3,988

Southwest Winter Haven Homes

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  • /21

    $365,000

    • 5 Beds
    • 3 Baths
    • 2,523 Sq Ft

    1404 Axel Cir, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Beautifully crafted, newly built home offering over 2,500 square feet of modern Florida living in the peaceful PINNACLE POINT neighborhood of Winter Haven, FL. This spacious 5-bedroom, 3-bathroom home features a thoughtfully designed layout that perfectly balances comfort, style, and functionality. Just off the foyer, a private guest suite with its

    Agent Photo

    Carlos DeJesus

    EXIT REALTY 4CORNERS

    (863) 204-5093

    1404 Axel Cir, Winter Haven, FL 33880
  • /35

    $1,099 - $1,549 per month

    Haven at Lake Deer

    Studio - 2 Beds

    350 24th St NW, Winter Haven, FL 33880

    Haven at Lake Deer is the retreat you've been looking for in Winter Haven, FL. Our lakeside community features studio, one and two bedroom homes complete with patios, wood-style flooring, and upgraded kitchens. What's more, as a member of the community you'll also have access to our sparkling swimming pools and a 24-hour gym. At Haven at Lake Deer, you're guaranteed to find a place to live with a

    350 24th St NW, Winter Haven, FL 33880
  • /2

    $164,500 Sold Sep 15, 2025

    • 1,456 Sq Ft
    • $113/SF
    • 43 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1989

    451 Village Cir SW, Winter Haven, FL 33880

    Well-maintained 2 bed, 2 bath home with stylish luxury vinyl plank flooring throughout. Enjoy a spacious screened-in lanai, two large storage sheds, and a $55/mo HOA that includes access to a sparkling pool and amenities. You own the land. Trailer/RV storage available (limited, first-come). Ideal for full-time living or a seasonal retreat. Community is perfectly located in Winter Haven Florida

    Carolyn Christian DALTON WADE INC

    451 Village Cir SW, Winter Haven, FL 33880
    • /40

      Est $274,980 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,531 Sq Ft

      1436 Wallace Manor Pass, Winter Haven, FL 33880

      1436 Wallace Manor Pass, Winter Haven, FL 33880
  • /10

    $199,900

    • 3 Beds
    • 1 Bath
    • 1,210 Sq Ft

    118 Orange Ave, Winter Haven, FL 33880

    BACK ON THE MARKET! INVESTORS SPECIAL! HANDYMAN SPECIAL! This cozy home is located just minutes from downtown Winter Haven. This cute home boast a 3 bedroom, 1 bath in the main house with screened in patio in the rear and two carports for parking currently rented under market rate. An additional highlight of this home is the de-attached 1br/1ba or mother-in-law suite, which includes a separate

    Agent Photo

    Sam Pergerson

    COLDWELL BANKER REALTY

    (863) 900-8957

    118 Orange Ave, Winter Haven, FL 33880
  • /7

    $1,395 per month

    • 1 Bed
    • 1 Bath
    • 360 Sq Ft
    • Townhouse for Rent

    320 Spirit Landings Cir, Winter Haven, FL 33880

    Make yourself at home in this charming 1 bed/1 bath unit located inside a quiet residential home. This fully furnished space is thoughtfully set up for comfortable, stress-free living! The unit features a cozy bedroom, a welcoming living area, and a well-equipped space perfect for everyday convenience. You’ll love the peaceful setting while still being close to shopping, dining, and local

    Kellie Hicks LOCKHART & ASSOCIATES INC

    320 Spirit Landings Cir, Winter Haven, FL 33880
  • /2

    $360,000 Sold Sep 12, 2025

    • 2,206 Sq Ft
    • $163/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    818 Summer Glen Dr, Winter Haven, FL 33880

    Stunning Fully Remodeled Pool Home – Move-In Ready!Welcome to this beautifully renovated property where every detail has been thoughtfully upgraded to provide the perfect balance of modern design, comfort, and functionality. This home is truly turn-key, offering peace of mind with a full remodel from top to bottom.As you arrive, you’ll immediately notice the brand-new roof and

    Robert McDugald FUTURE HOME REALTY INC

    818 Summer Glen Dr, Winter Haven, FL 33880
    • /16

      Est $236,295 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      108 4th St NE, Winter Haven, FL 33881

      108 4th St NE, Winter Haven, FL 33881
  • /43

    $375,000

    • 4 Beds
    • 3 Baths
    • 1,772 Sq Ft

    317 26th St SW, Winter Haven, FL 33880

    Welcome to this spacious and inviting 4-bedroom, 3 full-bath home, perfectly situated on more than one acre of land. Offering the best of comfort and privacy, this property is ideal for families, entertainers, or anyone looking to enjoy peaceful living with plenty of room to grow.Inside, you’ll find an open and functional layout with generously sized bedrooms, a bright kitchen, and

    Edward Tejada

    R&J REALTY AND PROPERTY MANAGEMENT LLC

    (863) 323-8452

    317 26th St SW, Winter Haven, FL 33880
  • /35

    $1,500 per month

    • 3 Beds
    • 1.5 Baths
    • 2,030 Sq Ft
    • Condo for Rent

    82 Coleman Rd, Winter Haven, FL 33880

    82 Coleman Rd, Winter Haven, FL 33880
  • /2

    $361,490 Sold Sep 12, 2025

    • 2,372 Sq Ft
    • $152/SF
    • 276 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2024

    2630 Sage Valley Way, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony on Lake Eloise is the perfect community to call home with its beautiful Florida lifestyle and amenities. This community boasts stunning home sites. You'll enjoy the sparkling local lakes practically i

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    2630 Sage Valley Way, Winter Haven, FL 33884
    • /20

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,012 Sq Ft

      124 6th Eloise St, Eloise, FL 33880

      124 6th Eloise St, Eloise, FL 33880
  • /37

    $410,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,534 Sq Ft

    5790 Crystal Beach Rd, Winter Haven, FL 33880

    Under contract-accepting backup offers. Welcome to your brand-new 2024 build on the serene shores of Eagle Lake! This thoughtfully designed 3-bedroom, 2-bathroom home offers modern living with stunning lakefront views and no HOA. Step into the inviting foyer, which opens to two guest bedrooms and a beautifully appointed kitchen. The kitchen is the heart of the home, featuring elegant quartz

    Agent Photo

    Cheyanne MacNeill

    THE AGENCY ORLANDO

    (863) 334-3328

    5790 Crystal Beach Rd, Winter Haven, FL 33880
  • /13

    $1,759 per month

    • 3 Beds
    • 2 Baths
    • 1,654 Sq Ft
    • House for Rent

    289 St Georges Cir, Eagle Lake, FL 33839

    Take a look at this beautiful home, Clean and Move-In Ready, split plan featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1672 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance

    Cathy Behe TAH FLORIDA LLC

    289 St Georges Cir, Eagle Lake, FL 33839
  • /2

    $270,000 Sold Aug 29, 2025

    • 1,420 Sq Ft
    • $190/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2007

    1533 Wallace Manor Ave, Winter Haven, FL 33880

    Welcome to this beautiful 3-bedroom, 2-bath home nestled on a spacious corner lot at the end of a quiet cul-de-sac! Step inside to discover stunning tile flooring throughout and soaring high ceilings that create an open and airy atmosphere. The updated kitchen features modern appliances, perfect for everyday living and entertaining. Enjoy peace of mind with a brand-new roof scheduled to be

    Darren Moreno KELLER WILLIAMS REALTY SMART

    1533 Wallace Manor Ave, Winter Haven, FL 33880
    • /37

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,314 Sq Ft

      503 Village Cir SW, Winter Haven, FL 33880

      503 Village Cir SW, Winter Haven, FL 33880
  • /36

    $245,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    728 Waterbridge Dr, Winter Haven, FL 33880

    Under contract-accepting backup offers. Perfect starter home in this quiet family friendly neighborhood of Whispering Lake. This 2 story home is Vacant and Move in ready and has all the conveniences of winter haven at your fingertips with close access to the US-17 and Polk Parkway. Home has 3 bedroom, 2 1/2 baths with a very low HOA fee & is conveniently located close to shopping, restaurants &

    Gregory Baker LIVE FLORIDA REALTY

    728 Waterbridge Dr, Winter Haven, FL 33880
  • /35

    $1,500 per month

    • 3 Beds
    • 1.5 Baths
    • 2,030 Sq Ft
    • Condo for Rent

    82 Coleman Rd, Winter Haven, FL 33880

    82 Coleman Rd, Winter Haven, FL 33880
  • /2

    $249,900 Sold Aug 25, 2025

    • 1,544 Sq Ft
    • $162/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    2424 Bates Ave SW, Winter Haven, FL 33880

    Welcome to 2424 Bates Ave – a well-maintained 3-bedroom, 2-bathroom home featuring a versatile mother-in-law suite, perfect for extended family, guests, or rental income potential. Nestled in a peaceful neighborhood just minutes from Winter Haven’s famous Chain of Lakes, this property offers both comfort and convenience.Inside, you’ll find a spacious and functional layout, a bright

    David Fleming BHHS FLORIDA PROPERTIES GROUP

    2424 Bates Ave SW, Winter Haven, FL 33880
    • /34

      Est $328,824 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,190 Sq Ft

      868 Buccaneer Blvd, Winter Haven, FL 33880

      868 Buccaneer Blvd, Winter Haven, FL 33880
  • /32

    $267,000

    • 3 Beds
    • 2 Baths
    • 1,718 Sq Ft

    269 Saint Georges Cir, Eagle Lake, FL 33839

    One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the heart of Eagle Lake, Florida. With 1,718 square feet of thoughtfully designed living space, this home offers a perfect combination of comfort, style, and functionality.The open floor plan seamlessly

    Kathi Zerilli REDFIN CORPORATION

    269 Saint Georges Cir, Eagle Lake, FL 33839
  • /11

    $1,750 per month

    • 4 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • House for Rent

    2460 Avenue E SW, Winter Haven, FL 33880

    Welcome to 2460 Avenue E SW in Winter Haven! A great 4 bedroom 2 bath home in a centralized location with close proximity to parks, shopping, medical facilities, and entertainment. Available for viewing 8/31/25. available to move in 8/31/25.

    Anya Kovalenko LPT REALTY, LLC

    2460 Avenue E SW, Winter Haven, FL 33880
  • /2

    $265,000 Sold Aug 19, 2025

    • 1,742 Sq Ft
    • $152/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1956

    2410 Avenue B NW, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Looking for your new home on a large lot with no HOA? Schedule your showing today! Cooperative Seller is willing to contribute towards closing costs or a rate buy down to help buyers. Don't miss out on this move in ready, renovated home in Winter Haven. Perfectly situated in a treelined neighborhood close to several lakes with public access, this 4

    MELANIE CARNEY JASON MITCHELL REAL ESTATE FLO

    2410 Avenue B NW, Winter Haven, FL 33880
    • /28

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,075 Sq Ft

      Unlisted Address

      Unlisted Address
  • /61

    $395,000

    • 4 Beds
    • 3 Baths
    • 2,226 Sq Ft

    230 Cove at Eagle Lake Cir, Eagle Lake, FL 33839

    MOTIVATED OWNERS! Welcome to 230 Cove at Eagle Lake Circle — a beautifully maintained 4-bedroom, 3-bathroom home built in 2022 by Southern Homes, located on a spacious 0.34-acre corner lot in the desirable gated community of The Cove at Eagle Lake. ••••SELLERS ARE OPEN TO CREATIVE FINANCING OR ASSUMABLE FHA MORTGAGE AT 3.5%. Several options available. ••••HOME FEATURES: • Open Layout for

    April Spaulding LPT REALTY, LLC

    230 Cove at Eagle Lake Cir, Eagle Lake, FL 33839
  • /8

    $750 per month

    • 3 Beds
    • 2 Baths
    • 1,184 Sq Ft
    • House for Rent

    1806 Wallace Manor Ln, Winter Haven, FL 33880

    Spacious, cozy and clean private master bedroom in a quiet neighborhood in WinterHaven. Room includes closet, dresser, 2 nightstands and queen bed (fully furnished). Room has wood flooring and bathroom is connected to bedroom. Bathroom private, toilet has a fully functional bidet installed. Comes with access to amenities including washer/dryer access, kitchenware (pots, pans, blender, cups,

    1806 Wallace Manor Ln, Winter Haven, FL 33880
  • /2

    $300,000 Sold Aug 18, 2025

    • 1,851 Sq Ft
    • $162/SF
    • 137 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2020

    301 St Georges Cir, Eagle Lake, FL 33839

    Don’t miss the chance to see this beautiful 4-bedroom, 2-bath home, ideally situated on a corner lot that combines both comfort and style. Offering 1,841 sqft of open-concept living space, this home features newly installed wood-like flooring throughout the living room, dining room, and three of the four bedrooms, creating a warm and welcoming atmosphere perfect for family living.The

    Jenna Henderson LIVE FLORIDA REALTY

    301 St Georges Cir, Eagle Lake, FL 33839
    • /49

      Est $305,541 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,685 Sq Ft

      996 Buccaneer Blvd, Winter Haven, FL 33880

      996 Buccaneer Blvd, Winter Haven, FL 33880
  • /40

    $430,000

    • 5 Beds
    • 3 Baths
    • 3,022 Sq Ft

    1396 Axel Cir, Winter Haven, FL 33880

    Seller Motivated! Discover 1396 Axel Cir, a beautifully upgraded 5-bedroom, 3-bath home in the sought-after Pinnacle Point community of Winter Haven. From the moment you walk in, you’ll be greeted by a spacious open living room that flows seamlessly into a large kitchen with sleek countertops, modern appliances, and a generous island. Perfect for family gatherings or entertaining guests.

    Shani Carty KELLER WILLIAMS REALTY AT THE PARKS

    1396 Axel Cir, Winter Haven, FL 33880
  • /16

    $1,705 per month

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • House for Rent

    956 Sunshine Way SW, Winter Haven, FL 33880

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    956 Sunshine Way SW, Winter Haven, FL 33880
  • /2

    $315,000 Sold Aug 14, 2025

    • 2,348 Sq Ft
    • $134/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2015

    1156 Normandy Heights Cir, Winter Haven, FL 33880

    Spacious 4-Bedroom Home with Bonus Room in a Prime Location! Welcome to this beautifully maintained 4-bedroom, 2-bathroom home with a large bonus room—perfect for a home office, playroom, or guest space. Located in an established and highly desirable community, this property offers the perfect blend of comfort, convenience, and space. Step inside to discover an open floor plan with soaring high

    Darren Moreno KELLER WILLIAMS REALTY SMART

    1156 Normandy Heights Cir, Winter Haven, FL 33880
    • /42

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,950 Sq Ft

      120 Pangola Dr, Winter Haven, FL 33880

      120 Pangola Dr, Winter Haven, FL 33880
  • /31

    $390,000

    • 4 Beds
    • 3 Baths
    • 2,447 Sq Ft

    804 Channing St, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Nestled amid lush greenery and meticulous landscaping, this 4-bedroom, 3-bathroom dream home offers numerous upgrades and over 2400 square feet of living space. Featuring a spacious two-car garage and thoughtful details throughout, this residence is designed for both everyday living and entertaining. Step inside to discover an inviting, open-concept

    Shanta Navarro KELLER WILLIAMS ADVANTAGE III

    804 Channing St, Winter Haven, FL 33880
  • /18

    $1,100 - $1,385 per month

    The Landings Apartment Homes

    1 - 2 Beds

    102 Landings Way, Winter Haven, FL 33880

    Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl

    102 Landings Way, Winter Haven, FL 33880
  • /2

    $274,000 Sold Aug 13, 2025

    • 1,768 Sq Ft
    • $155/SF
    • 126 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2018

    325 St Georges Cir, Eagle Lake, FL 33839

    Charm and curb appeal abound for this Eagle Lake home! Step inside into the inviting foyer and into the well-appointed living room, which sits at the center of the home. The kitchen features a four-piece appliance package, hard surface countertops, a pantry, and ample storage. Rounding out this ranch style floorplan is the home's laundry room, the primary suite, and three secondary bedrooms.

    Blake Keathley EVERYSTATE INC.

    325 St Georges Cir, Eagle Lake, FL 33839
    • /47

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,560 Sq Ft

      421 Village Cir SW, Winter Haven, FL 33880

      421 Village Cir SW, Winter Haven, FL 33880
  • /21

    $321,000

    • 3 Beds
    • 2 Baths
    • 1,859 Sq Ft

    1031 Normandy Heights Cir, Winter Haven, FL 33880

    Charm and curb appeal abound for this Winter Haven home! Step inside into the inviting foyer and into the well-appointed living room, positioned at the center of the home. The kitchen boasts stainless steel appliances, hard surface countertops, and ample storage. This split, ranch-style floorplan offers the primary suite on one side of the home and two secondary bedrooms on the other along with a

    Blake Keathley EVERYSTATE INC.

    1031 Normandy Heights Cir, Winter Haven, FL 33880
  • /16

    $1,900 per month

    • 4 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • House for Rent

    648 Lorient Dr, Eagle Lake, FL 33839

    Charming 2020 built home with 4 bedrooms and 2 bathrooms is move in ready! Open floor plan with living and dining areas open to kitchen. Kitchen features stainless steel appliances, island with bar counter, and closet pantry space. Primary bedroom with en-suite bathroom with double sink vanity and large glass enclosed shower stall. 3 additional bedrooms share a hall bathroom with a tub/shower

    Mary Rose Bianchi FLORIDA REALTY RESULTS LLC

    648 Lorient Dr, Eagle Lake, FL 33839
  • /2

    $302,500 Sold Aug 12, 2025

    • 1,768 Sq Ft
    • $171/SF
    • 62 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2018

    305 St Georges Cir, Eagle Lake, FL 33839

    $10,000 Price Reduction***This stunning, professionally designed and decorated Former Model Home is now available for sale in the sought-after Winter Haven area. The Parker is one of Highland Homes top-selling Florida home plans and offers a bright, open living space ideal for modern living. Key Features: 1. Open Concept Living: The spacious gathering room, dining cafe, and kitchen with a

    LaChelle Olivet PALERMO REAL ESTATE PROF. INC.

    305 St Georges Cir, Eagle Lake, FL 33839
    • /59

      Est $167,793 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 878 Sq Ft

      2938 Avenue G NW, Winter Haven, FL 33880

      2938 Avenue G NW, Winter Haven, FL 33880

Showing Results 1 - 40, Page 1 of 18

Home Trends in Southwest Winter Haven, FL

Housing Trends

Median Sale Price
$273,000
Median Single Family Sale Price
$275,000
Average Price Per Sq Ft
$185
Number of Homes for Sale
47
Last 12 months Home Sales
121
Months of Supply
4.70
Median List Price
$299,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-3%
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