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.

Single Family Homes for Sale in Winter Haven, FL

Search for Single Family Residential for Sale in Winter Haven, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 290 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
808 Overlook Grove Drive Winter Haven, FL Sparkling 4 bedroom, 3 bath home located on a quiet cul-de-sac with no rear neighbors. Thi...	4 beds \| 3 baths \| 2,093 sq.ft.	$360,000	Airbnb cash on cash: 9.16% Traditional cash on cash: 5.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2662 Airbnb ROI: 9.16% Traditional ROI: 5.23%
135 ELOISE OAKS DRIVE Winter Haven, FL ACCEPTING OFFERS NOW! PRICED TO SELL - NOW ONLY $369,900. ANNUAL HOA FEES PAID THROUGH DEC...	3 beds \| 2 baths \| 1,866 sq.ft.	$368,500	Airbnb cash on cash: 6.63% Traditional cash on cash: 4.28% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.63% Traditional ROI: 4.28%
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%
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.	$254,900	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.93% Airbnb Rental Income: $2962 Traditional Rental Income: $1751 Airbnb ROI: 6.13% Traditional ROI: 3.93%
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.	$278,000	Airbnb cash on cash: 9.26% Traditional cash on cash: 5.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2184 Airbnb ROI: 9.26% Traditional ROI: 5.55%
413 RUBY LAKE PLACE Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully maintained saltwater p...	4 beds \| 2 baths \| 2,172 sq.ft.	$465,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 2.26% Airbnb Rental Income: $5016 Traditional Rental Income: $2185 Airbnb ROI: 6.41% Traditional ROI: 2.26%
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.	$369,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 7.01% Airbnb Rental Income: $4015 Traditional Rental Income: $3175 Airbnb ROI: 6.96% Traditional ROI: 7.01%
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%
5813 WINDRIDGE DRIVE Winter Haven, FL Updated 3-Bedroom Home with Modern Touches & Energy Efficiency in Winter Haven, FL This b...	4 beds \| 3 baths \| 2,320 sq.ft.	$345,000	Airbnb cash on cash: 9.9% Traditional cash on cash: 6.39% Airbnb Rental Income: $5016 Traditional Rental Income: $2854 Airbnb ROI: 9.9% Traditional ROI: 6.39%
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.	$400,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 5.2% Airbnb Rental Income: $4015 Traditional Rental Income: $2647 Airbnb ROI: 6.56% Traditional ROI: 5.2%
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%
2023 LEISURE DRIVE Winter Haven, FL NO HOA and NO CDD! Sitting on a spacious .21-acre corner lot, this 3 bedroom, 2-bath home ...	3 beds \| 2 baths \| 1,410 sq.ft.	$275,000	Airbnb cash on cash: 9.56% Traditional cash on cash: 6.58% Airbnb Rental Income: $4015 Traditional Rental Income: $2383 Airbnb ROI: 9.56% Traditional ROI: 6.58%
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.	$180,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 5.78% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 8.5% Traditional ROI: 5.78%
1908 CROSSROADS BOULEVARD Winter Haven, FL SELLER MOTIVATED! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossro...	4 beds \| 3 baths \| 2,781 sq.ft.	$469,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 4.26% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 6.75% Traditional ROI: 4.26%
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.	$425,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 5.06% Airbnb Rental Income: $5016 Traditional Rental Income: $2856 Airbnb ROI: 7.91% Traditional ROI: 5.06%
128 LAKE RING DRIVE Winter Haven, FL Under contract-accepting backup offers. Back on the market no fault of the sellers! FHA ...	3 beds \| 2 baths \| 2,056 sq.ft.	$399,000	Airbnb cash on cash: 6.56% Traditional cash on cash: 4.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2496 Airbnb ROI: 6.56% Traditional ROI: 4.8%
2202 GARDEN LAKE DRIVE Winter Haven, FL Welcome to beautiful southeast Winter Haven, home to the Chain of Lakes and Legoland! This...	3 beds \| 2 baths \| 1,442 sq.ft.	$269,000	Airbnb cash on cash: 8.97% Traditional cash on cash: 4.88% Airbnb Rental Income: $4015 Traditional Rental Income: $2120 Airbnb ROI: 8.97% Traditional ROI: 4.88%
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.	$824,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.67% Airbnb Rental Income: $5016 Traditional Rental Income: $3702 Airbnb ROI: 3.05% Traditional ROI: 2.67%
1883 GALLOWAY TERRACE Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to this charming, well-maintained ...	3 beds \| 2 baths \| 1,521 sq.ft.	$285,000	Airbnb cash on cash: 9.38% Traditional cash on cash: 5.79% Airbnb Rental Income: $4015 Traditional Rental Income: $2194 Airbnb ROI: 9.38% Traditional ROI: 5.79%
232 TERRANOVA BOULEVARD Winter Haven, FL Under contract-accepting backup offers. Welcome to 232 Terranova Blvd, a beautifully maint...	4 beds \| 2 baths \| 2,327 sq.ft.	$424,900	Airbnb cash on cash: 7.41% Traditional cash on cash: 4.21% Airbnb Rental Income: $5016 Traditional Rental Income: $2717 Airbnb ROI: 7.41% Traditional ROI: 4.21%
3686 PLYMOUTH DRIVE Winter Haven, FL This beautifully updated 4-bedroom, 3-bath residence offers a spacious and thoughtfully de...	4 beds \| 3 baths \| 2,404 sq.ft.	$389,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.89% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.29% Traditional ROI: 3.89%
3211 HERON COVE Winter Haven, FL Gated custom home located within the peaceful and picturesque community of Heron Cay â w...	4 beds \| 4 baths \| 3,480 sq.ft.	$849,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 4.35% Airbnb Rental Income: $5016 Traditional Rental Income: $5223 Airbnb ROI: 2.79% Traditional ROI: 4.35%
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%
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.	$499,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 2.75% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.32% Traditional ROI: 2.75%
3912 BALDWIN LANE Winter Haven, FL What? Furniture and a golf cart? Just bring your toothbrush! Your maintenance-free lifesty...	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%
202 SAINT LUCIE ROAD Winter Haven, FL Corner Lot Charmer in SE Winter Haven â Price Improvement! NO HOA, Income Potential & Bu...	3 beds \| 2 baths \| 1,764 sq.ft.	$334,999	Airbnb cash on cash: 7.88% Traditional cash on cash: 6.16% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.88% Traditional ROI: 6.16%
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 Peaceful Waterfront Living! Many Beautiful Features & Oversized Living Areas Great for Ent...	4 beds \| 3 baths \| 3,034 sq.ft.	$399,900	Airbnb cash on cash: 7.76% Traditional cash on cash: 4.07% Airbnb Rental Income: $5016 Traditional Rental Income: $2611 Airbnb ROI: 7.76% Traditional ROI: 4.07%
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%
900 LAKE JESSIE DRIVE Winter Haven, FL Live the ultimate lakefront lifestyle on Lake Jessie. This beautifully maintained single-s...	3 beds \| 3 baths \| 1,828 sq.ft.	$545,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.63% Airbnb Rental Income: $4015 Traditional Rental Income: $3311 Airbnb ROI: 4.33% Traditional ROI: 4.63%
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%
272 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. A Home of Elegance and Timeless Views. Discover...	4 beds \| 4 baths \| 2,965 sq.ft.	$800,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.91% Airbnb Rental Income: $5016 Traditional Rental Income: $4653 Airbnb ROI: 3.03% Traditional ROI: 3.91%
403 SAINT ANNS DRIVE Winter Haven, FL Seller MOTIVATED!! BRING OFFERS!! NEW ROOF to be installed prior to closing with an appro...	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%
1152 BOWLINE STREET Winter Haven, FL PRICE IMPROVEMENT!!! Welcome Home! This 3BR/2BA home located on a corner lot in the gated...	3 beds \| 2 baths \| 1,585 sq.ft.	$314,900	Airbnb cash on cash: 7.87% Traditional cash on cash: 4.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2207 Airbnb ROI: 7.87% Traditional ROI: 4.67%
305 HERNANDO ROAD Winter Haven, FL Welcome to your Dream home!! Step into this stunning residence through a spacious, light-f...	4 beds \| 3 baths \| 2,569 sq.ft.	$485,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 5.79% Airbnb Rental Income: $5016 Traditional Rental Income: $3557 Airbnb ROI: 6.74% Traditional ROI: 5.79%
409 21ST STREET SW Winter Haven, FL Stunning 2 story 3 bath Spanish home with attention to details. This home has been complet...	4 beds \| 2 baths \| 2,706 sq.ft.	$550,000	Airbnb cash on cash: 5.71% Traditional cash on cash: 5.73% Airbnb Rental Income: $5016 Traditional Rental Income: $4002 Airbnb ROI: 5.71% Traditional ROI: 5.73%
6011 COUNTRY WALK LANE Winter Haven, FL Pride of ownership shines in this well-built and meticulously maintained 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,728 sq.ft.	$379,999	Airbnb cash on cash: 7.1% Traditional cash on cash: 4.41% Airbnb Rental Income: $4015 Traditional Rental Income: $2200 Airbnb ROI: 7.1% Traditional ROI: 4.41%
140 MORNING GLORY CIRCLE Winter Haven, FL WINTER HAVEN CHAIN OF LAKES ACCESS...Immaculate Winterset home with direct access to Lake ...	3 beds \| 2 baths \| 1,730 sq.ft.	$330,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 4.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2190 Airbnb ROI: 7.35% Traditional ROI: 4.23%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Haven, FL

808 Overlook Grove Drive

Winter Haven, FL

4 beds | 3 baths | 2,093 sq.ft.

$360,000

Airbnb cash on cash: 9.16%

Traditional cash on cash: 5.23%

Airbnb Rental Income: $5016

Traditional Rental Income: $2662

Airbnb ROI: 9.16%

Traditional ROI: 5.23%

135 ELOISE OAKS DRIVE

Winter Haven, FL

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

$368,500

Airbnb cash on cash: 6.63%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.63%

Traditional ROI: 4.28%

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%

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.

$254,900

Airbnb cash on cash: 6.13%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $2962

Traditional Rental Income: $1751

Airbnb ROI: 6.13%

Traditional ROI: 3.93%

1424 WALLACE MANOR PASS

Winter Haven, FL

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

$278,000

Airbnb cash on cash: 9.26%

Traditional cash on cash: 5.55%

Airbnb Rental Income: $4015

Traditional Rental Income: $2184

Airbnb ROI: 9.26%

Traditional ROI: 5.55%

413 RUBY LAKE PLACE

Winter Haven, FL

4 beds | 2 baths | 2,172 sq.ft.

$465,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $5016

Traditional Rental Income: $2185

Airbnb ROI: 6.41%