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.

Investment Property for Sale in Winter Haven, FL

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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%
379 WINTER RIDGE BOULEVARD #379 Winter Haven, FL LOW HOA WATERFRONT BRAND NEW ROOF 2025 Located in the wonderful Winter Ridge communi...	2 beds \| 2 baths \| 1,073 sq.ft.	$162,990	Airbnb cash on cash: 9.7% Traditional cash on cash: 5.26% Airbnb Rental Income: $2962 Traditional Rental Income: $1588 Airbnb ROI: 9.7% Traditional ROI: 5.26%
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%
2727 RUTLEDGE COURT Winter Haven, FL One or more photo(s) has been virtually staged. Welcome to 2727 Rutledge Court, a beautifu...	3 beds \| 2 baths \| 1,536 sq.ft.	$239,900	Airbnb cash on cash: 9.72% Traditional cash on cash: 5.12% Airbnb Rental Income: $4015 Traditional Rental Income: $2115 Airbnb ROI: 9.72% Traditional ROI: 5.12%
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%
714 MAGNOLIA PLACE #714 Winter Haven, FL Where Every Day Feels Like VacationâLakefront Condo! Desirable Upstairs condominium with...	2 beds \| 2 baths \| 1,078 sq.ft.	$235,000	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.2% Airbnb Rental Income: $2962 Traditional Rental Income: $1686 Airbnb ROI: 5.87% Traditional ROI: 3.2%
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%
1075 8TH STREET NW Winter Haven, FL Income-Generating Property with Two In-Law Suites, sitting on a huge lot with a pool!! Max...	4 beds \| N/A baths \| 1,985 sq.ft.	$480,000	Airbnb cash on cash: 7.04% Traditional cash on cash: 5.22% Airbnb Rental Income: $5016 Traditional Rental Income: $3171 Airbnb ROI: 7.04% Traditional ROI: 5.22%
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%
2025 SAN MARCOS DRIVE SE #27 Winter Haven, FL Welcome to this ground-floor 1 bedroom, 1 bathroom condo located at 2025 San Marcos Dr, Ap...	1 beds \| 1 baths \| 792 sq.ft.	$120,000	Airbnb cash on cash: 7.79% Traditional cash on cash: 7.66% Airbnb Rental Income: $1982 Traditional Rental Income: $1448 Airbnb ROI: 7.79% Traditional ROI: 7.66%
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%

Real Estate investment in Winter-haven, FL

There are 311 properties for sale in the city of Winter Haven . The median list price in Winter Haven is $284,900 and the average price per square foot is $167. In January 2026, the average monthly cash on cash return in Winter Haven is 6.00%. The average monthly rental income in Winter Haven is $2,174.

Winter-haven, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 311 investment properties available for sale in Winter-haven.

In 2026, the best neighborhood to buy investment property is Winter Haven.

The ROI for Long-Term is higher than the Short-Term in Winter-haven with average rental income of $2,174.

Your search for investment property begins and ends here

Investment Property 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%