Real Estate Investment Properties for Sale in Woodbridge, CT

Looking for investment property in Woodbridge, CT with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
40 Old Quarry Road Woodbridge, CT Welcome to 40 Old Quarry Rd! This custom built home features a two car finished garage, fu...	5 beds \| 6 baths \| 5,364 sq.ft.	$899,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 6.3% Airbnb Rental Income: $3575 Traditional Rental Income: $7899 Airbnb ROI: 0.2% Traditional ROI: 6.3%
827 Fountain Street Woodbridge, CT An exceptional opportunity awaits at 827 Fountain Street. Set on a spacious lot in a prime...	5 beds \| 5 baths \| 3,687 sq.ft.	$760,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 8.64% Airbnb Rental Income: $3575 Traditional Rental Income: $8379 Airbnb ROI: 0.75% Traditional ROI: 8.64%
71 Beecher Road Woodbridge, CT The Nathaniel Parks House circa 1706. Originally built in Guilford, CT, and painstakingly ...	5 beds \| 4 baths \| 3,892 sq.ft.	$1,075,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $3575 Traditional Rental Income: $5946 Airbnb ROI: -0.14% Traditional ROI: 3.02%
1166 Old Racebrook Road Woodbridge, CT Welcome home to this charming expanded cape! This unique and spacious 3-bedroom, 3-full-ba...	3 beds \| 3 baths \| 1,189 sq.ft.	$399,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 4.04% Airbnb Rental Income: $1022 Traditional Rental Income: $2744 Airbnb ROI: -1.51% Traditional ROI: 4.04%
268 Newton Road Woodbridge, CT Spacious Modern Colonial home with open layout floor plan. First and second floor both hav...	4 beds \| 3 baths \| 3,100 sq.ft.	$1,100,088	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $4471 Airbnb ROI: N/A Traditional ROI: 2.86%
11 Coachman Lane Woodbridge, CT Set against the scenic Woodbridge Land Trust, this spacious 5-bedroom, 3.5-bath home blend...	5 beds \| 4 baths \| 4,382 sq.ft.	$979,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.79% Airbnb Rental Income: $3575 Traditional Rental Income: $6663 Airbnb ROI: 0.54% Traditional ROI: 4.79%
68 Orchard Road Woodbridge, CT One of a kind Mid-Century Modern house designed by Vincent Scully and Albert Reese for the...	3 beds \| 1 baths \| 1,872 sq.ft.	$550,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 1.89% Airbnb Rental Income: $1022 Traditional Rental Income: $2455 Airbnb ROI: -1.59% Traditional ROI: 1.89%
489 Amity Road Woodbridge, CT The commanding presence of this stately brick Colonial will take your breath away.You are ...	4 beds \| 4 baths \| 6,011 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $5790 Airbnb ROI: N/A Traditional ROI: 1.39%

Real Estate investment in Woodbridge, CT

There are 8 properties for sale in the city of Woodbridge . The median list price in Woodbridge is $532,500 and the average price per square foot is $236. In February 2026, the average monthly cash on cash return in Woodbridge is 4.00%. The average monthly rental income in Woodbridge is $5,868.

Woodbridge, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 8 investment properties available for sale in Woodbridge.

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

The ROI for Short-Term is higher than the Long-Term in Woodbridge with average rental income of $3,575.

Your search for investment property begins and ends here

Investment Property for Sale in Woodbridge, CT

40 Old Quarry Road

Woodbridge, CT

5 beds | 6 baths | 5,364 sq.ft.

$899,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $3575

Traditional Rental Income: $7899

Airbnb ROI: 0.2%

Traditional ROI: 6.3%

827 Fountain Street

Woodbridge, CT

5 beds | 5 baths | 3,687 sq.ft.

$760,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 8.64%

Airbnb Rental Income: $3575

Traditional Rental Income: $8379

Airbnb ROI: 0.75%

Traditional ROI: 8.64%

71 Beecher Road

Woodbridge, CT

5 beds | 4 baths | 3,892 sq.ft.

$1,075,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $3575

Traditional Rental Income: $5946

Airbnb ROI: -0.14%

Traditional ROI: 3.02%

1166 Old Racebrook Road

Woodbridge, CT

3 beds | 3 baths | 1,189 sq.ft.

$399,900

Airbnb cash on cash: -1.51%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1022

Traditional Rental Income: $2744

Airbnb ROI: -1.51%

Traditional ROI: 4.04%

268 Newton Road

Woodbridge, CT

4 beds | 3 baths | 3,100 sq.ft.

$1,100,088

Airbnb cash on cash: N/A

Traditional cash on cash: 2.86%

Airbnb Rental Income: $null

Traditional Rental Income: $4471

Airbnb ROI: N/A

Traditional ROI: 2.86%

11 Coachman Lane

Woodbridge, CT

5 beds | 4 baths | 4,382 sq.ft.

$979,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $3575

Traditional Rental Income: $6663

Airbnb ROI: 0.54%

Traditional ROI: 4.79%

68 Orchard Road

Woodbridge, CT

3 beds | 1 baths | 1,872 sq.ft.

$550,000

Airbnb cash on cash: -1.59%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1022

Traditional Rental Income: $2455

Airbnb ROI: -1.59%

Traditional ROI: 1.89%

489 Amity Road

Woodbridge, CT

4 beds | 4 baths | 6,011 sq.ft.

$1,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.39%

Airbnb Rental Income: $null

Traditional Rental Income: $5790

Airbnb ROI: N/A