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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3041 EAGLE HAVEN DRIVE Winter Haven, FL NEW PRICE!!! Tucked behind citrus groves, your private, lakefront, DREAM home, situated on...	3 beds \| 4 baths \| 3,456 sq.ft.	$760,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 4.39% Airbnb Rental Income: $4015 Traditional Rental Income: $4310 Airbnb ROI: 2.77% Traditional ROI: 4.39%
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.	$388,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.97% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.2% Traditional ROI: 3.97%
1807 GARDEN LAKE DRIVE #1807 Winter Haven, FL Experience the pristine, resort-like lifestyle at Winterset! This beautifully updated, fir...	2 beds \| 2 baths \| 1,103 sq.ft.	$260,000	Airbnb cash on cash: 6.06% Traditional cash on cash: 5.39% Airbnb Rental Income: $2962 Traditional Rental Income: $2116 Airbnb ROI: 6.06% Traditional ROI: 5.39%
1429 WALLACE MANOR PASS Winter Haven, FL PRICED TO SELL! MOTIVATED SELLERS! This home has undergone several updates within the rece...	3 beds \| 2 baths \| 1,750 sq.ft.	$280,000	Airbnb cash on cash: 9.05% Traditional cash on cash: 4.35% Airbnb Rental Income: $4015 Traditional Rental Income: $1916 Airbnb ROI: 9.05% Traditional ROI: 4.35%
357 RUBY LAKE LOOP Winter Haven, FL Located in the gated community of Ruby Lake, this stunning 3-bedroom, 2-bath Cassidy Ox fl...	3 beds \| 2 baths \| 2,107 sq.ft.	$433,900	Airbnb cash on cash: 5.76% Traditional cash on cash: 4.35% Airbnb Rental Income: $4015 Traditional Rental Income: $2587 Airbnb ROI: 5.76% Traditional ROI: 4.35%
610 20TH STREET SW Winter Haven, FL One or more photo(s) has been virtually staged. Find your happy place on a sprawling near ...	3 beds \| 2 baths \| 2,181 sq.ft.	$295,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 6.76% Airbnb Rental Income: $4015 Traditional Rental Income: $2693 Airbnb ROI: 8.43% Traditional ROI: 6.76%
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.	$410,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 6.22% Airbnb Rental Income: $4015 Traditional Rental Income: $3175 Airbnb ROI: 6.17% Traditional ROI: 6.22%
1383 BUCKEYE TRACE BOULEVARD Winter Haven, FL Unique opportunity! This beautiful single family home 3 bedrooms and 2 bathrooms located ...	3 beds \| 2 baths \| 1,507 sq.ft.	$315,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 5.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2188 Airbnb ROI: 8.37% Traditional ROI: 5.1%
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.	$185,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 6.89% Airbnb Rental Income: $1982 Traditional Rental Income: $1607 Airbnb ROI: 6.07% Traditional ROI: 6.89%
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%
3309 RALEIGH DR Winter Haven, FL MOVE IN READY!! Don't miss this beautifully maintained 2 bedroom, 2 bathroom home with a F...	2 beds \| 2 baths \| 1,118 sq.ft.	$235,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 4.48% Airbnb Rental Income: $2962 Traditional Rental Income: $1905 Airbnb ROI: 6.17% Traditional ROI: 4.48%
1905 16TH STREET NW Winter Haven, FL Pride of Ownership here, this wonderfully renovated 3 bed/2 bath, solid concrete block hom...	3 beds \| 2 baths \| 1,418 sq.ft.	$280,000	Airbnb cash on cash: 9.76% Traditional cash on cash: 6.45% Airbnb Rental Income: $4015 Traditional Rental Income: $2283 Airbnb ROI: 9.76% Traditional ROI: 6.45%
3484 JULIUS ESTATES BOULEVARD Winter Haven, FL One or more photo(s) has been virtually staged. Experience serene living in this 2014-DR H...	4 beds \| 3 baths \| 2,900 sq.ft.	$329,000	Airbnb cash on cash: 9.58% Traditional cash on cash: 6.97% Airbnb Rental Income: $5016 Traditional Rental Income: $3184 Airbnb ROI: 9.58% Traditional ROI: 6.97%
157 BROWNING CIRCLE Winter Haven, FL Charming 2-Bedroom, 2-Bathroom Block Home in a Peaceful Southeast Winter Haven Neighborhoo...	2 beds \| 2 baths \| 1,134 sq.ft.	$240,000	Airbnb cash on cash: 7.95% Traditional cash on cash: 6.01% Airbnb Rental Income: $2962 Traditional Rental Income: $1839 Airbnb ROI: 7.95% Traditional ROI: 6.01%
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%
3537 RALEIGH DRIVE Winter Haven, FL Bring All Offers! Retired Couple Motivated to Move! Imagine the lifestyle you've been drea...	3 beds \| 3 baths \| 2,006 sq.ft.	$350,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.19% Airbnb Rental Income: $4015 Traditional Rental Income: $2584 Airbnb ROI: 5.93% Traditional ROI: 4.19%
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.	$427,500	Airbnb cash on cash: 7.69% Traditional cash on cash: 4.72% Airbnb Rental Income: $5016 Traditional Rental Income: $2802 Airbnb ROI: 7.69% Traditional ROI: 4.72%
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%
152 AUDUBON COURT Winter Haven, FL BACK ON THE MARKET!! Great Lake Daisy location - Located in prime SE Winter Haven on a lar...	3 beds \| 2 baths \| 2,538 sq.ft.	$379,900	Airbnb cash on cash: 7.15% Traditional cash on cash: 5.27% Airbnb Rental Income: $4015 Traditional Rental Income: $2488 Airbnb ROI: 7.15% Traditional ROI: 5.27%
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%
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%
1896 ELOISE LOOP ROAD Winter Haven, FL Price Reposition 9/12/24~Welcome to the Historical Pettigrew Home. Step back in time with ...	4 beds \| 2 baths \| 2,216 sq.ft.	$527,250	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.15% Airbnb Rental Income: $5016 Traditional Rental Income: $2649 Airbnb ROI: 5.87% Traditional ROI: 3.15%
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%
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%
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.	$475,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2645 Airbnb ROI: 4.89% Traditional ROI: 3.74%
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.	$650,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2841 Airbnb ROI: 3.26% Traditional ROI: 2.74%
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.	$280,000	Airbnb cash on cash: 9.22% Traditional cash on cash: 5.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2087 Airbnb ROI: 9.22% Traditional ROI: 5.17%
2010 OVERLOOK DRIVE Winter Haven, FL Welcome to this beautifully updated 3-bedroom, 3-bathroom home on the sought-after Overloo...	3 beds \| 3 baths \| 1,922 sq.ft.	$320,000	Airbnb cash on cash: 8.36% Traditional cash on cash: 6.53% Airbnb Rental Income: $4015 Traditional Rental Income: $2608 Airbnb ROI: 8.36% Traditional ROI: 6.53%
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%
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%
5726 CRYSTAL BEACH ROAD Winter Haven, FL Under contract-accepting backup offers. Come experience this fully renovated 4-bedroom, 2-...	4 beds \| 2 baths \| 1,964 sq.ft.	$449,000	Airbnb cash on cash: 7.36% Traditional cash on cash: 4.09% Airbnb Rental Income: $5016 Traditional Rental Income: $2618 Airbnb ROI: 7.36% Traditional ROI: 4.09%
859 VIENNA DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. This Home Can Be Yours with No Money Down ...	3 beds \| 2 baths \| 1,512 sq.ft.	$285,000	Airbnb cash on cash: 8.52% Traditional cash on cash: 4.91% Airbnb Rental Income: $4015 Traditional Rental Income: $2188 Airbnb ROI: 8.52% Traditional ROI: 4.91%
3136 COUNTRY CLUB CIRCLE Winter Haven, FL Are you looking for your dream home, look no further. This 3 bedroom 2 bath 2 car garage h...	3 beds \| 2 baths \| 1,690 sq.ft.	$314,900	Airbnb cash on cash: 8.09% Traditional cash on cash: 4.11% Airbnb Rental Income: $4015 Traditional Rental Income: $1978 Airbnb ROI: 8.09% Traditional ROI: 4.11%
2668 WHISPERING TRAILS DRIVE Winter Haven, FL Step into this beautifully renovated home in Winter Haven, FL, where charm meets modern co...	4 beds \| 3 baths \| 2,150 sq.ft.	$350,000	Airbnb cash on cash: 9.31% Traditional cash on cash: 5.05% Airbnb Rental Income: $5016 Traditional Rental Income: $2590 Airbnb ROI: 9.31% Traditional ROI: 5.05%
4034 DORAL Winter Haven, FL Welcome to this very well kept home located in the desirable SE Winter Haven community of ...	4 beds \| 3 baths \| 2,674 sq.ft.	$425,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 7.13% Airbnb Rental Income: $5016 Traditional Rental Income: $3389 Airbnb ROI: 8.65% Traditional ROI: 7.13%
2973 DAYTON DRIVE Winter Haven, FL Under contract-accepting backup offers. Only 6 years old and hardly used, this is the owne...	3 beds \| 3 baths \| 2,659 sq.ft.	$429,900	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.89% Airbnb Rental Income: $4015 Traditional Rental Income: $2793 Airbnb ROI: 3.79% Traditional ROI: 2.89%

Real Estate investment in Winter-haven, FL

There are 338 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $300,000 and the average price per square foot is $168. In December 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 338 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.

$760,000

Airbnb cash on cash: 2.77%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $4015

Traditional Rental Income: $4310

Airbnb ROI: 2.77%

Traditional ROI: 4.39%

135 ELOISE OAKS DRIVE

Winter Haven, FL

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

$388,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.2%

Traditional ROI: 3.97%

1807 GARDEN LAKE DRIVE #1807

Winter Haven, FL

2 beds | 2 baths | 1,103 sq.ft.

$260,000

Airbnb cash on cash: 6.06%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $2962

Traditional Rental Income: $2116

Airbnb ROI: 6.06%

Traditional ROI: 5.39%

1429 WALLACE MANOR PASS

Winter Haven, FL

3 beds | 2 baths | 1,750 sq.ft.

$280,000

Airbnb cash on cash: 9.05%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $4015

Traditional Rental Income: $1916

Airbnb ROI: 9.05%

Traditional ROI: 4.35%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$433,900

Airbnb cash on cash: 5.76%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $4015

Traditional Rental Income: $2587

Airbnb ROI: 5.76%

Traditional ROI: 4.35%

610 20TH STREET SW

Winter Haven, FL

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

$295,000

Airbnb cash on cash: 8.43%

Traditional cash on cash: 6.76%

Airbnb Rental Income: $4015

Traditional Rental Income: $2693

Airbnb ROI: 8.43%

Traditional ROI: 6.76%

1500 8TH STREET SE

Winter Haven, FL

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

$410,000

Airbnb cash on cash: 6.17%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $4015

Traditional Rental Income: $3175

Airbnb ROI: 6.17%

Traditional ROI: 6.22%

1383 BUCKEYE TRACE BOULEVARD

Winter Haven, FL

3 beds | 2 baths | 1,507 sq.ft.

$315,000

Airbnb cash on cash: 8.37%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $4015

Traditional Rental Income: $2188

Airbnb ROI: 8.37%