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
475 ARCHAIC DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to your perfect sanctuary in the h...	4 beds \| 3 baths \| 2,643 sq.ft.	$674,500	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.76% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.32% Traditional ROI: 3.76%
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.	$419,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2587 Airbnb ROI: 5.99% Traditional ROI: 4.54%
145 POLK DRIVE Winter Haven, FL Beautifully Remodeled, Move-In Ready Home in the Heart of Winter Haven! Welcome to this...	3 beds \| 2 baths \| 1,605 sq.ft.	$319,900	Airbnb cash on cash: 8.61% Traditional cash on cash: 5.63% Airbnb Rental Income: $4015 Traditional Rental Income: $2262 Airbnb ROI: 8.61% Traditional ROI: 5.63%
710 HERITAGE DRIVE NE Winter Haven, FL Seller Motivated! $5000 towards buyer concessions or buy down rate with approved offer. Dr...	4 beds \| 2 baths \| 2,736 sq.ft.	$647,499	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.21% Airbnb Rental Income: $5016 Traditional Rental Income: $3191 Airbnb ROI: 4.54% Traditional ROI: 3.21%
3830 OSPREY POINTE CIRCLE Winter Haven, FL Beautiful community of Osprey Pointe on Lake Ned. This 2 bedroom/2 bath home is move in re...	2 beds \| 2 baths \| 1,438 sq.ft.	$249,900	Airbnb cash on cash: 6.27% Traditional cash on cash: 4.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1751 Airbnb ROI: 6.27% Traditional ROI: 4.03%
2920 DAYTON DRIVE Winter Haven, FL Motivated Seller! This Fabulous 2 Bedroom with a Den Home is located on a Corner Lot in th...	2 beds \| 2 baths \| 1,935 sq.ft.	$259,999	Airbnb cash on cash: 3.61% Traditional cash on cash: 3.62% Airbnb Rental Income: $2962 Traditional Rental Income: $2281 Airbnb ROI: 3.61% Traditional ROI: 3.62%
1424 WALLACE MANOR PASS Winter Haven, FL Welcome to this charming 3 bedroom, 2 bath home built in 2014, offering almost 1600 sq. ft...	3 beds \| 2 baths \| 1,578 sq.ft.	$264,900	Airbnb cash on cash: 9.76% Traditional cash on cash: 5.87% Airbnb Rental Income: $4015 Traditional Rental Income: $2184 Airbnb ROI: 9.76% Traditional ROI: 5.87%
2343 SALZBURG LOOP Winter Haven, FL THIS WELL-MAINTAINED HOME IS LOCATED IN A GREAT 55+ COMMUNITY CENTRALLY LOCATED IN WINTER ...	3 beds \| 2 baths \| 1,948 sq.ft.	$327,500	Airbnb cash on cash: 7.71% Traditional cash on cash: 5.91% Airbnb Rental Income: $4015 Traditional Rental Income: $2603 Airbnb ROI: 7.71% Traditional ROI: 5.91%
457 ADRIEL AVENUE Winter Haven, FL Do not miss this nice size home with 4 bedrooms and 2 bathrooms. New Roof. Perfect layout,...	4 beds \| 2 baths \| 2,088 sq.ft.	$359,900	Airbnb cash on cash: 9.89% Traditional cash on cash: 5.15% Airbnb Rental Income: $5016 Traditional Rental Income: $2389 Airbnb ROI: 9.89% Traditional ROI: 5.15%
731 CANBERRA ROAD Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought...	3 beds \| 2 baths \| 2,140 sq.ft.	$335,000	Airbnb cash on cash: 8.02% Traditional cash on cash: 6.11% Airbnb Rental Income: $4015 Traditional Rental Income: $2555 Airbnb ROI: 8.02% Traditional ROI: 6.11%
379 WINTER RIDGE BOULEVARD #379 Winter Haven, FL LOW HOA WATERFRONT BRAND NEW ROOF 2025 Located in the wonderful Winter Ridge communi...	2 beds \| 2 baths \| 1,073 sq.ft.	$167,990	Airbnb cash on cash: 9.39% Traditional cash on cash: 5.08% Airbnb Rental Income: $2962 Traditional Rental Income: $1588 Airbnb ROI: 9.39% Traditional ROI: 5.08%
3334 FOX RIDGE DRIVE 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.	$375,000	Airbnb cash on cash: 7.05% Traditional cash on cash: 5.6% Airbnb Rental Income: $4015 Traditional Rental Income: $2647 Airbnb ROI: 7.05% Traditional ROI: 5.6%
113 CITRUS DRIVE Winter Haven, FL Conventional loans only. VERY MOTIVATED SELLER!! Welcome to this charming 3 Bedroom 2 Bath...	3 beds \| 2 baths \| 2,016 sq.ft.	$285,000	Airbnb cash on cash: 9.29% Traditional cash on cash: 7.53% Airbnb Rental Income: $4015 Traditional Rental Income: $2685 Airbnb ROI: 9.29% Traditional ROI: 7.53%
2282 FIRESTONE PLACE Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to Cypresswood Golf & Country Club...	2 beds \| 2 baths \| 1,164 sq.ft.	$170,000	Airbnb cash on cash: 9.04% Traditional cash on cash: 6.16% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 9.04% Traditional ROI: 6.16%
1908 CROSSROADS BOULEVARD Winter Haven, FL UP TO $5000 BUYER CONCESSION TOWARDS CLOSING COSTS WITH APPROVED OFFER!!! SELLER MOTIVATED...	4 beds \| 3 baths \| 2,781 sq.ft.	$454,900	Airbnb cash on cash: 6.98% Traditional cash on cash: 4.42% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 6.98% Traditional ROI: 4.42%
2014 8TH TERRACE SE Winter Haven, FL Experience the best of Winter Haven living in this beautifully updated 4 bedroom, 3.5 bath...	4 beds \| 4 baths \| 2,722 sq.ft.	$475,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 8.65% Airbnb Rental Income: $5016 Traditional Rental Income: $4761 Airbnb ROI: 6.92% Traditional ROI: 8.65%
114 BELMONT DRIVE Winter Haven, FL Welcome to this spacious and beautifully designed pool home, perfect for entertaining and ...	4 beds \| 2 baths \| 2,069 sq.ft.	$415,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 5.2% Airbnb Rental Income: $5016 Traditional Rental Income: $2856 Airbnb ROI: 8.12% Traditional ROI: 5.2%
220 RUBY LAKE LANE Winter Haven, FL Welcome to 220 Ruby Lake Lane, a stunning lakefront pool residence in the highly sought-af...	4 beds \| 3 baths \| 2,705 sq.ft.	$799,977	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.78% Airbnb Rental Income: $5016 Traditional Rental Income: $3702 Airbnb ROI: 3.17% Traditional ROI: 2.78%
4970 MANDOLIN COURT Winter Haven, FL Welcome to lakeside living in the Mandolin community! Inviting single story home with 4-be...	4 beds \| 2 baths \| 1,749 sq.ft.	$389,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 3.4% Airbnb Rental Income: $5016 Traditional Rental Income: $2223 Airbnb ROI: 8.24% Traditional ROI: 3.4%
3686 PLYMOUTH DRIVE Winter Haven, FL This spacious 4-bedroom, 3-bath home is located in the desirable 55+ gated community of Tr...	4 beds \| 3 baths \| 2,404 sq.ft.	$388,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.88% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.29% Traditional ROI: 3.88%
3211 HERON COVE Winter Haven, FL Welcome to 3211 Heron Cove, a custom gated estate in the exclusive community of Heron Cay,...	4 beds \| 4 baths \| 3,480 sq.ft.	$799,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 4.68% Airbnb Rental Income: $5016 Traditional Rental Income: $5223 Airbnb ROI: 3.03% Traditional ROI: 4.68%
3020 CANEEL STREET Winter Haven, FL GREAT OPPORTUNITY!!! Totally TURNKEY with all NEW FURNISHINGS!!! Welcome to carefree livin...	2 beds \| 2 baths \| 1,521 sq.ft.	$219,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 2.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1788 Airbnb ROI: 4.39% Traditional ROI: 2.03%
2013 MARILYN AVENUE Winter Haven, FL Welcome to 2013 Marilyn Ave in Winter Haven! BRAND NEW ROOF! (08/01/2025)This 3-bedroom, 3...	3 beds \| 3 baths \| 1,943 sq.ft.	$320,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.62% Airbnb Rental Income: $4015 Traditional Rental Income: $2173 Airbnb ROI: 7.89% Traditional ROI: 4.62%
130 AUDUBON ROAD Winter Haven, FL LOOK AT THIS BEAUTIFUL 4 BEDROOM 2 BATH HOME BOASTING 2,503 SqFt. SITUATED ON AN OVERSIZED...	4 beds \| 2 baths \| 2,503 sq.ft.	$347,900	Airbnb cash on cash: 9.61% Traditional cash on cash: 5.93% Airbnb Rental Income: $5016 Traditional Rental Income: $2787 Airbnb ROI: 9.61% Traditional ROI: 5.93%
714 MAGNOLIA PLACE #714 Winter Haven, FL Where Every Day Feels Like VacationâLakefront Condo! Desirable Upstairs condominium with...	2 beds \| 2 baths \| 1,078 sq.ft.	$235,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.2% Airbnb Rental Income: $2962 Traditional Rental Income: $1686 Airbnb ROI: 5.87% Traditional ROI: 3.2%
5357 HOGAN LANE Winter Haven, FL One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with...	3 beds \| 2 baths \| 2,363 sq.ft.	$489,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.82% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.43% Traditional ROI: 2.82%
3912 BALDWIN LANE Winter Haven, FL Under contract-accepting backup offers. What? Furniture and a golf cart? Just bring your t...	2 beds \| 2 baths \| 1,719 sq.ft.	$295,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.84% Airbnb Rental Income: $2962 Traditional Rental Income: $1837 Airbnb ROI: 3.43% Traditional ROI: 1.84%
273 MARIPOSA Winter Haven, FL LOVELY FULL-SIZE HOME ON A CORNER LOT. Step inside and you'll find a generous family room ...	3 beds \| 2 baths \| 1,966 sq.ft.	$294,000	Airbnb cash on cash: 9% Traditional cash on cash: 6.21% Airbnb Rental Income: $4015 Traditional Rental Income: $2385 Airbnb ROI: 9% Traditional ROI: 6.21%
1075 8TH STREET NW Winter Haven, FL Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Max...	4 beds \| N/A baths \| 1,985 sq.ft.	$498,999	Airbnb cash on cash: 6.74% Traditional cash on cash: 4.98% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 6.74% Traditional ROI: 4.98%
264 RUBY LAKE LANE Winter Haven, FL Lakefront Gem in Southeast Winter Haven! This Clean and ready to Move In 4 Bedroom, 2 bat...	4 beds \| 2 baths \| 2,217 sq.ft.	$750,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.56% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 3.73% Traditional ROI: 2.56%
5392 CHANDLER DRIVE Winter Haven, FL PRICE IMPROVEMENT!!! Peaceful Waterfront Living! Many Beautiful Features & Oversized Livi...	4 beds \| 3 baths \| 3,034 sq.ft.	$349,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 4.79% Airbnb Rental Income: $5016 Traditional Rental Income: $2611 Airbnb ROI: 8.99% Traditional ROI: 4.79%
108 LAKE SEARS DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. Live where lakefront serenity meets endles...	3 beds \| 2 baths \| 1,688 sq.ft.	$375,000	Airbnb cash on cash: 6.99% Traditional cash on cash: 5.03% Airbnb Rental Income: $4015 Traditional Rental Income: $2465 Airbnb ROI: 6.99% Traditional ROI: 5.03%
3201 OAK TREE LANE Winter Haven, FL Welcome to this well cared for three bedroom, two bathroom home offering 1376 square feet ...	3 beds \| 2 baths \| 1,376 sq.ft.	$265,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 4.99% Airbnb Rental Income: $4015 Traditional Rental Income: $2125 Airbnb ROI: 9.11% Traditional ROI: 4.99%
1062 MEDINAH DRIVE Winter Haven, FL * Major Price Reduction!! * Location, Lifestyle & Leisure â All in One! Discover the...	2 beds \| 2 baths \| 1,398 sq.ft.	$199,995	Airbnb cash on cash: 7.47% Traditional cash on cash: 6.26% Airbnb Rental Income: $2962 Traditional Rental Income: $2051 Airbnb ROI: 7.47% Traditional ROI: 6.26%
4009 BEDFORD AVENUE Winter Haven, FL This fabulous Eco-Smart home is nestled in the highly desirable, maintenance-free, gated c...	3 beds \| 2 baths \| 1,871 sq.ft.	$322,900	Airbnb cash on cash: 6.86% Traditional cash on cash: 3.93% Airbnb Rental Income: $4015 Traditional Rental Income: $2266 Airbnb ROI: 6.86% Traditional ROI: 3.93%
4105 OAK DRIVE Winter Haven, FL New Lower price!!! Looking for a charming home, with land? Come check out this cute home o...	2 beds \| 1 baths \| 1,253 sq.ft.	$258,000	Airbnb cash on cash: 7.06% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1809 Airbnb ROI: 7.06% Traditional ROI: 5.13%
905 HILLSIDE COURT S Winter Haven, FL Welcome to this lovely 3 bedroom and 2 bath home, where modern comfort meets spacious Flor...	3 beds \| 2 baths \| 2,077 sq.ft.	$384,999	Airbnb cash on cash: 6.51% Traditional cash on cash: 4.87% Airbnb Rental Income: $4015 Traditional Rental Income: $2564 Airbnb ROI: 6.51% Traditional ROI: 4.87%
2853 ATTWATER LOOP Winter Haven, FL Welcome to 2853 Attwater Loop â a warm and inviting home in Traditions at Lake Ruby, one...	2 beds \| 2 baths \| 1,385 sq.ft.	$215,000	Airbnb cash on cash: 4.92% Traditional cash on cash: 4.63% Airbnb Rental Income: $2962 Traditional Rental Income: $2220 Airbnb ROI: 4.92% Traditional ROI: 4.63%
403 SAINT ANNS DRIVE Winter Haven, FL Under contract-accepting backup offers. NEW ROOF to be installed 10-27-25. Welcome HOME!!...	3 beds \| 2 baths \| 1,596 sq.ft.	$275,000	Airbnb cash on cash: 9.53% Traditional cash on cash: 6.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2384 Airbnb ROI: 9.53% Traditional ROI: 6.55%
2512 SHERWOOD STREET Winter Haven, FL A beautiful family home is now available in the desirable gated community of Crossroads at...	4 beds \| 3 baths \| 2,697 sq.ft.	$479,900	Airbnb cash on cash: 5.9% Traditional cash on cash: 3.44% Airbnb Rental Income: $5016 Traditional Rental Income: $2883 Airbnb ROI: 5.9% Traditional ROI: 3.44%

Real Estate investment in Winter-haven, FL

There are 330 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $293,046 and the average price per square foot is $167. In December 2025, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,225.

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

There are 330 investment properties available for sale in Winter-haven.

In 2025, 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 $2,225.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Haven, FL

475 ARCHAIC DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,643 sq.ft.

$674,500

Airbnb cash on cash: 4.32%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.32%

Traditional ROI: 3.76%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$419,000

Airbnb cash on cash: 5.99%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $4015

Traditional Rental Income: $2587

Airbnb ROI: 5.99%

Traditional ROI: 4.54%

145 POLK DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,605 sq.ft.

$319,900

Airbnb cash on cash: 8.61%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $4015

Traditional Rental Income: $2262

Airbnb ROI: 8.61%

Traditional ROI: 5.63%

710 HERITAGE DRIVE NE

Winter Haven, FL

4 beds | 2 baths | 2,736 sq.ft.

$647,499

Airbnb cash on cash: 4.54%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $5016

Traditional Rental Income: $3191

Airbnb ROI: 4.54%

Traditional ROI: 3.21%

3830 OSPREY POINTE CIRCLE

Winter Haven, FL

2 beds | 2 baths | 1,438 sq.ft.

$249,900

Airbnb cash on cash: 6.27%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $2962

Traditional Rental Income: $1751

Airbnb ROI: 6.27%

Traditional ROI: 4.03%

2920 DAYTON DRIVE

Winter Haven, FL

2 beds | 2 baths | 1,935 sq.ft.

$259,999

Airbnb cash on cash: 3.61%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $2962

Traditional Rental Income: $2281

Airbnb ROI: 3.61%

Traditional ROI: 3.62%

1424 WALLACE MANOR PASS

Winter Haven, FL

3 beds | 2 baths | 1,578 sq.ft.

$264,900

Airbnb cash on cash: 9.76%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $4015

Traditional Rental Income: $2184

Airbnb ROI: 9.76%

Traditional ROI: 5.87%

2343 SALZBURG LOOP

Winter Haven, FL

3 beds | 2 baths | 1,948 sq.ft.

$327,500

Airbnb cash on cash: 7.71%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $4015

Traditional Rental Income: $2603

Airbnb ROI: 7.71%