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: 0.1% Traditional cash on cash: 6.2% Airbnb Rental Income: $3575 Traditional Rental Income: $7899 Airbnb ROI: 0.1% Traditional ROI: 6.2%
305 Rimmon Road Woodbridge, CT This stunning four-bedroom Colonial with contemporary flair sits on 2.5 picturesque acres ...	4 beds \| 4 baths \| 3,742 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.93% Airbnb Rental Income: $null Traditional Rental Income: $6647 Airbnb ROI: N/A Traditional ROI: 6.93%
11 Ariel Road Woodbridge, CT Hidden Gem in Woodbridge - Where Nature, Comfort & Elegance Align Welcome to a private pa...	4 beds \| 4 baths \| 3,428 sq.ft.	$1,149,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $6348 Airbnb ROI: N/A Traditional ROI: 2.72%
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: 0.68% Traditional cash on cash: 8.57% Airbnb Rental Income: $3575 Traditional Rental Income: $8379 Airbnb ROI: 0.68% Traditional ROI: 8.57%
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.	$1,125,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.47% Airbnb Rental Income: $3575 Traditional Rental Income: $5946 Airbnb ROI: -0.55% Traditional ROI: 2.47%
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: -1.6% Traditional cash on cash: 3.95% Airbnb Rental Income: $1022 Traditional Rental Income: $2744 Airbnb ROI: -1.6% Traditional ROI: 3.95%
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: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $4471 Airbnb ROI: N/A Traditional ROI: 1.15%
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: -0.17% Traditional cash on cash: 4.08% Airbnb Rental Income: $3575 Traditional Rental Income: $6663 Airbnb ROI: -0.17% Traditional ROI: 4.08%

Real Estate investment in Woodbridge, CT

There are 11 properties for sale in the city of Woodbridge . The median list price in Woodbridge is $899,000 and the average price per square foot is $257. In December 2025, the average monthly cash on cash return in Woodbridge is 4.00%. The average monthly rental income in Woodbridge is $6,348.

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

There are 11 investment properties available for sale in Woodbridge.

In 2025, 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: 0.1%

Traditional cash on cash: 6.2%

Airbnb Rental Income: $3575

Traditional Rental Income: $7899

Airbnb ROI: 0.1%

Traditional ROI: 6.2%

305 Rimmon Road

Woodbridge, CT

4 beds | 4 baths | 3,742 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.93%

Airbnb Rental Income: $null

Traditional Rental Income: $6647

Airbnb ROI: N/A

Traditional ROI: 6.93%

11 Ariel Road

Woodbridge, CT

4 beds | 4 baths | 3,428 sq.ft.

$1,149,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.72%

Airbnb Rental Income: $null

Traditional Rental Income: $6348

Airbnb ROI: N/A

Traditional ROI: 2.72%

827 Fountain Street

Woodbridge, CT

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

$760,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 8.57%

Airbnb Rental Income: $3575

Traditional Rental Income: $8379

Airbnb ROI: 0.68%

Traditional ROI: 8.57%

71 Beecher Road

Woodbridge, CT

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

$1,125,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $3575

Traditional Rental Income: $5946

Airbnb ROI: -0.55%

Traditional ROI: 2.47%

1166 Old Racebrook Road

Woodbridge, CT

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

$399,900

Airbnb cash on cash: -1.6%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1022

Traditional Rental Income: $2744

Airbnb ROI: -1.6%

Traditional ROI: 3.95%

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: 1.15%

Airbnb Rental Income: $null

Traditional Rental Income: $4471

Airbnb ROI: N/A

Traditional ROI: 1.15%

11 Coachman Lane

Woodbridge, CT

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

$979,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $3575

Traditional Rental Income: $6663

Airbnb ROI: -0.17%