Location: Winter Haven
Only Show: Short Sale
Do Not Show Listings
1507 VIENNA SQUARE DR, WINTER HAVEN, FL 33884
$185,0006 Days on yellowkey MLS ID: P4938251
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1231 Built: 2011Monthly Fee: $465 Tax: $2,013 (2025)Community: Vienna Square And The Villas At Vienna SVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,013
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner Villa with wooded view. The charming kitchen has upgraded wood cabinets, solid surface counter tops, breakfast bar, and two pantry storage closets. The spacious great room has recently updated Luxury Vinyl Plank floors for easy care. Other recent updates include AC system in 2022, and Roof 3/2026.This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Marti Sutton (863-206-0563)
140 KRENSON BAY LOOP N, WINTER HAVEN, FL 33881
$260,000Listed 04/01/2026 7:51PM MLS ID: S5146942
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1479 Built: 2022Monthly Fee: $83 Tax: $3,522 (2025)Community: Krenson BaySingle Family
Taxes:$3,522
Remarks: 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 garden tub, and a separate shower. The kitchen includes a range, dishwasher, and microwave. Located in Krenson Bay with convenient access to shopping, dining, major roadways, medical facilities, Polk State College, and downtown Winter Haven. Buyer and buyer’s agent should verify all measurements, HOA information, lease restrictions, and any other information important to them.
Listing is courtesy of: ZARZUELA REALTY, LLC (855-577-4549)
Listing Agent: Daniel Rivera Fontan (407-747-5408)
1987 8TH ST SE, WINTER HAVEN, FL 33880
$261,222316 Days on yellowkey MLS ID: P4934891
3 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2363 Built: 1959 Tax: $1,648 (2024)Community: Laha Wa ManorSingle Family
Taxes:$1,648
High School: Winter Haven Senior
Tax Year: 2024
Remarks: Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an amazing outdoor space. There is NO HOA, NO CDD and NO FLOOD ZONE is this well-established neighborhood. Located close to popular restaurants, shopping centers, and Legoland Florida Resort & Park, banks and lakes. It is tucked away, yet close to it ALL.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Kelly Hansell (863-557-1784)
31 LAKE LINK CIR SE, WINTER HAVEN, FL 33884
$300,000308 Days on yellowkey MLS ID: S5127874
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2223 Built: 1971 Tax: $4,080 (2024)Community: Lake Link EstatesSingle Family
Taxes:$4,080
Elementary School: Frank E. Brigham Academy
Middle School: Denison Middle
Remarks: 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 conservation views behind you, this spacious 4-bedroom, 2-bath home offers room to breathe, grow, and truly settle in. Inside, you’ll find more than 2,200 square feet of comfortable living space—plus a converted garage that gives you even more flexibility. Need a fifth bedroom? A home office? A workout room or game space? This home easily adapts to whatever stage of life you’re in. The heart of the home is the open kitchen, breakfast nook, and family room, designed for everyday living and easy entertaining. Large windows over the kitchen sink flood the space with natural light, while ample cabinetry and a charming barn-door pantry add both function and personality. The living room’s feature wall gives the space character, and luxury vinyl flooring throughout keeps things both stylish and practical. Every bedroom has ceiling fans, making the home comfortable year-round. One of the hidden gems here is the oversized laundry room—complete with built-in cabinets and direct access to the backyard—perfect for storage, projects, or keeping life organized. Major updates mean peace of mind: newer windows and sliding glass doors, updated insulation, a replaced sewer line, newer appliances, a 2021 roof, and solar panels installed in 2022. Even better? The solar panels often result in credits from the power company, helping keep monthly utility costs surprisingly low. Step outside and you’ll see where this home really shines. The backyard feels private and inviting, with a large screened porch, fire pit for cozy evenings, and two storage sheds for all your tools and toys. Whether you’re hosting friends, enjoying a quiet morning coffee, or winding down after a long day, there’s space here to enjoy Florida living your way. The wide driveway easily fits four or more vehicles, making gatherings easy. Located in a quiet non-HOA neighborhood, you’ll enjoy the freedom to live how you want—no HOA or CDD fees—while still being close to shopping, dining, schools, and local attractions. And if you love boating or an active outdoor lifestyle, you’ll appreciate the flexibility this neighborhood offers. This home isn’t just about square footage or upgrades—it’s about comfort, flexibility, and the feeling of finally finding the one. Come see it in person and imagine the life you could build here.
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Katie Sweet (863-990-5141)
1374 BENEVENTO DR, WINTER HAVEN, FL 33884
$199,9007 Days on yellowkey MLS ID: O6390730
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1849 Built: 2020Monthly Fee: $15 Tax: $5,650 (2025)Community: Villamar Ph 2Single Family
Taxes:$5,650
Remarks: 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, qualified buyers and must be coordinated with the listing agent. Property includes leased solar panels. Buyer to verify terms and assume existing lease. Buyer to verify all measurements, square footage, HOA, and property information.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Hien Nguyen (479-926-7079)
415 GARRETT RIDGE CT, WINTER HAVEN, FL 33880
$140,00041 Days on yellowkey MLS ID: O6383855
0 Days Off yellowkey (back on 3/6/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 2006 Tax: $3,078 (2025)Community: TanamoraSingle Family
Taxes:$3,078
Remarks: Short Sale. Investor opportunity in Winter Haven. Welcome to this 3 bedroom, 2 bath home offering an open and inviting layout with vaulted ceilings and a spacious family room designed for comfortable everyday living. Tile flooring flows seamlessly through the main living areas and into the galley kitchen, creating a bright and cohesive feel throughout the home. Built with durable block construction, this property also features a single car garage. Step outside to enjoy a beautifully shaded lot, perfect for relaxing or entertaining guests in a private outdoor setting. This is a Short Sale. Professionally processed by ARII SOLUTIONS, LLC. Buyer Responsible Short Sale Processing Fee of $5,000. Please review ''Presentation of Offers'' document before submitting offer. Property sold as-is
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Robert Arnold, Jr (407-389-7318)
5018 STRADA DR, WINTER HAVEN, FL 33880
$220,000505 Days on yellowkey MLS ID: TB8320717
0 Days Off yellowkey (back on 9/29/2025)
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3020 Built: 2004Monthly Fee: $14 Tax: $4,657 (2023)Community: Sunridge Village EastSingle Family
Taxes:$4,657
Elementary School: Eagle Lake Elem
High School: Lake Region High
Tax Year: 2023
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Short Sale. Packed with potential! This spacious two-story home, featuring 4 bedrooms, 2.5 baths, and a versatile bonus room needs some repairs, cleaning, and TLC, but that’s where the attractive price comes in! The main floor includes a large great room, white kitchen with granite countertops, front living room/den, laundry, enclosed bonus room and a 3-car garage. The lanai offers a great outdoor entertaining space. Upstairs, the primary suite offers dual sinks, tub and separate shower, and dual walk-in closets, and the other bedrooms. Not in a flood zone and low HOA fees of $165/year ensure long-term low cost of ownership. Trustee Sale, must sell!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Tanja Cisliek (727-480-4155)
3815 POMELO, WINTER HAVEN, FL 33884
$317,49038 Days on yellowkey MLS ID: O6384844
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1672 Built: 2026Monthly Fee: $30 Tax: $155 (2025)Community: Harmony On Lake EloiseSingle Family
Taxes:$155
Elementary School: John Snively Elem
Remarks: Short Sale. 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 in your backyard and the best local restaurants and shopping are just a short drive away. Love the outdoors? Explore nearby parks and farmer’s markets. Your home at Harmony on Lake Eloisewill be in the center of it all!!
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
4913 JACKSON ST, WINTER HAVEN, FL 33884
$239,90074 Days on yellowkey MLS ID: O6374521
2 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 2023Monthly Fee: $67 Tax: $3,152 (2025)Community: Jackson LndgSingle Family
Taxes:$3,152
Elementary School: Garden Grove Elem
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. 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.
Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)
Listing Agent: Wanda Turner (407-756-2194)
2005 CARNOSTIE RD, WINTER HAVEN, FL 33884
$330,000280 Days on yellowkey MLS ID: TB8400791
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2616 Built: 2022Monthly Fee: $16 Tax: $4,400 (2024)Community: Villamar Ph 3Single Family
Taxes:$4,400
Elementary School: Chain O Lakes Elem
Middle School: Mclaughlin Middle
Remarks: 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 guests, remote work, or playtime. The family-style kitchen is both beautiful and functional, showcasing granite countertops, upgraded cabinetry, and stainless steel appliances; the perfect space for cooking and connecting. Upstairs, the primary suite offers a comfortable retreat with dual vanities and two walk-in closets, while the loft and three additional bedrooms provide plenty of room for everyone to spread out and enjoy. This home has it all, space, comfort, and convenience, in one of the area’s most desirable communities. Don’t miss your chance to make it yours! The fenced backyard offers privacy for entertaining and is spacious enough for a future pool. A 10-year builder warranty provides added peace of mind. The community residents enjoy a lakeside pool and playground, all conveniently located near US-27 and Thompson Nursery Road. Priced to sell, don’t miss this opportunity!
Listing is courtesy of: ASCENSION REALTY INTERNATIONAL (863-513-0208)
Listing Agent: Sharonda Lawrence (863-513-0208)
1015 CAREFREE COVE DR, WINTER HAVEN, FL 33881
$199,90010 Days on yellowkey MLS ID: L4960484
Bed: 4 Bath: 1.5 Liv Area Sq Ft: 1104 Built: 1972 Tax: $3,182 (2025)Community: Carefree CoveSingle Family
Taxes:$3,182
Remarks: 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 countertops, stainless steel appliances, and updated cabinetry, perfect for both everyday living and entertaining. The functional layout includes four spacious bedrooms, a full bathroom, and an additional half bath for added convenience. Enjoy outdoor living in the fully fenced backyard, ideal for pets, gatherings, or simply relaxing in your private space. The home also includes a 1-car garage for storage and parking. Ideally situated near Lake Conine, part of Winter Haven’s famous Chain of Lakes, this property offers easy access to boating, fishing, and outdoor recreation. Conveniently located near major roadways, providing a quick commute to Orlando, Tampa, and world-renowned attractions like Disney. This move-in ready home combines modern updates, a great location, and no HOA restrictions—don’t miss your opportunity to make it yours!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Garrett Robinson (863-838-5210)
29 GOLF VIEW CIR NE, WINTER HAVEN, FL 33881
$300,000119 Days on yellowkey MLS ID: TB8453876
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1962 Tax: $4,496 (2024)Community: North Lake Elbert HeightsSingle Family
Taxes:$4,496
Elementary School: Elbert Elem
Remarks: 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 appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Chris Sakamoto (904-200-7535)
2350 SALZBURG LOOP, WINTER HAVEN, FL 33884
$245,00014 Days on yellowkey MLS ID: P4938176
1 Days Off yellowkey (back on 3/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1521 Built: 2010Monthly Fee: $290 Tax: $2,022 (2025)Community: Vienna SquareSingle Family
Taxes:$2,022
Remarks: Under contract-accepting backup offers. 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 season with electric hurricane shutters, and a 2020 Generac generator. The roof was replaced in 2024, hot water tank in 2024, and the AC system was replaced in 2020.This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low maintenance lifestyle, in a welcoming setting. The reasonable monthly fee includes all community amenities, lawn mowing, and a Spectrum Internet/Cable/TV package. Residents enjoy access to the community pool, fitness center, billiards, movie theater, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!
847 CHANNING ST, WINTER HAVEN, FL 33880
$265,000237 Days on yellowkey MLS ID: P4935775
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1478 Built: 2022Monthly Fee: $58 Tax: $3,439 (2024)Community: Village/Crystal BeachSingle Family
Taxes:$3,439
Remarks: 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 added privacy. You'll love the luxury vinyl flooring throughout the living areas, with cozy carpet in the bedrooms. Step outside to your large, fully fenced backyard—perfect for relaxation without any rear neighbors. Unwind in your spacious screened-in lanai, ideal for enjoying the outdoors year-round! Additional highlights include an 8 x 5 fireproof storage closet in the garage, providing peace of mind for your valuables, as well as a well-maintained irrigation system and beautiful landscaping that enhances the curb appeal. With quick access to the Polk Parkway and Interstate 4, Central Florida adventures are at your fingertips. Don’t miss out on this fantastic opportunity—schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
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