Real Estate Investment Properties for Sale in Old Greenwich, CT

Looking for investment property in Old Greenwich, CT with high ROI ?

Explore a variety of short-term homes & houses in Old Greenwich, CT. Invest wisely with VRBO & Old Greenwich, CT 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 Old Greenwich, CT

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
333 Sound Beach Avenue Old Greenwich, CT Ideally positioned in the heart of Old Greenwich, this charming residence offers an except...	4 beds \| 3 baths \| 2,965 sq.ft.	$3,850,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.72% Airbnb Rental Income: $null Traditional Rental Income: $8692 Airbnb ROI: N/A Traditional ROI: -0.72%
1535 E Putnam Avenue #304 Old Greenwich, CT Welcome to 1535 East Putnam Avenue in Old Greenwich. This charming 1 bedroom 1 bathroom co...	1 beds \| 1 baths \| 668 sq.ft.	$429,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 5.22% Airbnb Rental Income: $1498 Traditional Rental Income: $3444 Airbnb ROI: -0.71% Traditional ROI: 5.22%
Investment Properties for Sale in Other Cities of Connecticut
53 Canner Street unit: 4 New Haven , CT Recently updated East Rock two-bedroom condo with a private two car garage. Located on the...	2 beds \| 1 baths \| 890 sq.ft.	$365,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.88% Airbnb Rental Income: $1306 Traditional Rental Income: $1995 Airbnb ROI: -0.32% Traditional ROI: 2.88%
11 Ledgebrook Drive unit: 11 Norwalk , CT Don't miss this rare opportunity to own a completely updated two-bedroom townhouse with st...	2 beds \| 2 baths \| 1,173 sq.ft.	$459,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.4% Airbnb Rental Income: $2268 Traditional Rental Income: $2877 Airbnb ROI: -0.34% Traditional ROI: 2.4%
23 Heaton Street Waterbury , CT Beautiful 3-Bedroom Home Built in 2009 - Move-In Ready! Welcome to 23 Heaton Street, a wel...	3 beds \| 3 baths \| 1,716 sq.ft.	$374,995	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.94% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: -0.35% Traditional ROI: 3.94%
2 Elmwood Drive unit: 2 Fairfield , CT Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,399,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 0.1% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.79% Traditional ROI: 0.1%
89 Alma Street Naugatuck , CT *More Photos to come* 89 Alma Street is a charming Colonial in Naugatuck, CT. 3 Bedroo...	3 beds \| 3 baths \| 1,536 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.35% Airbnb Rental Income: $null Traditional Rental Income: $2984 Airbnb ROI: N/A Traditional ROI: 6.35%
286 Moose Hill Road Monroe , CT Welcome to this well maintained ranch style home nestled away from nearby amenities, but c...	2 beds \| 3 baths \| 1,012 sq.ft.	$549,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.7% Airbnb Rental Income: $2198 Traditional Rental Income: $2727 Airbnb ROI: 0.59% Traditional ROI: 2.7%
16 Marlene Drive Ledyard , CT RARE FIND! A 4-bedroom mobile home on its own land. You heard me right. Vinyl sided, newer...	4 beds \| 1 baths \| 1,260 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.16% Airbnb Rental Income: $null Traditional Rental Income: $2298 Airbnb ROI: N/A Traditional ROI: 10.16%
56 West Street Bolton , CT Beautifully renovated and move-in ready, 56 West Street offers the space, setting, and upd...	4 beds \| 2 baths \| 2,372 sq.ft.	$569,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.79% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 1.79%
32 WILLINGTON AVENUE Stafford Springs , CT Completely renovated old-style Colonial that sits on1.72 private acres. Nestled in the woo...	3 beds \| 2 baths \| 1,047 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 5.4%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.54% Airbnb Rental Income: $1388 Traditional Rental Income: $2560 Airbnb ROI: -0.23% Traditional ROI: 3.54%
198 Good Hill Road Oxford , CT Tranquility abounds on this sprawling old style cape home nestled in the hills of Oxford. ...	3 beds \| 2 baths \| 2,400 sq.ft.	$399,900	Airbnb cash on cash: -1.21% Traditional cash on cash: 5.87% Airbnb Rental Income: $1000 Traditional Rental Income: $3300 Airbnb ROI: -1.21% Traditional ROI: 5.87%
1200 Route 171 Woodstock , CT Adorable Country home on 3.22 acres with remodeled appliance eat in kitchen with large bre...	3 beds \| 1 baths \| 1,390 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.6% Airbnb Rental Income: $null Traditional Rental Income: $2212 Airbnb ROI: N/A Traditional ROI: 6.6%
36 Attawan Rd Niantic , CT Beautifully Renovated Year Round Beach Home! Move right into this charming Four Bedroom, ...	3 beds \| 2 baths \| 1,786 sq.ft.	$895,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.59% Airbnb Rental Income: $1952 Traditional Rental Income: $2800 Airbnb ROI: -0.05% Traditional ROI: 1.59%
106 Oakwood Road East Lyme , CT * OFFERS DUE BY MON, 3/30 AT 10am * Welcome to year-round coastal living in the highly...	3 beds \| 2 baths \| 1,636 sq.ft.	$459,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.26% Airbnb Rental Income: $2429 Traditional Rental Income: $2831 Airbnb ROI: 1.94% Traditional ROI: 4.26%

Real Estate investment in Old-greenwich, CT

There are 2 properties for sale in the city of Old Greenwich . The median list price in Old Greenwich is $2,572,500 and the average price per square foot is $919. In April 2026, the average monthly cash on cash return in Old Greenwich is -1.00%. The average monthly rental income in Old Greenwich is $3,444.

Old-greenwich, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Old-greenwich.

In 2026, the best neighborhood to buy investment property is Old Greenwich.

The ROI for Short-Term is higher than the Long-Term in Old-greenwich with average rental income of $1,498.

Your search for investment property begins and ends here

Investment Property for Sale in Old Greenwich, CT

333 Sound Beach Avenue

Old Greenwich, CT

4 beds | 3 baths | 2,965 sq.ft.

$3,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.72%

Airbnb Rental Income: $null

Traditional Rental Income: $8692

Airbnb ROI: N/A

Traditional ROI: -0.72%

1535 E Putnam Avenue #304

Old Greenwich, CT

1 beds | 1 baths | 668 sq.ft.

$429,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $1498

Traditional Rental Income: $3444

Airbnb ROI: -0.71%

Traditional ROI: 5.22%

Investment Properties for Sale in Other Cities of Connecticut

New Haven , CT

2 beds | 1 baths | 890 sq.ft.

$365,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $1306

Traditional Rental Income: $1995

Airbnb ROI: -0.32%

Traditional ROI: 2.88%

Norwalk , CT

2 beds | 2 baths | 1,173 sq.ft.

$459,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2268

Traditional Rental Income: $2877

Airbnb ROI: -0.34%

Traditional ROI: 2.4%

Waterbury , CT

3 beds | 3 baths | 1,716 sq.ft.

$374,995

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: -0.35%

Traditional ROI: 3.94%

Fairfield , CT

3 beds | 4 baths | 3,328 sq.ft.

$2,399,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.79%

Traditional ROI: 0.1%

Naugatuck , CT

3 beds | 3 baths | 1,536 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2984

Airbnb ROI: N/A

Traditional ROI: 6.35%

Monroe , CT

2 beds | 3 baths | 1,012 sq.ft.

$549,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2198

Traditional Rental Income: $2727

Airbnb ROI: 0.59%

Traditional ROI: 2.7%

Ledyard , CT

4 beds | 1 baths | 1,260 sq.ft.

$189,900

Airbnb cash on cash: N/A