Real Estate Investment Properties for Sale in Woodstock, CT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
53 Prospect Street Woodstock, CT Highest and Best Deadline, WEDNESDAY 4/29 at NOON East Woodstock Sweet Escape - Where...	3 beds \| 3 baths \| 1,736 sq.ft.	$425,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 6.23% Airbnb Rental Income: $2119 Traditional Rental Income: $3442 Airbnb ROI: 1.55% Traditional ROI: 6.23%
1605 Route 197 Woodstock, CT Tucked away on a private 1.3-acre lot in highly desirable Woodstock, this adorable ranch o...	2 beds \| 1 baths \| 920 sq.ft.	$329,900	Airbnb cash on cash: -1.12% Traditional cash on cash: 3.85% Airbnb Rental Income: $624 Traditional Rental Income: $1873 Airbnb ROI: -1.12% Traditional ROI: 3.85%
80 Bungay Hill Road Woodstock, CT Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct....	3 beds \| 5 baths \| 4,655 sq.ft.	$2,500,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.61% Airbnb Rental Income: $2119 Traditional Rental Income: $5688 Airbnb ROI: -1.16% Traditional ROI: 0.61%
Center Road Woodstock, CT TO BE BUILT Welcome to the quiet corner of Northeast Connecticut. Serene setting in Woodst...	3 beds \| 2 baths \| 1,500 sq.ft.	$489,900	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.53% Airbnb Rental Income: $2119 Traditional Rental Income: $3143 Airbnb ROI: 0.12% Traditional ROI: 3.53%
42 New Sweden Road Woodstock, CT Bright and Light. Charming Character. Beautifully Kept. Step into this home that has been ...	4 beds \| 2 baths \| 1,821 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $3511 Airbnb ROI: N/A Traditional ROI: 6.21%
83 Dodge Road Woodstock, CT Set in the charming town of Woodstock and minutes from the Massachusetts line, this 3-bedr...	3 beds \| 3 baths \| 2,240 sq.ft.	$465,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 5.65% Airbnb Rental Income: $2119 Traditional Rental Income: $3581 Airbnb ROI: 1.05% Traditional ROI: 5.65%
239 Barlow Cemetery Road Woodstock, CT Enjoy this beautiful, like-new, well-cared for 2250 square foot 3 bedroom, 3 full bath hom...	3 beds \| 3 baths \| 2,250 sq.ft.	$665,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.69% Airbnb Rental Income: $2119 Traditional Rental Income: $3984 Airbnb ROI: -0.19% Traditional ROI: 3.69%
9 Ellen Lane Woodstock, CT Discover a fantastic investment or owner-occupied opportunity in the heart of Woodstock, C...	6 beds \| 3 baths \| 3,214 sq.ft.	$450,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 8.93% Airbnb Rental Income: $3681 Traditional Rental Income: $4675 Airbnb ROI: 4.66% Traditional ROI: 8.93%
863 Route 198 Woodstock, CT Exceptional 2600+ SF Colonial on 2+ acres offering space, efficiency & a fantastic layout ...	3 beds \| 3 baths \| 2,672 sq.ft.	$599,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.52% Airbnb Rental Income: $2119 Traditional Rental Income: $3826 Airbnb ROI: 0.5% Traditional ROI: 4.52%

Real Estate investment in Woodstock, CT

There are 10 properties for sale in the city of Woodstock . The median list price in Woodstock is $484,900 and the average price per square foot is $198. In May 2026, the average monthly cash on cash return in Woodstock is 5.00%. The average monthly rental income in Woodstock is $3,546.

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

There are 10 investment properties available for sale in Woodstock.

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

The ROI for Long-Term is higher than the Short-Term in Woodstock with average rental income of $3,546.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, CT

53 Prospect Street

Woodstock, CT

3 beds | 3 baths | 1,736 sq.ft.

$425,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $2119

Traditional Rental Income: $3442

Airbnb ROI: 1.55%

Traditional ROI: 6.23%

1605 Route 197

Woodstock, CT

2 beds | 1 baths | 920 sq.ft.

$329,900

Airbnb cash on cash: -1.12%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $624

Traditional Rental Income: $1873

Airbnb ROI: -1.12%

Traditional ROI: 3.85%

80 Bungay Hill Road

Woodstock, CT

3 beds | 5 baths | 4,655 sq.ft.

$2,500,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2119

Traditional Rental Income: $5688

Airbnb ROI: -1.16%

Traditional ROI: 0.61%

Center Road

Woodstock, CT

3 beds | 2 baths | 1,500 sq.ft.

$489,900

Airbnb cash on cash: 0.12%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2119

Traditional Rental Income: $3143

Airbnb ROI: 0.12%

Traditional ROI: 3.53%

42 New Sweden Road

Woodstock, CT

4 beds | 2 baths | 1,821 sq.ft.

$440,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.21%

Airbnb Rental Income: $null

Traditional Rental Income: $3511

Airbnb ROI: N/A

Traditional ROI: 6.21%

83 Dodge Road

Woodstock, CT

3 beds | 3 baths | 2,240 sq.ft.

$465,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 5.65%

Airbnb Rental Income: $2119

Traditional Rental Income: $3581

Airbnb ROI: 1.05%

Traditional ROI: 5.65%

239 Barlow Cemetery Road

Woodstock, CT

3 beds | 3 baths | 2,250 sq.ft.

$665,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2119

Traditional Rental Income: $3984

Airbnb ROI: -0.19%

Traditional ROI: 3.69%

9 Ellen Lane

Woodstock, CT

6 beds | 3 baths | 3,214 sq.ft.

$450,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 8.93%

Airbnb Rental Income: $3681

Traditional Rental Income: $4675

Airbnb ROI: 4.66%