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 338 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
3041 EAGLE HAVEN DRIVE Winter Haven, FL PRICED BELOW APPRAISAL! Tucked behind citrus groves, your private, lakefront, DREAM ho...	3 beds \| 4 baths \| 3,456 sq.ft.	$725,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 4.65% Airbnb Rental Income: $4015 Traditional Rental Income: $4310 Airbnb ROI: 2.95% Traditional ROI: 4.65%
135 ELOISE OAKS DRIVE Winter Haven, FL Motivated Sellers! This impeccably maintained 3-bedroom, 2-bathroom custom home is packe...	3 beds \| 2 baths \| 1,866 sq.ft.	$380,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 4.07% Airbnb Rental Income: $4015 Traditional Rental Income: $2345 Airbnb ROI: 6.35% Traditional ROI: 4.07%
221 MCLEAN POINT Winter Haven, FL EXCLUSIVE GATED & GUARDED COMMUNITY \| TRANQUIL POND FRONTAGE \| EXTENSIVE HIGH-END FEATURES...	4 beds \| 4 baths \| 3,925 sq.ft.	$1,100,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 1.31% Airbnb Rental Income: $5016 Traditional Rental Income: $3713 Airbnb ROI: 1.58% Traditional ROI: 1.31%
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.	$429,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.42% Airbnb Rental Income: $4015 Traditional Rental Income: $2587 Airbnb ROI: 5.83% Traditional ROI: 4.42%
610 20TH STREET SW Winter Haven, FL One or more photo(s) has been virtually staged. Find your happy place on a sprawling near ...	3 beds \| 2 baths \| 2,181 sq.ft.	$275,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 7.32% Airbnb Rental Income: $4015 Traditional Rental Income: $2693 Airbnb ROI: 9.11% Traditional ROI: 7.32%
55 LAKE LINK CIRCLE SE Winter Haven, FL This charming and completely updated split-level home is ready to impress! From the moment...	3 beds \| 4 baths \| 2,550 sq.ft.	$460,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 7.86% Airbnb Rental Income: $4015 Traditional Rental Income: $4217 Airbnb ROI: 5.39% Traditional ROI: 7.86%
1500 8TH STREET SE Winter Haven, FL Beautiful Renovated 3Bed/2Bath Pool Home with 2,617 square feet of living area, this home ...	3 beds \| 2 baths \| 2,617 sq.ft.	$399,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 6.41% Airbnb Rental Income: $4015 Traditional Rental Income: $3175 Airbnb ROI: 6.37% Traditional ROI: 6.41%
42 ENCLAVE DRIVE Winter Haven, FL Luxury, Leisure & Little MaintenanceâWelcome to Cypresswood Living! Nestled in the hi...	3 beds \| 3 baths \| 2,370 sq.ft.	$300,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 2.55% Airbnb Rental Income: $4015 Traditional Rental Income: $1767 Airbnb ROI: 7.47% Traditional ROI: 2.55%
768 CANBERRA ROAD Winter Haven, FL Welcome to 768 Canberra Rd, located in the highly sought-after, gated/guarded community of...	3 beds \| 2 baths \| 1,888 sq.ft.	$339,000	Airbnb cash on cash: 7.49% Traditional cash on cash: 6.71% Airbnb Rental Income: $4015 Traditional Rental Income: $2909 Airbnb ROI: 7.49% Traditional ROI: 6.71%
112 WODEN WAY Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to this fabulous area! This home h...	2 beds \| 3 baths \| 3,222 sq.ft.	$416,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.47% Airbnb Rental Income: $2962 Traditional Rental Income: $2491 Airbnb ROI: 0.92% Traditional ROI: 1.47%
3711 JULIUS ESTATES BOULEVARD Winter Haven, FL This newly renovated home features 4 bedrooms, 2 baths, high ceilings, living area, dining...	4 beds \| 2 baths \| 1,842 sq.ft.	$330,000	Airbnb cash on cash: 9.92% Traditional cash on cash: 4.45% Airbnb Rental Income: $5016 Traditional Rental Income: $2295 Airbnb ROI: 9.92% Traditional ROI: 4.45%
128 LAKE RING DRIVE Winter Haven, FL What a fantastic property! A spacious 3-bedroom, 2-bathroom lakefront home with lots of u...	3 beds \| 2 baths \| 2,056 sq.ft.	$415,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 4.58% Airbnb Rental Income: $4015 Traditional Rental Income: $2496 Airbnb ROI: 6.27% Traditional ROI: 4.58%
5185 PEBBLE BEACH BOULEVARD Winter Haven, FL Golf course property! This charming 2-bed, 2-bath home backs up near the 17th green on the...	2 beds \| 2 baths \| 1,530 sq.ft.	$339,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.08% Airbnb Rental Income: $2962 Traditional Rental Income: $2205 Airbnb ROI: 4.31% Traditional ROI: 4.08%
1383 BUCKEYE TRACE BOULEVARD Winter Haven, FL Unique opportunity! This beautiful single family home 3 bedrooms and 2 bathrooms located ...	3 beds \| 2 baths \| 1,507 sq.ft.	$294,210	Airbnb cash on cash: 9.02% Traditional cash on cash: 5.52% Airbnb Rental Income: $4015 Traditional Rental Income: $2188 Airbnb ROI: 9.02% Traditional ROI: 5.52%
304 LAKE DAISY LOOP Winter Haven, FL NO HOA! Welcome home located in the beautiful city of Winter Haven, Florida! Offering 3 be...	3 beds \| 2 baths \| 1,474 sq.ft.	$315,000	Airbnb cash on cash: 8.35% Traditional cash on cash: 5.13% Airbnb Rental Income: $4015 Traditional Rental Income: $2205 Airbnb ROI: 8.35% Traditional ROI: 5.13%
3309 RALEIGH DR Winter Haven, FL MOVE IN READY!! Don't miss this beautifully maintained 2 bedroom, 2 bathroom home with a F...	2 beds \| 2 baths \| 1,118 sq.ft.	$225,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 4.72% Airbnb Rental Income: $2962 Traditional Rental Income: $1905 Airbnb ROI: 6.48% Traditional ROI: 4.72%
3416 GRENVILLE DRIVE Winter Haven, FL This stunning waterfront 2-bedroom, 2-bathroom home is located in the maintenance-free, ac...	2 beds \| 2 baths \| 1,315 sq.ft.	$264,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 4.57% Airbnb Rental Income: $2962 Traditional Rental Income: $2255 Airbnb ROI: 4.67% Traditional ROI: 4.57%
1001 MOCKINGBIRD CIRCLE Winter Haven, FL Discover your perfect Florida retreat in this charming 3-bedroom, 2-bathroom home located ...	3 beds \| 2 baths \| 1,853 sq.ft.	$350,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 5.66% Airbnb Rental Income: $4015 Traditional Rental Income: $2596 Airbnb ROI: 7.37% Traditional ROI: 5.66%
5891 FOREST RIDGE DRIVE Winter Haven, FL AMAZING OPPORTUNITY! Welcome home to 5891 Forest Ridge Dr. This stunning block home offers...	3 beds \| 2 baths \| 1,604 sq.ft.	$289,900	Airbnb cash on cash: 9.08% Traditional cash on cash: 5.37% Airbnb Rental Income: $4015 Traditional Rental Income: $2145 Airbnb ROI: 9.08% Traditional ROI: 5.37%
1905 16TH STREET NW Winter Haven, FL Under contract-accepting backup offers. Pride of Ownership! This wonderfully renovated 3 b...	3 beds \| 2 baths \| 1,418 sq.ft.	$275,000	Airbnb cash on cash: 9.96% Traditional cash on cash: 6.59% Airbnb Rental Income: $4015 Traditional Rental Income: $2283 Airbnb ROI: 9.96% Traditional ROI: 6.59%
3457 RALEIGH DRIVE Winter Haven, FL Upscale 55+ gated community of Traditions on Lake Ruby. Immaculate 2 bedroom 2 bath, 2 ca...	2 beds \| 2 baths \| 1,118 sq.ft.	$238,500	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.78% Airbnb Rental Income: $2962 Traditional Rental Income: $1878 Airbnb ROI: 5.56% Traditional ROI: 3.78%
3484 JULIUS ESTATES BOULEVARD Winter Haven, FL One or more photo(s) has been virtually staged. Experience serene living in this 2014-DR H...	4 beds \| 3 baths \| 2,900 sq.ft.	$319,900	Airbnb cash on cash: 9.87% Traditional cash on cash: 7.19% Airbnb Rental Income: $5016 Traditional Rental Income: $3184 Airbnb ROI: 9.87% Traditional ROI: 7.19%
503 HOLT CIRCLE Winter Haven, FL Cozy three bedrooms, 2 baths home, on a spacious fenced corner lot (0.22 acre). Total Upg...	3 beds \| 2 baths \| 1,305 sq.ft.	$269,900	Airbnb cash on cash: 9.95% Traditional cash on cash: 5.23% Airbnb Rental Income: $4015 Traditional Rental Income: $1955 Airbnb ROI: 9.95% Traditional ROI: 5.23%
3020 CANEEL STREET Winter Haven, FL PRICE IMPROVEMENT!!! Welcome to carefree living in this bright and airy super clean vill...	2 beds \| 2 baths \| 1,521 sq.ft.	$239,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 2.8% Airbnb Rental Income: $2962 Traditional Rental Income: $1788 Airbnb ROI: 4.97% Traditional ROI: 2.8%
3537 RALEIGH DRIVE Winter Haven, FL Welcome home! This wonderful 3 bedroom 2 bath home is located in the popular and gated 55+...	3 beds \| 2 baths \| 2,006 sq.ft.	$299,900	Airbnb cash on cash: 8.72% Traditional cash on cash: 6.69% Airbnb Rental Income: $4015 Traditional Rental Income: $2584 Airbnb ROI: 8.72% Traditional ROI: 6.69%
152 AUDUBON COURT Winter Haven, FL GREAT NEW PRICE!! Great Lake Daisy location - Located in prime SE Winter Haven on a large ...	3 beds \| 2 baths \| 2,538 sq.ft.	$350,000	Airbnb cash on cash: 7.83% Traditional cash on cash: 5.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2488 Airbnb ROI: 7.83% Traditional ROI: 5.8%
2237 AVENUE B NW Winter Haven, FL Make your appointment today to view this adorable 2 bedroom home that is filled with chara...	2 beds \| 2 baths \| 1,120 sq.ft.	$234,990	Airbnb cash on cash: 8.25% Traditional cash on cash: 3.85% Airbnb Rental Income: $2962 Traditional Rental Income: $1302 Airbnb ROI: 8.25% Traditional ROI: 3.85%
1012 ROBIN LANE Winter Haven, FL Priced Improvement This cozy 3-bedroom, 2-bath home in SE Winter Haven offers a peacef...	3 beds \| 2 baths \| 1,496 sq.ft.	$303,000	Airbnb cash on cash: 8.76% Traditional cash on cash: 5.02% Airbnb Rental Income: $4015 Traditional Rental Income: $2091 Airbnb ROI: 8.76% Traditional ROI: 5.02%
1396 LUCERNE LOOP ROAD NE Winter Haven, FL MOVE IN READY NO STORM DAMAGE! MOTIVATED SELLER OFFERING 2 YEAR HOME WARRANTY............	4 beds \| 3 baths \| 2,371 sq.ft.	$565,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 3.05% Airbnb Rental Income: $5016 Traditional Rental Income: $3251 Airbnb ROI: 4.45% Traditional ROI: 3.05%
3418 RALEIGH DRIVE Winter Haven, FL Located in the highly desirable, maintenance-free, gated community of Traditions on Lake R...	2 beds \| 2 baths \| 1,118 sq.ft.	$238,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.38% Airbnb Rental Income: $2962 Traditional Rental Income: $1917 Airbnb ROI: 4.99% Traditional ROI: 3.38%
2400 CRUMP ROAD Winter Haven, FL Under contract-accepting backup offers. Enjoy the Florida Lakefront Lifestyle in this meti...	3 beds \| 3 baths \| 2,175 sq.ft.	$565,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 4.88% Airbnb Rental Income: $4015 Traditional Rental Income: $3563 Airbnb ROI: 4.12% Traditional ROI: 4.88%
1201 GREY FOX HOLLOW DRIVE Winter Haven, FL Under contract-accepting backup offers. *Multiple offers received - please submit offers b...	4 beds \| 3 baths \| 3,252 sq.ft.	$595,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 2.17% Airbnb Rental Income: $5016 Traditional Rental Income: $2318 Airbnb ROI: 5.18% Traditional ROI: 2.17%
4545 MANDOLIN BOULEVARD Winter Haven, FL Under contract-accepting backup offers. Immaculate 3-Bedroom Home with Upgrades Galore in ...	3 beds \| 2 baths \| 1,760 sq.ft.	$370,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 3.55% Airbnb Rental Income: $4015 Traditional Rental Income: $2012 Airbnb ROI: 6.85% Traditional ROI: 3.55%
1421 AVENUE G NE Winter Haven, FL Great location! 3BD/2B home located at short walking distance from Lake Elbert. The family...	3 beds \| 2 baths \| 1,546 sq.ft.	$285,000	Airbnb cash on cash: 9.73% Traditional cash on cash: 5.97% Airbnb Rental Income: $4015 Traditional Rental Income: $2148 Airbnb ROI: 9.73% Traditional ROI: 5.97%
3717 HUNTINGTON LANE Winter Haven, FL Under contract-accepting backup offers. Back on the marketâ¦.Buyers sale contingency fell...	3 beds \| 2 baths \| 1,746 sq.ft.	$280,000	Airbnb cash on cash: 7.22% Traditional cash on cash: 3.73% Airbnb Rental Income: $4015 Traditional Rental Income: $2236 Airbnb ROI: 7.22% Traditional ROI: 3.73%
3834 BEDFORD AVENUE Winter Haven, FL This stunning 3-bedroom 2-bathroom home offers the perfect blend of modern upgrades and se...	3 beds \| 2 baths \| 1,831 sq.ft.	$405,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 2.9% Airbnb Rental Income: $4015 Traditional Rental Income: $2534 Airbnb ROI: 4.54% Traditional ROI: 2.9%
209 SANTA ROSA DRIVE Winter Haven, FL LOCATION,LOCATION,LOCATION.Welcome to your dream Home! Gated community. This 3/2.1 Pool ho...	3 beds \| 3 baths \| 2,338 sq.ft.	$435,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 5.84% Airbnb Rental Income: $4015 Traditional Rental Income: $3156 Airbnb ROI: 5.84% Traditional ROI: 5.84%
1437 GRAND CAYMAN CIRCLE Winter Haven, FL Under contract-accepting backup offers. Discover this stunning lakefront home on Lake Dext...	3 beds \| 2 baths \| 1,785 sq.ft.	$475,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.74% Airbnb Rental Income: $4015 Traditional Rental Income: $2645 Airbnb ROI: 4.89% Traditional ROI: 3.74%
1935 AUSTIN TERRACE Winter Haven, FL Nestled in the heart of Winter Haven, this exquisite residence beckons those with a pencha...	3 beds \| 3 baths \| 2,494 sq.ft.	$600,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 3.04% Airbnb Rental Income: $4015 Traditional Rental Income: $2841 Airbnb ROI: 3.61% Traditional ROI: 3.04%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Haven, FL

3041 EAGLE HAVEN DRIVE

Winter Haven, FL

3 beds | 4 baths | 3,456 sq.ft.

$725,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 4.65%

Airbnb Rental Income: $4015

Traditional Rental Income: $4310

Airbnb ROI: 2.95%

Traditional ROI: 4.65%

135 ELOISE OAKS DRIVE

Winter Haven, FL

3 beds | 2 baths | 1,866 sq.ft.

$380,000

Airbnb cash on cash: 6.35%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $4015

Traditional Rental Income: $2345

Airbnb ROI: 6.35%

Traditional ROI: 4.07%

221 MCLEAN POINT

Winter Haven, FL

4 beds | 4 baths | 3,925 sq.ft.

$1,100,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $5016

Traditional Rental Income: $3713

Airbnb ROI: 1.58%

Traditional ROI: 1.31%

357 RUBY LAKE LOOP

Winter Haven, FL

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

$429,000

Airbnb cash on cash: 5.83%

Traditional cash on cash: 4.42%

Airbnb Rental Income: $4015

Traditional Rental Income: $2587

Airbnb ROI: 5.83%

Traditional ROI: 4.42%

610 20TH STREET SW

Winter Haven, FL

3 beds | 2 baths | 2,181 sq.ft.

$275,000

Airbnb cash on cash: 9.11%

Traditional cash on cash: 7.32%

Airbnb Rental Income: $4015

Traditional Rental Income: $2693

Airbnb ROI: 9.11%

Traditional ROI: 7.32%

55 LAKE LINK CIRCLE SE

Winter Haven, FL

3 beds | 4 baths | 2,550 sq.ft.

$460,000

Airbnb cash on cash: 5.39%

Traditional cash on cash: 7.86%

Airbnb Rental Income: $4015

Traditional Rental Income: $4217

Airbnb ROI: 5.39%

Traditional ROI: 7.86%

1500 8TH STREET SE

Winter Haven, FL

3 beds | 2 baths | 2,617 sq.ft.

$399,000

Airbnb cash on cash: 6.37%

Traditional cash on cash: 6.41%

Airbnb Rental Income: $4015

Traditional Rental Income: $3175

Airbnb ROI: 6.37%

Traditional ROI: 6.41%

42 ENCLAVE DRIVE

Winter Haven, FL

3 beds | 3 baths | 2,370 sq.ft.

$300,000

Airbnb cash on cash: 7.47%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $4015

Traditional Rental Income: $1767

Airbnb ROI: 7.47%