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.	$299,500	Airbnb cash on cash: -0.15% Traditional cash on cash: 4.88% Airbnb Rental Income: $1015 Traditional Rental Income: $2076 Airbnb ROI: -0.15% Traditional ROI: 4.88%
2500 21ST Street NW #23 Winter Haven, FL PRICE REDUCTION!!!! Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartr...	2 beds \| 3 baths \| 1,334 sq.ft.	$169,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 6.87% Airbnb Rental Income: $1015 Traditional Rental Income: $1881 Airbnb ROI: -0.72% Traditional ROI: 6.87%
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.	$449,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.62% Airbnb Rental Income: $1015 Traditional Rental Income: $2369 Airbnb ROI: -0.45% Traditional ROI: 3.62%
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.	$399,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.37% Airbnb Rental Income: $1656 Traditional Rental Income: $2438 Airbnb ROI: 1.04% Traditional ROI: 4.37%
695 22ND ST NW Winter Haven, FL A 3 bedroom, 2 bathroom home featuring a separate BONUS ROOM and MUD ROOM is hard to find....	3 beds \| 2 baths \| 1,708 sq.ft.	$249,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 8.2% Airbnb Rental Income: $1656 Traditional Rental Income: $2430 Airbnb ROI: 2.95% Traditional ROI: 8.2%
408 LANIER Lane Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom block home perfectly position...	3 beds \| 2 baths \| 1,680 sq.ft.	$320,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.54% Airbnb Rental Income: $1656 Traditional Rental Income: $2273 Airbnb ROI: 1.94% Traditional ROI: 5.54%
4840 OLD LUCERNE PARK RD Winter Haven, FL Relax and Enjoy Lakefront Living on Beautiful Lake Lucerne! Situated on 0.84 acres, this u...	3 beds \| 2 baths \| 1,927 sq.ft.	$415,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.45% Airbnb Rental Income: $1656 Traditional Rental Income: $2803 Airbnb ROI: 1.3% Traditional ROI: 5.45%
1500 AVENUE G NE Winter Haven, FL Welcome to this spacious and beautifully maintained 3-bedroom, 2-bath home offering over 2...	3 beds \| 2 baths \| 2,280 sq.ft.	$359,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.17% Airbnb Rental Income: $1656 Traditional Rental Income: $2701 Airbnb ROI: 1.69% Traditional ROI: 6.17%
5203 WATERVIEW Way #5203 Winter Haven, FL PRICE DROP****Welcome to your private Florida condo! Ideally situated just minutes from LE...	2 beds \| 2 baths \| 930 sq.ft.	$159,900	Airbnb cash on cash: -1.09% Traditional cash on cash: 5.61% Airbnb Rental Income: $1015 Traditional Rental Income: $1679 Airbnb ROI: -1.09% Traditional ROI: 5.61%
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.	$214,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.6% Airbnb Rental Income: $1656 Traditional Rental Income: $2027 Airbnb ROI: 1.48% Traditional ROI: 5.6%
615 AVENUE A NE Winter Haven, FL Charming Historic Winter Haven Bungalow on a Great sized lot near Downtown Winter Haven - ...	3 beds \| 2 baths \| 1,848 sq.ft.	$265,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 4.93% Airbnb Rental Income: $1656 Traditional Rental Income: $1763 Airbnb ROI: 2.64% Traditional ROI: 4.93%
1908 CROSSROADS Boulevard Winter Haven, FL MAJOR PRICE DROP! SELLER MOTIVATED!!! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in...	4 beds \| 3 baths \| 2,781 sq.ft.	$395,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 4.89% Airbnb Rental Income: $2237 Traditional Rental Income: $2772 Airbnb ROI: 1.93% Traditional ROI: 4.89%
315 LANCEOLATE Drive Winter Haven, FL Saltwater pool. Boat parking. Private community boat ramp. Welcome to 315 Lanceolate Drive...	3 beds \| 2 baths \| 2,153 sq.ft.	$469,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.09% Airbnb Rental Income: $1656 Traditional Rental Income: $2901 Airbnb ROI: 0.2% Traditional ROI: 4.09%
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.	$259,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 8.59% Airbnb Rental Income: $2237 Traditional Rental Income: $2787 Airbnb ROI: 4.06% Traditional ROI: 8.59%
817 REFLECTIONS Loop E Winter Haven, FL FOR SALE - 4 Bedroom, 2 Bathroom Beautiful Home in One of Winter Haven's Most Desirable Ar...	4 beds \| 2 baths \| 1,937 sq.ft.	$379,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.88% Airbnb Rental Income: $2237 Traditional Rental Income: $2495 Airbnb ROI: 2.57% Traditional ROI: 4.88%
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.	$199,950	Airbnb cash on cash: -1.78% Traditional cash on cash: 5.38% Airbnb Rental Income: $1015 Traditional Rental Income: $2015 Airbnb ROI: -1.78% Traditional ROI: 5.38%
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: 1.26% Traditional cash on cash: 5.44% Airbnb Rental Income: $1656 Traditional Rental Income: $2174 Airbnb ROI: 1.26% 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: 2.07% Traditional cash on cash: 4.76% Airbnb Rental Income: $1656 Traditional Rental Income: $1874 Airbnb ROI: 2.07% Traditional ROI: 4.76%
4132 MARTINDALE Loop Winter Haven, FL Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the hig...	4 beds \| 3 baths \| 1,894 sq.ft.	$399,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.02% Airbnb Rental Income: $2237 Traditional Rental Income: $2413 Airbnb ROI: 1.06% Traditional ROI: 3.02%
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.	$524,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.59% Airbnb Rental Income: $2237 Traditional Rental Income: $3270 Airbnb ROI: 1.34% Traditional ROI: 4.59%
1028 S LAKE MARIAM Drive Winter Haven, FL Rare opportunity to own a direct-waterfront pool home on Lake Mariam, now offered at a red...	3 beds \| 3 baths \| 3,255 sq.ft.	$819,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.92% Airbnb Rental Income: $1656 Traditional Rental Income: $3641 Airbnb ROI: -0.29% Traditional ROI: 2.92%
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: 1.84% Traditional cash on cash: 6.68% Airbnb Rental Income: $1656 Traditional Rental Income: $2422 Airbnb ROI: 1.84% 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.	$699,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.23% Airbnb Rental Income: $2237 Traditional Rental Income: $4133 Airbnb ROI: 0.46% Traditional ROI: 4.23%
1015 ROBIN Lane Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home tucked away on a quiet c...	3 beds \| 2 baths \| 1,632 sq.ft.	$369,900	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.11% Airbnb Rental Income: $1656 Traditional Rental Income: $2252 Airbnb ROI: 1.05% Traditional ROI: 4.11%
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: 0.75% Traditional cash on cash: 4.74% Airbnb Rental Income: $1656 Traditional Rental Income: $2688 Airbnb ROI: 0.75% Traditional ROI: 4.74%
202 SAINT LUCIE Road Winter Haven, FL **Location, Location, Location! Seller offering closing costs assistance to help with prep...	3 beds \| 2 baths \| 1,764 sq.ft.	$309,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 6.67% Airbnb Rental Income: $1656 Traditional Rental Income: $2616 Airbnb ROI: 1.78% Traditional ROI: 6.67%
302 Sterling Drive Winter Haven, FL Under contract-accepting backup offers. Short Sale. Located in Winter Haven, this 4-bedroo...	4 beds \| 2 baths \| 2,460 sq.ft.	$315,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 7.29% Airbnb Rental Income: $2237 Traditional Rental Income: $2783 Airbnb ROI: 3.55% Traditional ROI: 7.29%
271 MARIPOSA Winter Haven, FL Welcome to your Home Sweet Home in Winter Haven, Florida! This 3-bedroom, 2-bath gem sits ...	3 beds \| 2 baths \| 1,571 sq.ft.	$249,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 6.74% Airbnb Rental Income: $1656 Traditional Rental Income: $2167 Airbnb ROI: 2.59% Traditional ROI: 6.74%
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.	$293,899	Airbnb cash on cash: 3.6% Traditional cash on cash: 5.95% Airbnb Rental Income: $2237 Traditional Rental Income: $2326 Airbnb ROI: 3.6% Traditional ROI: 5.95%
1646 TRESSEL Court Winter Haven, FL PRICE DROP!! Nestled within a secure, gated community with impressively low HOA fees, this...	4 beds \| 2 baths \| 1,846 sq.ft.	$275,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.4% Airbnb Rental Income: $2237 Traditional Rental Income: $2261 Airbnb ROI: 3.14% Traditional ROI: 5.4%
120 MORNING GLORY Circle Winter Haven, FL Every Detail Has Been Thoughtfully Designed. Every Upgrade Has Been Thoughtfully Completed...	3 beds \| 2 baths \| 1,930 sq.ft.	$345,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.79% Airbnb Rental Income: $1656 Traditional Rental Income: $2414 Airbnb ROI: 1.02% Traditional ROI: 4.79%
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.	$305,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 7.46% Airbnb Rental Income: $2237 Traditional Rental Income: $2970 Airbnb ROI: 2.95% Traditional ROI: 7.46%

Real Estate investment in Winter-haven, FL

There are 499 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 $174. In September 2026, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,136.

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

There are 499 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 $2,136.

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.

$299,500

Airbnb cash on cash: -0.15%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1015

Traditional Rental Income: $2076

Airbnb ROI: -0.15%

Traditional ROI: 4.88%

2500 21ST Street NW #23

Winter Haven, FL

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

$169,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 6.87%

Airbnb Rental Income: $1015

Traditional Rental Income: $1881

Airbnb ROI: -0.72%

Traditional ROI: 6.87%

1620 17TH Street NW

Winter Haven, FL

2 beds | 3 baths | 965 sq.ft.

$449,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1015

Traditional Rental Income: $2369

Airbnb ROI: -0.45%

Traditional ROI: 3.62%

357 RUBY LAKE Loop

Winter Haven, FL

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

$399,900

Airbnb cash on cash: 1.04%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1656

Traditional Rental Income: $2438

Airbnb ROI: 1.04%

Traditional ROI: 4.37%

695 22ND ST NW

Winter Haven, FL

3 beds | 2 baths | 1,708 sq.ft.

$249,900

Airbnb cash on cash: 2.95%

Traditional cash on cash: 8.2%

Airbnb Rental Income: $1656

Traditional Rental Income: $2430

Airbnb ROI: 2.95%

Traditional ROI: 8.2%

408 LANIER Lane

Winter Haven, FL

3 beds | 2 baths | 1,680 sq.ft.

$320,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1656

Traditional Rental Income: $2273

Airbnb ROI: 1.94%

Traditional ROI: 5.54%

4840 OLD LUCERNE PARK RD

Winter Haven, FL

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

$415,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $1656

Traditional Rental Income: $2803

Airbnb ROI: 1.3%

Traditional ROI: 5.45%

1500 AVENUE G NE

Winter Haven, FL

3 beds | 2 baths | 2,280 sq.ft.

$359,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $1656

Traditional Rental Income: $2701

Airbnb ROI: 1.69%