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.

Golden Highlands Investment Property for Sale in Winter Haven, FL

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

Showing 329 Golden Highlands Investment Property 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 STREET NW #23 Winter Haven, FL Welcome to Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to ...	2 beds \| 3 baths \| 1,334 sq.ft.	$178,000	Airbnb cash on cash: 8.84% Traditional cash on cash: 6.49% Airbnb Rental Income: $2962 Traditional Rental Income: $1881 Airbnb ROI: 8.84% Traditional ROI: 6.49%
404 TALAMONE DRIVE Winter Haven, FL BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in...	4 beds \| 3 baths \| 2,221 sq.ft.	$485,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.02% Airbnb Rental Income: $5016 Traditional Rental Income: $3098 Airbnb ROI: 5.98% Traditional ROI: 4.02%
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%
710 HERITAGE DRIVE NE Winter Haven, FL Under contract-accepting backup offers. Seller Motivated! $5000 towards buyer concessions ...	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%
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 *PRICE REDUCTION* Refined luxury meets modern efficiency in this stunning 4-bedroom, 3...	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%
731 CANBERRA ROAD Winter Haven, FL Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in th...	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.	$362,500	Airbnb cash on cash: 7.33% Traditional cash on cash: 6.25% Airbnb Rental Income: $4015 Traditional Rental Income: $2792 Airbnb ROI: 7.33% Traditional ROI: 6.25%
123 ELOISE OAKS DRIVE Winter Haven, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, ...	4 beds \| 3 baths \| 2,029 sq.ft.	$390,000	Airbnb cash on cash: 8.33% Traditional cash on cash: 4.59% Airbnb Rental Income: $5016 Traditional Rental Income: $2625 Airbnb ROI: 8.33% Traditional ROI: 4.59%
406 RUBY LAKE PLACE Winter Haven, FL Under contract-accepting backup offers. Welcome home to Ruby Lake, an established gated ne...	4 beds \| 3 baths \| 2,835 sq.ft.	$629,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 3.84% Airbnb Rental Income: $5016 Traditional Rental Income: $3695 Airbnb ROI: 4.35% Traditional ROI: 3.84%
503 HAMILTON SHORES COURT NE Winter Haven, FL Under contract-accepting backup offers. WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN O...	3 beds \| 3 baths \| 2,375 sq.ft.	$525,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 5.13% Airbnb Rental Income: $4015 Traditional Rental Income: $3374 Airbnb ROI: 4.69% Traditional ROI: 5.13%
321 ORANGE BLOSSOM DRIVE Winter Haven, FL Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is ...	2 beds \| 3 baths \| 1,407 sq.ft.	$220,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 4.81% Airbnb Rental Income: $2962 Traditional Rental Income: $2015 Airbnb ROI: 6.08% Traditional ROI: 4.81%
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%
2235 LAKERIDGE DRIVE Winter Haven, FL Welcome to 2235 Lakeridge Driveâan exceptional opportunity to own a beautifully designed...	3 beds \| 2 baths \| 1,893 sq.ft.	$315,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.36% Airbnb Rental Income: $4015 Traditional Rental Income: $2295 Airbnb ROI: 8.27% Traditional ROI: 5.36%
220 RUBY LAKE LANE Winter Haven, FL Welcome to this beautifully upgraded lakefront home nestled inside a private gated communi...	4 beds \| 3 baths \| 2,705 sq.ft.	$799,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.93% Airbnb Rental Income: $5016 Traditional Rental Income: $3807 Airbnb ROI: 3.17% Traditional ROI: 2.93%
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.	$355,000	Airbnb cash on cash: 9.11% Traditional cash on cash: 4.06% Airbnb Rental Income: $5016 Traditional Rental Income: $2306 Airbnb ROI: 9.11% Traditional ROI: 4.06%
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%
3211 HERON COVE Winter Haven, FL Under contract-accepting backup offers. Experience timeless elegance in this executive Med...	4 beds \| 4 baths \| 3,480 sq.ft.	$774,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 5.45% Airbnb Rental Income: $5016 Traditional Rental Income: $5654 Airbnb ROI: 3.15% Traditional ROI: 5.45%
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%
2735 RUTLEDGE COURT Winter Haven, FL Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available...	2 beds \| 2 baths \| 1,419 sq.ft.	$220,000	Airbnb cash on cash: 7.42% Traditional cash on cash: 6.03% Airbnb Rental Income: $2962 Traditional Rental Income: $1990 Airbnb ROI: 7.42% Traditional ROI: 6.03%
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.	$235,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.49% Airbnb Rental Income: $4015 Traditional Rental Income: $2168 Airbnb ROI: 9.94% Traditional ROI: 5.49%
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%
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.	$285,000	Airbnb cash on cash: 8.81% Traditional cash on cash: 6.34% Airbnb Rental Income: $4015 Traditional Rental Income: $2494 Airbnb ROI: 8.81% Traditional ROI: 6.34%
130 AUDUBON ROAD Winter Haven, FL BRAND NEW ROOF- 2026!!! LOOK AT THIS BEAUTIFUL 4 BEDROOM 2 BATH HOME BOASTING 2,503 SqFt....	4 beds \| 2 baths \| 2,503 sq.ft.	$346,000	Airbnb cash on cash: 9.67% Traditional cash on cash: 5.66% Airbnb Rental Income: $5016 Traditional Rental Income: $2689 Airbnb ROI: 9.67% Traditional ROI: 5.66%
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%
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.	$230,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 3.86% Airbnb Rental Income: $2962 Traditional Rental Income: $1934 Airbnb ROI: 5.45% Traditional ROI: 3.86%
221 WHITMAN ROAD Winter Haven, FL Under contract-accepting backup offers. Welcome to this well-maintained 3-bedroom, 2-bathr...	3 beds \| 2 baths \| 1,511 sq.ft.	$275,000	Airbnb cash on cash: 9.94% Traditional cash on cash: 5.8% Airbnb Rental Income: $4015 Traditional Rental Income: $2086 Airbnb ROI: 9.94% Traditional ROI: 5.8%
1051 LENA RUN COURT Winter Haven, FL Welcome home to this well-priced, beautifully maintained 4-bedroom, 2-bath residence locat...	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%
5357 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. WA...	3 beds \| 2 baths \| 2,363 sq.ft.	$440,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $4015 Traditional Rental Income: $2393 Airbnb ROI: 5.02% Traditional ROI: 3.17%
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%
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: 4.33% Airbnb Rental Income: $5016 Traditional Rental Income: $2772 Airbnb ROI: 7.04% Traditional ROI: 4.33%
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 Welcome to easy, low-maintenance living in the highly sought-after 55+ gated community of ...	2 beds \| 2 baths \| 1,118 sq.ft.	$210,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 5.06% Airbnb Rental Income: $2962 Traditional Rental Income: $1988 Airbnb ROI: 6.53% Traditional ROI: 5.06%
264 RUBY LAKE LANE Winter Haven, FL Under contract-accepting backup offers. Central Florida Lakefront home for sale now with a...	4 beds \| 2 baths \| 2,217 sq.ft.	$699,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.59% Airbnb Rental Income: $5016 Traditional Rental Income: $3025 Airbnb ROI: 4.07% Traditional ROI: 2.59%
5329 HOGAN LANE Winter Haven, FL Under contract-accepting backup offers. Welcome to 5329 Hogan Lane in the beautiful gated ...	3 beds \| 2 baths \| 1,847 sq.ft.	$349,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 3.72% Airbnb Rental Income: $4015 Traditional Rental Income: $2178 Airbnb ROI: 6.71% Traditional ROI: 3.72%
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%
2708 ATTWATER LOOP Winter Haven, FL Under contract-accepting backup offers. Impeccably maintained home in the sought-after Tra...	3 beds \| 2 baths \| 1,561 sq.ft.	$269,999	Airbnb cash on cash: 8.62% Traditional cash on cash: 5.21% Airbnb Rental Income: $4015 Traditional Rental Income: $2288 Airbnb ROI: 8.62% Traditional ROI: 5.21%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Winter Haven, FL

2500 21ST STREET NW #23

Winter Haven, FL

2 beds | 3 baths | 1,334 sq.ft.

$178,000

Airbnb cash on cash: 8.84%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $2962

Traditional Rental Income: $1881

Airbnb ROI: 8.84%

Traditional ROI: 6.49%

404 TALAMONE DRIVE

Winter Haven, FL

4 beds | 3 baths | 2,221 sq.ft.

$485,000

Airbnb cash on cash: 5.98%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $5016

Traditional Rental Income: $3098

Airbnb ROI: 5.98%

Traditional ROI: 4.02%

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%

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%

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%

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%