FL 33884
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
- Built 1986
5722 E Lake Fox Dr, Winter Haven, FL 33884

Last Sold Summary
- 68 Days On Market
Last Listing Agent Dolores Vogel LEGACY REAL ESTATE CENTER INC

/2
$50,000
- Land
- 10,018 Sq Ft
- $217,391 per Acre
138 1st Eloise St, Winter Haven, FL 33880

Really nice residential lot for sale close to all major attractions. A must see to appreciate value and area. All utilities are next door.

Franc Marrero

FREEDOM PROPERTY AGENT LLC

138 1st Eloise St, Winter Haven, FL 33880
/17
$2,466

Total Monthly Price
- 2 Beds
- 2 Baths
- 1,636 Sq Ft
- Condo for Rent
1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881

The advertised rate of $2,466/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881
/2
$495,000

Sold Jan 09, 2026

413 Horseshoe Ln NE, Winter Haven, FL 33881
- 4 Beds
- 2 Baths
- 2,336 Sq Ft
- Built 1991
Last Sold Summary
- 24% Below List Price
- $212/SF
- 132 Days On Market
Current Estimated Value $494,609

Last Listing Agent John Kelson KELLER WILLIAMS ADVANTAGE 2 REALTY

413 Horseshoe Ln NE, Winter Haven, FL 33881

/26
Est $313,413

Not Listed For Sale

1410 17th St NW, Winter Haven, FL 33881
- 3 Beds
- Built 1955
1410 17th St NW, Winter Haven, FL 33881

Last Sold Summary
- 17 Days On Market
Last Listing Agent Kaili Ross KELLER WILLIAMS REALTY SMART 1

/36
$326,900

$3K PRICE DROP
- 4 Beds
- 2 Baths
- 1,819 Sq Ft
2610 San Marco Way, Winter Haven, FL 33884

2610 San Marco Way is a beautifully maintained Highland Homes Raychel floor plan in the Villamar community of Winter Haven, offering 4 bedrooms, 2 bathrooms, an open layout, and several upgrades that have already been completed for the next owner.One feature that makes this home especially worth a look is the CDD. When the current owner purchased the home, the builder paid off the debt

Veronica Bard

LA ROSA REALTY PRESTIGE

2610 San Marco Way, Winter Haven, FL 33884
/15
$1,885 Per Month
- 3 Beds
- 2 Baths
- 1,678 Sq Ft
- House for Rent
324 Kensington View Dr, Winter Haven, FL 33880

Welcome to 324 Kensington View Drive, a spacious 1,678-square-foot home featuring 3 bedrooms and 2 bathrooms in the Kensington View community. The heart of the home is an open-concept kitchen equipped with stainless steel appliances and a center island that flows seamlessly into the main living area. Additional conveniences include in-home washer and dryer hookups, an attached 2-car garage for

324 Kensington View Dr, Winter Haven, FL 33880
/2
$272,000

Sold Dec 15, 2025

676 Augusta Rd, Winter Haven, FL 33884
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1985
Last Sold Summary
- 9% Below List Price
- $160/SF
- 108 Days On Market
Current Estimated Value $276,265

Last Listing Agent Dee Norris NEXTHOME NORRIS & COMPANY REAL

676 Augusta Rd, Winter Haven, FL 33884

/2
Not Listed For Sale

6032 Grand Oaks Dr SE, Winter Haven, FL 33884
- 2 Beds
- 2 Baths
- 1,448 Sq Ft
- Built 1982
6032 Grand Oaks Dr SE, Winter Haven, FL 33884

Last Sold Summary
- 2 Days On Market
Last Listing Agent Stephanie Lucas MUSIC REALTY

/5
$980,000

$130K PRICE INCREASE
- Land
- 9.8 Acres
- $100,000 per Acre
0 Brigham Rd NW, Winter Haven, FL 33881

9.8 ACRES (8.5 acres of R-3 + 1.3 acres of Conservation zoning) in the City of Winter Haven. Prime location and already zoned for multifamily development (R-3). Additional unit count with potential zoning change of 1.3 acre portion to R-3. WATER, SEWER & POWER readily available! Property fronts onto Brigham Road and backs up to a Conservation Area. All measurements including acreage count are

Steve Lockhart

LOCKHART & ASSOCIATES INC

0 Brigham Rd NW, Winter Haven, FL 33881
/20
$1,650 Per Month
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- House for Rent
1423-1426 26th St NW, Winter Haven, FL 33881

Property Id: 999583 Upcoming for middle of November. 2 Bedroom 1 Bathroom house, large fenced yard, Carport for rent. Taking applications. House will not be available until middle of November. Asking $1750 can leave it at $1650* per month. Outside showing and Driving at the moment. New floors planned to be installed. Area of Lake Cannon Winter Haven. If interested and for more information

1423-1426 26th St NW, Winter Haven, FL 33881
/2
$285,090

Sold Jun 22, 2026

4036 Giorgio Dr, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 1,665 Sq Ft
- Built 2025
Last Sold Summary
- 1% Above List Price
- $171/SF
- 241 Days On Market
Current Estimated Value $285,715

Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

4036 Giorgio Dr, Winter Haven, FL 33884

/2
Est $140,808

Not Listed For Sale

2037 San Marcos Dr SE Unit 443, Winter Haven, FL 33880
- 2 Beds
- 2 Baths
- 967 Sq Ft
- Built 1984
2037 San Marcos Dr SE Unit 443, Winter Haven, FL 33880

Last Sold Summary
- 37 Days On Market
Last Listing Agent Susan Brown COLDWELL BANKER REALTY

/67
$269,900

Under Contract
- 3 Beds
- 2 Baths
- 1,534 Sq Ft
106 Saint Kitts Cir, Winter Haven, FL 33884

Under contract-accepting backup offers. THIS WELL-KEPT HOME LOCATED ON A CUL-DE-SAC HAS A HUGE (ONE THIRD ACRE) LOT. THIS IS A SPLIT BEDROOM PLAN WITH THREE BEDROOMS AND TWO BATHS. KITCHEN AND BOTH BATHS HAVE BEEN UPDATED. THE PRIMARY BEDROOM HAS AN UPDATED EN SUITE WITH WALK-IN CLOSET. THE GREAT ROOM IS LARGE AND HAS A VAULTED CEILING. THERE IS AN EAT-IN AREA IN THE KITCHEN AS WELL AS A DINING

Brenda J. Quinn

QUINN & COMPANY REALTORS, LLC

106 Saint Kitts Cir, Winter Haven, FL 33884
/3
$1,550 Per Month
- 3 Beds
- 2 Baths
- 1,242 Sq Ft
- Condo for Rent
2007 9th St NE, Winter Haven, FL 33881

Welcome to your perfect rental in Winter Haven, Florida! This charming property offers a comfortable living space in a vibrant community, just minutes away from delightful dining options and major department stores. The Winter Haven Hospital is also conveniently located just six minutes from your doorstep, ensuring your peace of mind. Key property features include central heating and

2007 9th St NE, Winter Haven, FL 33881
/35
$265,990

Sold Apr 03, 2026

4517 Faith Dr, Lake Wales, FL 33859
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 5% Below List Price
- $200/SF
- 44 Days On Market
Current Estimated Value $263,781

D.R. Horton Annabelle Estates

4517 Faith Dr, Lake Wales, FL 33859

/52
Not Listed For Sale

6332 Grove Pointe Dr SE, Winter Haven, FL 33884
- 2 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1984
6332 Grove Pointe Dr SE, Winter Haven, FL 33884

Last Sold Summary
- 91 Days On Market
Last Listing Agent Nicole Ash BHHS FLORIDA PROPERTIES GROUP

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Winter Haven, FL Homes

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