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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Haven, FL

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

Showing 312 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
404 TALAMONE DRIVE Winter Haven, FL BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in...	4 beds \| 3 baths \| 2,221 sq.ft.	$485,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.02% Airbnb Rental Income: $5016 Traditional Rental Income: $3098 Airbnb ROI: 5.98% Traditional ROI: 4.02%
357 RUBY LAKE LOOP Winter Haven, FL Welcome to your dream home in the gated community of Ruby Lake! This beautifully designed ...	3 beds \| 2 baths \| 2,107 sq.ft.	$415,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 4.12% Airbnb Rental Income: $4015 Traditional Rental Income: $2419 Airbnb ROI: 6.02% Traditional ROI: 4.12%
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.	$304,900	Airbnb cash on cash: 9.07% Traditional cash on cash: 5.95% Airbnb Rental Income: $4015 Traditional Rental Income: $2262 Airbnb ROI: 9.07% Traditional ROI: 5.95%
710 HERITAGE DRIVE NE Winter Haven, FL Under contract-accepting backup offers. Seller Motivated! $5000 towards buyer concessions ...	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%
330 Sterling Drive Winter Haven, FL Beautiful and spacious home located in a great neighborhood with excellent schools and a g...	3 beds \| 2 baths \| 1,426 sq.ft.	$295,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 5.58% Airbnb Rental Income: $4015 Traditional Rental Income: $2304 Airbnb ROI: 8.65% Traditional ROI: 5.58%
2343 SALZBURG LOOP Winter Haven, FL Under contract-accepting backup offers. THIS WELL-MAINTAINED HOME IS LOCATED IN A GREAT 55...	3 beds \| 2 baths \| 1,948 sq.ft.	$317,500	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.14% Airbnb Rental Income: $4015 Traditional Rental Income: $2309 Airbnb ROI: 7.98% Traditional ROI: 5.14%
225 FRANKLIN COURT Winter Haven, FL *PRICE REDUCTION* Refined luxury meets modern efficiency in this stunning 4-bedroom, 3...	4 beds \| 3 baths \| 2,362 sq.ft.	$429,900	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.01% Airbnb Rental Income: $5016 Traditional Rental Income: $2683 Airbnb ROI: 7.26% Traditional ROI: 4.01%
2017 MISTY MORNING DRIVE Winter Haven, FL Under contract-accepting backup offers. RECENT $20K PRICE REDUCTION as of 3/10/2026!!...	3 beds \| 2 baths \| 1,728 sq.ft.	$360,000	Airbnb cash on cash: 6.83% Traditional cash on cash: 3.98% Airbnb Rental Income: $4015 Traditional Rental Income: $2193 Airbnb ROI: 6.83% Traditional ROI: 3.98%
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: 5.67% Airbnb Rental Income: $4015 Traditional Rental Income: $2419 Airbnb ROI: 8.02% Traditional ROI: 5.67%
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.	$362,500	Airbnb cash on cash: 7.33% Traditional cash on cash: 5.76% Airbnb Rental Income: $4015 Traditional Rental Income: $2623 Airbnb ROI: 7.33% Traditional ROI: 5.76%
2282 FIRESTONE PLACE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	2 beds \| 2 baths \| 1,164 sq.ft.	$165,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 6.37% Airbnb Rental Income: $2962 Traditional Rental Income: $1813 Airbnb ROI: 9.34% Traditional ROI: 6.37%
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.	$445,000	Airbnb cash on cash: 7.16% Traditional cash on cash: 4.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.16% Traditional ROI: 4.23%
406 RUBY LAKE PLACE Winter Haven, FL Under contract-accepting backup offers. Welcome home to Ruby Lake, an established gated ne...	4 beds \| 3 baths \| 2,835 sq.ft.	$629,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.84% Airbnb Rental Income: $5016 Traditional Rental Income: $3695 Airbnb ROI: 4.35% Traditional ROI: 3.84%
503 HAMILTON SHORES COURT NE Winter Haven, FL WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMIL...	3 beds \| 3 baths \| 2,375 sq.ft.	$525,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2868 Airbnb ROI: 4.69% Traditional ROI: 4.1%
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.	$465,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3352 Airbnb ROI: 7.09% Traditional ROI: 5.62%
321 ORANGE BLOSSOM DRIVE Winter Haven, FL Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is ...	2 beds \| 3 baths \| 1,407 sq.ft.	$220,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.6% Airbnb Rental Income: $2962 Traditional Rental Income: $1762 Airbnb ROI: 6.08% Traditional ROI: 3.6%
2202 GARDEN LAKE DRIVE Winter Haven, FL Experience resort-style living in the prestigious gated community of Winterset, just minut...	3 beds \| 2 baths \| 1,442 sq.ft.	$249,000	Airbnb cash on cash: 9.62% Traditional cash on cash: 5.41% Airbnb Rental Income: $4015 Traditional Rental Income: $2168 Airbnb ROI: 9.62% Traditional ROI: 5.41%
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.	$375,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 3.64% Airbnb Rental Income: $5016 Traditional Rental Income: $2254 Airbnb ROI: 8.58% Traditional ROI: 3.64%
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.	$535,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.52% Airbnb Rental Income: $5016 Traditional Rental Income: $3284 Airbnb ROI: 5.93% Traditional ROI: 4.52%
3686 PLYMOUTH DRIVE Winter Haven, FL One or more photo(s) has been virtually staged. This spacious 4-bedroom, 3-bath home is lo...	4 beds \| 3 baths \| 2,404 sq.ft.	$369,900	Airbnb cash on cash: 7.77% Traditional cash on cash: 3.8% Airbnb Rental Income: $5016 Traditional Rental Income: $2613 Airbnb ROI: 7.77% Traditional ROI: 3.8%
3211 HERON COVE Winter Haven, FL Experience timeless elegance in this executive Mediterranean-style home, where refined arc...	4 beds \| 4 baths \| 3,480 sq.ft.	$799,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.18% Airbnb Rental Income: $5016 Traditional Rental Income: $4107 Airbnb ROI: 3.03% Traditional ROI: 3.18%
1028 S LAKE MARIAM DRIVE Winter Haven, FL Welcome to your slice of LAKEFRONT, POOL HOME paradise on the pristine shores of Lake Mari...	3 beds \| 3 baths \| 3,255 sq.ft.	$850,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.06% Airbnb Rental Income: $4015 Traditional Rental Income: $3074 Airbnb ROI: 2.17% Traditional ROI: 2.06%
1444 KINGFISH LN Winter Haven, FL Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situate...	2 beds \| 2 baths \| 2,005 sq.ft.	$285,000	Airbnb cash on cash: 6.01% Traditional cash on cash: 5.9% Airbnb Rental Income: $2962 Traditional Rental Income: $2249 Airbnb ROI: 6.01% Traditional ROI: 5.9%
2735 RUTLEDGE COURT Winter Haven, FL Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available...	2 beds \| 2 baths \| 1,419 sq.ft.	$220,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 6.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1990 Airbnb ROI: 7.42% Traditional ROI: 6.03%
2727 RUTLEDGE COURT Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to 2727 Rutledge Court, a beautifu...	3 beds \| 2 baths \| 1,536 sq.ft.	$235,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.28% Airbnb Rental Income: $4015 Traditional Rental Income: $2123 Airbnb ROI: 9.94% Traditional ROI: 5.28%
207 24TH COURT SW Winter Haven, FL Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the...	3 beds \| 2 baths \| 1,296 sq.ft.	$285,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2334 Airbnb ROI: 8.81% Traditional ROI: 5.74%
130 AUDUBON ROAD Winter Haven, FL BRAND NEW ROOF- 2026!!! LOOK AT THIS BEAUTIFUL 4 BEDROOM 2 BATH HOME BOASTING 2,503 SqFt....	4 beds \| 2 baths \| 2,503 sq.ft.	$346,000	Airbnb cash on cash: 9.67% Traditional cash on cash: 5.39% Airbnb Rental Income: $5016 Traditional Rental Income: $2602 Airbnb ROI: 9.67% Traditional ROI: 5.39%
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.	$230,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 3.71% Airbnb Rental Income: $2962 Traditional Rental Income: $1900 Airbnb ROI: 5.45% Traditional ROI: 3.71%
1051 LENA RUN COURT Winter Haven, FL Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence locat...	4 beds \| 2 baths \| 2,428 sq.ft.	$477,555	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.02% Airbnb Rental Income: $5016 Traditional Rental Income: $2360 Airbnb ROI: 6.67% Traditional ROI: 3.02%
5357 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WA...	3 beds \| 2 baths \| 2,363 sq.ft.	$440,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2393 Airbnb ROI: 5.02% Traditional ROI: 3.17%
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.	$289,900	Airbnb cash on cash: 9.13% Traditional cash on cash: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2365 Airbnb ROI: 9.13% Traditional ROI: 6.23%
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: 6.16% Airbnb Rental Income: $5016 Traditional Rental Income: $3594 Airbnb ROI: 7.04% Traditional ROI: 6.16%
250 VOLUSIA DRIVE Winter Haven, FL SELLER IS OFFERING $10K IN CONCESSIONS! Welcome to this charming 3-bedroom, 2-bathroom hom...	3 beds \| 2 baths \| 1,449 sq.ft.	$299,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.18% Airbnb Rental Income: $4015 Traditional Rental Income: $2050 Airbnb ROI: 9.11% Traditional ROI: 5.18%
3473 RALEIGH DRIVE Winter Haven, FL Welcome to easy, low-maintenance living in the highly sought-after 55+ gated community of ...	2 beds \| 2 baths \| 1,118 sq.ft.	$215,000	Airbnb cash on cash: 6.36% Traditional cash on cash: 4.24% Airbnb Rental Income: $2962 Traditional Rental Income: $1849 Airbnb ROI: 6.36% Traditional ROI: 4.24%
264 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a...	4 beds \| 2 baths \| 2,217 sq.ft.	$699,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3025 Airbnb ROI: 4.07% Traditional ROI: 2.59%
5329 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to 5329 Hogan Lane in the beautiful gated ...	3 beds \| 2 baths \| 1,847 sq.ft.	$349,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 3.72% Airbnb Rental Income: $4015 Traditional Rental Income: $2178 Airbnb ROI: 6.71% Traditional ROI: 3.72%
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.	$349,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 5.87% Airbnb Rental Income: $5016 Traditional Rental Income: $2967 Airbnb ROI: 8.99% Traditional ROI: 5.87%
5828 MARSH LANDING DRIVE Winter Haven, FL Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakes...	4 beds \| 2 baths \| 2,078 sq.ft.	$387,500	Airbnb cash on cash: 7.94% Traditional cash on cash: 3.42% Airbnb Rental Income: $5016 Traditional Rental Income: $2350 Airbnb ROI: 7.94% Traditional ROI: 3.42%
2452 SALZBURG LOOP Winter Haven, FL AMAZING OPPORTUNITY! ONE OF THE ONLY POOL HOMES LOCATED IN VIENNA SQUARE!!! This lovely ho...	2 beds \| 2 baths \| 1,729 sq.ft.	$332,452	Airbnb cash on cash: 4.13% Traditional cash on cash: 5.51% Airbnb Rental Income: $2962 Traditional Rental Income: $2710 Airbnb ROI: 4.13% Traditional ROI: 5.51%
2853 ATTWATER LOOP Winter Haven, FL Looking for a low-maintenance home in a 55+ community in Winter Haven, Florida? This 2019-...	2 beds \| 2 baths \| 1,385 sq.ft.	$210,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.87% Airbnb Rental Income: $2962 Traditional Rental Income: $2241 Airbnb ROI: 5.06% Traditional ROI: 4.87%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Haven, FL

404 TALAMONE DRIVE

Winter Haven, FL

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

$485,000

Airbnb cash on cash: 5.98%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $5016

Traditional Rental Income: $3098

Airbnb ROI: 5.98%

Traditional ROI: 4.02%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$415,000

Airbnb cash on cash: 6.02%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $4015

Traditional Rental Income: $2419

Airbnb ROI: 6.02%

Traditional ROI: 4.12%

145 POLK DRIVE

Winter Haven, FL

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

$304,900

Airbnb cash on cash: 9.07%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $4015

Traditional Rental Income: $2262

Airbnb ROI: 9.07%

Traditional ROI: 5.95%

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%

330 Sterling Drive

Winter Haven, FL

3 beds | 2 baths | 1,426 sq.ft.

$295,000

Airbnb cash on cash: 8.65%

Traditional cash on cash: 5.58%

Airbnb Rental Income: $4015

Traditional Rental Income: $2304

Airbnb ROI: 8.65%

Traditional ROI: 5.58%

2343 SALZBURG LOOP

Winter Haven, FL

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

$317,500

Airbnb cash on cash: 7.98%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $4015

Traditional Rental Income: $2309

Airbnb ROI: 7.98%

Traditional ROI: 5.14%

225 FRANKLIN COURT

Winter Haven, FL

4 beds | 3 baths | 2,362 sq.ft.

$429,900

Airbnb cash on cash: 7.26%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $5016

Traditional Rental Income: $2683

Airbnb ROI: 7.26%

Traditional ROI: 4.01%

2017 MISTY MORNING DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,728 sq.ft.

$360,000

Airbnb cash on cash: 6.83%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $4015

Traditional Rental Income: $2193

Airbnb ROI: 6.83%