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Winter Haven, FL Short Sale Homes for Sale

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  • /49

    $279,900

    $80K PRICE DROP
    • 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

    $260,000

    $39K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - 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

    Agent Photo

    Jon McCall PA

    DALTON WADE INC

    (863) 250-1507

    3180 Country Club Cir, Winter Haven, FL 33881
  • /20

    $195,000

    $54K PRICE DROP
    • 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
  • /24

    $310,000

    $100K PRICE DROP
    • 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
  • /19

    $220,000

    $45K PRICE DROP
    • 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
  • /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
  • /13

    $275,000

    $50K PRICE DROP
    • 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
  • /2

    $197,500

    • 3 Beds
    • 2 Baths
    • 2,082 Sq Ft

    820 Avenue Z NW, Winter Haven, FL 33881

    Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking

    Cesar Estrada, PA EXP REALTY LLC

    820 Avenue Z NW, Winter Haven, FL 33881
  • /20

    $239,900

    $50K PRICE DROP
    • 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
  • /46

    $270,000

    $63K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft

    1596 Leamington Ln, Winter Haven, FL 33884

    Short Sale. Motivated Sellers- well below appraisal price - Price 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 dog park, creating an active and

    Christian Clay DALTON WADE INC

    1596 Leamington Ln, Winter Haven, FL 33884
  • /23

    $265,000

    $80K PRICE DROP
    • 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
  • /7

    $245,000

    $35K PRICE INCREASE
    • 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
  • /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
  • /9

    $242,000

    $47K PRICE DROP
    • 3 Beds
    • 2 Baths

    3829 Giorgio Dr, Winter Haven, FL 33884

    PROPERTY IS ALMOST BRAND NEW, SO NOTHING NEEDS TO BE DONE, NO REPAIRS!TAKE ADVANTAGE OF THIS GREAT PROPERTY, IN EXCELLENT LOCATION.

    Ivette Loaiza First Pro International Rlty

    3829 Giorgio Dr, Winter Haven, FL 33884
  • /21

    $110,000

    $10K PRICE DROP
    • 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
  • /16

    $185,000

    • 4 Beds
    • 2 Baths
    • 1,304 Sq Ft

    505 Holt Cir, Winter Haven, FL 33880

    Short Sale. This 4-bedroom, 2-bath home with a versatile bonus room is situated on a desirable corner lot with no HOA restrictions. Featuring a newer roof installed in 2022, this property offers incredible potential for homeowners and investors alike. Conveniently located near major highways, shopping, and grocery stores, the home also provides plenty of outdoor space with endless possibilities

    Melissa Victor MMV REAL ESTATE GROUP LLC

    505 Holt Cir, Winter Haven, FL 33880
  • /9

    $250,000

    $81K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 1,520 Sq Ft

    119 Allen Ave, Winter Haven, FL 33880

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

    Randy Patrick WESTBAY REAL ESTATE

    119 Allen Ave, Winter Haven, FL 33880
  • /26

    $275,000

    • 4 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    884 Cambridge Dr, Winter Haven, FL 33881

    Short Sale. SHORT SALE OPPORTUNITY PRICED TO SELL! This is a great opportunity to walk into equity in a newer home. Needs some minor TLC. Lucerne Park Reserve is located in historic Winter Haven only one mile from US-27 providing easy access to major employment centers. The home is located closely to town centers with plenty of restaurant and retail options. Meritage Home is Known for their

    Dana Cates FOUNDATION REALTY GROUP

    884 Cambridge Dr, Winter Haven, FL 33881
  • /3

    $288,000

    $49K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    113 Citrus Dr, Winter Haven, FL 33884

    Short Sale. SHORT SALE APPROVED. LIST PRICE APPROVED BY BANK. Amazing opportunity to purchase a 3 bedroom, 2 bath home situated on a spacious 1⁄4 acre lot with NO HOA. Priced to sell and offering exceptional value, this property will not last long. The home features an open floor plan with a spacious living room, kitchen and dining combination, and additional family room space. The primary

    Cristina Porretto THE AGENCY FL

    113 Citrus Dr, Winter Haven, FL 33884
  • /19

    $330,000

    • 4 Beds
    • 2.5 Baths
    • 2,832 Sq Ft

    1965 Carnostie Rd, Winter Haven, FL 33884

    **Short Sale Opportunity - Villamar, Winter Haven** Welcome to this beautiful home in the Villamar community of Winter Haven. This property features a spacious layout, abundant natural light, and comfortable living areas-perfect for both everyday living and entertaining. The backyard offers excellent potential for outdoor enjoyment or customization. Conveniently located near shopping, dining,

    Chris Johnson PLATINUM PEAK PROPERTIES LLC

    1965 Carnostie Rd, Winter Haven, FL 33884
  • /62

    $320,000

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

    3365 Costello Cir, Winter Haven, FL 33884

    Short Sale. Discover this beautifully designed 2023-built 5-bedroom, 3-bathroom home located in the highly sought-after Villamar community in Winter Haven, Florida. This spacious two-story home offers the perfect blend of modern style, functional living space, and scenic water views. The welcoming foyer opens into a bright and airy open-concept floor plan ideal for both entertaining and everyday

    Emily Lietz ENGEL & VOELKERS LAKELAND

    3365 Costello Cir, Winter Haven, FL 33884
  • /29

    $249,000

    $85K PRICE DROP
    • 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
  • /38

    $284,999

    $20K PRICE DROP
    • 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
  • /27

    $300,000

    $25K PRICE DROP
    • 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
  • /22

    $285,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,453 Sq Ft

    541 Heather Glen Dr, Winter Haven, FL 33884

    Short Sale. SHORT SALE!! SUBMIT YOUR OFFER & WE WILL SUBMIT TO THE BANK. Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation

    Jeavanna Lanza PA EXP REALTY LLC

    541 Heather Glen Dr, 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
  • /6

    $292,000

    $2K PRICE INCREASE
    • 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
  • /13

    $390,000

    $12K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,242 Sq Ft

    Unlisted Address

    Short Sale. Over a half-acre fenced in lot with a 4 bedroom 2 1/2 bath home with an office or den. Large family room with a separate formal dining room. Eat in kitchen with 2 pantry's. New roof in 2017-2018 and a new air conditioner in 2019. Great location minutesfrom State Road 60 and close to all the dining and theme parks and spring baseball field in Winter Haven.

    Erica W Ranson BROOKS REALTY GROUP LLC

    Unlisted Address
  • /34

    $220,000

    $20K PRICE INCREASE
    • 4 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    1015 Carefree Cove Dr, Winter Haven, FL 33881

    Short Sale. Bank approved price! 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

    Garrett Robinson KELLER WILLIAMS REALTY SMART

    1015 Carefree Cove Dr, Winter Haven, FL 33881
  • /20

    $260,000

    $11K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,713 Sq Ft

    3732 Giorgio Dr, Winter Haven, FL 33884

    Short Sale. Welcome to this beautiful Winter Haven home! VillamarThis property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways.Short Sale opportunity — perfect for buyers looking for value and

    Yoja Mirabal MY REALTY GROUP, LLC.

    3732 Giorgio Dr, 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
  • /35

    $325,000

    $75K PRICE DROP
    • 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
  • /17

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft

    307 Sterling Dr, Winter Haven, FL 33884

    Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living

    Krichely Gonzalez Rodriguez KELLER WILLIAMS ADVANTAGE III

    307 Sterling Dr, Winter Haven, FL 33884
  • /33

    $199,000

    $71K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    3025 Silverado Terrace, Winter Haven, FL 33884

    Short Sale. SHORT SALE!! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect

    Malak Benbachir KELLER WILLIAMS REALTY SMART 1

    3025 Silverado Terrace, Winter Haven, FL 33884
  • /23

    $298,900

    $51K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,707 Sq Ft

    2638 San Marco Way, Winter Haven, FL 33884

    Short Sale. Welcome to this stunning 4-bedroom, 2-bathroom home featuring an open-concept layout perfect for modern living.Enjoy a spacious living room with a ceiling fan and decorative lighting, seamlessly flowing into the open kitchen equipped with shaker-style stone cabinets, Silestone countertops, stainless steel appliances, a large island, walk-in pantry, and an inviting dining area. The

    Shirley Beckford LOKATION

    2638 San Marco Way, Winter Haven, FL 33884
  • /35

    $276,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft

    909 Cambridge Dr, Winter Haven, FL 33881

    Short Sale. – PRICED TO SELL! Welcome to this 2022-built 3-bedroom, 2-bathroom home located in the growing Lucerne Park Reserve community of Winter Haven. This newer construction single-story home features a desirable open-concept floor plan, perfect for comfortable everyday living and easy entertaining. The spacious kitchen overlooks the living and dining areas, creating a bright and inviting

    Mariel Espinal LPT REALTY, LLC

    909 Cambridge Dr, Winter Haven, FL 33881

Home Prices in Winter Haven, FL

Home Price Trends

Median Sale Price
$294,990
Median Single Family Sale Price
$299,999
Median Townhouse Sale Price
$244,990
Median 2 Bedroom Sale Price
$187,900
Median 1 Bedroom Sale Price
$95,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
848
Last 12 months Home Sales
2,119
Months of Supply
4.80
Median List Price
$307,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
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