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 354 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
132 DUVAL Road Winter Haven, FL This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearl...	2 beds \| 2 baths \| 1,260 sq.ft.	$299,500	Airbnb cash on cash: -0.15% Traditional cash on cash: 4.88% Airbnb Rental Income: $1015 Traditional Rental Income: $2076 Airbnb ROI: -0.15% Traditional ROI: 4.88%
1620 17TH Street NW Winter Haven, FL New Lake Life listing, two houses one price. Must see property with no HOA. Chain of lakes...	2 beds \| 3 baths \| 965 sq.ft.	$449,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.62% Airbnb Rental Income: $1015 Traditional Rental Income: $2369 Airbnb ROI: -0.45% Traditional ROI: 3.62%
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.	$399,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.37% Airbnb Rental Income: $1656 Traditional Rental Income: $2438 Airbnb ROI: 1.04% Traditional ROI: 4.37%
695 22ND ST NW Winter Haven, FL A 3 bedroom, 2 bathroom home featuring a separate BONUS ROOM and MUD ROOM is hard to find....	3 beds \| 2 baths \| 1,708 sq.ft.	$249,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 8.2% Airbnb Rental Income: $1656 Traditional Rental Income: $2430 Airbnb ROI: 2.95% Traditional ROI: 8.2%
408 LANIER Lane Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom block home perfectly position...	3 beds \| 2 baths \| 1,680 sq.ft.	$320,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.54% Airbnb Rental Income: $1656 Traditional Rental Income: $2273 Airbnb ROI: 1.94% Traditional ROI: 5.54%
4840 OLD LUCERNE PARK RD Winter Haven, FL Relax and Enjoy Lakefront Living on Beautiful Lake Lucerne! Situated on 0.84 acres, this u...	3 beds \| 2 baths \| 1,927 sq.ft.	$415,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.45% Airbnb Rental Income: $1656 Traditional Rental Income: $2803 Airbnb ROI: 1.3% Traditional ROI: 5.45%
1500 AVENUE G NE Winter Haven, FL Welcome to this spacious and beautifully maintained 3-bedroom, 2-bath home offering over 2...	3 beds \| 2 baths \| 2,280 sq.ft.	$359,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.17% Airbnb Rental Income: $1656 Traditional Rental Income: $2701 Airbnb ROI: 1.69% Traditional ROI: 6.17%
615 AVENUE A NE Winter Haven, FL Charming Historic Winter Haven Bungalow on a Great sized lot near Downtown Winter Haven - ...	3 beds \| 2 baths \| 1,848 sq.ft.	$265,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 4.93% Airbnb Rental Income: $1656 Traditional Rental Income: $1763 Airbnb ROI: 2.64% Traditional ROI: 4.93%
1908 CROSSROADS Boulevard Winter Haven, FL MAJOR PRICE DROP! SELLER MOTIVATED!!! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in...	4 beds \| 3 baths \| 2,781 sq.ft.	$395,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 4.89% Airbnb Rental Income: $2237 Traditional Rental Income: $2772 Airbnb ROI: 1.93% Traditional ROI: 4.89%
315 LANCEOLATE Drive Winter Haven, FL Saltwater pool. Boat parking. Private community boat ramp. Welcome to 315 Lanceolate Drive...	3 beds \| 2 baths \| 2,153 sq.ft.	$469,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.09% Airbnb Rental Income: $1656 Traditional Rental Income: $2901 Airbnb ROI: 0.2% Traditional ROI: 4.09%
511 MARCIA Loop Winter Haven, FL 4 bedrooms, private backyard retreat with a hot tub, expansive Florida room, and solar-pow...	4 beds \| 3 baths \| 2,159 sq.ft.	$259,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 8.59% Airbnb Rental Income: $2237 Traditional Rental Income: $2787 Airbnb ROI: 4.06% Traditional ROI: 8.59%
817 REFLECTIONS Loop E Winter Haven, FL FOR SALE - 4 Bedroom, 2 Bathroom Beautiful Home in One of Winter Haven's Most Desirable Ar...	4 beds \| 2 baths \| 1,937 sq.ft.	$379,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.88% Airbnb Rental Income: $2237 Traditional Rental Income: $2495 Airbnb ROI: 2.57% Traditional ROI: 4.88%
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: 1.26% Traditional cash on cash: 5.44% Airbnb Rental Income: $1656 Traditional Rental Income: $2174 Airbnb ROI: 1.26% Traditional ROI: 5.44%
4132 MARTINDALE Loop Winter Haven, FL Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the hig...	4 beds \| 3 baths \| 1,894 sq.ft.	$399,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.02% Airbnb Rental Income: $2237 Traditional Rental Income: $2413 Airbnb ROI: 1.06% Traditional ROI: 3.02%
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.	$524,900	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.59% Airbnb Rental Income: $2237 Traditional Rental Income: $3270 Airbnb ROI: 1.34% Traditional ROI: 4.59%
1028 S LAKE MARIAM Drive Winter Haven, FL Rare opportunity to own a direct-waterfront pool home on Lake Mariam, now offered at a red...	3 beds \| 3 baths \| 3,255 sq.ft.	$819,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.92% Airbnb Rental Income: $1656 Traditional Rental Income: $3641 Airbnb ROI: -0.29% Traditional ROI: 2.92%
811 22ND Street NW Winter Haven, FL "Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven...	3 beds \| 3 baths \| 1,408 sq.ft.	$269,990	Airbnb cash on cash: 1.84% Traditional cash on cash: 6.68% Airbnb Rental Income: $1656 Traditional Rental Income: $2422 Airbnb ROI: 1.84% Traditional ROI: 6.68%
1095 W LAKE HAMILTON Drive Winter Haven, FL Welcome to this exceptional 4-bedroom, 3-bath home set on over half an acre, offering a ra...	4 beds \| 4 baths \| 2,363 sq.ft.	$699,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.23% Airbnb Rental Income: $2237 Traditional Rental Income: $4133 Airbnb ROI: 0.46% Traditional ROI: 4.23%
1015 ROBIN Lane Winter Haven, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home tucked away on a quiet c...	3 beds \| 2 baths \| 1,632 sq.ft.	$369,900	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.11% Airbnb Rental Income: $1656 Traditional Rental Income: $2252 Airbnb ROI: 1.05% Traditional ROI: 4.11%
4111 ISLAND LAKES Drive Winter Haven, FL Welcome to this beautifully maintained waterfront home on an oversized lot in the desirabl...	3 beds \| 2 baths \| 1,998 sq.ft.	$399,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.74% Airbnb Rental Income: $1656 Traditional Rental Income: $2688 Airbnb ROI: 0.75% Traditional ROI: 4.74%
202 SAINT LUCIE Road Winter Haven, FL **Location, Location, Location! Seller offering closing costs assistance to help with prep...	3 beds \| 2 baths \| 1,764 sq.ft.	$309,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 6.67% Airbnb Rental Income: $1656 Traditional Rental Income: $2616 Airbnb ROI: 1.78% Traditional ROI: 6.67%
271 MARIPOSA Winter Haven, FL Welcome to your Home Sweet Home in Winter Haven, Florida! This 3-bedroom, 2-bath gem sits ...	3 beds \| 2 baths \| 1,571 sq.ft.	$249,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 6.74% Airbnb Rental Income: $1656 Traditional Rental Income: $2167 Airbnb ROI: 2.59% Traditional ROI: 6.74%
1382 SALISBURY Drive Winter Haven, FL *SELLER'S ARE VERY MOTIVATED DUE TO JOB TRANSFER*Welcome to this updated 4-bedroom, 2....	4 beds \| 3 baths \| 1,764 sq.ft.	$293,899	Airbnb cash on cash: 3.6% Traditional cash on cash: 5.95% Airbnb Rental Income: $2237 Traditional Rental Income: $2326 Airbnb ROI: 3.6% Traditional ROI: 5.95%
1646 TRESSEL Court Winter Haven, FL PRICE DROP!! Nestled within a secure, gated community with impressively low HOA fees, this...	4 beds \| 2 baths \| 1,846 sq.ft.	$275,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.4% Airbnb Rental Income: $2237 Traditional Rental Income: $2261 Airbnb ROI: 3.14% Traditional ROI: 5.4%
120 MORNING GLORY Circle Winter Haven, FL Every Detail Has Been Thoughtfully Designed. Every Upgrade Has Been Thoughtfully Completed...	3 beds \| 2 baths \| 1,930 sq.ft.	$345,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.79% Airbnb Rental Income: $1656 Traditional Rental Income: $2414 Airbnb ROI: 1.02% Traditional ROI: 4.79%
5780 LAKESIDE LANDINGS Boulevard Winter Haven, FL From the moment you walk through the door, this home welcomes you with space, comfort, and...	4 beds \| 3 baths \| 2,526 sq.ft.	$305,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 7.46% Airbnb Rental Income: $2237 Traditional Rental Income: $2970 Airbnb ROI: 2.95% Traditional ROI: 7.46%
5638 ROYAL HILLS Street Winter Haven, FL WELCOME TO THIS WELL-KEPT PROPERTY WITH LOW HOA FEE. THIS IS A SPLIT PLAN FOUR BEDROOM/TWO...	4 beds \| 2 baths \| 2,012 sq.ft.	$316,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 5.53% Airbnb Rental Income: $2237 Traditional Rental Income: $2447 Airbnb ROI: 2.95% Traditional ROI: 5.53%
3129 AVENUE W NW Winter Haven, FL Virtually Staged. 3129 Avenue W NW is a residence with a functional layout and modern fini...	3 beds \| 1 baths \| 1,500 sq.ft.	$230,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 6.23% Airbnb Rental Income: $1656 Traditional Rental Income: $1818 Airbnb ROI: 3.35% Traditional ROI: 6.23%
3004 AVENUE S NW Winter Haven, FL Move right in and enjoy this charming 3-bedroom, 2-bathroom concrete block home in a conve...	3 beds \| 2 baths \| 1,153 sq.ft.	$219,900	Airbnb cash on cash: 3.63% Traditional cash on cash: 8.17% Airbnb Rental Income: $1656 Traditional Rental Income: $2136 Airbnb ROI: 3.63% Traditional ROI: 8.17%
961 DREXEL Avenue NE Winter Haven, FL >>>>Huge Price Reduction<<<< Check out this unique 2-story home in Winter Haven is full of...	3 beds \| 2 baths \| 1,856 sq.ft.	$290,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 6.46% Airbnb Rental Income: $1656 Traditional Rental Income: $2448 Airbnb ROI: 1.86% Traditional ROI: 6.46%
1394 OAKMONT Drive Winter Haven, FL Under contract-accepting backup offers. Experience resort-style living in the highly sough...	3 beds \| 2 baths \| 2,606 sq.ft.	$549,500	Airbnb cash on cash: -0.8% Traditional cash on cash: 1.77% Airbnb Rental Income: $1656 Traditional Rental Income: $2511 Airbnb ROI: -0.8% Traditional ROI: 1.77%
415 8TH Street NE Winter Haven, FL Welcome home to this charming bungalow-style 3-bedroom, 2-bath residence offering comfort,...	3 beds \| 2 baths \| 1,652 sq.ft.	$265,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 3.83% Airbnb Rental Income: $1656 Traditional Rental Income: $1570 Airbnb ROI: 2.31% Traditional ROI: 3.83%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Haven, FL

132 DUVAL Road

Winter Haven, FL

2 beds | 2 baths | 1,260 sq.ft.

$299,500

Airbnb cash on cash: -0.15%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1015

Traditional Rental Income: $2076

Airbnb ROI: -0.15%

Traditional ROI: 4.88%

1620 17TH Street NW

Winter Haven, FL

2 beds | 3 baths | 965 sq.ft.

$449,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1015

Traditional Rental Income: $2369

Airbnb ROI: -0.45%

Traditional ROI: 3.62%

357 RUBY LAKE Loop

Winter Haven, FL

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

$399,900

Airbnb cash on cash: 1.04%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1656

Traditional Rental Income: $2438

Airbnb ROI: 1.04%

Traditional ROI: 4.37%

695 22ND ST NW

Winter Haven, FL

3 beds | 2 baths | 1,708 sq.ft.

$249,900

Airbnb cash on cash: 2.95%

Traditional cash on cash: 8.2%

Airbnb Rental Income: $1656

Traditional Rental Income: $2430

Airbnb ROI: 2.95%

Traditional ROI: 8.2%

408 LANIER Lane

Winter Haven, FL

3 beds | 2 baths | 1,680 sq.ft.

$320,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1656

Traditional Rental Income: $2273

Airbnb ROI: 1.94%

Traditional ROI: 5.54%

4840 OLD LUCERNE PARK RD

Winter Haven, FL

3 beds | 2 baths | 1,927 sq.ft.

$415,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $1656

Traditional Rental Income: $2803

Airbnb ROI: 1.3%

Traditional ROI: 5.45%

1500 AVENUE G NE

Winter Haven, FL

3 beds | 2 baths | 2,280 sq.ft.

$359,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $1656

Traditional Rental Income: $2701

Airbnb ROI: 1.69%

Traditional ROI: 6.17%

615 AVENUE A NE

Winter Haven, FL

3 beds | 2 baths | 1,848 sq.ft.

$265,000

Airbnb cash on cash: 2.64%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $1656

Traditional Rental Income: $1763

Airbnb ROI: 2.64%