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 281 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
3304 FOX RIDGE DRIVE Winter Haven, FL Great home available in Fox Ridge. This 2 bedroom, 2 bath, 2 car garage home is very well ...	2 beds \| 2 baths \| 1,153 sq.ft.	$239,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 6% Airbnb Rental Income: $2962 Traditional Rental Income: $1860 Airbnb ROI: 7.85% Traditional ROI: 6%
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: 4.49% Traditional cash on cash: 3.91% Airbnb Rental Income: $5016 Traditional Rental Income: $3637 Airbnb ROI: 4.49% Traditional ROI: 3.91%
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.	$489,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.09% Airbnb Rental Income: $5016 Traditional Rental Income: $3150 Airbnb ROI: 5.93% Traditional ROI: 4.09%
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%
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! This home offer...	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%
2017 MISTY MORNING DRIVE Winter Haven, FL Located on a quiet cul-de-sac within a small, quaint HOA, this beautifully remodeled 3-bed...	3 beds \| 2 baths \| 1,728 sq.ft.	$380,000	Airbnb cash on cash: 6.42% Traditional cash on cash: 3.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2178 Airbnb ROI: 6.42% Traditional ROI: 3.68%
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%
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%
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.	$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.	$448,900	Airbnb cash on cash: 7.09% Traditional cash on cash: 4.49% Airbnb Rental Income: $5016 Traditional Rental Income: $2898 Airbnb ROI: 7.09% Traditional ROI: 4.49%
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.	$470,000	Airbnb cash on cash: 7% Traditional cash on cash: 8.75% Airbnb Rental Income: $5016 Traditional Rental Income: $4761 Airbnb ROI: 7% Traditional ROI: 8.75%
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.	$264,900	Airbnb cash on cash: 9.05% Traditional cash on cash: 4.9% Airbnb Rental Income: $4015 Traditional Rental Income: $2120 Airbnb ROI: 9.05% Traditional ROI: 4.9%
107 MANDOLIN DRIVE Winter Haven, FL JUST LISTED! New Roof, New Interior Paint, Move-In Ready, SE Winter Haven Gated Community!...	4 beds \| 2 baths \| 1,665 sq.ft.	$345,000	Airbnb cash on cash: 9.55% Traditional cash on cash: 3.26% Airbnb Rental Income: $5016 Traditional Rental Income: $1953 Airbnb ROI: 9.55% Traditional ROI: 3.26%
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.	$379,000	Airbnb cash on cash: 8.48% Traditional cash on cash: 3.51% Airbnb Rental Income: $5016 Traditional Rental Income: $2223 Airbnb ROI: 8.48% Traditional ROI: 3.51%
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: 7.34% Traditional cash on cash: 3.94% Airbnb Rental Income: $5016 Traditional Rental Income: $2748 Airbnb ROI: 7.34% Traditional ROI: 3.94%
3211 HERON COVE Winter Haven, FL Executive-level gated pool home located in the exclusive community of Heron Cay! Welcome t...	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%
2735 RUTLEDGE COURT Winter Haven, FL Move-in-ready villa now available in the highly sought-after Verandahs at Lake Reeves comm...	2 beds \| 2 baths \| 1,419 sq.ft.	$225,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 6.05% Airbnb Rental Income: $2962 Traditional Rental Income: $2027 Airbnb ROI: 7.24% Traditional ROI: 6.05%
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%
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.	$290,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 3.33% Airbnb Rental Income: $4015 Traditional Rental Income: $1705 Airbnb ROI: 8.64% Traditional ROI: 3.33%
168 LAKE DAISY TERRACE Winter Haven, FL Spacious 4-bedroom, 2.5-bath home with 2,360 sq. ft. of living space in the sought-after L...	4 beds \| 3 baths \| 2,360 sq.ft.	$360,000	Airbnb cash on cash: 9.42% Traditional cash on cash: 6.34% Airbnb Rental Income: $5016 Traditional Rental Income: $2952 Airbnb ROI: 9.42% Traditional ROI: 6.34%
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.	$459,000	Airbnb cash on cash: 4.78% Traditional cash on cash: 3.07% Airbnb Rental Income: $4015 Traditional Rental Income: $2424 Airbnb ROI: 4.78% Traditional ROI: 3.07%
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%
264 RUBY LAKE LANE Winter Haven, FL Discover a lakefront retreat in Southeast Winter Haven! This pristine, move-in-ready 4 Be...	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 home to this beautiful three bedroom, two bathroom single family residence located...	3 beds \| 2 baths \| 1,376 sq.ft.	$260,000	Airbnb cash on cash: 9.3% Traditional cash on cash: 5.1% Airbnb Rental Income: $4015 Traditional Rental Income: $2125 Airbnb ROI: 9.3% Traditional ROI: 5.1%
1062 MEDINAH DRIVE Winter Haven, FL Location, Lifestyle & Leisure â All in One! Discover the perfect blend of comfort, conv...	2 beds \| 2 baths \| 1,398 sq.ft.	$219,500	Airbnb cash on cash: 6.73% Traditional cash on cash: 5.63% Airbnb Rental Income: $2962 Traditional Rental Income: $2051 Airbnb ROI: 6.73% Traditional ROI: 5.63%
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: 6.93% Traditional cash on cash: 4% Airbnb Rental Income: $4015 Traditional Rental Income: $2266 Airbnb ROI: 6.93% Traditional ROI: 4%
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 Looking for a low-maintenance home in a 55+ community in Winter Haven, Florida? This 2019-...	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%
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%
4034 DORAL Winter Haven, FL Welcome to this very well kept home located in the desirable SE Winter Haven community of ...	4 beds \| 3 baths \| 2,674 sq.ft.	$399,900	Airbnb cash on cash: 9.22% Traditional cash on cash: 7.61% Airbnb Rental Income: $5016 Traditional Rental Income: $3389 Airbnb ROI: 9.22% Traditional ROI: 7.61%
6011 COUNTRY WALK LANE Winter Haven, FL Welcome to this beautifully updated and immaculately maintained home that truly stands out...	3 beds \| 2 baths \| 1,728 sq.ft.	$370,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 4.31% Airbnb Rental Income: $4015 Traditional Rental Income: $2200 Airbnb ROI: 7.07% Traditional ROI: 4.31%
10 JIMMY LEE ROAD Winter Haven, FL Experience the best of both worlds â peaceful country living just minutes from town! Tuc...	3 beds \| 2 baths \| 1,680 sq.ft.	$439,000	Airbnb cash on cash: 5.61% Traditional cash on cash: 3.49% Airbnb Rental Income: $4015 Traditional Rental Income: $2286 Airbnb ROI: 5.61% Traditional ROI: 3.49%
1156 BRENTON MANOR DRIVE Winter Haven, FL Seller will contribute up to $5,000 BUYER CLOSING COSTS WITH AN ACCEPTABLE OFFER. This mov...	3 beds \| 2 baths \| 1,770 sq.ft.	$312,000	Airbnb cash on cash: 7.74% Traditional cash on cash: 4.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2253 Airbnb ROI: 7.74% Traditional ROI: 4.66%
751 AVENUE B SW Winter Haven, FL Charming property with plenty of desirable features! This 3 bedrooms 2 baths remodeled hom...	3 beds \| 2 baths \| 1,361 sq.ft.	$295,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 5.97% Airbnb Rental Income: $4015 Traditional Rental Income: $2310 Airbnb ROI: 9.01% Traditional ROI: 5.97%
1211 LAKE LOOP Winter Haven, FL Welcome to this beautifully maintained 3-bed, 2-bath home on a spacious fenced corner lot....	3 beds \| 2 baths \| 1,547 sq.ft.	$329,999	Airbnb cash on cash: 8.09% Traditional cash on cash: 4.69% Airbnb Rental Income: $4015 Traditional Rental Income: $2103 Airbnb ROI: 8.09% Traditional ROI: 4.69%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Haven, FL

3304 FOX RIDGE DRIVE

Winter Haven, FL

2 beds | 2 baths | 1,153 sq.ft.

$239,900

Airbnb cash on cash: 7.85%

Traditional cash on cash: 6%

Airbnb Rental Income: $2962

Traditional Rental Income: $1860

Airbnb ROI: 7.85%

Traditional ROI: 6%

475 ARCHAIC DRIVE

Winter Haven, FL

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

$649,500

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $5016

Traditional Rental Income: $3637

Airbnb ROI: 4.49%

Traditional ROI: 3.91%

404 TALAMONE DRIVE

Winter Haven, FL

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

$489,000

Airbnb cash on cash: 5.93%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $5016

Traditional Rental Income: $3150

Airbnb ROI: 5.93%

Traditional ROI: 4.09%

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%

2343 SALZBURG LOOP

Winter Haven, FL

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

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%

2017 MISTY MORNING DRIVE

Winter Haven, FL

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

$380,000

Airbnb cash on cash: 6.42%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $4015

Traditional Rental Income: $2178

Airbnb ROI: 6.42%