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
3041 EAGLE HAVEN DRIVE Winter Haven, FL Tucked behind citrus groves, your private, lakefront, DREAM home, situated on over an acre...	3 beds \| 4 baths \| 3,456 sq.ft.	$799,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.13% Airbnb Rental Income: $4015 Traditional Rental Income: $4310 Airbnb ROI: 2.58% Traditional ROI: 4.13%
135 ELOISE OAKS DRIVE Winter Haven, FL Motivated Sellers! This impeccably maintained 3-bedroom, 2-bathroom custom home is packe...	3 beds \| 2 baths \| 1,866 sq.ft.	$389,900	Airbnb cash on cash: 6.16% Traditional cash on cash: 3.94% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.16% Traditional ROI: 3.94%
610 20TH STREET SW Winter Haven, FL One or more photo(s) has been virtually staged. BACK ON MARKET! 2017 ROOF, 2024 Interior P...	3 beds \| 2 baths \| 2,181 sq.ft.	$298,000	Airbnb cash on cash: 8.34% Traditional cash on cash: 6.69% Airbnb Rental Income: $4015 Traditional Rental Income: $2693 Airbnb ROI: 8.34% Traditional ROI: 6.69%
1500 8TH STREET SE Winter Haven, FL Beautiful Renovated 3Bed/2Bath Pool Home with 2,617 square feet of living area, this home ...	3 beds \| 2 baths \| 2,617 sq.ft.	$415,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 6.13% Airbnb Rental Income: $4015 Traditional Rental Income: $3175 Airbnb ROI: 6.09% Traditional ROI: 6.13%
261 GERBER DAIRY ROAD Winter Haven, FL Under contract-accepting backup offers. Welcome Home! This beautifully remodeled 4 Bedroom...	4 beds \| 2 baths \| 2,139 sq.ft.	$599,900	Airbnb cash on cash: 5.51% Traditional cash on cash: 2.77% Airbnb Rental Income: $5016 Traditional Rental Income: $2458 Airbnb ROI: 5.51% Traditional ROI: 2.77%
625 KINGS LANE SW Winter Haven, FL Welcome to your future haven. This property boasts a fresh, neutral color paint scheme bot...	2 beds \| 2 baths \| 979 sq.ft.	$232,000	Airbnb cash on cash: 7.8% Traditional cash on cash: 5.91% Airbnb Rental Income: $2962 Traditional Rental Income: $1863 Airbnb ROI: 7.8% Traditional ROI: 5.91%
1963 8TH STREET SE Winter Haven, FL Under contract-accepting backup offers. This POOL house exudes mid-century charm, features...	3 beds \| 2 baths \| 1,759 sq.ft.	$325,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 5.94% Airbnb Rental Income: $4015 Traditional Rental Income: $2428 Airbnb ROI: 8.32% Traditional ROI: 5.94%
3711 JULIUS ESTATES BOULEVARD Winter Haven, FL SELLER OFFERING $5,000 TO BUYERS CLOSING COSTS. This newly renovated home features 4 ...	4 beds \| 2 baths \| 1,842 sq.ft.	$342,000	Airbnb cash on cash: 9.54% Traditional cash on cash: 4.26% Airbnb Rental Income: $5016 Traditional Rental Income: $2295 Airbnb ROI: 9.54% Traditional ROI: 4.26%
8507 Waterview Way Winter Haven, FL This charming condo offers a unique layout with 1 bedroom, 1 full bath, and an open floor ...	1 beds \| 2 baths \| 793 sq.ft.	$189,900	Airbnb cash on cash: 5.89% Traditional cash on cash: 6.69% Airbnb Rental Income: $1982 Traditional Rental Income: $1607 Airbnb ROI: 5.89% Traditional ROI: 6.69%
101 SUGAR CREEK ROAD Winter Haven, FL LOCATION LOCATION!!! This beautiful 3 bedroom 2 bathroom brick home spans over 2400 sq ft ...	3 beds \| 2 baths \| 1,581 sq.ft.	$369,900	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.41% Airbnb Rental Income: $4015 Traditional Rental Income: $2189 Airbnb ROI: 7.19% Traditional ROI: 4.41%
304 LAKE DAISY LOOP Winter Haven, FL Welcome to your dream home located at 304 Lake Daisy Loop in the beautiful city of Winter ...	3 beds \| 2 baths \| 1,474 sq.ft.	$315,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 5.22% Airbnb Rental Income: $4015 Traditional Rental Income: $2205 Airbnb ROI: 8.43% Traditional ROI: 5.22%
1908 EMILY BOULEVARD Winter Haven, FL GREAT OPPORTUNITY for the first-time buyer!! 3Bed/2Bath featuring an open floor plan with ...	3 beds \| 2 baths \| 1,636 sq.ft.	$280,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 5.72% Airbnb Rental Income: $4015 Traditional Rental Income: $2087 Airbnb ROI: 9.77% Traditional ROI: 5.72%
1 Lake Eloise Lane Winter Haven, FL PRICE REDUCED! SELLER MOTIVATED!! This amazing home in Southeast Winter Haven is basically...	4 beds \| 3 baths \| 2,550 sq.ft.	$577,500	Airbnb cash on cash: 5.51% Traditional cash on cash: 2.99% Airbnb Rental Income: $5016 Traditional Rental Income: $2631 Airbnb ROI: 5.51% Traditional ROI: 2.99%
503 HOLT CIRCLE Winter Haven, FL Cozy three bedrooms, 2 baths home, on a spacious fenced corner lot (0.22 acre). Upon enter...	3 beds \| 2 baths \| 1,305 sq.ft.	$279,900	Airbnb cash on cash: 9.66% Traditional cash on cash: 5.1% Airbnb Rental Income: $4015 Traditional Rental Income: $1955 Airbnb ROI: 9.66% Traditional ROI: 5.1%
555 HEATHER GLEN DRIVE Winter Haven, FL Step into your dream Florida retreat in the sought-after gated community of Heather Glen! ...	3 beds \| 2 baths \| 1,514 sq.ft.	$300,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 6.3% Airbnb Rental Income: $4015 Traditional Rental Income: $2403 Airbnb ROI: 8.97% Traditional ROI: 6.3%
744 SANTA MARIA DRIVE Winter Haven, FL Under contract-accepting backup offers. Stunning 3 Bedroom, 2 Bath Pool Home, Located on a...	3 beds \| 2 baths \| 2,018 sq.ft.	$409,900	Airbnb cash on cash: 6.15% Traditional cash on cash: 6.06% Airbnb Rental Income: $4015 Traditional Rental Income: $3120 Airbnb ROI: 6.15% Traditional ROI: 6.06%
3537 RALEIGH DRIVE Winter Haven, FL Imagine waking up every day to a community that invites you to embrace a lifestyle of ease...	3 beds \| 3 baths \| 2,006 sq.ft.	$362,990	Airbnb cash on cash: 5.68% Traditional cash on cash: 4% Airbnb Rental Income: $4015 Traditional Rental Income: $2584 Airbnb ROI: 5.68% Traditional ROI: 4%
191 LAKE THOMAS DRIVE Winter Haven, FL Charming 4-Bedroom Home with Screened-In Pool on Corner Lot! Welcome to your dream home! ...	4 beds \| 2 baths \| 2,201 sq.ft.	$430,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 4.69% Airbnb Rental Income: $5016 Traditional Rental Income: $2802 Airbnb ROI: 7.64% Traditional ROI: 4.69%
480 Lake Eloise Pointe Boulevard Winter Haven, FL Beautiful single-family home with open floor plan in well-kept neighborhood. This home boa...	3 beds \| 2 baths \| 1,266 sq.ft.	$291,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 4.3% Airbnb Rental Income: $4015 Traditional Rental Income: $1865 Airbnb ROI: 9.01% Traditional ROI: 4.3%
1422 GRAND CAYMAN CIRCLE Winter Haven, FL Home is in great condition after Hurricane Milton and did not sustain any damages!!Discove...	3 beds \| 2 baths \| 1,615 sq.ft.	$295,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 6.06% Airbnb Rental Income: $4015 Traditional Rental Income: $2218 Airbnb ROI: 9.44% Traditional ROI: 6.06%
1396 LUCERNE LOOP ROAD NE Winter Haven, FL MOVE IN READY NO STORM DAMAGE! MOTIVATED SELLER OFFERING 2 YEAR HOME WARRANTY............	4 beds \| 3 baths \| 2,371 sq.ft.	$565,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.05% Airbnb Rental Income: $5016 Traditional Rental Income: $3251 Airbnb ROI: 4.45% Traditional ROI: 3.05%
142 AVENUE F SW Winter Haven, FL Conveniently located near countless shopping, dining, and entertainment options, this Wint...	2 beds \| 1 baths \| 1,114 sq.ft.	$210,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 7.5% Airbnb Rental Income: $2962 Traditional Rental Income: $1880 Airbnb ROI: 9.51% Traditional ROI: 7.5%
1075 8TH STREET NW Winter Haven, FL Price Adjustment and $4000 Seller Concession to Buyer. Gorgeous 4 Bedroom, 3 Bathroom, Sin...	4 beds \| 3 baths \| 1,985 sq.ft.	$545,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 4.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 6.23% Traditional ROI: 4.62%
1421 AVENUE G NE Winter Haven, FL Great location! 3BD/2B home located at short walking distance from Lake Elbert. The family...	3 beds \| 2 baths \| 1,546 sq.ft.	$289,500	Airbnb cash on cash: 9.56% Traditional cash on cash: 5.86% Airbnb Rental Income: $4015 Traditional Rental Income: $2148 Airbnb ROI: 9.56% Traditional ROI: 5.86%
3461 RALEIGH DRIVE Winter Haven, FL Under contract-accepting backup offers. This Delightful 2 Bedroom/ 2 Bath home is sited in...	2 beds \| 2 baths \| 1,275 sq.ft.	$249,900	Airbnb cash on cash: 5.03% Traditional cash on cash: 3.5% Airbnb Rental Income: $2962 Traditional Rental Income: $1918 Airbnb ROI: 5.03% Traditional ROI: 3.5%
3717 HUNTINGTON LANE Winter Haven, FL Looking to live the Florida retirement lifestyle and maintenance free? This sought after 5...	3 beds \| 2 baths \| 1,746 sq.ft.	$280,000	Airbnb cash on cash: 7.22% Traditional cash on cash: 3.73% Airbnb Rental Income: $4015 Traditional Rental Income: $2236 Airbnb ROI: 7.22% Traditional ROI: 3.73%
2014 BARDMOOR Winter Haven, FL Welcome to 2014 Bardmoor in Winter Haven, FL! This 3-bed, 2-bath home boasts 1,880 sq ft o...	3 beds \| 2 baths \| 1,880 sq.ft.	$317,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 6.75% Airbnb Rental Income: $4015 Traditional Rental Income: $2685 Airbnb ROI: 8.33% Traditional ROI: 6.75%
209 SANTA ROSA DRIVE Winter Haven, FL LOCATION,LOCATION,LOCATION.Welcome to your dream Home! Gated community. This 3/2.1 Pool ho...	3 beds \| 3 baths \| 2,338 sq.ft.	$440,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 5.76% Airbnb Rental Income: $4015 Traditional Rental Income: $3156 Airbnb ROI: 5.76% Traditional ROI: 5.76%
1437 GRAND CAYMAN CIRCLE Winter Haven, FL Discover this stunning lakefront home on Lake Dexter, a serene 166-acre lake nestled in so...	3 beds \| 2 baths \| 1,785 sq.ft.	$490,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 3.6% Airbnb Rental Income: $4015 Traditional Rental Income: $2645 Airbnb ROI: 4.71% Traditional ROI: 3.6%
1935 AUSTIN TERRACE Winter Haven, FL Nestled in the heart of Winter Haven, this exquisite residence beckons those with a pencha...	3 beds \| 3 baths \| 2,494 sq.ft.	$750,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.24% Airbnb Rental Income: $4015 Traditional Rental Income: $2841 Airbnb ROI: 2.69% Traditional ROI: 2.24%
4072 LAKE MARIANNA DRIVE Winter Haven, FL Welcome to lake life! This fully remodeled home has a peaceful lake view that is great fo...	3 beds \| 2 baths \| 1,900 sq.ft.	$539,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 3.65% Airbnb Rental Income: $4015 Traditional Rental Income: $2674 Airbnb ROI: 4.61% Traditional ROI: 3.65%
55 ENCLAVE DRIVE Winter Haven, FL Under contract-accepting backup offers. It is a wonderful opportunity for YOU to be a part...	2 beds \| 2 baths \| 1,444 sq.ft.	$246,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 2.67% Airbnb Rental Income: $2962 Traditional Rental Income: $1581 Airbnb ROI: 5.68% Traditional ROI: 2.67%
3806 OSPREY POINTE CIRCLE Winter Haven, FL Step into your welcoming home in the serene Osprey Pointe community, where accessibility a...	3 beds \| 2 baths \| 1,635 sq.ft.	$285,000	Airbnb cash on cash: 9.05% Traditional cash on cash: 5.06% Airbnb Rental Income: $4015 Traditional Rental Income: $2087 Airbnb ROI: 9.05% Traditional ROI: 5.06%
1237 N LAKE ELBERT DRIVE NE Winter Haven, FL Under contract-accepting backup offers. Breath taking sunsets on Lake Elbert from your fro...	3 beds \| 3 baths \| 2,255 sq.ft.	$439,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 5.25% Airbnb Rental Income: $4015 Traditional Rental Income: $3271 Airbnb ROI: 4.97% Traditional ROI: 5.25%
524 HAINES TRAIL Winter Haven, FL THIS IS THE ONE!! MUST SEE THIS BREATHTAKING EXTREMELY WELL KEPT and HIGHLY UPGRADED HOME ...	4 beds \| 2 baths \| 1,980 sq.ft.	$370,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.88% Airbnb Rental Income: $5016 Traditional Rental Income: $2405 Airbnb ROI: 9.44% Traditional ROI: 4.88%
123 OLD SPANISH WAY Winter Haven, FL Located in the prestigious gated community of The Trails of Lake Daisy, this custom-built ...	4 beds \| 3 baths \| 2,916 sq.ft.	$668,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 1.9% Airbnb Rental Income: $5016 Traditional Rental Income: $2529 Airbnb ROI: 4.25% Traditional ROI: 1.9%
208 SHELLEY DRIVE Winter Haven, FL This charming single-story home features three spacious bedrooms and two well-appointed ba...	3 beds \| 2 baths \| 1,364 sq.ft.	$289,900	Airbnb cash on cash: 9.48% Traditional cash on cash: 5.69% Airbnb Rental Income: $4015 Traditional Rental Income: $2122 Airbnb ROI: 9.48% Traditional ROI: 5.69%
150 EL DORADO #107 Winter Haven, FL This desirable ground floor 2-bedroom, 2-bathroom condo is located in a 55+ community with...	2 beds \| 2 baths \| 1,372 sq.ft.	$151,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 6.88% Airbnb Rental Income: $2962 Traditional Rental Income: $1904 Airbnb ROI: 9.48% Traditional ROI: 6.88%
5289 PEBBLE BEACH BOULEVARD Winter Haven, FL Welcome to your new home in the beautiful 55+ Golf Community of Lake Ashton. This stunnin...	3 beds \| 2 baths \| 2,002 sq.ft.	$369,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 4.04% Airbnb Rental Income: $4015 Traditional Rental Income: $2422 Airbnb ROI: 6.16% Traditional ROI: 4.04%
205 HIBISCUS STREET Winter Haven, FL Welcome to this desirable property, a meticulously maintained home ready for a fresh start...	3 beds \| 2 baths \| 1,636 sq.ft.	$281,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 4.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2087 Airbnb ROI: 8.78% Traditional ROI: 4.74%

Real Estate investment in Winter-haven, FL

There are 341 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $304,900 and the average price per square foot is $172. In November 2024, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,273.

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

There are 341 investment properties available for sale in Winter-haven.

In 2024, the best neighborhood to buy investment property is Winter Haven.

The ROI for Short-Term is higher than the Long-Term in Winter-haven with average rental income of $4,015.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Haven, FL

3041 EAGLE HAVEN DRIVE

Winter Haven, FL

3 beds | 4 baths | 3,456 sq.ft.

$799,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $4015

Traditional Rental Income: $4310

Airbnb ROI: 2.58%

Traditional ROI: 4.13%

135 ELOISE OAKS DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,866 sq.ft.

$389,900

Airbnb cash on cash: 6.16%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.16%

Traditional ROI: 3.94%

610 20TH STREET SW

Winter Haven, FL

3 beds | 2 baths | 2,181 sq.ft.

$298,000

Airbnb cash on cash: 8.34%

Traditional cash on cash: 6.69%

Airbnb Rental Income: $4015

Traditional Rental Income: $2693

Airbnb ROI: 8.34%

Traditional ROI: 6.69%

1500 8TH STREET SE

Winter Haven, FL

3 beds | 2 baths | 2,617 sq.ft.

$415,000

Airbnb cash on cash: 6.09%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $4015

Traditional Rental Income: $3175

Airbnb ROI: 6.09%

Traditional ROI: 6.13%

261 GERBER DAIRY ROAD

Winter Haven, FL

4 beds | 2 baths | 2,139 sq.ft.

$599,900

Airbnb cash on cash: 5.51%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $5016

Traditional Rental Income: $2458

Airbnb ROI: 5.51%

Traditional ROI: 2.77%

625 KINGS LANE SW

Winter Haven, FL

2 beds | 2 baths | 979 sq.ft.

$232,000

Airbnb cash on cash: 7.8%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $2962

Traditional Rental Income: $1863

Airbnb ROI: 7.8%

Traditional ROI: 5.91%

1963 8TH STREET SE

Winter Haven, FL

3 beds | 2 baths | 1,759 sq.ft.

$325,900

Airbnb cash on cash: 8.32%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $4015

Traditional Rental Income: $2428

Airbnb ROI: 8.32%

Traditional ROI: 5.94%

3711 JULIUS ESTATES BOULEVARD

Winter Haven, FL

4 beds | 2 baths | 1,842 sq.ft.

$342,000

Airbnb cash on cash: 9.54%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $5016

Traditional Rental Income: $2295

Airbnb ROI: 9.54%