Real Estate Investment Properties for Sale in Woodbury, CT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
54 Mountain Road Woodbury, CT Investors take note! 54 Mountain Road, Woodbury, CT Inside, it's nearly complete-outside,...	2 beds \| 1 baths \| 1,080 sq.ft.	$339,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 1.25% Airbnb Rental Income: $3375 Traditional Rental Income: $1484 Airbnb ROI: 4.83% Traditional ROI: 1.25%
45 North Gate Road Woodbury, CT Welcome to Woodbury, a quintessential New England town. This house is located in a very de...	4 beds \| 3 baths \| 3,545 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.71% Airbnb Rental Income: $null Traditional Rental Income: $4025 Airbnb ROI: N/A Traditional ROI: 0.71%
105 Minortown Road Woodbury, CT NEW PRICE! Don't wait! This ranch-style home might be the perfect fit! Just minutes from t...	3 beds \| 3 baths \| 2,227 sq.ft.	$599,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 3.96% Airbnb Rental Income: $1611 Traditional Rental Income: $4053 Airbnb ROI: -1.23% Traditional ROI: 3.96%
2 Linden Road Woodbury, CT Calling All Investors! Opportunity knocks with this spacious corner lot duplex offering gr...	5 beds \| 2 baths \| 2,760 sq.ft.	$315,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 9.43% Airbnb Rental Income: $2710 Traditional Rental Income: $3811 Airbnb ROI: 3.56% Traditional ROI: 9.43%
393 Middle Road Turnpike Woodbury, CT The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's hist...	4 beds \| 4 baths \| 3,280 sq.ft.	$849,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $6609 Airbnb ROI: N/A Traditional ROI: 5.11%
2 Judd Hill Road Woodbury, CT Charm and modern comfort come together in this beautifully renovated 3BR, 2BA home set on ...	3 beds \| 2 baths \| 1,470 sq.ft.	$569,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 2.64% Airbnb Rental Income: $1611 Traditional Rental Income: $3156 Airbnb ROI: -1.13% Traditional ROI: 2.64%
819 Main Street North Woodbury, CT Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and mo...	3 beds \| 3 baths \| 2,992 sq.ft.	$1,925,000	Airbnb cash on cash: -2.54% Traditional cash on cash: -0.9% Airbnb Rental Income: $1611 Traditional Rental Income: $4073 Airbnb ROI: -2.54% Traditional ROI: -0.9%
360 Old Sherman Hill Road Woodbury, CT Come view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! ...	3 beds \| 2 baths \| 1,296 sq.ft.	$499,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.58% Airbnb Rental Income: $1611 Traditional Rental Income: $2755 Airbnb ROI: -0.85% Traditional ROI: 2.58%
4 Fox Run #4 Woodbury, CT Welcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominiu...	2 beds \| 2 baths \| 1,182 sq.ft.	$299,990	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.73% Airbnb Rental Income: $3375 Traditional Rental Income: $2423 Airbnb ROI: 4.44% Traditional ROI: 3.73%

Real Estate investment in Woodbury, CT

There are 12 properties for sale in the city of Woodbury . The median list price in Woodbury is $534,000 and the average price per square foot is $238. In December 2025, the average monthly cash on cash return in Woodbury is 3.00%. The average monthly rental income in Woodbury is $3,918.

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

There are 12 investment properties available for sale in Woodbury.

In 2025, the best neighborhood to buy investment property is Woodbury.

The ROI for Short-Term is higher than the Long-Term in Woodbury with average rental income of $1,611.

Your search for investment property begins and ends here

Investment Property for Sale in Woodbury, CT

54 Mountain Road

Woodbury, CT

2 beds | 1 baths | 1,080 sq.ft.

$339,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $3375

Traditional Rental Income: $1484

Airbnb ROI: 4.83%

Traditional ROI: 1.25%

45 North Gate Road

Woodbury, CT

4 beds | 3 baths | 3,545 sq.ft.

$1,100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.71%

Airbnb Rental Income: $null

Traditional Rental Income: $4025

Airbnb ROI: N/A

Traditional ROI: 0.71%

105 Minortown Road

Woodbury, CT

3 beds | 3 baths | 2,227 sq.ft.

$599,000

Airbnb cash on cash: -1.23%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $1611

Traditional Rental Income: $4053

Airbnb ROI: -1.23%

Traditional ROI: 3.96%

2 Linden Road

Woodbury, CT

5 beds | 2 baths | 2,760 sq.ft.

$315,000

Airbnb cash on cash: 3.56%

Traditional cash on cash: 9.43%

Airbnb Rental Income: $2710

Traditional Rental Income: $3811

Airbnb ROI: 3.56%

Traditional ROI: 9.43%

393 Middle Road Turnpike

Woodbury, CT

4 beds | 4 baths | 3,280 sq.ft.

$849,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.11%

Airbnb Rental Income: $null

Traditional Rental Income: $6609

Airbnb ROI: N/A

Traditional ROI: 5.11%

2 Judd Hill Road

Woodbury, CT

3 beds | 2 baths | 1,470 sq.ft.

$569,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $1611

Traditional Rental Income: $3156

Airbnb ROI: -1.13%

Traditional ROI: 2.64%

819 Main Street North

Woodbury, CT

3 beds | 3 baths | 2,992 sq.ft.

$1,925,000

Airbnb cash on cash: -2.54%

Traditional cash on cash: -0.9%

Airbnb Rental Income: $1611

Traditional Rental Income: $4073

Airbnb ROI: -2.54%

Traditional ROI: -0.9%

360 Old Sherman Hill Road

Woodbury, CT

3 beds | 2 baths | 1,296 sq.ft.

$499,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $1611

Traditional Rental Income: $2755

Airbnb ROI: -0.85%