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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
31 McVeigh Rd Woodbury, CT Well maintained and updated Colonial on Level lot. Formal living room with fireplace, Dini...	4 beds \| 2 baths \| 2,256 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2824 Airbnb ROI: N/A Traditional ROI: 3.05%
74 Middle Quarter Rd Woodbury, CT Just Reduced! Beautiful 1835 Mini Farm, updated Farmhouse with four bedrooms, a three bay ...	4 beds \| 2 baths \| 2,874 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3575 Airbnb ROI: N/A Traditional ROI: 3.26%
27 Middle Quarter Rd Woodbury, CT 4 Bedroom 1.5 Bath Colonial Built in 1825 on 1.32 Acres with 2 Large Barns on the property...	3 beds \| 2 baths \| 2,042 sq.ft.	$999,900	Airbnb cash on cash: -2.09% Traditional cash on cash: 0.44% Airbnb Rental Income: $1611 Traditional Rental Income: $3745 Airbnb ROI: -2.09% Traditional ROI: 0.44%
45 North Gate Rd Woodbury, CT Welcome to Woodbury, a quintessential New England town. This house is located in a very de...	4 beds \| 2 baths \| 3,545 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $4025 Airbnb ROI: N/A Traditional ROI: 1.81%
105 Minortown Rd 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: -0.54% Traditional cash on cash: 4.64% Airbnb Rental Income: $1611 Traditional Rental Income: $4053 Airbnb ROI: -0.54% Traditional ROI: 4.64%
819 Main St N 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: -1.02% Traditional cash on cash: 0.61% Airbnb Rental Income: $1611 Traditional Rental Income: $4073 Airbnb ROI: -1.02% Traditional ROI: 0.61%
360 Old Sherman Hill Rd Woodbury, CT Come view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! ...	3 beds \| 1 baths \| 1,296 sq.ft.	$449,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 3.74% Airbnb Rental Income: $1611 Traditional Rental Income: $2755 Airbnb ROI: 0.3% Traditional ROI: 3.74%
126 Sherman Hill Rd Apt B12 Woodbury, CT This second level unit offers a living and dining combo, kitchen, two bedrooms and one ful...	2 beds \| 1 baths \| 1,150 sq.ft.	$200,000	Airbnb cash on cash: 6.46% Traditional cash on cash: 3.31% Airbnb Rental Income: $3375 Traditional Rental Income: $1982 Airbnb ROI: 6.46% Traditional ROI: 3.31%
90 Rowley Rd Woodbury, CT 90 Rowley Rd, Woodbury, CT 06798 \| Single Family Residential	4 beds \| 4 baths \| 2,695 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.36% Airbnb Rental Income: $null Traditional Rental Income: $4484 Airbnb ROI: N/A Traditional ROI: 9.36%
10 Hazel Plain Rd Woodbury, CT 10 Hazel Plain Rd, Woodbury, CT 06798 \| Single Family Residential	2 beds \| 2 baths \| 1,267 sq.ft.	$339,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 3.28% Airbnb Rental Income: $3375 Traditional Rental Income: $2129 Airbnb ROI: 4.83% Traditional ROI: 3.28%
5 Upper Cmns Woodbury, CT 5 Upper Cmns, Woodbury, CT 06798 \| Condo/Coop	2 beds \| 2 baths \| 1,182 sq.ft.	$260,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 2.95% Airbnb Rental Income: $3375 Traditional Rental Income: $2006 Airbnb ROI: 5.42% Traditional ROI: 2.95%
34 Transylvania Rd Woodbury, CT 34 Transylvania Rd, Woodbury, CT 06798 \| Single Family Residential	3 beds \| 2 baths \| 2,016 sq.ft.	$499,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.5% Airbnb Rental Income: $1611 Traditional Rental Income: $2715 Airbnb ROI: -0.85% Traditional ROI: 2.5%
92 Minortown Rd Woodbury, CT 92 Minortown Rd, Woodbury, CT 06798 \| Single Family Residential	3 beds \| 2 baths \| 2,448 sq.ft.	$799,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 0.4% Airbnb Rental Income: $1611 Traditional Rental Income: $2719 Airbnb ROI: -1.7% Traditional ROI: 0.4%
439 Washington Rd Woodbury, CT 439 Washington Rd, Woodbury, CT 06798 \| Single Family Residential	2 beds \| 1 baths \| 1,920 sq.ft.	$314,900	Airbnb cash on cash: 5.43% Traditional cash on cash: 1.47% Airbnb Rental Income: $3375 Traditional Rental Income: $1452 Airbnb ROI: 5.43% Traditional ROI: 1.47%
2 South Mdws #107B Woodbury, CT 2 South Mdws #107B, Woodbury, CT 06798 \| Condo/Coop	3 beds \| 2 baths \| 2,069 sq.ft.	$377,750	Airbnb cash on cash: -1.38% Traditional cash on cash: 2.96% Airbnb Rental Income: $1611 Traditional Rental Income: $2693 Airbnb ROI: -1.38% Traditional ROI: 2.96%
8 Tamarack Ln #8 Woodbury, CT 8 Tamarack Ln #8, Woodbury, CT 06798 \| Condo/Coop	2 beds \| 2 baths \| 2,118 sq.ft.	$355,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.3% Airbnb Rental Income: $3375 Traditional Rental Income: $2314 Airbnb ROI: 3.23% Traditional ROI: 2.3%
337 Main St S Woodbury, CT 337 Main St S, Woodbury, CT 06798 \| Single Family Residential	4 beds \| 2 baths \| 3,700 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.48% Airbnb Rental Income: $null Traditional Rental Income: $3118 Airbnb ROI: N/A Traditional ROI: 0.48%
373 Transylvania Rd Woodbury, CT 373 Transylvania Rd, Woodbury, CT 06798 \| Single Family Residential	3 beds \| 3 baths \| 4,059 sq.ft.	$1,275,000	Airbnb cash on cash: -2.23% Traditional cash on cash: -0.34% Airbnb Rental Income: $1611 Traditional Rental Income: $3395 Airbnb ROI: -2.23% Traditional ROI: -0.34%
74 Woodbury Hill unit: 74 #74 Woodbury, CT Beautiful Woodbury Hill condo located in a desirable, small, and quiet complex offering a ...	2 beds \| 3 baths \| 2,463 sq.ft.	$490,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 3.85% Airbnb Rental Income: $3375 Traditional Rental Income: $3513 Airbnb ROI: 1.91% Traditional ROI: 3.85%
13 Park Lane Woodbury, CT Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautif...	3 beds \| 3 baths \| 2,264 sq.ft.	$649,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.65% Airbnb Rental Income: $1611 Traditional Rental Income: $4090 Airbnb ROI: -0.19% Traditional ROI: 4.65%
148 Flanders Rd Woodbury, CT 148 Flanders Rd, Woodbury, CT 06798 \| Single Family Residential	3 beds \| 4 baths \| 3,082 sq.ft.	$849,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 2.38% Airbnb Rental Income: $1611 Traditional Rental Income: $4446 Airbnb ROI: -1.79% Traditional ROI: 2.38%
14 Meadow Crest Dr Woodbury, CT 14 Meadow Crest Dr, Woodbury, CT 06798 \| Single Family Residential	3 beds \| 1 baths \| 2,102 sq.ft.	$499,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.65% Airbnb Rental Income: $1611 Traditional Rental Income: $1945 Airbnb ROI: -0.96% Traditional ROI: 0.65%
Carmel Hill Rd Woodbury, CT Carmel Hill Rd, Woodbury, CT 06798 \| Other	N/A beds \| N/A baths \| N/A	$179,900	Airbnb cash on cash: 2.78% Traditional cash on cash: 1.52% Airbnb Rental Income: $1545 Traditional Rental Income: $883 Airbnb ROI: 2.78% Traditional ROI: 1.52%
9 Highpoint Ct #116E Woodbury, CT 9 Highpoint Ct #116E, Woodbury, CT 06798 \| Condo/Coop	2 beds \| 2 baths \| 1,182 sq.ft.	$275,000	Airbnb cash on cash: 5.11% Traditional cash on cash: 2.73% Airbnb Rental Income: $3375 Traditional Rental Income: $2006 Airbnb ROI: 5.11% Traditional ROI: 2.73%
229 Bacon Pond Rd #312 Woodbury, CT 229 Bacon Pond Rd #312, Woodbury, CT 06798 \| Condo/Coop	2 beds \| 1 baths \| 913 sq.ft.	$160,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 1.68% Airbnb Rental Income: $3375 Traditional Rental Income: $1377 Airbnb ROI: 9.84% Traditional ROI: 1.68%

Real Estate investment in Woodbury, CT

There are 29 properties for sale in the city of Woodbury . The median list price in Woodbury is $425,000 and the average price per square foot is $182. In March 2026, the average monthly cash on cash return in Woodbury is 2.00%. The average monthly rental income in Woodbury is $2,719.

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

There are 29 investment properties available for sale in Woodbury.

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

The ROI for Long-Term is higher than the Short-Term in Woodbury with average rental income of $2,719.

Your search for investment property begins and ends here

Investment Property for Sale in Woodbury, CT

31 McVeigh Rd

Woodbury, CT

4 beds | 2 baths | 2,256 sq.ft.

$559,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2824

Airbnb ROI: N/A

Traditional ROI: 3.05%

74 Middle Quarter Rd

Woodbury, CT

4 beds | 2 baths | 2,874 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.26%

Airbnb Rental Income: $null

Traditional Rental Income: $3575

Airbnb ROI: N/A

Traditional ROI: 3.26%

27 Middle Quarter Rd

Woodbury, CT

3 beds | 2 baths | 2,042 sq.ft.

$999,900

Airbnb cash on cash: -2.09%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $1611

Traditional Rental Income: $3745

Airbnb ROI: -2.09%

Traditional ROI: 0.44%

45 North Gate Rd

Woodbury, CT

4 beds | 2 baths | 3,545 sq.ft.

$1,100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.81%

Airbnb Rental Income: $null

Traditional Rental Income: $4025

Airbnb ROI: N/A

Traditional ROI: 1.81%

105 Minortown Rd

Woodbury, CT

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

$599,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1611

Traditional Rental Income: $4053

Airbnb ROI: -0.54%

Traditional ROI: 4.64%

819 Main St N

Woodbury, CT

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

$1,925,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1611

Traditional Rental Income: $4073

Airbnb ROI: -1.02%

Traditional ROI: 0.61%

360 Old Sherman Hill Rd

Woodbury, CT

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

$449,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $1611

Traditional Rental Income: $2755

Airbnb ROI: 0.3%

Traditional ROI: 3.74%

126 Sherman Hill Rd Apt B12

Woodbury, CT

2 beds | 1 baths | 1,150 sq.ft.

$200,000

Airbnb cash on cash: 6.46%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3375

Traditional Rental Income: $1982

Airbnb ROI: 6.46%