Real Estate Investment Properties for Sale in Winter Haven, FL

Looking for investment property in Winter Haven, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Haven, FL. Invest wisely with VRBO & Winter Haven, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Winter Haven, FL

Search for Single Family Residential for Sale in Winter Haven, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 577 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
132 Duval Rd Winter Haven, FL This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearl...	2 beds \| 2 baths \| 1,260 sq.ft.	$309,500	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.69% Airbnb Rental Income: $897 Traditional Rental Income: $2076 Airbnb ROI: -0.52% Traditional ROI: 4.69%
5872 ROYAL HILLS CIRCLE Winter Haven, FL Seller Motivated!! Welcome to Royal Hills, where comfort, space, and convenience come toge...	4 beds \| 2 baths \| 1,730 sq.ft.	$290,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 6.08% Airbnb Rental Income: $2995 Traditional Rental Income: $2403 Airbnb ROI: 5.73% Traditional ROI: 6.08%
254 CLOVERDALE ROAD Winter Haven, FL Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2-bath home loca...	3 beds \| 2 baths \| 1,463 sq.ft.	$259,900	Airbnb cash on cash: 2.18% Traditional cash on cash: 4.55% Airbnb Rental Income: $1757 Traditional Rental Income: $1858 Airbnb ROI: 2.18% Traditional ROI: 4.55%
357 Ruby Lake Loop Winter Haven, FL Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed ...	3 beds \| 2 baths \| 2,107 sq.ft.	$415,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.17% Airbnb Rental Income: $1757 Traditional Rental Income: $2438 Airbnb ROI: 1.18% Traditional ROI: 4.17%
225 FRANKLIN COURT Winter Haven, FL Under contract-accepting backup offers. *PRICE REDUCTION* Refined luxury meets modern ...	4 beds \| 3 baths \| 2,362 sq.ft.	$427,500	Airbnb cash on cash: 3.1% Traditional cash on cash: 4.23% Airbnb Rental Income: $2995 Traditional Rental Income: $2761 Airbnb ROI: 3.1% Traditional ROI: 4.23%
4840 Old Lucerne Park Rd Winter Haven, FL Lakefront Retreat on Beautiful Lake Lucerne! Situated on 0.84 acres, this updated 3-bedro...	3 beds \| 2 baths \| 1,927 sq.ft.	$425,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 5.3% Airbnb Rental Income: $1757 Traditional Rental Income: $2803 Airbnb ROI: 1.46% Traditional ROI: 5.3%
731 Canberra Rd Winter Haven, FL Under contract-accepting backup offers. Just REDUCED!! Welcome to this beautifully maintai...	3 beds \| 2 baths \| 2,140 sq.ft.	$325,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 6.38% Airbnb Rental Income: $1757 Traditional Rental Income: $2573 Airbnb ROI: 2.13% Traditional ROI: 6.38%
1908 Crossroads Blvd Winter Haven, FL Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region...	4 beds \| 3 baths \| 2,781 sq.ft.	$395,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 4.55% Airbnb Rental Income: $2995 Traditional Rental Income: $2772 Airbnb ROI: 3.37% Traditional ROI: 4.55%
1280 W LAKE HAMILTON DRIVE Winter Haven, FL Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come tog...	5 beds \| 4 baths \| 5,416 sq.ft.	$1,259,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.44% Airbnb Rental Income: $5523 Traditional Rental Income: $5937 Airbnb ROI: 2.14% Traditional ROI: 3.44%
511 Marcia Loop Winter Haven, FL 4 bedrooms, private backyard retreat with a hot tub, expansive Florida room, and solar-pow...	4 beds \| 2 baths \| 2,159 sq.ft.	$279,900	Airbnb cash on cash: 6.1% Traditional cash on cash: 7.92% Airbnb Rental Income: $2995 Traditional Rental Income: $2787 Airbnb ROI: 6.1% Traditional ROI: 7.92%
136 MADERA DRIVE Winter Haven, FL Under contract-accepting backup offers. Short Sale. BANK APPROVED PRICE! Take a look at th...	3 beds \| 2 baths \| 1,448 sq.ft.	$175,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 9.14% Airbnb Rental Income: $1757 Traditional Rental Income: $2029 Airbnb ROI: 4.62% Traditional ROI: 9.14%
2202 Garden Lake Dr Winter Haven, FL Experience resort-style living in the prestigious gated community of Winterset, just minut...	3 beds \| 2 baths \| 1,442 sq.ft.	$249,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.44% Airbnb Rental Income: $1757 Traditional Rental Income: $2174 Airbnb ROI: 1.62% Traditional ROI: 5.44%
1716 Terry Cir NE Winter Haven, FL Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and full...	3 beds \| 2 baths \| 1,065 sq.ft.	$270,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 4.76% Airbnb Rental Income: $1757 Traditional Rental Income: $1874 Airbnb ROI: 2.4% Traditional ROI: 4.76%
1 Lake Eloise Ln Winter Haven, FL Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in wint...	4 beds \| 3 baths \| 2,550 sq.ft.	$535,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 4.49% Airbnb Rental Income: $2995 Traditional Rental Income: $3270 Airbnb ROI: 2.56% Traditional ROI: 4.49%
3686 PLYMOUTH DRIVE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	4 beds \| 3 baths \| 2,404 sq.ft.	$369,900	Airbnb cash on cash: 2.91% Traditional cash on cash: 4.45% Airbnb Rental Income: $2995 Traditional Rental Income: $2841 Airbnb ROI: 2.91% Traditional ROI: 4.45%
1028 S Lake Mariam Dr Winter Haven, FL Welcome to your slice of LAKEFRONT, LAKE VIEW, POOL HOME paradise on the pristine shores o...	3 beds \| 2 baths \| 3,255 sq.ft.	$850,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.78% Airbnb Rental Income: $1757 Traditional Rental Income: $3641 Airbnb ROI: -0.21% Traditional ROI: 2.78%
811 22nd St NW Winter Haven, FL "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven...	3 beds \| 3 baths \| 1,408 sq.ft.	$269,990	Airbnb cash on cash: 2.17% Traditional cash on cash: 6.68% Airbnb Rental Income: $1757 Traditional Rental Income: $2422 Airbnb ROI: 2.17% Traditional ROI: 6.68%
1095 W Lake Hamilton Dr Winter Haven, FL Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a ra...	4 beds \| 3 baths \| 2,363 sq.ft.	$739,900	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.88% Airbnb Rental Income: $2995 Traditional Rental Income: $4133 Airbnb ROI: 1.27% Traditional ROI: 3.88%
1051 LENA RUN COURT Winter Haven, FL Under contract-accepting backup offers. Welcome home to this well-priced, beautifully main...	4 beds \| 2 baths \| 2,428 sq.ft.	$477,555	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.56% Airbnb Rental Income: $2995 Traditional Rental Income: $2604 Airbnb ROI: 2.9% Traditional ROI: 3.56%
202 Saint Lucie Rd Winter Haven, FL **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepai...	3 beds \| 2 baths \| 1,764 sq.ft.	$328,999	Airbnb cash on cash: 1.9% Traditional cash on cash: 6.23% Airbnb Rental Income: $1757 Traditional Rental Income: $2616 Airbnb ROI: 1.9% Traditional ROI: 6.23%
250 Volusia Dr Winter Haven, FL PRICE DROP! SELLER OFFERS $15,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYERâS CHOIC...	3 beds \| 2 baths \| 1,449 sq.ft.	$279,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 5.77% Airbnb Rental Income: $1757 Traditional Rental Income: $2186 Airbnb ROI: 2.48% Traditional ROI: 5.77%
3311 Queens Cove Loop Winter Haven, FL Don't miss this move-in ready, recently updated 3 bedroom, 2 bathroom block home with a 2-...	3 beds \| 2 baths \| 1,109 sq.ft.	$239,999	Airbnb cash on cash: 2.93% Traditional cash on cash: 5.69% Airbnb Rental Income: $1757 Traditional Rental Income: $1926 Airbnb ROI: 2.93% Traditional ROI: 5.69%
2011 9TH STREET NE Winter Haven, FL Welcome to this well-maintained 3 bedroom, 2 bath home located on a quiet, established str...	3 beds \| 2 baths \| 1,415 sq.ft.	$233,995	Airbnb cash on cash: 3.11% Traditional cash on cash: 7.27% Airbnb Rental Income: $1757 Traditional Rental Income: $2196 Airbnb ROI: 3.11% Traditional ROI: 7.27%
1382 Salisbury Dr Winter Haven, FL *SELLER'S ARE VERY MOTIVATED DUE TO JOB TRANSFER*Welcome to this updated 4-bedroom, 2....	4 beds \| 2 baths \| 1,764 sq.ft.	$294,999	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.81% Airbnb Rental Income: $2995 Traditional Rental Income: $2326 Airbnb ROI: 5.75% Traditional ROI: 5.81%
1646 Tressel Ct Winter Haven, FL Nestled within a secure, gated community with impressively low HOA fees, this beautiful 4-...	4 beds \| 2 baths \| 1,846 sq.ft.	$280,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 5.08% Airbnb Rental Income: $2995 Traditional Rental Income: $2261 Airbnb ROI: 5.25% Traditional ROI: 5.08%
5780 Lakeside Landings Blvd Winter Haven, FL From the moment you walk through the door, this home welcomes you with space, comfort, and...	4 beds \| 2 baths \| 2,526 sq.ft.	$305,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 7.19% Airbnb Rental Income: $2995 Traditional Rental Income: $2970 Airbnb ROI: 4.96% Traditional ROI: 7.19%
5828 MARSH LANDING DRIVE Winter Haven, FL Under contract-accepting backup offers. Welcome to refined Florida living in the serene, g...	4 beds \| 2 baths \| 2,078 sq.ft.	$387,500	Airbnb cash on cash: 3.3% Traditional cash on cash: 5.58% Airbnb Rental Income: $2995 Traditional Rental Income: $3135 Airbnb ROI: 3.3% Traditional ROI: 5.58%
524 Haines Trl Winter Haven, FL Beautifully maintained, highly upgraded home in a quiet, conveniently located community. F...	4 beds \| 2 baths \| 1,980 sq.ft.	$279,999	Airbnb cash on cash: 2.02% Traditional cash on cash: 5.84% Airbnb Rental Income: $1757 Traditional Rental Income: $2405 Airbnb ROI: 2.02% Traditional ROI: 5.84%
961 Drexel Ave NE Winter Haven, FL *PRICE DECREASE* This unique 2-story home in Winter Haven is full of character and cha...	3 beds \| 2 baths \| 1,856 sq.ft.	$305,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 6.1% Airbnb Rental Income: $1757 Traditional Rental Income: $2448 Airbnb ROI: 2.01% Traditional ROI: 6.1%
1394 OAKMONT DRIVE Winter Haven, FL Experience resort-style living in the highly sought-after gated 55+ golf community of Lake...	3 beds \| 2 baths \| 2,606 sq.ft.	$549,500	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.77% Airbnb Rental Income: $1757 Traditional Rental Income: $2511 Airbnb ROI: -0.64% Traditional ROI: 1.77%
3425 COVE COURT E Winter Haven, FL Under contract-accepting backup offers. *UNDER CONTRACT ACCEPTING BACK UP OFFERS* Tuck...	3 beds \| 2 baths \| 1,109 sq.ft.	$255,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 6.09% Airbnb Rental Income: $1757 Traditional Rental Income: $2083 Airbnb ROI: 2.74% Traditional ROI: 6.09%
340 Vail Dr Winter Haven, FL Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar C...	4 beds \| 3 baths \| 2,042 sq.ft.	$365,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 5.03% Airbnb Rental Income: $1757 Traditional Rental Income: $2545 Airbnb ROI: 1.32% Traditional ROI: 5.03%
3136 Country Club Cir Winter Haven, FL Welcome to a home that makes everyday living simple and enjoyable. Located in the establis...	3 beds \| 2 baths \| 1,690 sq.ft.	$290,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.47% Airbnb Rental Income: $1757 Traditional Rental Income: $1978 Airbnb ROI: 1.9% Traditional ROI: 4.47%
802 Marcia Loop Winter Haven, FL Welcome to 802 Marcia Loop, a LAKEFRONT property located in southeast Winter Haven! The pr...	3 beds \| 2 baths \| 1,539 sq.ft.	$349,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 4.71% Airbnb Rental Income: $1757 Traditional Rental Income: $2269 Airbnb ROI: 1.68% Traditional ROI: 4.71%
505 MAGGIE CIRCLE Winter Haven, FL Under contract-accepting backup offers. MAKE YOUR APPOINTMENT NOW TO VIEW THIS WELL-MAINTA...	3 beds \| 2 baths \| 1,592 sq.ft.	$249,900	Airbnb cash on cash: 2.93% Traditional cash on cash: 6.48% Airbnb Rental Income: $1757 Traditional Rental Income: $2113 Airbnb ROI: 2.93% Traditional ROI: 6.48%
305 Hernando Rd Winter Haven, FL Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step i...	4 beds \| 3 baths \| 2,569 sq.ft.	$479,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 6.35% Airbnb Rental Income: $2995 Traditional Rental Income: $3792 Airbnb ROI: 3.04% Traditional ROI: 6.35%
409 21st St SW Winter Haven, FL Stunning 2 story 3 bath Spanish home with attention to details. This home has been renova...	4 beds \| 1 baths \| 2,322 sq.ft.	$550,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 5.68% Airbnb Rental Income: $2995 Traditional Rental Income: $4002 Airbnb ROI: 2.39% Traditional ROI: 5.68%
725 Heritage Dr NE Winter Haven, FL One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe c...	4 beds \| 2 baths \| 3,114 sq.ft.	$559,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 4.62% Airbnb Rental Income: $2995 Traditional Rental Income: $3730 Airbnb ROI: 1.9% Traditional ROI: 4.62%
306 Palmetto Ave NW Winter Haven, FL Located in the desirable Harrington subdivision of Winter Haven, this beautifully single-f...	3 beds \| 1 baths \| 768 sq.ft.	$179,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 6.39% Airbnb Rental Income: $1757 Traditional Rental Income: $1602 Airbnb ROI: 4.48% Traditional ROI: 6.39%
525 Squires Grove Dr Winter Haven, FL Welcome home to 525 Squires Grove Dr! This well-maintained property offers a great blend o...	4 beds \| 2 baths \| 1,872 sq.ft.	$290,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 5.83% Airbnb Rental Income: $2995 Traditional Rental Income: $2425 Airbnb ROI: 5.4% Traditional ROI: 5.83%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Haven, FL

132 Duval Rd

Winter Haven, FL

2 beds | 2 baths | 1,260 sq.ft.

$309,500

Airbnb cash on cash: -0.52%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $897

Traditional Rental Income: $2076

Airbnb ROI: -0.52%

Traditional ROI: 4.69%

5872 ROYAL HILLS CIRCLE

Winter Haven, FL

4 beds | 2 baths | 1,730 sq.ft.

$290,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 6.08%

Airbnb Rental Income: $2995

Traditional Rental Income: $2403

Airbnb ROI: 5.73%

Traditional ROI: 6.08%

254 CLOVERDALE ROAD

Winter Haven, FL

3 beds | 2 baths | 1,463 sq.ft.

$259,900

Airbnb cash on cash: 2.18%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $1757

Traditional Rental Income: $1858

Airbnb ROI: 2.18%

Traditional ROI: 4.55%

357 Ruby Lake Loop

Winter Haven, FL

3 beds | 2 baths | 2,107 sq.ft.

$415,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $1757

Traditional Rental Income: $2438

Airbnb ROI: 1.18%

Traditional ROI: 4.17%

225 FRANKLIN COURT

Winter Haven, FL

4 beds | 3 baths | 2,362 sq.ft.

$427,500

Airbnb cash on cash: 3.1%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $2995

Traditional Rental Income: $2761

Airbnb ROI: 3.1%

Traditional ROI: 4.23%

4840 Old Lucerne Park Rd

Winter Haven, FL

3 beds | 2 baths | 1,927 sq.ft.

$425,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $1757

Traditional Rental Income: $2803

Airbnb ROI: 1.46%

Traditional ROI: 5.3%

731 Canberra Rd

Winter Haven, FL

3 beds | 2 baths | 2,140 sq.ft.

$325,000

Airbnb cash on cash: 2.13%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $1757

Traditional Rental Income: $2573

Airbnb ROI: 2.13%

Traditional ROI: 6.38%

1908 Crossroads Blvd

Winter Haven, FL

4 beds | 3 baths | 2,781 sq.ft.

$395,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $2995

Traditional Rental Income: $2772

Airbnb ROI: 3.37%