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.

Condos for Sale in Winter Haven, FL

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

Showing 38 Condo 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
2500 21st St NW #23 Winter Haven, FL Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to ...	2 beds \| 2 baths \| 1,334 sq.ft.	$169,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 6.49% Airbnb Rental Income: $897 Traditional Rental Income: $1881 Airbnb ROI: -1.32% Traditional ROI: 6.49%
333 Lake Howard Dr NW #203C Winter Haven, FL Under contract-accepting backup offers. Enjoy a relaxed, maintenance-free lifestyle in thi...	2 beds \| 2 baths \| 1,030 sq.ft.	$109,900	Airbnb cash on cash: -1.59% Traditional cash on cash: 8.62% Airbnb Rental Income: $897 Traditional Rental Income: $1645 Airbnb ROI: -1.59% Traditional ROI: 8.62%
1776 6TH STREET NW #303 Winter Haven, FL Under contract-accepting backup offers. Improved Price!! All new window in the building......	2 beds \| 2 baths \| 1,347 sq.ft.	$115,000	Airbnb cash on cash: -3.95% Traditional cash on cash: 8.81% Airbnb Rental Income: $897 Traditional Rental Income: $1976 Airbnb ROI: -3.95% Traditional ROI: 8.81%
200 EL CAMINO DRIVE #101 Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. TH...	3 beds \| 3 baths \| 1,617 sq.ft.	$134,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 8.49% Airbnb Rental Income: $1757 Traditional Rental Income: $2059 Airbnb ROI: 2.44% Traditional ROI: 8.49%
1100 MARTINIQUE DRIVE #208 Winter Haven, FL Under contract-accepting backup offers. Spacious 2-bedroom, 2-bath upper corner condo in t...	2 beds \| 2 baths \| 1,024 sq.ft.	$94,750	Airbnb cash on cash: -0.84% Traditional cash on cash: 11.72% Airbnb Rental Income: $897 Traditional Rental Income: $1718 Airbnb ROI: -0.84% Traditional ROI: 11.72%
1700 6th St NW #C31 Winter Haven, FL HUGE PRICE DROP! Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community ...	2 beds \| 1 baths \| 840 sq.ft.	$99,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 9.2% Airbnb Rental Income: $897 Traditional Rental Income: $1599 Airbnb ROI: -1.51% Traditional ROI: 9.2%
702 Country Ln NE #702 Winter Haven, FL LAKEFRONT LIVING AT IT'S BEST! REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING A...	2 beds \| 2 baths \| 1,252 sq.ft.	$169,500	Airbnb cash on cash: -1.82% Traditional cash on cash: 8.78% Airbnb Rental Income: $897 Traditional Rental Income: $2272 Airbnb ROI: -1.82% Traditional ROI: 8.78%
700 MIRROR TERRACE NW #505 Winter Haven, FL Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, ...	2 beds \| 2 baths \| 1,190 sq.ft.	$109,900	Airbnb cash on cash: -5.43% Traditional cash on cash: 8.88% Airbnb Rental Income: $897 Traditional Rental Income: $2082 Airbnb ROI: -5.43% Traditional ROI: 8.88%
404 COUNTRY LANE NE #404 Winter Haven, FL Short Sale. Welcome to your new home in this peaceful and well-maintained community! This ...	2 beds \| 2 baths \| 1,252 sq.ft.	$110,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 11.35% Airbnb Rental Income: $897 Traditional Rental Income: $1903 Airbnb ROI: -1.28% Traditional ROI: 11.35%
2500 21ST STREET NW #47 Winter Haven, FL Nestled on beautiful Lake Hartridge, is this completely remodeled and move-in ready, stunn...	2 beds \| 3 baths \| 1,229 sq.ft.	$177,000	Airbnb cash on cash: -2.58% Traditional cash on cash: 5.46% Airbnb Rental Income: $897 Traditional Rental Income: $1915 Airbnb ROI: -2.58% Traditional ROI: 5.46%
831 Orchid Springs Dr #831 Winter Haven, FL Whether you are looking for your first home or first rental property, this condominium is ...	2 beds \| 1 baths \| 851 sq.ft.	$113,000	Airbnb cash on cash: -2.46% Traditional cash on cash: 7.37% Airbnb Rental Income: $897 Traditional Rental Income: $1642 Airbnb ROI: -2.46% Traditional ROI: 7.37%
333 Lake Howard Dr NW #314D Winter Haven, FL Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, n...	3 beds \| 2 baths \| 1,226 sq.ft.	$99,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 10.93% Airbnb Rental Income: $1757 Traditional Rental Income: $1996 Airbnb ROI: 3.45% Traditional ROI: 10.93%
1700 6th St NW #C1 Winter Haven, FL Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is ...	2 beds \| 1 baths \| 840 sq.ft.	$109,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 9.69% Airbnb Rental Income: $897 Traditional Rental Income: $1689 Airbnb ROI: -0.93% Traditional ROI: 9.69%
1710 GARDEN LAKE DRIVE #1710 Winter Haven, FL One or more photo(s) has been virtually staged. Short Sale. Back on the market with renewe...	2 beds \| 2 baths \| 1,103 sq.ft.	$169,900	Airbnb cash on cash: -2.05% Traditional cash on cash: 4.91% Airbnb Rental Income: $897 Traditional Rental Income: $1685 Airbnb ROI: -2.05% Traditional ROI: 4.91%
8304 Waterview Way #8304 Winter Haven, FL A Cozy Condo nestled in the back corner of the popular community of Winterset. Forgot your...	2 beds \| 2 baths \| 930 sq.ft.	$154,900	Airbnb cash on cash: -1.36% Traditional cash on cash: 6.87% Airbnb Rental Income: $897 Traditional Rental Income: $1776 Airbnb ROI: -1.36% Traditional ROI: 6.87%
1700 6th St NW #C26 Winter Haven, FL This fully remodeled condo offers comfortable and stylish living with two bedrooms and one...	2 beds \| 1 baths \| 840 sq.ft.	$116,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 7.76% Airbnb Rental Income: $897 Traditional Rental Income: $1533 Airbnb ROI: -0.94% Traditional ROI: 7.76%
700 Mirror Ter NW #303 Winter Haven, FL Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a...	2 beds \| 2 baths \| 1,029 sq.ft.	$99,900	Airbnb cash on cash: -3.84% Traditional cash on cash: 9.47% Airbnb Rental Income: $897 Traditional Rental Income: $1852 Airbnb ROI: -3.84% Traditional ROI: 9.47%
1100 MARTINIQUE DRIVE #203 Winter Haven, FL SO close to HWY 27, Legoland, shopping, golf, and MORE! This beautifully renovated 2/1 c...	2 beds \| 1 baths \| 826 sq.ft.	$115,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 8.05% Airbnb Rental Income: $897 Traditional Rental Income: $1527 Airbnb ROI: -0.66% Traditional ROI: 8.05%
1550 11TH STREET NE #F2 Winter Haven, FL Under contract-accepting backup offers. Welcome to this 2-bedroom, 2-bathroom ground-floor...	2 beds \| 2 baths \| 1,148 sq.ft.	$119,000	Airbnb cash on cash: -2.38% Traditional cash on cash: 8.65% Airbnb Rental Income: $897 Traditional Rental Income: $1825 Airbnb ROI: -2.38% Traditional ROI: 8.65%
413 WINTER RIDGE BOULEVARD #413 Winter Haven, FL Under contract-accepting backup offers. PRICE REDUCED on this wonderful opportunity! Welc...	2 beds \| 2 baths \| 1,073 sq.ft.	$144,500	Airbnb cash on cash: -0.96% Traditional cash on cash: 8.38% Airbnb Rental Income: $897 Traditional Rental Income: $1852 Airbnb ROI: -0.96% Traditional ROI: 8.38%
628 Ridge Ter Winter Haven, FL Updated 3-Bed, 2-Bath Condo in a Lakefront Community! Experience easy Florida livin...	3 beds \| 2 baths \| 1,073 sq.ft.	$169,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 7.52% Airbnb Rental Income: $1757 Traditional Rental Income: $1875 Airbnb ROI: 3.8% Traditional ROI: 7.52%
1700 6th St NW #B24 Winter Haven, FL 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, an...	2 beds \| 2 baths \| 960 sq.ft.	$105,000	Airbnb cash on cash: -2.52% Traditional cash on cash: 9.39% Airbnb Rental Income: $897 Traditional Rental Income: $1772 Airbnb ROI: -2.52% Traditional ROI: 9.39%
100 EL Camino Dr #111 Winter Haven, FL Owner motivated and ready to negotiate â WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR ...	1 beds \| 1 baths \| 931 sq.ft.	$65,000	Airbnb cash on cash: -8.11% Traditional cash on cash: 7.37% Airbnb Rental Income: $800 Traditional Rental Income: $1481 Airbnb ROI: -8.11% Traditional ROI: 7.37%
2040 SAN MARCOS DRIVE SE #206 Winter Haven, FL Under contract-accepting backup offers. This move-in-ready home features fresh interior pa...	2 beds \| 2 baths \| 1,276 sq.ft.	$166,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 7.92% Airbnb Rental Income: $897 Traditional Rental Income: $1853 Airbnb ROI: -0.25% Traditional ROI: 7.92%
1700 6TH STREET NW #C2 Winter Haven, FL Welcome to easy, low-maintenance Florida living in this fully furnished 1 bedroom, 1 bathr...	1 beds \| 1 baths \| 640 sq.ft.	$79,900	Airbnb cash on cash: -0.85% Traditional cash on cash: 11.55% Airbnb Rental Income: $800 Traditional Rental Income: $1453 Airbnb ROI: -0.85% Traditional ROI: 11.55%
607 Country Ln NE #607 Winter Haven, FL WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF...	2 beds \| 2 baths \| 1,252 sq.ft.	$149,500	Airbnb cash on cash: -1.51% Traditional cash on cash: 7.9% Airbnb Rental Income: $897 Traditional Rental Income: $1905 Airbnb ROI: -1.51% Traditional ROI: 7.9%
900 Avenue Z SE #A1 Winter Haven, FL Condo located in Winter Haven FL, the Water Ski Capital of the World and only 6 minutes fr...	2 beds \| 1 baths \| 840 sq.ft.	$124,900	Airbnb cash on cash: -1.88% Traditional cash on cash: 5.26% Airbnb Rental Income: $897 Traditional Rental Income: $1418 Airbnb ROI: -1.88% Traditional ROI: 5.26%
75 Sunset View Dr #75 Winter Haven, FL Beautiful lakefront living awaits in the gated community of Winterset! This beautifully ma...	2 beds \| 2 baths \| 2,249 sq.ft.	$405,000	Airbnb cash on cash: -2.39% Traditional cash on cash: 2.45% Airbnb Rental Income: $897 Traditional Rental Income: $2396 Airbnb ROI: -2.39% Traditional ROI: 2.45%
150 EL Dorado #105 Winter Haven, FL Discover this charming first-floor corner unit condo in the highly sought after Orchid Spr...	2 beds \| 2 baths \| 1,372 sq.ft.	$100,000	Airbnb cash on cash: -3.92% Traditional cash on cash: 10.31% Airbnb Rental Income: $897 Traditional Rental Income: $1942 Airbnb ROI: -3.92% Traditional ROI: 10.31%
306 Eagle Pond Dr Winter Haven, FL Beautiful completely updated condo in the highly desirable gated community of Cypresswood ...	2 beds \| 2 baths \| 1,017 sq.ft.	$211,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 5.21% Airbnb Rental Income: $897 Traditional Rental Income: $1857 Airbnb ROI: -1.28% Traditional ROI: 5.21%
1550 11TH STREET NE #H1 Winter Haven, FL Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully main...	2 beds \| 2 baths \| 1,148 sq.ft.	$115,000	Airbnb cash on cash: -2.34% Traditional cash on cash: 8.27% Airbnb Rental Income: $897 Traditional Rental Income: $1737 Airbnb ROI: -2.34% Traditional ROI: 8.27%
115 WINTER RIDGE DRIVE #115 Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully updated 3-bedroom, 2-b...	3 beds \| 2 baths \| 1,073 sq.ft.	$162,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 7.2% Airbnb Rental Income: $1757 Traditional Rental Income: $1791 Airbnb ROI: 3.86% Traditional ROI: 7.2%
645 Broadmoor Cir #645 Winter Haven, FL FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath...	2 beds \| 2 baths \| 1,278 sq.ft.	$189,900	Airbnb cash on cash: -1.84% Traditional cash on cash: 5.21% Airbnb Rental Income: $897 Traditional Rental Income: $1831 Airbnb ROI: -1.84% Traditional ROI: 5.21%

Your search for investment property begins and ends here

Condos for Sale in Winter Haven, FL

2500 21st St NW #23

Winter Haven, FL

2 beds | 2 baths | 1,334 sq.ft.

$169,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $897

Traditional Rental Income: $1881

Airbnb ROI: -1.32%

Traditional ROI: 6.49%

333 Lake Howard Dr NW #203C

Winter Haven, FL

2 beds | 2 baths | 1,030 sq.ft.

$109,900

Airbnb cash on cash: -1.59%

Traditional cash on cash: 8.62%

Airbnb Rental Income: $897

Traditional Rental Income: $1645

Airbnb ROI: -1.59%

Traditional ROI: 8.62%

1776 6TH STREET NW #303

Winter Haven, FL

2 beds | 2 baths | 1,347 sq.ft.

$115,000

Airbnb cash on cash: -3.95%

Traditional cash on cash: 8.81%

Airbnb Rental Income: $897

Traditional Rental Income: $1976

Airbnb ROI: -3.95%

Traditional ROI: 8.81%

200 EL CAMINO DRIVE #101

Winter Haven, FL

3 beds | 3 baths | 1,617 sq.ft.

$134,900

Airbnb cash on cash: 2.44%

Traditional cash on cash: 8.49%

Airbnb Rental Income: $1757

Traditional Rental Income: $2059

Airbnb ROI: 2.44%

Traditional ROI: 8.49%

1100 MARTINIQUE DRIVE #208

Winter Haven, FL

2 beds | 2 baths | 1,024 sq.ft.

$94,750

Airbnb cash on cash: -0.84%

Traditional cash on cash: 11.72%

Airbnb Rental Income: $897

Traditional Rental Income: $1718

Airbnb ROI: -0.84%

Traditional ROI: 11.72%

1700 6th St NW #C31

Winter Haven, FL

2 beds | 1 baths | 840 sq.ft.

$99,900

Airbnb cash on cash: -1.51%

Traditional cash on cash: 9.2%

Airbnb Rental Income: $897

Traditional Rental Income: $1599

Airbnb ROI: -1.51%

Traditional ROI: 9.2%

702 Country Ln NE #702

Winter Haven, FL

2 beds | 2 baths | 1,252 sq.ft.

$169,500

Airbnb cash on cash: -1.82%

Traditional cash on cash: 8.78%

Airbnb Rental Income: $897

Traditional Rental Income: $2272

Airbnb ROI: -1.82%

Traditional ROI: 8.78%

700 MIRROR TERRACE NW #505

Winter Haven, FL

2 beds | 2 baths | 1,190 sq.ft.

$109,900

Airbnb cash on cash: -5.43%

Traditional cash on cash: 8.88%

Airbnb Rental Income: $897

Traditional Rental Income: $2082

Airbnb ROI: -5.43%