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 260 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.	$315,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.59% Airbnb Rental Income: $2962 Traditional Rental Income: $2076 Airbnb ROI: 5.28% Traditional ROI: 4.59%
254 CLOVERDALE ROAD Winter Haven, FL Beautifully maintained 3-bedroom, 2-bath home located in the desirable Savanna Pointe comm...	3 beds \| 2 baths \| 1,463 sq.ft.	$259,900	Airbnb cash on cash: 9.85% Traditional cash on cash: 4.55% Airbnb Rental Income: $4015 Traditional Rental Income: $1858 Airbnb ROI: 9.85% Traditional ROI: 4.55%
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: 4.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2438 Airbnb ROI: 6.02% Traditional ROI: 4.17%
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: 5.26% Airbnb Rental Income: $4015 Traditional Rental Income: $2215 Airbnb ROI: 8.65% Traditional ROI: 5.26%
225 FRANKLIN COURT Winter Haven, FL Under contract-accepting backup offers. *PRICE REDUCTION* Refined luxury meets modern ...	4 beds \| 3 baths \| 2,362 sq.ft.	$427,500	Airbnb cash on cash: 7.3% Traditional cash on cash: 4.23% Airbnb Rental Income: $5016 Traditional Rental Income: $2761 Airbnb ROI: 7.3% Traditional ROI: 4.23%
1368 INNSBRUCK CT Winter Haven, FL POND VIEW END UNIT Villa in beautiful Vienna Square, Winter Haven's most charming 55+ comm...	2 beds \| 2 baths \| 1,369 sq.ft.	$219,900	Airbnb cash on cash: 6.03% Traditional cash on cash: 1.33% Airbnb Rental Income: $2962 Traditional Rental Income: $1302 Airbnb ROI: 6.03% Traditional ROI: 1.33%
731 CANBERRA ROAD Winter Haven, FL Under contract-accepting backup offers. Just REDUCED!! Welcome to this beautifully maintai...	3 beds \| 2 baths \| 2,140 sq.ft.	$325,000	Airbnb cash on cash: 8.29% Traditional cash on cash: 6.38% Airbnb Rental Income: $4015 Traditional Rental Income: $2573 Airbnb ROI: 8.29% Traditional ROI: 6.38%
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.	$349,900	Airbnb cash on cash: 7.62% Traditional cash on cash: 6.51% Airbnb Rental Income: $4015 Traditional Rental Income: $2792 Airbnb ROI: 7.62% Traditional ROI: 6.51%
1908 CROSSROADS BOULEVARD Winter Haven, FL Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region...	4 beds \| 3 baths \| 2,781 sq.ft.	$419,000	Airbnb cash on cash: 7.66% Traditional cash on cash: 4.55% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.66% Traditional ROI: 4.55%
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: 5.44% Airbnb Rental Income: $4015 Traditional Rental Income: $2174 Airbnb ROI: 9.62% Traditional ROI: 5.44%
220 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully upgraded lakefront hom...	4 beds \| 3 baths \| 2,705 sq.ft.	$789,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 2.97% Airbnb Rental Income: $5016 Traditional Rental Income: $3807 Airbnb ROI: 3.22% Traditional ROI: 2.97%
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: 4.49% Airbnb Rental Income: $5016 Traditional Rental Income: $3270 Airbnb ROI: 5.93% Traditional ROI: 4.49%
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: 4.45% Airbnb Rental Income: $5016 Traditional Rental Income: $2841 Airbnb ROI: 7.77% Traditional ROI: 4.45%
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: 2.78% Airbnb Rental Income: $4015 Traditional Rental Income: $3641 Airbnb ROI: 2.17% Traditional ROI: 2.78%
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.	$270,000	Airbnb cash on cash: 6.4% Traditional cash on cash: 6.28% Airbnb Rental Income: $2962 Traditional Rental Income: $2249 Airbnb ROI: 6.4% Traditional ROI: 6.28%
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: 9.56% Traditional cash on cash: 6.68% Airbnb Rental Income: $4015 Traditional Rental Income: $2422 Airbnb ROI: 9.56% 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.	$777,700	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.71% Airbnb Rental Income: $5016 Traditional Rental Income: $4133 Airbnb ROI: 3.51% Traditional ROI: 3.71%
1051 LENA RUN COURT Winter Haven, FL Under contract-accepting backup offers. Welcome home to this well-priced, beautifully main...	4 beds \| 2 baths \| 2,428 sq.ft.	$477,555	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.56% Airbnb Rental Income: $5016 Traditional Rental Income: $2604 Airbnb ROI: 6.67% Traditional ROI: 3.56%
202 SAINT LUCIE ROAD Winter Haven, FL **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepai...	3 beds \| 2 baths \| 1,764 sq.ft.	$328,999	Airbnb cash on cash: 7.98% Traditional cash on cash: 6.23% Airbnb Rental Income: $4015 Traditional Rental Income: $2616 Airbnb ROI: 7.98% Traditional ROI: 6.23%
250 VOLUSIA DRIVE Winter Haven, FL SELLER OFFERS $10,000 CREDIT TOWARD CLOSING COSTS OR UPGRADES, BUYERâS CHOICE PRIOR TO C...	3 beds \| 2 baths \| 1,449 sq.ft.	$299,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 5.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2186 Airbnb ROI: 9.11% Traditional ROI: 5.66%
3473 RALEIGH DRIVE Winter Haven, FL Under contract-accepting backup offers. Welcome to easy, low-maintenance living in the hig...	2 beds \| 2 baths \| 1,118 sq.ft.	$207,500	Airbnb cash on cash: 6.62% Traditional cash on cash: 5.13% Airbnb Rental Income: $2962 Traditional Rental Income: $1988 Airbnb ROI: 6.62% Traditional ROI: 5.13%
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: 5.58% Airbnb Rental Income: $5016 Traditional Rental Income: $3135 Airbnb ROI: 7.94% Traditional ROI: 5.58%
524 HAINES TRAIL Winter Haven, FL Beautifully maintained, highly upgraded home in a quiet, conveniently located community. F...	3 beds \| 2 baths \| 1,980 sq.ft.	$329,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 5.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2405 Airbnb ROI: 7.98% Traditional ROI: 5.55%
961 DREXEL AVENUE NE Winter Haven, FL ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-stor...	3 beds \| 2 baths \| 1,856 sq.ft.	$315,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.88% Airbnb Rental Income: $4015 Traditional Rental Income: $2448 Airbnb ROI: 8.27% Traditional ROI: 5.88%
1394 OAKMONT DRIVE Winter Haven, FL Experience resort-style living in the highly sought-after gated 55+ golf community of Lake...	3 beds \| 2 baths \| 2,606 sq.ft.	$549,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 1.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2511 Airbnb ROI: 3.03% Traditional ROI: 1.77%
802 MARCIA LOOP Winter Haven, FL Welcome to 802 Marcia Loop, a LAKEFRONT property located in southeast Winter Haven! The pr...	3 beds \| 2 baths \| 1,539 sq.ft.	$349,900	Airbnb cash on cash: 7.41% Traditional cash on cash: 4.71% Airbnb Rental Income: $4015 Traditional Rental Income: $2269 Airbnb ROI: 7.41% Traditional ROI: 4.71%
305 HERNANDO ROAD Winter Haven, FL Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step i...	4 beds \| 3 baths \| 2,569 sq.ft.	$479,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 6.35% Airbnb Rental Income: $5016 Traditional Rental Income: $3792 Airbnb ROI: 6.79% Traditional ROI: 6.35%
409 21ST STREET SW Winter Haven, FL Stunning 2 story 3 bath Spanish home with attention to details. This home has been renova...	4 beds \| 1 baths \| 2,322 sq.ft.	$550,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 5.68% Airbnb Rental Income: $5016 Traditional Rental Income: $4002 Airbnb ROI: 5.66% Traditional ROI: 5.68%
725 HERITAGE DRIVE NE Winter Haven, FL One or more photo(s) has been virtually staged. Located in the desirable Hamilton Pointe c...	4 beds \| 3 baths \| 3,114 sq.ft.	$559,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.62% Airbnb Rental Income: $5016 Traditional Rental Income: $3730 Airbnb ROI: 5.12% Traditional ROI: 4.62%
3208 TIMBERLINE ROAD Winter Haven, FL MOVE-IN READY & COMPLETELY REMODELED! This stunning home features a bright, open layout w...	2 beds \| 2 baths \| 1,043 sq.ft.	$240,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.56% Airbnb Rental Income: $2962 Traditional Rental Income: $1845 Airbnb ROI: 7.47% Traditional ROI: 5.56%
4 CASARENA COURT Winter Haven, FL This dynamically unique home in Winter Haven offers waterfront living, with direct access ...	3 beds \| 3 baths \| 3,911 sq.ft.	$524,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.77% Airbnb Rental Income: $4015 Traditional Rental Income: $2691 Airbnb ROI: 3.72% Traditional ROI: 2.77%
144 BEVERLY DRIVE Winter Haven, FL FLORIDA LIVING AT ITS BEST! Pool home + oversized lot + NO HOA + Chain of Lakes access jus...	4 beds \| 3 baths \| 2,492 sq.ft.	$399,500	Airbnb cash on cash: 8.47% Traditional cash on cash: 7.91% Airbnb Rental Income: $5016 Traditional Rental Income: $3781 Airbnb ROI: 8.47% Traditional ROI: 7.91%
3843 ELOISE ESTATES COURT Winter Haven, FL HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern upda...	3 beds \| 2 baths \| 1,600 sq.ft.	$280,000	Airbnb cash on cash: 9.09% Traditional cash on cash: 5.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2273 Airbnb ROI: 9.09% Traditional ROI: 5.74%
851 VIENNA DRIVE Winter Haven, FL Better Than New 2022 Home â Move-In Ready! VA Assumable Mortgage!!! Welcome to this b...	3 beds \| 2 baths \| 1,569 sq.ft.	$279,900	Airbnb cash on cash: 8.35% Traditional cash on cash: 4.54% Airbnb Rental Income: $4015 Traditional Rental Income: $2151 Airbnb ROI: 8.35% Traditional ROI: 4.54%
2218 ABBEY ROAD Winter Haven, FL Turnkey Villa in Stonebridge â Low Maintenance Living, Prime Location Step into easy ...	2 beds \| 2 baths \| 1,252 sq.ft.	$182,990	Airbnb cash on cash: 9.28% Traditional cash on cash: 7.57% Airbnb Rental Income: $2962 Traditional Rental Income: $1982 Airbnb ROI: 9.28% Traditional ROI: 7.57%
525 DRAYTON ROAD Winter Haven, FL Under contract-accepting backup offers. BEAT NEW CONSTRUCTION COSTS! Seller offering up to...	3 beds \| 2 baths \| 1,876 sq.ft.	$289,900	Airbnb cash on cash: 8.53% Traditional cash on cash: 5.3% Airbnb Rental Income: $4015 Traditional Rental Income: $2273 Airbnb ROI: 8.53% Traditional ROI: 5.3%
1590 VIENNA SQUARE DRIVE Winter Haven, FL Welcome to Vienna Square, a beautifully maintained 55+ gated community offering resort-sty...	2 beds \| 2 baths \| 1,231 sq.ft.	$210,000	Airbnb cash on cash: 7.97% Traditional cash on cash: 6.6% Airbnb Rental Income: $2962 Traditional Rental Income: $2006 Airbnb ROI: 7.97% Traditional ROI: 6.6%
1806 17TH STREET NW Winter Haven, FL Mediterranean Revival residence combining historic charm, remarkable updates, and an ideal...	3 beds \| 2 baths \| 1,750 sq.ft.	$360,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 6.04% Airbnb Rental Income: $4015 Traditional Rental Income: $2730 Airbnb ROI: 7.3% Traditional ROI: 6.04%
339 LAKE SMART CIRCLE Winter Haven, FL Motivated Seller. Introducing a beautifully maintained home offering an excellent and func...	3 beds \| 3 baths \| 2,173 sq.ft.	$338,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 5.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2626 Airbnb ROI: 7.34% Traditional ROI: 5.66%
2349 SALZBURG LOOP Winter Haven, FL HERONS, CRANES, EGRETS, AND DUCKS! You'll have a birds eye view of Florida's most beautifu...	3 beds \| 3 baths \| 1,724 sq.ft.	$309,900	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.62% Airbnb Rental Income: $4015 Traditional Rental Income: $2139 Airbnb ROI: 7.11% Traditional ROI: 3.62%

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.

$315,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $2962

Traditional Rental Income: $2076

Airbnb ROI: 5.28%

Traditional ROI: 4.59%

254 CLOVERDALE ROAD

Winter Haven, FL

3 beds | 2 baths | 1,463 sq.ft.

$259,900

Airbnb cash on cash: 9.85%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $4015

Traditional Rental Income: $1858

Airbnb ROI: 9.85%

Traditional ROI: 4.55%

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: 4.17%

Airbnb Rental Income: $4015

Traditional Rental Income: $2438

Airbnb ROI: 6.02%

Traditional ROI: 4.17%

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: 5.26%

Airbnb Rental Income: $4015

Traditional Rental Income: $2215

Airbnb ROI: 8.65%

Traditional ROI: 5.26%

225 FRANKLIN COURT

Winter Haven, FL

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

$427,500

Airbnb cash on cash: 7.3%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $5016

Traditional Rental Income: $2761

Airbnb ROI: 7.3%

Traditional ROI: 4.23%

1368 INNSBRUCK CT

Winter Haven, FL

2 beds | 2 baths | 1,369 sq.ft.

$219,900

Airbnb cash on cash: 6.03%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $2962

Traditional Rental Income: $1302

Airbnb ROI: 6.03%

Traditional ROI: 1.33%

731 CANBERRA ROAD

Winter Haven, FL

3 beds | 2 baths | 2,140 sq.ft.

$325,000

Airbnb cash on cash: 8.29%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $4015

Traditional Rental Income: $2573

Airbnb ROI: 8.29%

Traditional ROI: 6.38%

3334 FOX RIDGE DRIVE

Winter Haven, FL

3 beds | 3 baths | 1,542 sq.ft.

$349,900

Airbnb cash on cash: 7.62%

Traditional cash on cash: 6.51%

Airbnb Rental Income: $4015

Traditional Rental Income: $2792

Airbnb ROI: 7.62%