Southeast Winterhaven Homes

/79
$299,900
- 3 Beds
- 2 Baths
- 1,556 Sq Ft
4294 Berwick Dr, Lake Wales, FL 33859

Begin the next exciting chapter of your life in Lake Ashton, Central Florida's premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with a den enjoys a desirable location overlooking the Lake Ashton East Golf Course. From the moment you arrive, you'll appreciate the care and quality found throughout. The updated kitchen features newer

Brad Kirwan

GLOBAL LIFESTYLE LLC

4294 Berwick Dr, Lake Wales, FL 33859
/26
Starting at $1,269 Per Month
- 1 - 3 Beds
1015 Lake Forest Blvd, Winter Haven, FL 33884

Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer.At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and

The Waverly at Winter Haven

1015 Lake Forest Blvd, Winter Haven, FL 33884
/2
$260,000

Sold Mar 23, 2026

565 Terranova Cir, Winter Haven, FL 33884
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
- Built 2003
Last Sold Summary
- 7% Below List Price
- $180/SF
- 113 Days On Market
Current Estimated Value $260,237

Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

565 Terranova Cir, Winter Haven, FL 33884

/2
Est $337,984

Not Listed For Sale

3507 Costello Cir, Winter Haven, FL 33884
- 5 Beds
- 3 Baths
- 2,447 Sq Ft
- Built 2025
3507 Costello Cir, Winter Haven, FL 33884

Last Sold Summary
- 17 Days On Market
Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

/86
$720,000
- 4 Beds
- 4 Baths
- 2,961 Sq Ft
237 Mclean Point, Winter Haven, FL 33884

MUST SEE! Beautiful Custom-Built Home in the Renaissance Subdivision! Welcome to your dream home nestled in the serene community of Renaissance in lovely Winter Haven, Florida. This stunning 4-bedroom, 4-bathroom model home offers the perfect blend of privacy, convenience, and resort-style living, complete with a spectacular pool area. Key Features: • Prime Location: Enjoy boat access to Lake

Luis Perez Garcia

EXP Realty LLC

237 Mclean Point, Winter Haven, FL 33884
/15
$1,200 Per Month
- 2 Beds
- 2 Baths
- 930 Sq Ft
- Condo for Rent
8402 Waterview Way Unit 8402, Winter Haven, FL 33884

2 bedroom 2 bath ground floor condo located in gated Winterset on the Shores of Lake Winterset.Enjoy a community pool, club house, tennis courts and community boat ramp.Partially furnished or furniture can be removed.

Steven Smith, PA

LOCKHART & ASSOCIATES INC

8402 Waterview Way Unit 8402, Winter Haven, FL 33884
/2
$280,000

Sold Mar 05, 2026

6654 Crescent Loop, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 1,820 Sq Ft
- Built 2014
Last Sold Summary
- 7% Below List Price
- $154/SF
- 138 Days On Market
Current Estimated Value $287,322

Last Listing Agent Cindy Thornton AGILE GROUP REALTY

6654 Crescent Loop, Winter Haven, FL 33884

/17
Not Listed For Sale

5006 Abigail Dr, Winter Haven, FL 33859
- 4 Beds
- 2 Baths
- 1,938 Sq Ft
- Built 2025
5006 Abigail Dr, Winter Haven, FL 33859

Last Sold Summary
- 30 Days On Market

/39
$295,000

$23K PRICE DROP
- 4 Beds
- 2 Baths
- 1,680 Sq Ft
1799 Carnostie Rd, Winter Haven, FL 33884

PRICE LOWERED JUST FOR YOU! Move right into this pristine, turnkey oasis. Built in 2022, this beautifully maintained home in the peaceful Villa Mar community features a bright, open floor plan and four spacious bedrooms. The modern kitchen flows effortlessly into the main living areas, which boast durable ceramic tile flooring for a sleek, low-maintenance finish. Relax on your private,

Twanna Dewdney

LA ROSA REALTY PRESTIGE

1799 Carnostie Rd, Winter Haven, FL 33884
/22
Starting at $1,441

Total Monthly Price
- 1 - 2 Beds
3110 Gowan Dr, Winter Haven, FL 33884

Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness

Prose Cypress Pointe

3110 Gowan Dr, Winter Haven, FL 33884
/21
$299,490

Sold May 28, 2026

6216 Botticella Blvd, Winter Haven, FL 33884
- 5 Beds
- 2 Baths
- 2,326 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $129/SF
- 7 Days On Market
Lennar Villa Mar

6216 Botticella Blvd, Winter Haven, FL 33884

/2
Est $305,539

Not Listed For Sale

308 Corso Loop, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 1,828 Sq Ft
- Built 2024
308 Corso Loop, Winter Haven, FL 33884

Last Sold Summary
- 241 Days On Market
Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

/100
$224,900

$5K PRICE DROP Pending
- 2 Beds
- 2 Baths
- 1,109 Sq Ft
4201 Berwick Dr, Lake Wales, FL 33859

THE CDD BOND IS FULLY PAID on this unique one-owner Marbella floor plan home. As one arrives and tours this home, the pride of ownership is evident. This 2-bedroom, 2-bath open-floor-plan home is located on a large corner lot at the end of a dead-end street. Curb appeal comes from the paver drive and walk, quality plantings, and well-maintained landscaping beds. The lawn and landscaping are

Michael Krigelski

A+ REALTY LLC

4201 Berwick Dr, Lake Wales, FL 33859
/44
$1,400 Per Month
- 2 Beds
- 2 Baths
- 930 Sq Ft
- Condo for Rent
8302 Waterview Way, Winter Haven, FL 33884

Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer &

CarLee Marchetti

STAR REALTY OF WINTER HAVEN

8302 Waterview Way, Winter Haven, FL 33884
/16
$272,490

Sold Apr 08, 2026

2154 Chris Dr, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 1,880 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 5% Below List Price
- $145/SF
- 38 Days On Market
Current Estimated Value $275,224

2154 Chris Dr, Winter Haven, FL 33884

/17
Est $220,855

Not Listed For Sale

3004 Caneel St, Winter Haven, FL 33884
- 2 Beds
- 2 Baths
- 1,521 Sq Ft
- Built 2018
3004 Caneel St, Winter Haven, FL 33884

Last Sold Summary
- 47 Days On Market
Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP

/62
$359,000

$16K PRICE DROP
- 3 Beds
- 2 Baths
- 1,914 Sq Ft
131 Ruby Lake Dr, Winter Haven, FL 33884

Virtually Staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest.Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A

CarLee Marchetti

STAR REALTY OF WINTER HAVEN

131 Ruby Lake Dr, Winter Haven, FL 33884
/54
Starting at $1,455 Per Month
- 1 - 3 Beds
1015 Mahaffey Rd, Winter Haven, FL 33884

A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

The Carlton at Lake Dexter

1015 Mahaffey Rd, Winter Haven, FL 33884
/28
$279,490

Sold Sep 24, 2025

4144 Giorgio Dr, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 1,665 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $168/SF
- 13 Days On Market
D.R. Horton VillaMar

4144 Giorgio Dr, Winter Haven, FL 33884

/2
Est $418,637

Not Listed For Sale

2973 Dayton Dr, Winter Haven, FL 33884
- 3 Beds
- 3 Baths
- 2,659 Sq Ft
- Built 2018
2973 Dayton Dr, Winter Haven, FL 33884

Last Sold Summary
- 99 Days On Market
Last Listing Agent Assunta Zaghet STATION SQUARE REALTY LLC

/40
$235,000

$20K PRICE DROP Under Contract
- 2 Beds
- 2 Baths
- 1,118 Sq Ft
3363 Livingston Way, Winter Haven, FL 33884

Under contract-accepting backup offers. Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years

Beena Kokeram

VREELAND REAL ESTATE LLC

3363 Livingston Way, Winter Haven, FL 33884
/6
$1,300 Per Month
- 1 Bed
- 1 Bath
- 2,109 Sq Ft
- House for Rent
1453 Austin St Unit B, Winter Haven, FL 33884

Charming PRIVATE ENTRANCE 1 - NEW bedroom apartment available for rent! Welcome to your new home! This beautiful apartment with living room, kitchen, 1 bathroom and 1 bedroom. Located in a quiet and friendly neighborhood in Eagle Lake, this space offers all the comfort and convenience you need. As for the location, it is close to shopping centers, restaurants, parks and public transportation.

Isabel Melin Mora

MELIN REALTY LLC

1453 Austin St Unit B, Winter Haven, FL 33884
/2
$249,490

Sold May 14, 2026

6473 Domizio Dr, Winter Haven, FL 33884
- 4 Beds
- 2.5 Baths
- 1,880 Sq Ft
- Built 2026
Last Sold Summary
- 7% Below List Price
- $133/SF
- 5 Days On Market
Current Estimated Value $249,802

Last Listing Agent Ben Goldstein LENNAR REALTY

6473 Domizio Dr, Winter Haven, FL 33884

/2
Not Listed For Sale

2735 Nursery Rd, Lake Wales, FL 33859
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1981
2735 Nursery Rd, Lake Wales, FL 33859

Last Sold Summary
- 42 Days On Market
Last Listing Agent Craig Burke CRAIG BURKE REAL ESTATE GROUP, LLC

/32
$399,900

$15K PRICE DROP
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
357 Ruby Lake Loop, Winter Haven, FL 33884

Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed 3-bedroom, 2-bath Cassidy “Ox” floor plan perfectly balances elegance and everyday comfort. Step inside to discover a spacious layout featuring formal living and dining rooms, along with a generous family room—ideal for both entertaining and relaxed living. The updated kitchen is truly the heart of the home,

Steve Lockhart

LOCKHART & ASSOCIATES INC

357 Ruby Lake Loop, Winter Haven, FL 33884
/56
Starting at $1,430 Per Month
- 1 - 3 Beds
3005 Willow Glen Cir, Lake Wales, FL 33859

Set Your Own Pace at Alera at Hunters GlenDiscover a modern vision for upscale apartment living at Alera at Hunters Glen—where style meets simplicity in Lake Wales, FL. Embrace the freedom of a lock-and-leave lifestyle in a sophisticated community designed for those who live life on their own terms. With a seamless blend of contemporary design and refined elegance, Alera is where your

Alera at Hunters Glen

3005 Willow Glen Cir, Lake Wales, FL 33859
/34
$329,990

Sold Apr 30, 2026

4422 Blackwell Ave, Lake Wales, FL 33859
- 5 Beds
- 3 Baths
- 2,077 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 7% Below List Price
- $159/SF
- 71 Days On Market
Current Estimated Value $332,000

D.R. Horton Annabelle Estates

4422 Blackwell Ave, Lake Wales, FL 33859

/2
Est $280,714

Not Listed For Sale

256 Ruby Lake Ln, Winter Haven, FL 33884
256 Ruby Lake Ln, Winter Haven, FL 33884

Last Sold Summary
- 15 Days On Market
Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

/33
$280,000

$5K PRICE DROP
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
140 Morning Glory Cir, Winter Haven, FL 33884

PRICE DROP OF $5,000! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly desirable Morningside at Winterset, a 24/7 gated community offering comfort, security, and resort-style living. This spacious property features an inviting foyer that opens into a bright great room and dining area, enhanced by elegant plant shelves and sliding glass doors leading to a large

Fabiana Cuevas

NEW HEIGHTS REALTY GROUP

140 Morning Glory Cir, Winter Haven, FL 33884
/26
$2,175 Per Month
- 4 Beds
- 2.5 Baths
- 1,880 Sq Ft
- House for Rent
6220 Botticella Blvd, Winter Haven, FL 33884

Brand-new two-story home located in the sought-after Villamar community of Winter Haven. This residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and a 2-car garage with approximately 1,880 square feet of living space.The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating a functional layout for everyday living and entertaining. The kitchen

Maritza Monzon

INTERNATIONAL EXECUTIVE REALTY

6220 Botticella Blvd, Winter Haven, FL 33884
/17
$319,950

Sold Aug 04, 2026

5135 Kinsley Dr, Lake Wales, FL 33859
- 4 Beds
- 2 Baths
- 1,910 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $168/SF
- 13 Days On Market
Richmond American Annabelle Estates

5135 Kinsley Dr, Lake Wales, FL 33859

/46
Est $233,437

Not Listed For Sale

3389 Raleigh Dr, Winter Haven, FL 33884
- 2 Beds
- 2 Baths
- 1,295 Sq Ft
- Built 2017
3389 Raleigh Dr, Winter Haven, FL 33884

Last Sold Summary
- 40 Days On Market
Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

/48
$300,000
- 3 Beds
- 2 Baths
- 1,898 Sq Ft
4465 Strathmore Dr, Lake Wales, FL 33859

Virtually Staged. Discover easy Florida living in this beautifully maintained home in Lake Ashton featuring the popular expanded Hemingway floor plan with 2 bedrooms, 2 baths, and a versatile den perfect for a home office, hobby room, or guest space. Best of all, the CDD bond debt is fully paid. Pride of ownership shines throughout, from the landscaping and paver driveway to the move-in ready

Jared Rutherford

KELLER WILLIAMS TAMPA PROPERTIES

4465 Strathmore Dr, Lake Wales, FL 33859
/65
Starting at $959 Per Month
- Studio - 3 Beds
7676 Carlton Arms Blvd, Winter Haven, FL 33884

Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.

Carlton Arms Of Winter Haven

7676 Carlton Arms Blvd, Winter Haven, FL 33884
/12
$265,000

Sold Sep 23, 2025

4981 Kaia Ave, Winter Haven, FL 33884
- 3 Beds
- 2 Baths
- 1,269 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $209/SF
- 145 Days On Market
Current Estimated Value $237,410

Meritage Homes VillaMar - Classic Series

4981 Kaia Ave, Winter Haven, FL 33884

/2
Est $373,627

Not Listed For Sale

359 Mandolin Ln, Winter Haven, FL 33884
- 4 Beds
- 2 Baths
- 2,356 Sq Ft
- Built 2009
359 Mandolin Ln, Winter Haven, FL 33884

Last Sold Summary
- 60 Days On Market
Last Listing Agent Renee Butler BROKERS REALTY OF CENTRAL FLOR

/32
$1,200,000
- 3 Beds
- 2 Baths
- 2,129 Sq Ft
4401 Chambliss Rd, Winter Haven, FL 33884

Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future

Cyleste Goodson

FLORIDA REAL ESTATE COMPANY

4401 Chambliss Rd, Winter Haven, FL 33884
/47
$1,700 Per Month
- 2 Beds
- 2 Baths
- 1,078 Sq Ft
- Condo for Rent
715 Magnolia Place Unit 715, Winter Haven, FL 33884

Gorgeous sunset views over Lake Winterset... this is the kind of rental you don’t come across often. Located in the gated Winterset community, this well-maintained 2-bedroom, 2-bath upstairs condo with a private one-car garage offers easy, low-maintenance lakeview living. Inside, you’ll find an open and airy layout with vaulted ceilings, skylights, and large sliding glass doors that bring in tons

CarLee Marchetti

STAR REALTY OF WINTER HAVEN

715 Magnolia Place Unit 715, Winter Haven, FL 33884
/2
$369,999

Sold Oct 20, 2025

5465 San Pietro Dr, Winter Haven, FL 33884
- 4 Beds
- 3 Baths
- 2,292 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $161/SF
- 10 Days On Market
Current Estimated Value $346,763

Casa Fresca Homes Villa Mar

5465 San Pietro Dr, Winter Haven, FL 33884

/2
Est $290,587

Not Listed For Sale

4723 Mandolin Loop, Winter Haven, FL 33884
- 4 Beds
- 2.5 Baths
- 1,860 Sq Ft
- Built 2011
4723 Mandolin Loop, Winter Haven, FL 33884

Last Sold Summary
- 24 Days On Market
Last Listing Agent Lesley Guarino CITRAVEST MANAGEMENT LLC

Showing Results 1 - 40, Page 1 of 18

Florida Polk County Winter Haven

Learn more about living in Southeast Winterhaven

Home Prices in Southeast Winterhaven, FL

The median home sale price in Southeast Winterhaven, Winter Haven is $299,000, down 2% year-over-year. Homes in Southeast Winterhaven sell in 87 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $299,000	Median Single Family Sale Price $301,552
Median Townhouse Sale Price $243,990	Median 2 Bedroom Sale Price $235,000
Median 1 Bedroom Sale Price $170,000	Average Price Per Sq Ft $166
Number of Homes for Sale 10,001	Last 12 months Home Sales 1,172
Months of Supply 3.60	Median List Price $312,740
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change -2%

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Southeast Winterhaven Homes

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Home Prices in Southeast Winterhaven, FL

Home Price Trends