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Winter Haven, FL Short Sale Homes for Sale

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  • /15

    $260,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft

    3180 Country Club Cir, Winter Haven, FL 33881

    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 Kitchen

    Agent Photo

    Jon McCall PA

    Dalton Wade Inc

    3180 Country Club Cir, Winter Haven, FL 33881
  • /36

    $180,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,306 Sq Ft

    124 Center St, Winter Haven, FL 33880

    Virtually Staged. Short Sale. Investor Special! (short sale requiring 3rd party approval) Don't miss this opportunity to transform this 3-bedroom, 2-bath block home into something truly special. Featuring a newer roof and AC system, some of the major improvements have already been completed, providing a solid foundation for your renovation plans. Whether you're an investor searching for your next

    Agent Photo

    Stephen Novak

    LIVE FLORIDA REALTY

    124 Center St, Winter Haven, FL 33880
  • /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

    1109 5th St SW, 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

    $245,000

    $80K 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
  • /43

    $290,000

    $35K PRICE DROP
    • 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
  • /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
  • /19

    $245,000

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    878 Killearn Blvd, Winter Haven, FL 33880

    Short Sale. Great opportunity to own this spacious home! Please note this is a short sale and purchase is subject to lender/bank approval. Property is being sold strictly in As-Is condition, and buyer is responsible for all municipal inspections. Bring your vision and custom touches to make this home your own! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established

    Barbi Rodriguez SIGNATURE INTERNATIONAL REAL E

    878 Killearn Blvd, Winter Haven, FL 33880
  • /15

    $270,000

    $20K PRICE INCREASE
    • 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
  • /13

    $365,000

    • 4 Beds
    • 2 Baths
    • 2,460 Sq Ft

    302 Sterling Dr, Winter Haven, FL 33884

    Short Sale. Located in Winter Haven, this 4-bedroom, 2-bath home offers approximately 2,460 square feet of living space with a two-car garage, spacious layout, and private pool. The home's generous floor plan provides multiple living areas and ample space for everyday living, entertaining, or accommodating a variety of household needs. Based on available information and photographs, the property

    Jonathon, PA McLeod KELLER WILLIAMS ELITE REALTY

    302 Sterling Dr, Winter Haven, FL 33884
  • /21

    $105,000

    $15K 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

    $287,500

    $13K PRICE INCREASE
    • 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

    $263,500

    $25K 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
  • /23

    $290,000

    $110K PRICE DROP
    • 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
  • /31

    $280,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,543 Sq Ft

    111 Krenson Bay Loop, Winter Haven, FL 33881

    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 flooring throughout the main

    Carolina Flores, LLC LPT REALTY, LLC

    111 Krenson Bay Loop, Winter Haven, FL 33881
  • /22

    $269,999

    $20K 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
  • /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.

    3829 Giorgio Dr, Winter Haven, FL 33884
  • /6

    $287,000

    $3K PRICE DROP
    • 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

    $250,000

    $21K 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
  • /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
  • /51

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    1912 Carnostie Rd, Winter Haven, FL 33884

    Short Sale. This home is located in Villamar Subdivision in Southeast Winter Haven. It was built in 2022, and it features a nice open concept with split bedroom plan, inside laundry room, and an open kitchen with a large island. The home has ceramic tile and wood flooring throughout for ease of living. The kitchen features stainless steel appliances package with granite countertops. Other

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    1912 Carnostie Rd, Winter Haven, FL 33884
  • /2

    $315,000

    • 4 Beds
    • 2 Baths
    • 1,822 Sq Ft

    3530 Evening Star Dr, Winter Haven, FL 33881

    Short Sale. Short Sale: roomy single-story residence crafted for ease and elegance. Its 4-bedroom design boasts an open-concept kitchen, dining, and family area perfect for gatherings and daily life. The sleek kitchen includes granite counters, stainless appliances, and premium cabinetry. Three bedrooms sit upfront, with the secluded primary suite featuring a walk-in closet and luxurious bath.

    Salvador Aguilar FAIR FEE REALTY

    3530 Evening Star Dr, Winter Haven, FL 33881
  • /35

    $266,900

    $25K 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 Price Trends

Median Sale Price
$294,990
Median Single Family Sale Price
$299,900
Median Townhouse Sale Price
$244,945
Median 2 Bedroom Sale Price
$190,000
Median 1 Bedroom Sale Price
$96,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
866
Last 12 months Home Sales
2,188
Months of Supply
4.70
Median List Price
$305,640
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
3%
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