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
2500 21st St NW #23 Winter Haven, FL Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to ...	2 beds \| 2 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%
404 TALAMONE DRIVE Winter Haven, FL BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in...	4 beds \| 3 baths \| 2,221 sq.ft.	$485,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.02% Airbnb Rental Income: $5016 Traditional Rental Income: $3098 Airbnb ROI: 5.98% Traditional ROI: 4.02%
254 Cloverdale Rd Winter Haven, FL Beautifully maintained 3-bedroom, 2-bath home located in the desirable Savanna Pointe comm...	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%
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%
330 Sterling Dr Winter Haven, FL Beautiful and spacious home located in a great neighborhood with excellent schools and a g...	3 beds \| 2 baths \| 1,426 sq.ft.	$295,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 5.26% Airbnb Rental Income: $4015 Traditional Rental Income: $2215 Airbnb ROI: 8.65% Traditional ROI: 5.26%
225 Franklin Ct Winter Haven, FL *PRICE REDUCTION* Refined luxury meets modern efficiency in this stunning 4-bedroom, 3...	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%
21 Casarena Ct Winter Haven, FL HUGE PRICE REDUCTION!!! CHAIN OF LAKES COMMUNITY...2 Bedroom/2.5 bath home nestled in the ...	2 beds \| 2 baths \| 2,045 sq.ft.	$285,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 4.09% Airbnb Rental Income: $2962 Traditional Rental Income: $2084 Airbnb ROI: 4.81% Traditional ROI: 4.09%
2348 Isle Royale Ct SE Winter Haven, FL Park Lake Townhome is move-in ready! Across the quiet, landscaped grounds you will find a ...	2 beds \| 2 baths \| 1,281 sq.ft.	$212,900	Airbnb cash on cash: 7.62% Traditional cash on cash: 5.79% Airbnb Rental Income: $2962 Traditional Rental Income: $1909 Airbnb ROI: 7.62% Traditional ROI: 5.79%
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%
3334 Fox Ridge Dr Winter Haven, FL LAKEFRONT LIVING WITH NO HOA Welcome to 3334 Fox Ridge Drive â a beautifully maintained...	3 beds \| 3 baths \| 1,542 sq.ft.	$362,500	Airbnb cash on cash: 7.33% Traditional cash on cash: 6.25% Airbnb Rental Income: $4015 Traditional Rental Income: $2792 Airbnb ROI: 7.33% Traditional ROI: 6.25%
455 Majestic Gardens Blvd Winter Haven, FL WELCOME HOME! Well maintained 3/2 with pool plus spa in Desirable gated Winter Haven commu...	3 beds \| 2 baths \| 1,625 sq.ft.	$349,900	Airbnb cash on cash: 7.64% Traditional cash on cash: 4.72% Airbnb Rental Income: $4015 Traditional Rental Income: $2200 Airbnb ROI: 7.64% Traditional ROI: 4.72%
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.	$419,900	Airbnb cash on cash: 7.64% Traditional cash on cash: 4.54% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.64% Traditional ROI: 4.54%
469 Muirfield Ct Winter Haven, FL Immaculate home located in Cypresswood. Home features engineered hardwood flooring. Large ...	2 beds \| 2 baths \| 1,293 sq.ft.	$299,999	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.55% Airbnb Rental Income: $2962 Traditional Rental Income: $1899 Airbnb ROI: 5.9% Traditional ROI: 4.55%
503 HAMILTON SHORES COURT NE Winter Haven, FL Under contract-accepting backup offers. WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN O...	3 beds \| 3 baths \| 2,375 sq.ft.	$525,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 5.13% Airbnb Rental Income: $4015 Traditional Rental Income: $3374 Airbnb ROI: 4.69% Traditional ROI: 5.13%
321 Orange Blossom Dr Winter Haven, FL Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is ...	2 beds \| 2 baths \| 1,407 sq.ft.	$215,500	Airbnb cash on cash: 6.22% Traditional cash on cash: 4.93% Airbnb Rental Income: $2962 Traditional Rental Income: $2015 Airbnb ROI: 6.22% Traditional ROI: 4.93%
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: 9.62% Traditional cash on cash: 5.44% Airbnb Rental Income: $4015 Traditional Rental Income: $2174 Airbnb ROI: 9.62% Traditional ROI: 5.44%
2235 Lakeridge Dr Winter Haven, FL Welcome to 2235 Lakeridge Driveâan exceptional opportunity to own a beautifully designed...	3 beds \| 2 baths \| 1,893 sq.ft.	$315,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.36% Airbnb Rental Income: $4015 Traditional Rental Income: $2295 Airbnb ROI: 8.27% Traditional ROI: 5.36%
220 Ruby Lake Ln Winter Haven, FL Welcome to this beautifully upgraded lakefront home nestled inside a private gated communi...	4 beds \| 3 baths \| 2,705 sq.ft.	$789,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.93% Airbnb Rental Income: $5016 Traditional Rental Income: $3807 Airbnb ROI: 3.17% Traditional ROI: 2.93%
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: 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 Dr Winter Haven, FL One or more photo(s) has been virtually staged. This spacious 4-bedroom, 3-bath home is lo...	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 Dr Winter Haven, FL Welcome to your slice of LAKEFRONT, POOL HOME paradise on the pristine shores of Lake Mari...	3 beds \| 2 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%
1444 Kingfish Ln Winter Haven, FL Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situate...	2 beds \| 2 baths \| 2,005 sq.ft.	$270,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 6.28% Airbnb Rental Income: $2962 Traditional Rental Income: $2249 Airbnb ROI: 6.4% Traditional ROI: 6.28%
2735 RUTLEDGE COURT Winter Haven, FL Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available...	2 beds \| 2 baths \| 1,419 sq.ft.	$220,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 6.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1990 Airbnb ROI: 7.42% Traditional ROI: 6.03%
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: 9.56% Traditional cash on cash: 6.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2422 Airbnb ROI: 9.56% Traditional ROI: 6.68%
207 24TH COURT SW Winter Haven, FL Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the...	3 beds \| 2 baths \| 1,296 sq.ft.	$285,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 6.34% Airbnb Rental Income: $4015 Traditional Rental Income: $2494 Airbnb ROI: 8.81% Traditional ROI: 6.34%
2118 Edgewater Cir Winter Haven, FL This beautiful custom built 4 Bdrm/3 Bath home in Edgewater Manor neighborhood in Winter H...	4 beds \| 3 baths \| 2,763 sq.ft.	$399,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 4.76% Airbnb Rental Income: $5016 Traditional Rental Income: $2770 Airbnb ROI: 8.03% Traditional ROI: 4.76%
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.	$777,700	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.71% Airbnb Rental Income: $5016 Traditional Rental Income: $4133 Airbnb ROI: 3.51% Traditional ROI: 3.71%
221 WHITMAN ROAD Winter Haven, FL Under contract-accepting backup offers. Welcome to this well-maintained 3-bedroom, 2-bathr...	3 beds \| 2 baths \| 1,511 sq.ft.	$275,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2086 Airbnb ROI: 9.94% Traditional ROI: 5.8%
1051 Lena Run Ct Winter Haven, FL Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence locat...	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%
5357 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WA...	3 beds \| 2 baths \| 2,363 sq.ft.	$440,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2393 Airbnb ROI: 5.02% Traditional ROI: 3.17%
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: 7.98% Traditional cash on cash: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.98% Traditional ROI: 6.23%
2642 Rutledge Ct Winter Haven, FL Great opportunity to own a beautiful low maintenance townhouse in SE Winter Haven! Excelle...	2 beds \| 2 baths \| 1,419 sq.ft.	$189,900	Airbnb cash on cash: 8.6% Traditional cash on cash: 6.28% Airbnb Rental Income: $2962 Traditional Rental Income: $1860 Airbnb ROI: 8.6% Traditional ROI: 6.28%
1075 8th St NW Winter Haven, FL Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Max...	4 beds \| 3 baths \| 1,985 sq.ft.	$480,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 4.33% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.04% Traditional ROI: 4.33%
250 Volusia Dr Winter Haven, FL SELLER OFFERS $10,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYERâS CHOICE PRIOR TO C...	3 beds \| 2 baths \| 1,449 sq.ft.	$299,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2186 Airbnb ROI: 9.11% Traditional ROI: 5.66%
3473 Raleigh Dr Winter Haven, FL Welcome to easy, low-maintenance living in the highly sought-after 55+ gated community of ...	2 beds \| 2 baths \| 1,118 sq.ft.	$207,500	Airbnb cash on cash: 6.62% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1988 Airbnb ROI: 6.62% Traditional ROI: 5.13%
264 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a...	4 beds \| 2 baths \| 2,217 sq.ft.	$699,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3025 Airbnb ROI: 4.07% Traditional ROI: 2.59%
900 Lake Jessie Dr Winter Haven, FL Live the ultimate lakefront lifestyle on Lake Jessie. This beautifully maintained single-s...	3 beds \| 3 baths \| 1,828 sq.ft.	$469,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 5.52% Airbnb Rental Income: $4015 Traditional Rental Income: $3311 Airbnb ROI: 5.17% Traditional ROI: 5.52%
2708 ATTWATER LOOP Winter Haven, FL Under contract-accepting backup offers. Impeccably maintained home in the sought-after Tra...	3 beds \| 2 baths \| 1,561 sq.ft.	$269,999	Airbnb cash on cash: 8.62% Traditional cash on cash: 5.21% Airbnb Rental Income: $4015 Traditional Rental Income: $2288 Airbnb ROI: 8.62% Traditional ROI: 5.21%
2452 Salzburg Loop Winter Haven, FL AMAZING OPPORTUNITY! ONE OF THE ONLY POOL HOMES LOCATED IN VIENNA SQUARE!!! This lovely ho...	2 beds \| 2 baths \| 1,729 sq.ft.	$332,452	Airbnb cash on cash: 4.13% Traditional cash on cash: 5.7% Airbnb Rental Income: $2962 Traditional Rental Income: $2771 Airbnb ROI: 4.13% Traditional ROI: 5.7%
524 Haines Trl Winter Haven, FL Beautifully maintained, highly upgraded home in a quiet, conveniently located community. F...	3 beds \| 2 baths \| 1,980 sq.ft.	$329,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2405 Airbnb ROI: 7.98% Traditional ROI: 5.55%

Real Estate investment in Winter-haven, FL

There are 562 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $295,000 and the average price per square foot is $165. In May 2026, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,194.

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

There are 562 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 $2,194.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Haven, FL

2500 21st St NW #23

Winter Haven, FL

2 beds | 2 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%

404 TALAMONE DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,221 sq.ft.

$485,000

Airbnb cash on cash: 5.98%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $5016

Traditional Rental Income: $3098

Airbnb ROI: 5.98%

Traditional ROI: 4.02%

254 Cloverdale Rd

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%

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%

330 Sterling Dr

Winter Haven, FL

3 beds | 2 baths | 1,426 sq.ft.

$295,000

Airbnb cash on cash: 8.65%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $4015

Traditional Rental Income: $2215

Airbnb ROI: 8.65%

Traditional ROI: 5.26%

225 Franklin Ct

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%

21 Casarena Ct

Winter Haven, FL

2 beds | 2 baths | 2,045 sq.ft.

$285,000

Airbnb cash on cash: 4.81%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2962

Traditional Rental Income: $2084

Airbnb ROI: 4.81%

Traditional ROI: 4.09%

2348 Isle Royale Ct SE

Winter Haven, FL

2 beds | 2 baths | 1,281 sq.ft.

$212,900

Airbnb cash on cash: 7.62%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $2962

Traditional Rental Income: $1909

Airbnb ROI: 7.62%