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: 5.39% Traditional cash on cash: 4.69% Airbnb Rental Income: $2962 Traditional Rental Income: $2076 Airbnb ROI: 5.39% 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: 8.84% Traditional cash on cash: 6.49% Airbnb Rental Income: $2962 Traditional Rental Income: $1881 Airbnb ROI: 8.84% Traditional ROI: 6.49%
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: 9.85% Traditional cash on cash: 4.55% Airbnb Rental Income: $4015 Traditional Rental Income: $1858 Airbnb ROI: 9.85% Traditional ROI: 4.55%
1620 17TH STREET NW Winter Haven, FL New Lake Life listing, two houses one price. Must see property with no HOA. Chain of lakes...	2 beds \| 3 baths \| 965 sq.ft.	$479,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 3.34% Airbnb Rental Income: $2962 Traditional Rental Income: $2369 Airbnb ROI: 3.14% Traditional ROI: 3.34%
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: 6.02% Traditional cash on cash: 4.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2438 Airbnb ROI: 6.02% 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: 7.3% Traditional cash on cash: 4.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2761 Airbnb ROI: 7.3% 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: 6.19% Traditional cash on cash: 5.3% Airbnb Rental Income: $4015 Traditional Rental Income: $2803 Airbnb ROI: 6.19% 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: 5.85% Traditional cash on cash: 5.01% Airbnb Rental Income: $2962 Traditional Rental Income: $2090 Airbnb ROI: 5.85% Traditional ROI: 5.01%
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: 8.29% Traditional cash on cash: 6.38% Airbnb Rental Income: $4015 Traditional Rental Income: $2573 Airbnb ROI: 8.29% Traditional ROI: 6.38%
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: 7.66% Traditional cash on cash: 4.55% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.66% 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: 3.25% Traditional cash on cash: 3.44% Airbnb Rental Income: $7079 Traditional Rental Income: $5937 Airbnb ROI: 3.25% Traditional ROI: 3.44%
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: 6.59% Traditional cash on cash: 5.23% Airbnb Rental Income: $2962 Traditional Rental Income: $2015 Airbnb ROI: 6.59% 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: 9.62% Traditional cash on cash: 5.44% Airbnb Rental Income: $4015 Traditional Rental Income: $2174 Airbnb ROI: 9.62% 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: 9.79% Traditional cash on cash: 4.76% Airbnb Rental Income: $4015 Traditional Rental Income: $1874 Airbnb ROI: 9.79% 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: 5.93% Traditional cash on cash: 4.49% Airbnb Rental Income: $5016 Traditional Rental Income: $3270 Airbnb ROI: 5.93% 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: 7.77% Traditional cash on cash: 4.45% Airbnb Rental Income: $5016 Traditional Rental Income: $2841 Airbnb ROI: 7.77% 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: 2.17% Traditional cash on cash: 2.78% Airbnb Rental Income: $4015 Traditional Rental Income: $3641 Airbnb ROI: 2.17% 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: 9.56% Traditional cash on cash: 6.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2422 Airbnb ROI: 9.56% 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: 3.68% Traditional cash on cash: 3.88% Airbnb Rental Income: $5016 Traditional Rental Income: $4133 Airbnb ROI: 3.68% Traditional ROI: 3.88%
4111 ISLAND LAKES DRIVE Winter Haven, FL Welcome to this beautifully maintained waterfront home on an oversized lot in the desirabl...	3 beds \| 2 baths \| 1,998 sq.ft.	$399,900	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2688 Airbnb ROI: 5.99% Traditional ROI: 4.74%
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: 6.67% Traditional cash on cash: 3.56% Airbnb Rental Income: $5016 Traditional Rental Income: $2604 Airbnb ROI: 6.67% 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: 7.98% Traditional cash on cash: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.98% Traditional ROI: 6.23%
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: 9.28% Traditional cash on cash: 5.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2186 Airbnb ROI: 9.28% Traditional ROI: 5.77%
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: 7.94% Traditional cash on cash: 5.58% Airbnb Rental Income: $5016 Traditional Rental Income: $3135 Airbnb ROI: 7.94% Traditional ROI: 5.58%
2500 21ST STREET NW #22 Winter Haven, FL Welcome to easy Florida living at this beautifully updated 2-bedroom, 2.5-bath townhome wi...	2 beds \| 3 baths \| 1,334 sq.ft.	$179,990	Airbnb cash on cash: 8.23% Traditional cash on cash: 6.02% Airbnb Rental Income: $2962 Traditional Rental Income: $1900 Airbnb ROI: 8.23% Traditional ROI: 6.02%
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: 8.38% Traditional cash on cash: 5.84% Airbnb Rental Income: $4015 Traditional Rental Income: $2405 Airbnb ROI: 8.38% 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: 8.57% Traditional cash on cash: 6.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2448 Airbnb ROI: 8.57% 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: 3.03% Traditional cash on cash: 1.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2511 Airbnb ROI: 3.03% Traditional ROI: 1.77%
340 Vail Dr Winter Haven, FL Beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar C...	3 beds \| 3 baths \| 2,042 sq.ft.	$365,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 5.03% Airbnb Rental Income: $4015 Traditional Rental Income: $2545 Airbnb ROI: 6.82% Traditional ROI: 5.03%
3136 COUNTRY CLUB CIRCLE 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: 8.79% Traditional cash on cash: 4.47% Airbnb Rental Income: $4015 Traditional Rental Income: $1978 Airbnb ROI: 8.79% 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: 7.41% Traditional cash on cash: 4.71% Airbnb Rental Income: $4015 Traditional Rental Income: $2269 Airbnb ROI: 7.41% Traditional ROI: 4.71%
305 HERNANDO ROAD 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: 6.79% Traditional cash on cash: 6.35% Airbnb Rental Income: $5016 Traditional Rental Income: $3792 Airbnb ROI: 6.79% Traditional ROI: 6.35%
409 21ST STREET 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: 5.66% Traditional cash on cash: 5.68% Airbnb Rental Income: $5016 Traditional Rental Income: $4002 Airbnb ROI: 5.66% Traditional ROI: 5.68%
725 HERITAGE DRIVE NE Winter Haven, FL One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe c...	4 beds \| 3 baths \| 3,114 sq.ft.	$559,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3730 Airbnb ROI: 5.12% Traditional ROI: 4.62%
3208 TIMBERLINE ROAD Winter Haven, FL MOVE-IN READY & COMPLETELY REMODELED! This stunning home features a bright, open layout w...	2 beds \| 2 baths \| 1,043 sq.ft.	$240,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.56% Airbnb Rental Income: $2962 Traditional Rental Income: $1845 Airbnb ROI: 7.47% Traditional ROI: 5.56%
4 CASARENA COURT Winter Haven, FL This dynamically unique home in Winter Haven offers waterfront living, with direct access ...	3 beds \| 3 baths \| 3,911 sq.ft.	$524,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2691 Airbnb ROI: 3.72% Traditional ROI: 2.77%
144 BEVERLY DRIVE Winter Haven, FL NO HOA + POOL HOME + MINUTES TO THE CHAIN OF LAKES! This updated 4-bedroom, 3-bath Winter ...	4 beds \| 3 baths \| 2,492 sq.ft.	$389,900	Airbnb cash on cash: 8.7% Traditional cash on cash: 8.12% Airbnb Rental Income: $5016 Traditional Rental Income: $3781 Airbnb ROI: 8.7% Traditional ROI: 8.12%
3843 ELOISE ESTATES COURT Winter Haven, FL HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern upda...	3 beds \| 2 baths \| 1,600 sq.ft.	$280,000	Airbnb cash on cash: 9.09% Traditional cash on cash: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2273 Airbnb ROI: 9.09% Traditional ROI: 5.74%
851 VIENNA DRIVE Winter Haven, FL Better Than New 2022 Home â Move-In Ready! VA Assumable Mortgage!!! Welcome to this b...	3 beds \| 2 baths \| 1,569 sq.ft.	$279,900	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2151 Airbnb ROI: 8.35% Traditional ROI: 4.54%
2218 ABBEY ROAD Winter Haven, FL Turnkey Villa in Stonebridge â Low Maintenance Living, Prime Location Step into easy ...	2 beds \| 2 baths \| 1,252 sq.ft.	$179,999	Airbnb cash on cash: 9.45% Traditional cash on cash: 7.71% Airbnb Rental Income: $2962 Traditional Rental Income: $1982 Airbnb ROI: 9.45% Traditional ROI: 7.71%

Real Estate investment in Winter-haven, FL

There are 294 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $294,838 and the average price per square foot is $171. In June 2026, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,207.

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

There are 294 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 $2,207.

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: 5.39%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $2962

Traditional Rental Income: $2076

Airbnb ROI: 5.39%

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: 8.84%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $2962

Traditional Rental Income: $1881

Airbnb ROI: 8.84%

Traditional ROI: 6.49%

254 CLOVERDALE ROAD

Winter Haven, FL

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

$259,900

Airbnb cash on cash: 9.85%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4015

Traditional Rental Income: $1858

Airbnb ROI: 9.85%

Traditional ROI: 4.55%

1620 17TH STREET NW

Winter Haven, FL

2 beds | 3 baths | 965 sq.ft.

$479,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $2962

Traditional Rental Income: $2369

Airbnb ROI: 3.14%

Traditional ROI: 3.34%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$415,000

Airbnb cash on cash: 6.02%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $4015

Traditional Rental Income: $2438

Airbnb ROI: 6.02%

Traditional ROI: 4.17%

225 FRANKLIN COURT

Winter Haven, FL

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

$427,500

Airbnb cash on cash: 7.3%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $5016

Traditional Rental Income: $2761

Airbnb ROI: 7.3%

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: 6.19%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $4015

Traditional Rental Income: $2803

Airbnb ROI: 6.19%

Traditional ROI: 5.3%

2634 RUTLEDGE COURT

Winter Haven, FL

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

$240,000

Airbnb cash on cash: 5.85%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $2962

Traditional Rental Income: $2090

Airbnb ROI: 5.85%