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
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%
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%
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 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%
1503 EAGLE POND DRIVE #1503 Winter Haven, FL Under contract-accepting backup offers. Introducing a must-see condo in the esteemed gated...	2 beds \| 2 baths \| 1,017 sq.ft.	$169,500	Airbnb cash on cash: 9.67% Traditional cash on cash: 6.83% Airbnb Rental Income: $2962 Traditional Rental Income: $1821 Airbnb ROI: 9.67% Traditional ROI: 6.83%
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%

Real Estate investment in Winter-haven, FL

There are 318 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $289,900 and the average price per square foot is $166. In October 2025, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,210.

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

There are 318 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 $2,210.

Your search for investment property begins and ends here

Investment Property 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%