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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
170 Lyon Hill Road Woodstock, CT This original 1811 Colonial, surrounded by nature's beauty, will welcome and captivate in ...	3 beds \| 3 baths \| 2,960 sq.ft.	$679,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 0.31% Airbnb Rental Income: $6015 Traditional Rental Income: $2267 Airbnb ROI: 4.34% Traditional ROI: 0.31%
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: -1.09% Traditional cash on cash: -0.72% Airbnb Rental Income: $6015 Traditional Rental Income: $5688 Airbnb ROI: -1.09% Traditional ROI: -0.72%
64 May Brook Woodstock, CT Welcome to 64 May Brook, a beautiful home set on a cul-de-sac in Woodstock with one of the...	4 beds \| 5 baths \| 3,795 sq.ft.	$719,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 8.45% Airbnb Rental Income: $3137 Traditional Rental Income: $7863 Airbnb ROI: 0.35% Traditional ROI: 8.45%
56 Laurel Hill Drive Woodstock, CT Charming 3-Bedroom Home on Double Lot - Lake Bunggee Waterfront Access! Discover the pote...	3 beds \| 2 baths \| 1,008 sq.ft.	$475,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 2.62% Airbnb Rental Income: $6015 Traditional Rental Income: $2644 Airbnb ROI: 7.52% Traditional ROI: 2.62%
1669 Route 169 Woodstock, CT Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut...	2 beds \| 2 baths \| 2,340 sq.ft.	$1,250,000	Airbnb cash on cash: -2.23% Traditional cash on cash: -0.75% Airbnb Rental Income: $1588 Traditional Rental Income: $2860 Airbnb ROI: -2.23% Traditional ROI: -0.75%
70 Laurel Hill Drive Woodstock, CT Get ready to fall in love with this fully renovated colonial, just one minute from the bea...	3 beds \| 3 baths \| 1,682 sq.ft.	$449,900	Airbnb cash on cash: 8.11% Traditional cash on cash: 4.35% Airbnb Rental Income: $6015 Traditional Rental Income: $3238 Airbnb ROI: 8.11% Traditional ROI: 4.35%
4 Perrin Road Woodstock, CT Seller is highly motivated! Price has been adjusted! Bring all offers! Welcome to the exqu...	5 beds \| 4 baths \| 4,172 sq.ft.	$535,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 8.97% Airbnb Rental Income: $4090 Traditional Rental Income: $6137 Airbnb ROI: 3.13% Traditional ROI: 8.97%
36 Dunleavy Drive Woodstock, CT Discover this charming colonial Lakefront home on Roseland Lake, offering 2,036 sq ft of l...	3 beds \| 2 baths \| 2,036 sq.ft.	$524,900	Airbnb cash on cash: 6.52% Traditional cash on cash: 4.26% Airbnb Rental Income: $6015 Traditional Rental Income: $3717 Airbnb ROI: 6.52% Traditional ROI: 4.26%
285 East Quasset Road Woodstock, CT Discover the charm of lakeside living on peaceful Quasset Lake in Woodstock, CT. This cozy...	4 beds \| 1 baths \| 1,144 sq.ft.	$425,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 2.73% Airbnb Rental Income: $3137 Traditional Rental Income: $2465 Airbnb ROI: 2.63% Traditional ROI: 2.73%
50 Crooked Trail Woodstock, CT This is a large raised ranch with all 3 bedrooms on the main level. The primary bedroom ha...	3 beds \| 3 baths \| 2,339 sq.ft.	$399,900	Airbnb cash on cash: 9.5% Traditional cash on cash: 6.69% Airbnb Rental Income: $6015 Traditional Rental Income: $3770 Airbnb ROI: 9.5% Traditional ROI: 6.69%
130 Tripp Road Woodstock, CT Great location in South Woodstock, if being close to town is important. Live comfortably i...	2 beds \| 1 baths \| 1,222 sq.ft.	$338,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.51% Airbnb Rental Income: $1588 Traditional Rental Income: $2197 Airbnb ROI: 0.16% Traditional ROI: 3.51%
9 Sherman Road Woodstock, CT Investor Opportunity in Woodstock! Set on a corner lot on a quiet country road, this 2-bed...	2 beds \| 1 baths \| 888 sq.ft.	$175,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 7.63% Airbnb Rental Income: $1588 Traditional Rental Income: $1881 Airbnb ROI: 3.15% Traditional ROI: 7.63%
42 Woodstock Meadows #42 Woodstock, CT No more leaf-raking, mowing, gutter clean-outs or snowplowing for you! Experience the ease...	2 beds \| 2 baths \| 1,541 sq.ft.	$339,500	Airbnb cash on cash: -0.98% Traditional cash on cash: 4.12% Airbnb Rental Income: $1588 Traditional Rental Income: $2760 Airbnb ROI: -0.98% Traditional ROI: 4.12%
115 Crooked Trail Extension Woodstock, CT This charming, year-round lake front home located at 115 Crooked Trail Ext in Woodstock, ...	3 beds \| 2 baths \| 1,922 sq.ft.	$659,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 2.32% Airbnb Rental Income: $6015 Traditional Rental Income: $3439 Airbnb ROI: 4.57% Traditional ROI: 2.32%
19 A Route Woodstock, CT Country living in Woodstock means more than just a house it's a lifestyle of privacy, spac...	2 beds \| 1 baths \| 708 sq.ft.	$299,999	Airbnb cash on cash: 0.58% Traditional cash on cash: 2.44% Airbnb Rental Income: $1588 Traditional Rental Income: $1661 Airbnb ROI: 0.58% Traditional ROI: 2.44%
189 Center Road Woodstock, CT A beautifully maintained colonial nestled in one of Woodstock's most picturesque settings ...	4 beds \| 3 baths \| 3,662 sq.ft.	$799,900	Airbnb cash on cash: 0% Traditional cash on cash: 3.06% Airbnb Rental Income: $3137 Traditional Rental Income: $4701 Airbnb ROI: 0% Traditional ROI: 3.06%
69 Lyon Hill Road Woodstock, CT Nestled on a picturesque 1.75-acre lot in the heart of Woodstock, Connecticut, this loving...	3 beds \| 2 baths \| 1,210 sq.ft.	$440,000	Airbnb cash on cash: 8.36% Traditional cash on cash: 3.33% Airbnb Rental Income: $6015 Traditional Rental Income: $2750 Airbnb ROI: 8.36% Traditional ROI: 3.33%
211 New Sweden Road Woodstock, CT Welcome home to this classic Colonial nestled on a 2-acre country lot in desirable Woodsto...	3 beds \| 3 baths \| 2,016 sq.ft.	$494,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 4.28% Airbnb Rental Income: $6015 Traditional Rental Income: $3521 Airbnb ROI: 7.1% Traditional ROI: 4.28%

Real Estate investment in Woodstock, CT

There are 21 properties for sale in the city of Woodstock . The median list price in Woodstock is $494,900 and the average price per square foot is $224. In October 2025, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $3,238.

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

There are 21 investment properties available for sale in Woodstock.

In 2025, 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 $3,238.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, CT

170 Lyon Hill Road

Woodstock, CT

3 beds | 3 baths | 2,960 sq.ft.

$679,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $6015

Traditional Rental Income: $2267

Airbnb ROI: 4.34%

Traditional ROI: 0.31%

80 Bungay Hill Road

Woodstock, CT

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

$2,500,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: -0.72%

Airbnb Rental Income: $6015

Traditional Rental Income: $5688

Airbnb ROI: -1.09%

Traditional ROI: -0.72%

64 May Brook

Woodstock, CT

4 beds | 5 baths | 3,795 sq.ft.

$719,900

Airbnb cash on cash: 0.35%

Traditional cash on cash: 8.45%

Airbnb Rental Income: $3137

Traditional Rental Income: $7863

Airbnb ROI: 0.35%

Traditional ROI: 8.45%

56 Laurel Hill Drive

Woodstock, CT

3 beds | 2 baths | 1,008 sq.ft.

$475,000

Airbnb cash on cash: 7.52%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $6015

Traditional Rental Income: $2644

Airbnb ROI: 7.52%

Traditional ROI: 2.62%

1669 Route 169

Woodstock, CT

2 beds | 2 baths | 2,340 sq.ft.

$1,250,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: -0.75%

Airbnb Rental Income: $1588

Traditional Rental Income: $2860

Airbnb ROI: -2.23%

Traditional ROI: -0.75%

70 Laurel Hill Drive

Woodstock, CT

3 beds | 3 baths | 1,682 sq.ft.

$449,900

Airbnb cash on cash: 8.11%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $6015

Traditional Rental Income: $3238

Airbnb ROI: 8.11%

Traditional ROI: 4.35%

4 Perrin Road

Woodstock, CT

5 beds | 4 baths | 4,172 sq.ft.

$535,000

Airbnb cash on cash: 3.13%

Traditional cash on cash: 8.97%

Airbnb Rental Income: $4090

Traditional Rental Income: $6137

Airbnb ROI: 3.13%

Traditional ROI: 8.97%

36 Dunleavy Drive

Woodstock, CT

3 beds | 2 baths | 2,036 sq.ft.

$524,900

Airbnb cash on cash: 6.52%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $6015

Traditional Rental Income: $3717

Airbnb ROI: 6.52%