Real Estate Investment Properties for Sale in Chesapeake, VA

Looking for investment property in Chesapeake, VA with high ROI ?

Explore a variety of short-term homes & houses in Chesapeake, VA. Invest wisely with VRBO & Chesapeake, VA 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 Chesapeake, VA

Search for Golden Highlands Investment Property for Sale in Chesapeake, Virginia. 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 448 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
622 Marcus Street Chesapeake, VA Welcome to this move-in ready 3-bedroom, 2-bath ranch style home in Chesapeake, offering t...	3 beds \| 2 baths \| 1,130 sq.ft.	$315,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.41% Airbnb Rental Income: $1466 Traditional Rental Income: $1920 Airbnb ROI: 1.41% Traditional ROI: 4.41%
2856 Flag Road Chesapeake, VA Welcome Home! This charming 3-bedroom, 1-bathroom ranch-style home is in the heart of Deep...	3 beds \| 1 baths \| 1,319 sq.ft.	$325,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.52% Airbnb Rental Income: $1357 Traditional Rental Income: $1695 Airbnb ROI: 1.06% Traditional ROI: 3.52%
1813 Sunsprite Loop Chesapeake, VA This Beautiful 4 bedroom 2 1/2 bath traditional style home located in the Landing at Grass...	4 beds \| 3 baths \| 2,446 sq.ft.	$624,999	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.41% Airbnb Rental Income: $1233 Traditional Rental Income: $2693 Airbnb ROI: -0.77% Traditional ROI: 2.41%
1002 Whitburn Terrace #373 Chesapeake, VA Energy-efficient single-family home on a premium cul-de-sac lot with scenic views! Located...	3 beds \| 3 baths \| 2,159 sq.ft.	$545,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.42% Airbnb Rental Income: $1370 Traditional Rental Income: $2790 Airbnb ROI: -0.19% Traditional ROI: 3.42%
812 Hardwood Drive Chesapeake, VA Welcome to this beautifully maintained 4-bedroom, 3 full bath ranch in the highly desirabl...	4 beds \| 3 baths \| 1,921 sq.ft.	$440,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 3.94% Airbnb Rental Income: $2643 Traditional Rental Income: $2573 Airbnb ROI: 2.58% Traditional ROI: 3.94%
627 Emerald Court Chesapeake, VA Motivated seller-bring your buyers! This 4-bedroom, 3 full bath home is ideally located in...	4 beds \| 3 baths \| 2,887 sq.ft.	$550,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.07% Airbnb Rental Income: $2643 Traditional Rental Income: $3176 Airbnb ROI: 1.81% Traditional ROI: 4.07%
1016 Middle Street Chesapeake, VA Beautifully designed 4-bedroom, 2.5-bath home with a bright, open layout perfect for enter...	4 beds \| 3 baths \| 1,835 sq.ft.	$365,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 5.09% Airbnb Rental Income: $1084 Traditional Rental Income: $2479 Airbnb ROI: -0.06% Traditional ROI: 5.09%
1125 Sutherlyn Court Chesapeake, VA This stunning all-brick home sits at the end of a quiet cul-de-sac on a beautifully mainta...	4 beds \| 3 baths \| 3,000 sq.ft.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $2655 Airbnb ROI: N/A Traditional ROI: 1.91%
641 Gallbush Road Chesapeake, VA Come View your new home in HICKORY! Spacious 4 bedroom 2 1/2 baths. Open floor plan featur...	4 beds \| 3 baths \| 2,200 sq.ft.	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 2.8%
1024 Middle Street Chesapeake, VA What a find! Spacious and modern colonial style home in a great location near shopping, sc...	3 beds \| 3 baths \| 1,500 sq.ft.	$329,900	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.4% Airbnb Rental Income: $1153 Traditional Rental Income: $2046 Airbnb ROI: 0.29% Traditional ROI: 4.4%
1000 York Drive Chesapeake, VA Here is the cutest 4-bedroom ranch you'll find in Greenbrier, tucked on a quiet cul-de-sac...	4 beds \| 3 baths \| 1,682 sq.ft.	$440,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.78% Airbnb Rental Income: $2643 Traditional Rental Income: $2400 Airbnb ROI: 2.84% Traditional ROI: 3.78%
426 San Roman Drive Chesapeake, VA Discover this stunning, renovated townhouse in the sought-after Las Gaviotas community, 1,...	3 beds \| 3 baths \| 1,540 sq.ft.	$359,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.77% Airbnb Rental Income: $1370 Traditional Rental Income: $2357 Airbnb ROI: 0.62% Traditional ROI: 4.77%
1016 Thoroughgood Way #307 Chesapeake, VA Beautifully maintained, one-owner, 3rd-floor condo with elevator access in a secure-entry ...	2 beds \| 2 baths \| 1,255 sq.ft.	$245,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 6.28% Airbnb Rental Income: $824 Traditional Rental Income: $2004 Airbnb ROI: -0.23% Traditional ROI: 6.28%
2712 Mark Street Chesapeake, VA Charming ranch-style home offering one-level living! The kitchen flows into the family roo...	4 beds \| 2 baths \| 1,550 sq.ft.	$315,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 5.39% Airbnb Rental Income: $1084 Traditional Rental Income: $2263 Airbnb ROI: 0.17% Traditional ROI: 5.39%
801 Poindexter Street #314 Chesapeake, VA Spacious, move-in ready condo just minutes from Norfolk Naval Base, Portsmouth Shipyard, a...	1 beds \| 1 baths \| 1,135 sq.ft.	$159,500	Airbnb cash on cash: 2.93% Traditional cash on cash: 8.31% Airbnb Rental Income: $1237 Traditional Rental Income: $1661 Airbnb ROI: 2.93% Traditional ROI: 8.31%
2218 Vicker Avenue Chesapeake, VA Fully remodeled in 2018. This contemporary open floor plan has 2 large living areas and 26...	4 beds \| 2 baths \| 2,692 sq.ft.	$440,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.61% Airbnb Rental Income: $1689 Traditional Rental Income: $2730 Airbnb ROI: 0.94% Traditional ROI: 4.61%
3313 Dodd Drive Chesapeake, VA Welcome Home! Step into this stunning home featuring soaring ceilings and a chef inspired ...	4 beds \| 3 baths \| 2,862 sq.ft.	$550,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.9% Airbnb Rental Income: $1233 Traditional Rental Income: $3014 Airbnb ROI: -0.34% Traditional ROI: 3.9%
1333 Great Bridge Boulevard Chesapeake, VA Welcome to Crestwood Gardens in Chesapeake! This home features major updates made within t...	3 beds \| 2 baths \| 1,317 sq.ft.	$279,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 6.14% Airbnb Rental Income: $1466 Traditional Rental Income: $2226 Airbnb ROI: 1.6% Traditional ROI: 6.14%
1108 Anne Avenue Chesapeake, VA Cute ranch home in Southern Chesapeake with new paint thought out. Incredible backyard for...	3 beds \| 1 baths \| 900 sq.ft.	$285,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 4.27% Airbnb Rental Income: $1153 Traditional Rental Income: $1736 Airbnb ROI: 0.68% Traditional ROI: 4.27%
2417 Baum Road Chesapeake, VA Comfort, luxury and space come together in this move-in-ready home. Vaulted ceilings and f...	4 beds \| 4 baths \| 3,985 sq.ft.	$980,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.67% Airbnb Rental Income: $null Traditional Rental Income: $3393 Airbnb ROI: N/A Traditional ROI: 1.67%
2145 Docking Post Drive Chesapeake, VA This meticulously maintained home radiates pride of ownership, move-in ready and perfect f...	4 beds \| 3 baths \| 2,359 sq.ft.	$575,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.27% Airbnb Rental Income: $1233 Traditional Rental Income: $2876 Airbnb ROI: -0.52% Traditional ROI: 3.27%
2807 Omar Street Chesapeake, VA Great Starter home, this 2-bedroom, 1 bath bungalow style home sits on a nice lot, minutes...	2 beds \| 1 baths \| 672 sq.ft.	$185,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 6.2% Airbnb Rental Income: $1444 Traditional Rental Income: $1516 Airbnb ROI: 3.35% Traditional ROI: 6.2%
3320 Daystone Arch Chesapeake, VA Welcome to 3320 Daystone Arch! Stunning 5 bedroom 2.5 bath nestled on a quiet street in th...	5 beds \| 3 baths \| 3,400 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 3.3%
4332 Hillingdon Bend #104 Chesapeake, VA Discover this BEAUTIFUL 2-bedroom home in the sought-after Western Branch area! This gem f...	2 beds \| 2 baths \| 1,367 sq.ft.	$232,700	Airbnb cash on cash: 1.26% Traditional cash on cash: 6.62% Airbnb Rental Income: $1189 Traditional Rental Income: $1982 Airbnb ROI: 1.26% Traditional ROI: 6.62%
1972 Beechwood Road Chesapeake, VA This charming four-bedroom Stephen Alexander Walnut model in the desirable Summer Park com...	4 beds \| 3 baths \| 3,114 sq.ft.	$689,900	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.83% Airbnb Rental Income: $1233 Traditional Rental Income: $3186 Airbnb ROI: -0.82% Traditional ROI: 2.83%
4000 Hamilton Street Chesapeake, VA This stunning 3-bed, 2-bath single-family home was completely transformed in 2023 - new ro...	3 beds \| 2 baths \| 1,235 sq.ft.	$335,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.4% Airbnb Rental Income: $1153 Traditional Rental Income: $1722 Airbnb ROI: 0.38% Traditional ROI: 3.4%
2432 Lakewood Lane Chesapeake, VA Beautifully updated and maintained brick ranch in highly desirable neighborhood. You will ...	4 beds \| 2 baths \| 1,887 sq.ft.	$420,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.02% Airbnb Rental Income: $2104 Traditional Rental Income: $2405 Airbnb ROI: 1.89% Traditional ROI: 4.02%
1327 HAZEL AVE Chesapeake, VA Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,176 sq.ft.	$291,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 4.8% Airbnb Rental Income: $1123 Traditional Rental Income: $1866 Airbnb ROI: 0.72% Traditional ROI: 4.8%
1310 Elder Avenue Chesapeake, VA This centrally located 3 bedroom 1 bathroom ranch style home is ready for you! Fresh paint...	3 beds \| 1 baths \| 1,140 sq.ft.	$275,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 4.7% Airbnb Rental Income: $1123 Traditional Rental Income: $1800 Airbnb ROI: 0.64% Traditional ROI: 4.7%
2041 Lockard Avenue Chesapeake, VA Great investment opportunity! This 3 bedroom, 1 bath ranch comes with a tenant in place th...	3 beds \| 1 baths \| 1,000 sq.ft.	$230,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.29% Airbnb Rental Income: $1123 Traditional Rental Income: $1675 Airbnb ROI: 1.03% Traditional ROI: 5.29%
1101 Park Avenue Chesapeake, VA Great investment! This 2-story duplex sits on a large corner lot in a quiet residential co...	N/A beds \| N/A baths \| 1,790 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $1379 Airbnb ROI: N/A Traditional ROI: 3.28%
327 Esplanade Place Chesapeake, VA Discover this stunning 3-bedroom, 2.5-bath townhome in the highly desirable Riverwalk neig...	3 beds \| 3 baths \| 2,100 sq.ft.	$370,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 5.11% Airbnb Rental Income: $1466 Traditional Rental Income: $2639 Airbnb ROI: 0.48% Traditional ROI: 5.11%
4314 Farringdon Way Chesapeake, VA RARE 1,870 sq ft layout with dual-primary suites! Two full upstairs suites provide privacy...	3 beds \| 3 baths \| 1,870 sq.ft.	$305,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 5.82% Airbnb Rental Income: $1175 Traditional Rental Income: $2244 Airbnb ROI: 0.76% Traditional ROI: 5.82%
4606 Olde Stone Way Chesapeake, VA This beautifully maintained 3-bedroom, 2-bath, move-in ready home instantly feels warm and...	3 beds \| 2 baths \| 1,245 sq.ft.	$250,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 5.05% Airbnb Rental Income: $1175 Traditional Rental Income: $1737 Airbnb ROI: 1.04% Traditional ROI: 5.05%
1920 Crayton Way Chesapeake, VA This is a home that immediately captures your attention and continues to impress at every ...	4 beds \| 3 baths \| 2,787 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $3158 Airbnb ROI: N/A Traditional ROI: 2.53%
1731 Woodmill Street Chesapeake, VA Located in the heart of Chesapeake's Greenbrier area, this meticulously maintained detache...	3 beds \| 3 baths \| 1,867 sq.ft.	$390,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 4.29% Airbnb Rental Income: $1951 Traditional Rental Income: $2315 Airbnb ROI: 1.89% Traditional ROI: 4.29%
1308 Seaboard Avenue Chesapeake, VA Remodeled in 2019, this updated home offers just over 2,000 sq ft of inviting living space...	4 beds \| 3 baths \| 2,002 sq.ft.	$355,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 5.72% Airbnb Rental Income: $1084 Traditional Rental Income: $2638 Airbnb ROI: -0.05% Traditional ROI: 5.72%
4134 Everett Street Chesapeake, VA Charming 3-bedroom, 2.5-bath home built in 2005, featuring a brand-new roof (2026) and HVA...	3 beds \| 3 baths \| 1,544 sq.ft.	$325,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 4.73% Airbnb Rental Income: $1153 Traditional Rental Income: $2105 Airbnb ROI: 0.37% Traditional ROI: 4.73%
401 Pelican Circle Chesapeake, VA This meticulously maintained 4-bedroom, 2.5-bath home offers approximately 2,400 square fe...	4 beds \| 3 baths \| 2,400 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $3133 Airbnb ROI: N/A Traditional ROI: 3.61%
1229 Decatur Street Chesapeake, VA This is such a lovely home with a fantastic backyard and oversized detached garage conveni...	3 beds \| 2 baths \| 1,332 sq.ft.	$270,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 5.47% Airbnb Rental Income: $1153 Traditional Rental Income: $1943 Airbnb ROI: 0.87% Traditional ROI: 5.47%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Chesapeake, VA

622 Marcus Street

Chesapeake, VA

3 beds | 2 baths | 1,130 sq.ft.

$315,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1466

Traditional Rental Income: $1920

Airbnb ROI: 1.41%

Traditional ROI: 4.41%

2856 Flag Road

Chesapeake, VA

3 beds | 1 baths | 1,319 sq.ft.

$325,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $1357

Traditional Rental Income: $1695

Airbnb ROI: 1.06%

Traditional ROI: 3.52%

1813 Sunsprite Loop

Chesapeake, VA

4 beds | 3 baths | 2,446 sq.ft.

$624,999

Airbnb cash on cash: -0.77%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $1233

Traditional Rental Income: $2693

Airbnb ROI: -0.77%

Traditional ROI: 2.41%

1002 Whitburn Terrace #373

Chesapeake, VA

3 beds | 3 baths | 2,159 sq.ft.

$545,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $1370

Traditional Rental Income: $2790

Airbnb ROI: -0.19%

Traditional ROI: 3.42%

812 Hardwood Drive

Chesapeake, VA

4 beds | 3 baths | 1,921 sq.ft.

$440,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2643

Traditional Rental Income: $2573

Airbnb ROI: 2.58%

Traditional ROI: 3.94%

627 Emerald Court

Chesapeake, VA

4 beds | 3 baths | 2,887 sq.ft.

$550,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $2643

Traditional Rental Income: $3176

Airbnb ROI: 1.81%

Traditional ROI: 4.07%

1016 Middle Street

Chesapeake, VA

4 beds | 3 baths | 1,835 sq.ft.

$365,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $1084

Traditional Rental Income: $2479

Airbnb ROI: -0.06%

Traditional ROI: 5.09%

1125 Sutherlyn Court

Chesapeake, VA

4 beds | 3 baths | 3,000 sq.ft.

$720,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2655

Airbnb ROI: N/A