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Winter Haven, FL Short Sale Homes for Sale

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  • /49

    $300,000

    • 4 Beds
    • 2 Baths
    • 2,223 Sq Ft

    31 Lake Link Cir SE, Winter Haven, FL 33884

    Short Sale. Lender has provided preliminary net guidance based on a recent appraisal. Offers will be reviewed in accordance with lender and VA guidelines. Buyer is encouraged to submit highest and best offer. Final approval subject to lender review.This is the kind of home that just feels right the moment you pull in. Set on an oversized .29-acre lot with no rear neighbors and peaceful

    Agent Photo

    Katie Sweet

    WATSON REALTY CORP.

    (863) 265-5379

    31 Lake Link Cir SE, Winter Haven, FL 33884
  • /15

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    BANKRUPTCY SHORT SALE! Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space.

    Agent Photo

    Jon McCall PA

    Dalton Wade Inc

    (863) 250-1507

    3180 Country Club Cir, Winter Haven, FL 33881
  • /24

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    4612 Reynosa Dr SW, Winter Haven, FL 33880

    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 the back patio into the living room,

    Agent Photo

    Trent Shackelford

    LPT REALTY LLC

    (863) 417-4589

    4612 Reynosa Dr SW, Winter Haven, FL 33880
  • /20

    $195,000

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft

    1109 5th St SW, Winter Haven, FL 33880

    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 home features a spacious living area, an

    Agent Photo

    Carlos DeJesus

    EXIT REALTY 4CORNERS

    (863) 267-9625

    1109 5th St SW, Winter Haven, FL 33880
  • /29

    $389,900

    • 5 Beds
    • 3 Baths
    • 1,703 Sq Ft

    1501 7th St SE, Winter Haven, FL 33880

    Short Sale. Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT,2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shakercabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and

    Laura Auten ELEVATE REALTY LLC

    1501 7th St SE, Winter Haven, FL 33880
  • /13

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft

    3098 Laurel Oak Ln, Winter Haven, FL 33884

    Short Sale. Located in the Villamar community of Winter Haven, this 3-bedroom, 2-bath home built in 2023 offers modern construction with a two-car garage and a functional layout designed for everyday living. The home features open living spaces, well-sized bedrooms, and contemporary finishes typical of newer construction. The property appears to require cosmetic refreshing, presenting an

    Jonathon, PA McLeod KELLER WILLIAMS ELITE REALTY

    3098 Laurel Oak Ln, Winter Haven, FL 33884
  • /21

    $120,000

    • 2 Beds
    • 2 Baths
    • 1,252 Sq Ft

    404 Country Ln NE Unit 404, Winter Haven, FL 33881

    Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary

    Casandra Vann KELLER WILLIAMS REALTY SMART

    404 Country Ln NE Unit 404, Winter Haven, FL 33881
  • /2

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft

    140 Krenson Bay Loop, Winter Haven, FL 33881

    Short Sale. 3-bedroom, 2-bath Adams Homes 1512 floor plan in Winter Haven offering 1,512 square feet of living space, a split-bedroom layout, and a 2-car attached garage. Interior features include tile flooring in the main living areas, carpet in the bedrooms, and an open kitchen with pantry and dining area. The primary suite includes a walk-in closet, and the primary bath features dual sinks, a

    Daniel Rivera Fontan ZARZUELA REALTY, LLC

    140 Krenson Bay Loop, Winter Haven, FL 33881
  • /3

    $199,900

    • 4 Beds
    • 2 Baths
    • 1,849 Sq Ft

    1374 Benevento Dr, Winter Haven, FL 33884

    Short Sale. Subject to lender approval. Property has sustained prior storm-related damage with documented mold and interior environmental conditions. Due to these conditions, interior access is limited and not suitable for routine showings. Property is being sold AS-IS and will require substantial remediation, including potential structural and electrical work. Access is restricted to serious,

    Hien Nguyen FLORIDA REALTY INVESTMENTS

    1374 Benevento Dr, Winter Haven, FL 33884
  • /34

    $199,900

    • 4 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    1015 Carefree Cove Dr, Winter Haven, FL 33881

    Short Sale. Welcome to this beautifully updated 4-bedroom, 1.5-bath single-family home located in Winter Haven with NO HOA! This solid block construction home offers peace of mind with a new roof and AC installed in 2024. Inside, you’ll find newer flooring throughout along with a recently renovated kitchen and bathrooms, giving the home a fresh, modern feel. The kitchen features quartz

    Garrett Robinson KELLER WILLIAMS REALTY SMART

    1015 Carefree Cove Dr, Winter Haven, FL 33881
  • /66

    $245,000 Open Sat 2AM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft

    2350 Salzburg Loop, Winter Haven, FL 33884

    Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner 2 bedroom 2 bath home. The charming kitchen has a breakfast nook with bay window, breakfast bar, generous countertops, and cabinet space. The bright, and open great room as well as both bedrooms have recently updated Luxury Vinyl Plank floors for easy care. You'll be snug, and secure during storm

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    2350 Salzburg Loop, Winter Haven, FL 33884
  • /15

    $250,000

    • 4 Beds
    • 2 Baths
    • 1,846 Sq Ft

    920 Cambridge Dr, Winter Haven, FL 33881

    SHORT SALE OPPORTUNITY PRICED TO SELL! Welcome to this 2021 built 4-bed 2 bath home located in the growing Windridge community of Winter Haven. This newer construction single story home offers a desirable open-concept floor plan designed for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the main living and dining areas, creating a bright and inviting central

    Briana Willis Global Advantage Realty LLC

    920 Cambridge Dr, Winter Haven, FL 33881
  • /43

    $290,000

    • 5 Beds
    • 3 Baths
    • 2,601 Sq Ft

    3935 Palazzo Place, Winter Haven, FL 33884

    Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen

    Casandra Vann KELLER WILLIAMS REALTY SMART

    3935 Palazzo Place, Winter Haven, FL 33884
  • /38

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,543 Sq Ft

    111 Krenson Bay Loop, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile

    Carolina Flores, LLC LPT REALTY, LLC

    111 Krenson Bay Loop, Winter Haven, FL 33881
  • /13

    $210,000

    • 4 Beds
    • 3 Baths
    • 1,703 Sq Ft

    125 Edgewater Dr, Winter Haven, FL 33881

    Short Sale. This property presents a great opportunity for buyers looking to renovate and add value. With a functional floor plan and generous living areas, it offers a solid starting point for updates and improvements. The layout provides flexibility to reimagine the space to suit your needs and design preferences. Spacious rooms allow for creative customization throughout. The kitchen area

    Cesar Estrada, PA EXP REALTY LLC

    125 Edgewater Dr, Winter Haven, FL 33881
  • /29

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft

    6518 Crescent Loop, Winter Haven, FL 33884

    Short Sale. Charming, move-in ready 3-bed, 2-bath home in a peaceful Winter Haven community. Features an open living/dining layout, updated kitchen with modern finishes, and spacious bedrooms. Enjoy plenty of natural light, a private backyard perfect for gatherings and outdoor living, and an attached 2-car garage. Well-maintained and thoughtfully updated, this home offers both comfort and

    Mona Cherkaoui WORLD PROPERTIES GROUP

    6518 Crescent Loop, Winter Haven, FL 33884
  • /14

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft

    273 Hayley St, Winter Haven, FL 33884

    Short Sale. ...Exceptional Corner-Lot Home in Peace Creek Reserve. A beautifully maintained, move-in ready 3 bedroom, 2 bath home. Just a short stroll from the resort-style pool and playground, this home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is ideal for entertaining, highlighted by a gourmet kitchen with a spacious center island overlooking the

    Robert Bretz, PA EXP REALTY LLC

    273 Hayley St, Winter Haven, FL 33884
  • /35

    $400,000

    • 5 Beds
    • 3 Baths
    • 2,579 Sq Ft

    129 Lake Otis Rd, Winter Haven, FL 33884

    Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it

    Kelley Vogel Blackburn COLDWELL BANKER REALTY

    129 Lake Otis Rd, Winter Haven, FL 33884
  • /7

    $255,000

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft

    405 Hickory Ln, Winter Haven, FL 33880

    Short Sale. Finding a 3-bedroom, 2-bathroom home with a 2-car garage in a community with no HOA and no CDD fees that includes lake access is a rare but available opportunity in Florida with this home! This property offers freedom from restrictive covenants and extra monthly fees while providing recreational water access. Come check it out today!

    Susan Brown COLDWELL BANKER REALTY

    405 Hickory Ln, Winter Haven, FL 33880
  • /32

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    440 Kensington View Dr, Winter Haven, FL 33880

    Short Sale. SHORT SALE BANK APPROVED AT 269K --VACANT---ON A CORNER LOT--delightful home boasting a private vinyl fenced side and backyard. Step inside to find three bedrooms and two bathrooms, where the primary suite offers serene privacy and comfort. The kitchen is a homeowner’s dream with upgraded granite countertops, complemented by stylish brown cabinets. Hard flooring flows throughout most

    Michael Huculak PREFERRED RE BROKERS III

    440 Kensington View Dr, Winter Haven, FL 33880
  • /23

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    29 Golfview Cir NE, Winter Haven, FL 33881

    Short Sale. We are in the process of getting a short sale approved. So expect delays.Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel

    Chris Sakamoto MARK SPAIN REAL ESTATE

    29 Golfview Cir NE, Winter Haven, FL 33881
  • /20

    $239,900

    • 4 Beds
    • 2 Baths
    • 1,599 Sq Ft

    306 Fern Rd, Winter Haven, FL 33880

    Short Sale. ***SHORT SALE *** BEAUTIFUL HOUSE COMPLETELY REMODELED, stainless steel appliances, wooden cabinets and whole house Laminate flooring.

    Consuelo Zea ZEA REALTY & ASSOCIATES

    306 Fern Rd, Winter Haven, FL 33880
  • /19

    $249,900

    • 4 Beds
    • 2 Baths
    • 2,225 Sq Ft

    116 Hampden Rd, Winter Haven, FL 33884

    Short Sale. ***THIS IS AN UNAPPROVED SHORT SALE TRANSACTION***Spacious 4/2 with a duplex layout. an impressive 12,000sqft+ lot that includes a covered back patio, nice sized pool, and detached garaged.Property needs new roof, pool work, and a variety of other repairs throughout the property. Tenant occupied. 24hr notice needed

    Brandon Ford TOWER TEAM REALTY, LLC

    116 Hampden Rd, Winter Haven, FL 33884
  • /47

    $325,000

    • 5 Beds
    • 3 Baths
    • 2,522 Sq Ft

    4223 San Rocco Way, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Short Sale. Welcome home to Villa Mar, a vibrant and growing community in beautiful Winter Haven! Built in 2023 and occupied for just one year, this 5-bedroom, 3-bathroom home offers that “like-new” feel with thoughtful upgrades throughout. As you step inside, you’re greeted by an inviting open-concept layout designed for both comfort and

    Brianna Perez Montalvo EXP REALTY LLC

    4223 San Rocco Way, Winter Haven, FL 33884
  • /27

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,829 Sq Ft

    3112 Saint Charles Place, Winter Haven, FL 33884

    Short Sale. Perfect starter home or investment property! Welcome to this 4-bedroom, 2-bathroom residence located in the desirable Orleans community. Built in 2023, this charming corner-lot home offers an open floor plan with a spacious living area, kitchen, and dinette—all featuring easy-to-maintain tile flooring. A sliding glass door leads to the covered lanai, perfect for relaxing or

    Veronica Figueroa EXP REALTY LLC

    3112 Saint Charles Place, Winter Haven, FL 33884
  • /19

    $220,000

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft

    602 Taylor Blvd, Winter Haven, FL 33880

    Short Sale. Welcome to this charming three-bedroom, two-bathroom home, perfectly situated for comfortable living. The inviting open concept layout seamlessly integrates the kitchen, living, and dining areas, adorned with luxury vinyl plank flooring that adds both style and durability. The well-appointed kitchen features beautiful granite countertops, complemented by sleek black appliances, crisp

    David Small KELLER WILLIAMS REALTY SMART 1

    602 Taylor Blvd, Winter Haven, FL 33880
  • /23

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,478 Sq Ft

    847 Channing St, Winter Haven, FL 33880

    Short Sale. $50,000 PRICE REDUCTION! Welcome to your perfect retreat in this exclusive gated community, where tranquility meets convenience! Enjoy easy access to shopping, dining, and the exciting attractions of Winter Haven, including Legoland Theme Park, all just minutes away. This charming three-bedroom, two-bathroom home features a modern open-concept layout and a split bedroom design for

    David Small KELLER WILLIAMS REALTY SMART 1

    847 Channing St, Winter Haven, FL 33880
  • /46

    $297,000

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft

    1596 Leamington Ln, Winter Haven, FL 33884

    Short Sale. Motivated Sellers- Listing reflects appraisal price for Short Sale - Price is negotiable, requires bank approval - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned

    Christian Clay DALTON WADE INC

    1596 Leamington Ln, Winter Haven, FL 33884
  • /49

    $330,000

    • 5 Beds
    • 3 Baths
    • 2,616 Sq Ft

    2005 Carnostie Rd, Winter Haven, FL 33884

    Short Sale. Welcome home to this inviting 5-bedroom, 3-bath family home offering 2,601 sq. ft. of comfortable living on an oversized lot. This move-in ready home is priced to sell fast, and the seller is motivated; don’t wait on this one! Step inside and enjoy the spacious, open-concept layout designed with families in mind. The main floor features a bedroom and office/bonus room, perfect for

    Sharonda Lawrence ASCENSION REALTY INTERNATIONAL

    2005 Carnostie Rd, Winter Haven, FL 33884
  • /9

    $270,000

    • 4 Beds
    • 2 Baths
    • 1,520 Sq Ft

    119 Allen Ave, Winter Haven, FL 33880

    Short Sale. Verbally Approved Short Sale. Requires a some TLC & Refresh. Pool Home.

    Randy Patrick WESTBAY REAL ESTATE

    119 Allen Ave, Winter Haven, FL 33880
  • /70

    $185,000

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft

    503 Holt Cir, Winter Haven, FL 33880

    Short Sale. Welcome to 503 Holt Circle! This corner-lot property boasts 3 bedrooms, 2 full bathrooms and an abundance of outdoor space. There are plenty of windows to let the natural light in, and a sliding glass door to access the screened-in patio. Enjoy peace of mind with a 2024 roof, 2023 A/C and 2023 electric water heater. Both bathrooms contain thoughtful upgrades for design and

    Adam Faucett EXP REALTY LLC

    503 Holt Cir, Winter Haven, FL 33880
  • /39

    $299,000

    • 4 Beds
    • 3 Baths
    • 2,332 Sq Ft

    292 Spirit Landings Cir, Winter Haven, FL 33880

    Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek

    Marisol Rivera KELLER WILLIAMS ADVANTAGE III

    292 Spirit Landings Cir, Winter Haven, FL 33880
  • /39

    $259,000

    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft

    3161 Royal Tern Dr, Winter Haven, FL 33881

    Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area

    Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

    3161 Royal Tern Dr, Winter Haven, FL 33881
  • /7

    $245,000

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

    1540 Avenue C NE, Winter Haven, FL 33881

    Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

    Robert Miller MILLSHIRE REALTY

    1540 Avenue C NE, Winter Haven, FL 33881
  • /12

    $70,000

    • 3 Beds
    • 2 Baths
    • 1,330 Sq Ft

    333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880

    Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures

    Anthony Giglio REALTY COOPERATIVE

    333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880
  • /2

    $292,000

    • 3 Beds
    • 2 Baths
    • 1,919 Sq Ft

    123 Ruby Lake Dr, Winter Haven, FL 33884

    APPROVED SHORT SALE. THIS BEAUTIFUL HOME IS A 3 BEDROOM TWO BATH HOME WITH AN OFFICE. CAN BE USED AS A 4TH BEDROOM. LARGE OVERSIZED LOT IN A GATED COMMUNITY.

    Lisa Gonzalez Signature Realty Group

    123 Ruby Lake Dr, Winter Haven, FL 33884

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$292,945
Median Single Family Sale Price
$299,990
Median Townhouse Sale Price
$252,445
Median 2 Bedroom Sale Price
$136,670
Median 1 Bedroom Sale Price
$96,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
849
Last 12 months Home Sales
2,035
Months of Supply
5.00
Median List Price
$306,955
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
1%
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