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.

Mt.morris Investment Property for Sale in Winter Haven, FL

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

Showing 330 Mt.morris 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
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.	$649,500	Airbnb cash on cash: 4.52% Traditional cash on cash: 3.94% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.52% Traditional ROI: 3.94%
404 TALAMONE DRIVE Winter Haven, FL MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny,...	4 beds \| 3 baths \| 2,221 sq.ft.	$499,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.99% Airbnb Rental Income: $5016 Traditional Rental Income: $3150 Airbnb ROI: 5.79% Traditional ROI: 3.99%
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.	$480,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 5.22% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 7.04% Traditional ROI: 5.22%
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%
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 Under contract-accepting backup offers. Welcome to this lovely 3 bedroom and 2 bath home, ...	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%

Your search for investment property begins and ends here

Mt.morris Investment Property for Sale in Winter Haven, FL

475 ARCHAIC DRIVE

Winter Haven, FL

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

$649,500

Airbnb cash on cash: 4.52%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.52%

Traditional ROI: 3.94%

404 TALAMONE DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,221 sq.ft.

$499,000

Airbnb cash on cash: 5.79%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $5016

Traditional Rental Income: $3150

Airbnb ROI: 5.79%

Traditional ROI: 3.99%

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%