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.

Investment Property for Sale in Winter Haven, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
132 DUVAL ROAD 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%
2500 21ST STREET NW #23 Winter Haven, FL Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to ...	2 beds \| 3 baths \| 1,334 sq.ft.	$178,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 6.49% Airbnb Rental Income: $897 Traditional Rental Income: $1881 Airbnb ROI: -1.32% Traditional ROI: 6.49%
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%
2634 RUTLEDGE COURT Winter Haven, FL Welcome to easy, maintenance-free living in the highly sought-after Verandahs at Tradition...	2 beds \| 2 baths \| 1,536 sq.ft.	$240,000	Airbnb cash on cash: -1.74% Traditional cash on cash: 5.01% Airbnb Rental Income: $897 Traditional Rental Income: $2090 Airbnb ROI: -1.74% Traditional ROI: 5.01%
2739 RUTLEDGE COURT Winter Haven, FL Welcome to this charming three-bedroom, two-bath townhome nestled in the desirable Traditi...	3 beds \| 2 baths \| 1,419 sq.ft.	$224,800	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.3% Airbnb Rental Income: $1757 Traditional Rental Income: $2027 Airbnb ROI: 1.77% Traditional ROI: 5.3%
731 CANBERRA ROAD 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%
333 LAKE HOWARD DRIVE NW #203C Winter Haven, FL Under contract-accepting backup offers. Enjoy a relaxed, maintenance-free lifestyle in thi...	2 beds \| 2 baths \| 1,030 sq.ft.	$109,900	Airbnb cash on cash: -1.59% Traditional cash on cash: 8.62% Airbnb Rental Income: $897 Traditional Rental Income: $1645 Airbnb ROI: -1.59% Traditional ROI: 8.62%
1908 CROSSROADS BOULEVARD 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.	$419,000	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 \| 3 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%
321 ORANGE BLOSSOM DRIVE Winter Haven, FL Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is ...	2 beds \| 3 baths \| 1,407 sq.ft.	$205,000	Airbnb cash on cash: -2.26% Traditional cash on cash: 5.23% Airbnb Rental Income: $897 Traditional Rental Income: $2015 Airbnb ROI: -2.26% Traditional ROI: 5.23%
2202 GARDEN LAKE DRIVE 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 \| 1,507 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 LANE 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 DRIVE Winter Haven, FL Welcome to your slice of LAKEFRONT, LAKE VIEW, POOL HOME paradise on the pristine shores o...	3 beds \| 3 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 STREET 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 DRIVE Winter Haven, FL Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a ra...	4 beds \| 4 baths \| 2,363 sq.ft.	$749,900	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 ROAD 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%
1776 6TH STREET NW #303 Winter Haven, FL Under contract-accepting backup offers. Improved Price!! All new window in the building......	2 beds \| 2 baths \| 1,347 sq.ft.	$115,000	Airbnb cash on cash: -3.95% Traditional cash on cash: 8.81% Airbnb Rental Income: $897 Traditional Rental Income: $1976 Airbnb ROI: -3.95% Traditional ROI: 8.81%
250 VOLUSIA DRIVE 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.	$294,000	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.	$249,999	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%
200 EL CAMINO DRIVE #101 Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. TH...	3 beds \| 3 baths \| 1,617 sq.ft.	$134,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 8.49% Airbnb Rental Income: $1757 Traditional Rental Income: $2059 Airbnb ROI: 2.44% Traditional ROI: 8.49%
1100 MARTINIQUE DRIVE #208 Winter Haven, FL Under contract-accepting backup offers. Spacious 2-bedroom, 2-bath upper corner condo in t...	2 beds \| 2 baths \| 1,024 sq.ft.	$94,750	Airbnb cash on cash: -0.84% Traditional cash on cash: 11.72% Airbnb Rental Income: $897 Traditional Rental Income: $1718 Airbnb ROI: -0.84% Traditional ROI: 11.72%
1382 SALISBURY DRIVE Winter Haven, FL *SELLER'S ARE VERY MOTIVATED DUE TO JOB TRANSFER*Welcome to this updated 4-bedroom, 2....	4 beds \| 3 baths \| 1,764 sq.ft.	$299,900	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 COURT 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.	$290,000	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 BOULEVARD Winter Haven, FL From the moment you walk through the door, this home welcomes you with space, comfort, and...	4 beds \| 3 baths \| 2,526 sq.ft.	$315,000	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%
1700 6TH STREET NW #C31 Winter Haven, FL HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community ...	2 beds \| 2 baths \| 840 sq.ft.	$99,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 9.2% Airbnb Rental Income: $897 Traditional Rental Income: $1599 Airbnb ROI: -1.51% Traditional ROI: 9.2%
524 HAINES TRAIL Winter Haven, FL Beautifully maintained, highly upgraded home in a quiet, conveniently located community. F...	3 beds \| 2 baths \| 1,980 sq.ft.	$315,000	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 AVENUE 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%

Real Estate investment in Winter-haven, FL

There are 479 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $294,814 and the average price per square foot is $173. In July 2026, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,125.

Winter-haven, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 479 investment properties available for sale in Winter-haven.

In 2026, the best neighborhood to buy investment property is Winter Haven.

The ROI for Long-Term is higher than the Short-Term in Winter-haven with average rental income of $2,125.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Haven, FL

132 DUVAL ROAD

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%

2500 21ST STREET NW #23

Winter Haven, FL

2 beds | 3 baths | 1,334 sq.ft.

$178,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $897

Traditional Rental Income: $1881

Airbnb ROI: -1.32%

Traditional ROI: 6.49%

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%

2634 RUTLEDGE COURT

Winter Haven, FL

2 beds | 2 baths | 1,536 sq.ft.

$240,000

Airbnb cash on cash: -1.74%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $897

Traditional Rental Income: $2090

Airbnb ROI: -1.74%