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.

Fort Worth Investment Property for Sale in Winter Haven, FL

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

Showing 326 Fort Worth Investment Property 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.	$369,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 4.26% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.6% Traditional ROI: 4.26%
475 ARCHAIC DRIVE Winter Haven, FL Welcome to your perfect sanctuary in the heart of Central Florida! With a freshly repainte...	4 beds \| 3 baths \| 2,643 sq.ft.	$699,500	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.13% Traditional ROI: 3.59%
3324 OAK HILL PLACE Winter Haven, FL Under contract-accepting backup offers. Upgraded Pool Home in Cypresswood Golf & Country C...	3 beds \| 2 baths \| 1,675 sq.ft.	$339,000	Airbnb cash on cash: 6.62% Traditional cash on cash: 4.35% Airbnb Rental Income: $4015 Traditional Rental Income: $2433 Airbnb ROI: 6.62% 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.	$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.	$265,000	Airbnb cash on cash: 5.86% Traditional cash on cash: 3.75% Airbnb Rental Income: $2962 Traditional Rental Income: $1751 Airbnb ROI: 5.86% Traditional ROI: 3.75%
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.	$285,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 5.39% Airbnb Rental Income: $4015 Traditional Rental Income: $2184 Airbnb ROI: 9.01% Traditional ROI: 5.39%
413 RUBY LAKE PLACE Winter Haven, FL Welcome to this beautifully maintained saltwater pool home offering comfort, style, and a ...	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%
934 LAKE ELBERT DRIVE SE Winter Haven, FL Under contract-accepting backup offers. Welcome to a one-of-a-kind lakeside retreat in the...	4 beds \| 2 baths \| 3,198 sq.ft.	$495,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.15% Airbnb Rental Income: $5016 Traditional Rental Income: $3322 Airbnb ROI: 6.59% Traditional ROI: 5.15%
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%
112 WODEN WAY Winter Haven, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	2 beds \| 3 baths \| 3,222 sq.ft.	$372,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.75% Airbnb Rental Income: $2962 Traditional Rental Income: $2491 Airbnb ROI: 1.15% Traditional ROI: 1.75%
113 CITRUS DRIVE Winter Haven, FL VERY MOTIVATED SELLER!! Welcome to this charming 3 Bedroom 2 Bath single-family home, wher...	3 beds \| 2 baths \| 2,016 sq.ft.	$289,900	Airbnb cash on cash: 9.11% Traditional cash on cash: 7.39% Airbnb Rental Income: $4015 Traditional Rental Income: $2685 Airbnb ROI: 9.11% Traditional ROI: 7.39%
2282 FIRESTONE PLACE Winter Haven, FL Welcome to Cypresswood Golf & Country Club Living! Discover this charming 2-bed, 2-bath, ...	2 beds \| 2 baths \| 1,164 sq.ft.	$205,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.97% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 7.37% Traditional ROI: 4.97%
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%
3372 LIVINGSTON WAY Winter Haven, FL Under contract-accepting backup offers. Welcome to this well-maintained 2-bedroom, 2-bath ...	2 beds \| 2 baths \| 1,275 sq.ft.	$250,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.37% Airbnb Rental Income: $2962 Traditional Rental Income: $1967 Airbnb ROI: 5.69% Traditional ROI: 4.37%
104 MORNING GLORY CIRCLE Winter Haven, FL Under contract-accepting backup offers. NEW ROOF ~PERFECT FOR BUYERS INSURANCE PREMIUM! Ju...	3 beds \| 2 baths \| 1,806 sq.ft.	$299,900	Airbnb cash on cash: 8.71% Traditional cash on cash: 5.84% Airbnb Rental Income: $4015 Traditional Rental Income: $2348 Airbnb ROI: 8.71% Traditional ROI: 5.84%
128 LAKE RING DRIVE Winter Haven, FL Back on the market no fault of the sellers! FHA appraisal complete and inspections too! ...	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%
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%
1383 BUCKEYE TRACE BOULEVARD Winter Haven, FL Under contract-accepting backup offers. Rare Find in a Gated Community! This beautiful 3-...	3 beds \| 2 baths \| 1,507 sq.ft.	$280,000	Airbnb cash on cash: 9.5% Traditional cash on cash: 5.82% Airbnb Rental Income: $4015 Traditional Rental Income: $2188 Airbnb ROI: 9.5% Traditional ROI: 5.82%
4007 CYPRESS LANDING S Winter Haven, FL Under contract-accepting backup offers. Welcome to your beautiful new home in the highly s...	2 beds \| 2 baths \| 1,578 sq.ft.	$234,900	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.09% Airbnb Rental Income: $2962 Traditional Rental Income: $1569 Airbnb ROI: 7.29% Traditional ROI: 4.09%
1 LAKE ELOISE LANE Winter Haven, FL Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in wint...	4 beds \| 3 baths \| 2,550 sq.ft.	$544,900	Airbnb cash on cash: 5.84% Traditional cash on cash: 3.17% Airbnb Rental Income: $5016 Traditional Rental Income: $2631 Airbnb ROI: 5.84% Traditional ROI: 3.17%
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 ESTATE â EXCLUSIVE HERON CAY ON LAKE ELOISE- WELCOME TO 3211 HERON COVE: Tu...	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%
152 AUDUBON COURT Winter Haven, FL GREAT 3 BEDROOM, 2 BATHROOM HOME ON AN OVERSIZED (.42 AC) CORNER LOT WITH PEACEFUL VIEWS O...	3 beds \| 2 baths \| 2,490 sq.ft.	$337,500	Airbnb cash on cash: 7.96% Traditional cash on cash: 5.85% Airbnb Rental Income: $4015 Traditional Rental Income: $2488 Airbnb ROI: 7.96% Traditional ROI: 5.85%
5609 FOREST RIDGE DRIVE Winter Haven, FL Under contract-accepting backup offers. AMAZING OPPORTUNITY IN WINTER HAVEN. NEW A/C!! Thi...	3 beds \| 2 baths \| 1,534 sq.ft.	$287,000	Airbnb cash on cash: 9.4% Traditional cash on cash: 5.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2149 Airbnb ROI: 9.4% Traditional ROI: 5.67%
1012 ROBIN LANE Winter Haven, FL PRICED BELOW APPRAISED VALUE; SELLER OFFERING CLOSING COST ASSISTANCE -Priced in the $200'...	3 beds \| 2 baths \| 1,496 sq.ft.	$295,500	Airbnb cash on cash: 9% Traditional cash on cash: 5.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2091 Airbnb ROI: 9% Traditional ROI: 5.17%
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.	$520,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 2.6% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.11% Traditional ROI: 2.6%
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, Major Upgrades & Clos...	3 beds \| 2 baths \| 1,764 sq.ft.	$349,999	Airbnb cash on cash: 7.5% Traditional cash on cash: 5.86% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.5% Traditional ROI: 5.86%
1075 8TH STREET NW Winter Haven, FL Income-Generating Property with Two In-Law Suites!! Maximize your rental income potential ...	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%
2 BRIDGEWATER DRIVE Winter Haven, FL Under contract-accepting backup offers. * SIGNIFICANT SAVINGS-HUGE PRICE REDUCTION* ...	4 beds \| 3 baths \| 3,472 sq.ft.	$484,900	Airbnb cash on cash: 7.35% Traditional cash on cash: 6.34% Airbnb Rental Income: $5016 Traditional Rental Income: $3534 Airbnb ROI: 7.35% Traditional ROI: 6.34%
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 Introducing a must-see condo in the esteemed gated community of Cypress Wood, this charmin...	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.	$335,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 3.75% Airbnb Rental Income: $4015 Traditional Rental Income: $2266 Airbnb ROI: 6.58% Traditional ROI: 3.75%
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%

Your search for investment property begins and ends here

Fort Worth 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.

$369,900

Airbnb cash on cash: 6.6%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.6%

Traditional ROI: 4.26%

475 ARCHAIC DRIVE

Winter Haven, FL

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

$699,500

Airbnb cash on cash: 4.13%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.13%

Traditional ROI: 3.59%

3324 OAK HILL PLACE

Winter Haven, FL

3 beds | 2 baths | 1,675 sq.ft.

$339,000

Airbnb cash on cash: 6.62%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $4015

Traditional Rental Income: $2433

Airbnb ROI: 6.62%

Traditional ROI: 4.35%

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.

$265,000

Airbnb cash on cash: 5.86%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2962

Traditional Rental Income: $1751

Airbnb ROI: 5.86%

Traditional ROI: 3.75%

1424 WALLACE MANOR PASS

Winter Haven, FL

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

$285,000

Airbnb cash on cash: 9.01%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $4015

Traditional Rental Income: $2184

Airbnb ROI: 9.01%