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$295,000
4 Beds ⋅ 2 Baths ⋅ Tangerine Pkwy SubDv. ⋅ 33881 Zip Code
Located near Polk State College and close to downtown Winter Haven, this duplex offers a great income-producing property. Each unit is a 2-bed, 1-bath, approximately 850 sq.ft. of living, with 1-car garage and screened in rear patio. Each unit is currently under lease until October 31, 2026, with 1254 getting $1,100 and 1256 renting at $1,150. Roof was replaced in 2022 and both A/C units done in 2020. The property with its location has potential for even more profit. Call today to view this opportunity. *Agents, please read MLS remarks.*

1254/1256 Tangerine Parkway Ne, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Howard Cannon Park Resub SubDv. ⋅ 33881 Zip Code
Located on a spacious corner lot in the heart of Winter Haven, this income-producing duplex offers an unbeatable combination of location, and long-term potential. One unit is currently rented for $1,300 on a month to month lease. The other unit is currently vacant. Featuring a brand-new roof and easy access to Winter Haven’s famous Chain of Lakes, including Lake Howard and Lake Cannon. Residents can enjoy boating, fishing, and waterfront dining. Ideally situated only about 8 minutes from Downtown Winter Haven, residents can also enjoy local restaurants, shops, entertainment, and community events while still having quick access to major roadways for an easy commute throughout Polk County. The property also offers convenient access to nearby schools, including Inwood Elementary just 2 minutes away, Westwood Middle approximately 4 minutes away, and Winter Haven Senior High around 8 minutes away. Whether you’re looking to expand your investment portfolio or secure a property in one of Central Florida’s fastest-growing lakefront communities, This property has exceptional value with its prime location, recent improvements, and proximity to Winter Haven’s iconic lakes and downtown district.

2097 Avenue H Nw, Winter Haven
$329,900
4 Beds ⋅ 2 Baths ⋅ Haven Terrace SubDv. ⋅ 33880 Zip Code
INVESTOR OPPORTUNITY, HOUSE HACK DREAM, OR MULTI-GENERATIONAL LIVING! Welcome to 113 Avenue C SE, Winter Haven, FL, a beautifully maintained and FULLY FURNISHED income-producing property offering exceptional flexibility and value! Situated on a single parcel, this unique property features a charming 3 BEDROOM, 1 BATH main home currently operating as a successful AIRBNB, along with a DETACHED 1 BEDROOM, 1 BATH IN-LAW SUITE with its own private entrance, separate address (258 1st St S, Winter Haven, FL 33880), and alley access, currently rented for $1,100 /MONTH. Both units have been UPDATED, with ROOFS AND A/C SYSTEMS REPLACED WITHIN THE LAST 3 YEARS, allowing peace of mind for years to come. The front home showcases beautiful ORIGINAL HARDWOOD FLOORS, while the rear apartment features attractive WOOD-LOOK TILE flooring. Built in 1950, this property has been exceptionally cared for and is in GREAT CONDITION while maintaining its timeless character. Whether you're looking to HOUSE HACK, generate immediate RENTAL INCOME, accommodate extended family, or expand your investment portfolio, this property checks every box. Located just a SHORT WALK TO DOWNTOWN WINTER HAVEN, you'll enjoy local restaurants, breweries, coffee shops, farmers markets, and year-round community events. Winter Haven continues to experience tremendous growth with ongoing DOWNTOWN REDEVELOPMENT, major investments in public amenities and infrastructure, expanding logistics and employment opportunities through the Central Florida Integrated Logistics Park, and continued economic development expected over the coming years. Conveniently located approximately 10 minutes from LEGOLAND Florida Resort, 45-60 minutes to Walt Disney World, 50-60 minutes to Orlando International Airport, and about 1 hour to Tampa International Airport, this location offers easy access to Central Florida's world-famous attractions while benefiting from Winter Haven's rapidly expanding job market, vibrant downtown, and outstanding quality of life. Whether you're an investor seeking multiple income streams or a homeowner looking for a property that helps pay for itself, this is a RARE opportunity you won't want to miss!

113 Avenue C Se, Winter Haven
$319,900
4 Beds ⋅ 2 Baths ⋅ Fanning Sub SubDv. ⋅ 33880 Zip Code
Welcome to an exceptional HOUSE HACKING and INVESTMENT OPPORTUNITY in the heart of Winter Haven! Legally classified as a SINGLE-FAMILY HOME, this unique property is GRANDFATHERED FOR MULTI-FAMILY USE and is currently configured as two separate living units, making it ideal for INVESTORS, OWNER-OCCUPANTS, or MULTI-GENERATIONAL LIVING. The front unit features 3 BEDROOMS, 1 BATHROOM, its own PRIVATE CARPORT, LAUNDRY ROOM, separate entrance, and private backyard, while the rear unit offers 1 BEDROOM, 1 BATHROOM, a private entrance, private backyard, and is currently rented for OVER $1,200 /MONTH. For added comfort, energy efficiency, and long-term value, the rear unit has been upgraded with a NEW MINI-SPLIT A/C SYSTEM, providing efficient climate control for tenants. The front unit has an estimated rental value of $1,650-$1,750 /MONTH, creating a projected combined rental income of approximately $2,850-$3,000+ /MONTH. Looking for additional upside? One of the bedrooms in the front unit has its OWN EXTERIOR ENTRANCE leading to the patio and offers exciting VALUE-ADD POTENTIAL for a future studio or efficiency conversion by adding a bathroom and kitchenette (buyer to verify all permitting, zoning, and city requirements). Recent 2023 UPDATES include updated kitchen countertops, fresh exterior paint, new flooring and interior paint in the rear unit, along with the installation of the NEW MINI-SPLIT A/C, making this property truly move-in and rent-ready. The home is serviced by ONE WATER METER and TWO SEPARATE ELECTRICAL METERS, allowing each unit to maintain its own electrical service. Perfectly situated just minutes from DOWNTOWN WINTER HAVEN, the famous Chain of Lakes, shopping, dining, healthcare, and schools, you'll also enjoy convenient access to US-27, I-4, Orlando International Airport, Downtown Orlando, and Walt Disney World, along with many of Central Florida's top attractions. As Winter Haven continues to experience significant residential, commercial, and economic growth, this property presents an outstanding opportunity to capitalize on both IMMEDIATE CASH FLOW and LONG-TERM APPRECIATION, whether you're looking to LIVE IN ONE UNIT WHILE RENTING THE OTHER, expand your investment portfolio, or own a versatile income-producing property with exceptional future potential. For added flexibility, the front 3-bedroom unit is also being offered FOR RENT, creating additional options for investors or future owner-occupants. Front Unit was Virtually Staged.

501 Avenue G Se, Winter Haven
$339,000
4 Beds ⋅ 4 Baths ⋅ Saxon-Myers Rep Ph 1 SubDv. ⋅ 33881 Zip Code
Income-Producing Duplex on Corner Lot – No HOA! Exceptional opportunity in Winter Haven! This well-maintained duplex at 2021/2023 Buckeye Rd NE features two spacious 2-bedroom, 2-bathroom units — 1,070 sq ft each — both with the convenience of indoor laundry hookup. Unit 2021 is vacant and move-in ready, while Unit 2023 is occupied by a reliable tenant who just renewed their lease at $1,300/month for another full year — instant income from day one! With market rents for comparable renovated units ranging from $1,400–$1,500, there's built-in upside on both sides. Perfect for the savvy house hacker: live in one unit while your tenant covers a significant portion of your mortgage. Investors will love the turnkey setup — lease the vacant unit at market rate and enjoy strong dual rental income with room to grow. Situated on a desirable fenced corner lot with no HOA fees or restrictions. Roof replaced in 2018, keeping maintenance minimal and insurance affordable. Opportunities like this — generously sized units, in-place income, and rent upside — don't last long. Schedule your showing today!

2021 Buckeye Road Ne, Winter Haven
$455,000
6 Beds ⋅ 2 Baths ⋅ Laramore Sub SubDv. ⋅ 33881 Zip Code
Calling all investors and house-hackers! Welcome to 1830 2nd St NW, a fantastic multi-family investment opportunity located right in the heart of Winter Haven. This well-maintained duplex features two spacious, mirror-image units, each offering a highly desirable 3-bedroom, 1-bathroom layout perfect for maximizing rental income and attracting long-term tenants! Both units boast bright, open-concept floor plans designed for easy living and low maintenance. Step inside to find durable ceramic tile flooring flowing seamlessly throughout the main living areas and kitchens, paired with crisp, neutral paint that makes the space feel fresh and inviting. The kitchens are fully equipped with rich wood cabinetry, ample counter prep space, white appliances (including dishwashers!), and a convenient breakfast bar/passthrough that overlooks the spacious family room. To top it off, each unit includes its own dedicated in-unit laundry closet with a stackable washer and dryer—a major premium for prospective renters.

1830 2nd Street Nw Unit A, Winter Haven
$459,000
6 Beds ⋅ 5 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

1339 7th Street Sw, Winter Haven
$579,000
9 Beds ⋅ 6 Baths ⋅ Coker A B Add SubDv. ⋅ 33881 Zip Code
Virtually Staged. Rare opportunity to own a 5-unit multifamily investment property situated on an oversized lot in the rapidly growing and expanding City of Winter Haven. The property consists of three separate buildings, providing flexibility, privacy, and multiple income streams. Currently, three units are leased with one vacant unit available for immediate occupancy or additional rental income potential , air b n b options as well . Recent renovations and updates completed within the past year include a new metal roof, updated HVAC systems, and numerous interior and exterior improvements, helping minimize deferred maintenance and enhance long-term value. Located near shopping, restaurants, schools, medical facilities, and major roadways, this property is positioned in one of Central Florida's strongest and fastest-growing rental markets. The versatile layout presents numerous possibilities for investors seeking cash flow, portfolio expansion, house-hacking opportunities, or potential short-term rental and Airbnb use, subject to local regulations and buyer verification. With strong income potential, multiple buildings, recent capital improvements, and a prime Winter Haven location near attractions, employment centers, and everyday conveniences, this is a unique opportunity to acquire a well-maintained multifamily asset with both immediate income and future upside.

514 Avenue C Ne, Winter Haven
$295,700
4 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.

3356 Avenue Q Nw, Winter Haven