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Winter Haven, FL Short Sale Homes for Sale

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  • /32

    $235,000

    $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    1533 Majestic Ln, Winter Haven, FL 33880

    Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to the community of Eagle Landing in beautiful SE Winter Haven, Florida. This newer home features 4 Bedrooms/2.5 Bathrooms with a spacious two-story layout that maximizes space and natural light perfect for any lifestyle with Low HOA and NO CDD. The modern kitchen design with Island and Breakfast Bar

    Agent Photo

    Cheryl Brewer

    COLDWELL BANKER REALTY

    1533 Majestic Ln, 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
  • /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
  • /13

    $175,000

    $60K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 2,200 Sq Ft

    128 Avenue D SW, Winter Haven, FL 33880

    Short Sale. Hard to beat this combination of size, location, and upside. Located just one street from Winter Haven’s growing downtown district, this spacious approximately 2,200-square-foot home offers investors a rare opportunity to acquire a large property in an increasingly desirable area. The home is vacant and ready for renovation. Major system updates, including dual-zone air conditioning,

    Chad Lindsey LOKATION

    128 Avenue D SW, Winter Haven, FL 33880
  • /33

    $96,000

    $39K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    400 El Camino Dr Unit 210, Winter Haven, FL 33884

    Short Sale. Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy & a peaceful feel while enjoying the security & convenience of community living. Inside you will find updated luxury vinyl

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    400 El Camino Dr Unit 210, Winter Haven, FL 33884
  • /13

    $220,000

    $105K 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 NEXTHOME LUXE COASTAL

    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
  • /59

    $198,900

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft

    1307 Innsbruck Ct, Winter Haven, FL 33884

    Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    1307 Innsbruck Ct, Winter Haven, FL 33884
  • /20

    $229,900

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,599 Sq Ft

    306 Fern Rd, Winter Haven, FL 33880

    Short Sale. ***SHORT SALE *** Easy to show, beautiful completely remodeled home, No Homeowner association -- everything was updated

    Consuelo Zea ZEA REALTY & ASSOCIATES

    306 Fern Rd, Winter Haven, FL 33880
  • /43

    $280,000

    $45K 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

    3935 Palazzo Place, Winter Haven, FL 33884
  • /16

    $250,000

    $15K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft

    1973 Carnostie Rd, Winter Haven, FL 33884

    Short Sale. Calling all investors, flippers, and renovation enthusiasts! This 4 bedroom, 2 bathroom home in Winter Haven presents an outstanding opportunity to add value and build equity. With a spacious floor plan and solid footprint, this property is ready for a complete transformation. Whether you're looking for your next fix and flip, rental investment, or renovation project, the

    Casandra Vann KELLER WILLIAMS REALTY

    1973 Carnostie Rd, Winter Haven, FL 33884
  • /5

    $225,000

    • 3 Beds
    • 2 Baths
    • 2,006 Sq Ft

    2824 San Marco Way, Winter Haven, FL 33884

    Virtually Staged. Short Sale. Welcome to Villamar, a growing community in Winter Haven where convenience, modern living and peaceful pond views come together. This single-story 3-bedroom, 2-bath home offers an inviting open floor plan with spacious living areas designed for comfortable everyday living and easy entertaining. The kitchen features an oversized island, granite countertops, stainless

    Alexis Claire FATHOM REALTY FL LLC

    2824 San Marco Way, Winter Haven, FL 33884
  • /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
  • /13

    $340,000

    $25K PRICE DROP
    • 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

    Jonathon, PA McLeod NEXTHOME LUXE COASTAL

    302 Sterling Dr, Winter Haven, FL 33884
  • /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
  • /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
  • /9

    $240,000

    $71K 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.

    Randall 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
  • /62

    $285,000

    $35K PRICE DROP
    • 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

    $270,000

    $130K 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
  • /40

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft

    573 Lucerne Blvd, Winter Haven, FL 33881

    Virtually Staged. Short Sale. Welcome to 573 Lucerne Blvd, a well-maintained single-story home offering 4 bedrooms and 2 bathrooms with a comfortable layout designed for everyday living. Recent improvements provide added peace of mind, including an HVAC system installed in 2018, updated flooring in the main living areas in 2018, interior paint completed in 2019, and exterior paint refreshed in

    Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

    573 Lucerne Blvd, 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

    Carolina Flores, LLC LPT REALTY, LLC

    111 Krenson Bay Loop, Winter Haven, FL 33881
  • /10

    $232,000

    $38K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft

    4913 Jackson St, Winter Haven, FL 33884

    Short Sale. Back on the market -Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.

    Wanda Turner NONA LEGACY POWERED BY LA ROSA

    4913 Jackson St, Winter Haven, FL 33884
  • /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
  • /29

    $350,000

    • 5 Beds
    • 3 Baths
    • 2,577 Sq Ft

    6022 Grey Heron Dr, Winter Haven, FL 33881

    Short Sale. Opportunity awaits more photos coming soon! This 5-bedroom, 3-bathroom home offers incredible potential for homeowners and investors!Please note that this property is being sold as a non-approved short sale, and all offers are subject to third-party lender approval.With a spacious layout this home is an excellent opportunity to build equity and make it your

    Xiomara Pichardo AXEN REALTY, LLC

    6022 Grey Heron Dr, Winter Haven, FL 33881
  • /5

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,954 Sq Ft

    26 Saint Kitts Cir, Winter Haven, FL 33884

    Short Sale. This is a 3-bedroom, 2-bathroom home nestled in Winter Haven, FL. Built in 1993, this property offers a comfortable floor plan with great bones and exciting potential for the right buyer. This short sale opportunity presents an excellent chance to acquire a Winter Haven home at an improved price point in an established neighborhood. The layout provides functional living spaces

    Don Jerue KELLER WILLIAMS REALTY SMART 1

    26 Saint Kitts Cir, Winter Haven, FL 33884
  • /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

    $204,900

    $5K 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

    Garrett Robinson KELLER WILLIAMS REALTY

    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
  • /13

    $210,000

    $15K PRICE DROP
    • 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
  • /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

    $256,900

    $35K 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
$292,999
Median Single Family Sale Price
$299,490
Median Townhouse Sale Price
$244,990
Median 2 Bedroom Sale Price
$185,000
Median 1 Bedroom Sale Price
$95,000
Average Price Per Sq Ft
$168
Number of Homes for Sale
881
Last 12 months Home Sales
2,190
Months of Supply
4.80
Median List Price
$304,990
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
2%
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