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: 2.46% Traditional cash on cash: 6.23% Airbnb Rental Income: $2553 Traditional Rental Income: $3442 Airbnb ROI: 2.46% 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: 2.46% Traditional cash on cash: 3.85% Airbnb Rental Income: $1957 Traditional Rental Income: $1873 Airbnb ROI: 2.46% Traditional ROI: 3.85%
23 Senexet Road Woodstock, CT Welcome to this stunning 2022-built Colonial set on 2.42 private acres in desirable Woodst...	3 beds \| 3 baths \| 2,626 sq.ft.	$674,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.14% Airbnb Rental Income: $2553 Traditional Rental Income: $4133 Airbnb ROI: 0.65% Traditional ROI: 4.14%
70 Red Cedar Road Woodstock, CT Nestled in the serene landscape with views of Bunggee Lake, this Cape-style residence offe...	3 beds \| 2 baths \| 1,685 sq.ft.	$390,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.56% Airbnb Rental Income: $2553 Traditional Rental Income: $2311 Airbnb ROI: 2.54% Traditional ROI: 3.56%
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: 0.91% Traditional cash on cash: 3.53% Airbnb Rental Income: $2553 Traditional Rental Income: $3143 Airbnb ROI: 0.91% Traditional ROI: 3.53%
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.	$450,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 5.87% Airbnb Rental Income: $2553 Traditional Rental Income: $3581 Airbnb ROI: 1.97% Traditional ROI: 5.87%
863 Route 198 Woodstock, CT Exceptional 2600+ SF Colonial on 2+ acres in desirable Woodstock commuter location about 4...	3 beds \| 3 baths \| 2,672 sq.ft.	$589,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.61% Airbnb Rental Income: $2553 Traditional Rental Income: $3826 Airbnb ROI: 1.19% Traditional ROI: 4.61%
57 Beaver Dam Road Woodstock, CT Adorable year-round home on Lake Bunggee, ideally located across from a private beach with...	2 beds \| 1 baths \| 888 sq.ft.	$355,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.56% Airbnb Rental Income: $1957 Traditional Rental Income: $1735 Airbnb ROI: 1.68% Traditional ROI: 2.56%
1226 169 Route Woodstock, CT First time offered under the community District (Woodstock Zoning Regulations Aricle II, s...	2 beds \| 1 baths \| 1,248 sq.ft.	$199,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 8.96% Airbnb Rental Income: $1957 Traditional Rental Income: $2196 Airbnb ROI: 4.98% Traditional ROI: 8.96%
1393 Route 169 Woodstock, CT Set far off the road down a beautifully paved driveway, this classic New England Colonial ...	3 beds \| 3 baths \| 2,464 sq.ft.	$595,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.63% Airbnb Rental Income: $2553 Traditional Rental Income: $3807 Airbnb ROI: 1.26% Traditional ROI: 4.63%
20 Crooked Trail Woodstock, CT Enjoy lake living in this charming Woodstock retreat located directly across the street fr...	3 beds \| 2 baths \| 1,352 sq.ft.	$425,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.5% Airbnb Rental Income: $2553 Traditional Rental Income: $2750 Airbnb ROI: 2.46% Traditional ROI: 4.5%
186 Brickyard Road Woodstock, CT Enjoy the beautiful landscaping of this custom oversized ranch. Located on 6 acres, Recent...	3 beds \| 2 baths \| 1,970 sq.ft.	$579,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 3.83% Airbnb Rental Income: $2553 Traditional Rental Income: $3262 Airbnb ROI: 1.38% Traditional ROI: 3.83%
608 English Neighborhood Road Woodstock, CT OPEN HOUSE IS CANCELED. Welcome to this spacious Colonial set on a peaceful 1.21-acre lot ...	4 beds \| 4 baths \| 1,728 sq.ft.	$440,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.52% Airbnb Rental Income: $null Traditional Rental Income: $4131 Airbnb ROI: N/A Traditional ROI: 7.52%
133 Route 198 Woodstock, CT This sprawling country style ranch home has plenty of space! Over 1800 sq.ft of living spa...	2 beds \| 2 baths \| 1,894 sq.ft.	$349,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 6.28% Airbnb Rental Income: $1957 Traditional Rental Income: $2826 Airbnb ROI: 2.07% Traditional ROI: 6.28%
158 W Quasset Road Woodstock, CT Extraordinary Waterfront Estate. Set on an exceptional 5.5-acre private lot with 265 feet ...	4 beds \| 4 baths \| 3,723 sq.ft.	$2,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $6671 Airbnb ROI: N/A Traditional ROI: 1.12%
259 Old Hall Road Woodstock, CT Pretty lot in South Woodstock, that abuts the Mill Brook on the west, and has a pretty vie...	2 beds \| 1 baths \| 1,024 sq.ft.	$200,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 8.55% Airbnb Rental Income: $1957 Traditional Rental Income: $2175 Airbnb ROI: 4.69% Traditional ROI: 8.55%
48 Grey Fox Landing Woodstock, CT Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peacefu...	4 beds \| 5 baths \| 5,087 sq.ft.	$880,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.89% Airbnb Rental Income: $null Traditional Rental Income: $7592 Airbnb ROI: N/A Traditional ROI: 6.89%
229 Woodstock Road Woodstock, CT Proudly owned by the original owner, the Cape sites sweetly in East Woodstock. The origina...	3 beds \| 2 baths \| 1,693 sq.ft.	$500,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 4.28% Airbnb Rental Income: $2553 Traditional Rental Income: $3074 Airbnb ROI: 1.85% Traditional ROI: 4.28%
5 Beaver Dam Road Woodstock, CT Experience year-round vacation vibes in this warm and inviting 3-bedroom lakeside retreat ...	3 beds \| 2 baths \| 1,098 sq.ft.	$525,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.31% Airbnb Rental Income: $2553 Traditional Rental Income: $2553 Airbnb ROI: 2.06% Traditional ROI: 3.31%

Real Estate investment in Woodstock, CT

There are 26 properties for sale in the city of Woodstock . The median list price in Woodstock is $482,999 and the average price per square foot is $200. In June 2026, the average monthly cash on cash return in Woodstock is 5.00%. The average monthly rental income in Woodstock is $3,007.

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

There are 26 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 $3,007.

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: 2.46%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $2553

Traditional Rental Income: $3442

Airbnb ROI: 2.46%

Traditional ROI: 6.23%

1605 Route 197

Woodstock, CT

2 beds | 1 baths | 920 sq.ft.

$329,900

Airbnb cash on cash: 2.46%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1957

Traditional Rental Income: $1873

Airbnb ROI: 2.46%

Traditional ROI: 3.85%

23 Senexet Road

Woodstock, CT

3 beds | 3 baths | 2,626 sq.ft.

$674,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $2553

Traditional Rental Income: $4133

Airbnb ROI: 0.65%

Traditional ROI: 4.14%

70 Red Cedar Road

Woodstock, CT

3 beds | 2 baths | 1,685 sq.ft.

$390,000

Airbnb cash on cash: 2.54%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $2553

Traditional Rental Income: $2311

Airbnb ROI: 2.54%

Traditional ROI: 3.56%

Center Road

Woodstock, CT

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

$489,900

Airbnb cash on cash: 0.91%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2553

Traditional Rental Income: $3143

Airbnb ROI: 0.91%

Traditional ROI: 3.53%

83 Dodge Road

Woodstock, CT

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

$450,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $2553

Traditional Rental Income: $3581

Airbnb ROI: 1.97%

Traditional ROI: 5.87%

863 Route 198

Woodstock, CT

3 beds | 3 baths | 2,672 sq.ft.

$589,900

Airbnb cash on cash: 1.19%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $2553

Traditional Rental Income: $3826

Airbnb ROI: 1.19%

Traditional ROI: 4.61%

57 Beaver Dam Road

Woodstock, CT

2 beds | 1 baths | 888 sq.ft.

$355,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $1957

Traditional Rental Income: $1735

Airbnb ROI: 1.68%