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
417 Dugg Hill Road Woodstock, CT There's such a great layout in this spacious contemporary raised ranch! It has vaulted cei...	3 beds \| 2 baths \| 1,506 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.92% Airbnb Rental Income: $null Traditional Rental Income: $2470 Airbnb ROI: N/A Traditional ROI: 2.92%
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: N/A Traditional cash on cash: -0.72% Airbnb Rental Income: $null Traditional Rental Income: $5688 Airbnb ROI: N/A Traditional ROI: -0.72%
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: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $2644 Airbnb ROI: N/A Traditional ROI: 2.62%
19 Hiawatha Heights Woodstock, CT Price Improvement!!! RARE PRIVATE LAKEFRONT GEM: PICTURE WINDOWS FRAME PANORAMIC VIEWS & ...	4 beds \| 3 baths \| 3,480 sq.ft.	$999,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 2.06% Airbnb Rental Income: $2220 Traditional Rental Income: $5083 Airbnb ROI: -1.62% Traditional ROI: 2.06%
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: -2.39% Traditional cash on cash: -0.75% Airbnb Rental Income: $1363 Traditional Rental Income: $2860 Airbnb ROI: -2.39% 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.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $3238 Airbnb ROI: N/A Traditional ROI: 4.87%
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: 1.38% Traditional cash on cash: 8.97% Airbnb Rental Income: $3040 Traditional Rental Income: $6137 Airbnb ROI: 1.38% Traditional ROI: 8.97%
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: -0.43% Traditional cash on cash: 3.51% Airbnb Rental Income: $1363 Traditional Rental Income: $2197 Airbnb ROI: -0.43% Traditional ROI: 3.51%
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: -1.57% Traditional cash on cash: 4.12% Airbnb Rental Income: $1363 Traditional Rental Income: $2760 Airbnb ROI: -1.57% Traditional ROI: 4.12%
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.	$774,900	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.25% Airbnb Rental Income: $2220 Traditional Rental Income: $4701 Airbnb ROI: -0.95% Traditional ROI: 3.25%
211 New Sweden Road Woodstock, CT Sellers are motivated! Welcome home to this classic Colonial nestled on a 2-acre country l...	3 beds \| 3 baths \| 2,016 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $3521 Airbnb ROI: N/A Traditional ROI: 5.02%
55 Pond View Drive Woodstock, CT Nestled in a quiet corner of the waterfront community of Muddy Pond, this beautifully main...	3 beds \| 2 baths \| 1,476 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2915 Airbnb ROI: N/A Traditional ROI: 4.9%
1820 Route 197 Woodstock, CT 2003 Built Ranch on 4.04 Acres with Solar Panels completely owned by the seller. NO Solar ...	3 beds \| 2 baths \| 2,006 sq.ft.	$394,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $3505 Airbnb ROI: N/A Traditional ROI: 6.1%
134 New Sweden Road Woodstock, CT Charming Cape on a Beautiful Level Lot! Welcome home to this inviting Cape featuring a war...	2 beds \| 2 baths \| 1,306 sq.ft.	$439,900	Airbnb cash on cash: -1.05% Traditional cash on cash: 3.4% Airbnb Rental Income: $1363 Traditional Rental Income: $2780 Airbnb ROI: -1.05% Traditional ROI: 3.4%
172 Peake Brook Road Woodstock, CT Location is key. Woodstock one owner cozy ranch house. Close to town built in 1954 on 0.7 ...	2 beds \| 2 baths \| 1,073 sq.ft.	$279,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 5.5% Airbnb Rental Income: $1363 Traditional Rental Income: $2359 Airbnb ROI: 0.13% Traditional ROI: 5.5%
145 Perrin Road Woodstock, CT Stunning Equestrian Estate on 26.54 Acres - Woodstock, CT 4 Beds 3 Baths Potential In-Law ...	4 beds \| 3 baths \| 1,574 sq.ft.	$949,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.52% Airbnb Rental Income: $2220 Traditional Rental Income: $3317 Airbnb ROI: -1.35% Traditional ROI: 0.52%
104 Pulpit Rock Road Woodstock, CT Experience family living in this beautifully updated 4 bed & 2.5 bath Colonial, perfectly ...	4 beds \| 3 baths \| 2,016 sq.ft.	$560,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.91% Airbnb Rental Income: $2220 Traditional Rental Income: $3773 Airbnb ROI: -0.13% Traditional ROI: 3.91%

Real Estate investment in Woodstock, CT

There are 19 properties for sale in the city of Woodstock . The median list price in Woodstock is $450,000 and the average price per square foot is $214. In December 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 19 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

417 Dugg Hill Road

Woodstock, CT

3 beds | 2 baths | 1,506 sq.ft.

$420,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2470

Airbnb ROI: N/A

Traditional ROI: 2.92%

80 Bungay Hill Road

Woodstock, CT

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

$2,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.72%

Airbnb Rental Income: $null

Traditional Rental Income: $5688

Airbnb ROI: N/A

Traditional ROI: -0.72%

56 Laurel Hill Drive

Woodstock, CT

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

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.62%

Airbnb Rental Income: $null

Traditional Rental Income: $2644

Airbnb ROI: N/A

Traditional ROI: 2.62%

19 Hiawatha Heights

Woodstock, CT

4 beds | 3 baths | 3,480 sq.ft.

$999,000

Airbnb cash on cash: -1.62%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $2220

Traditional Rental Income: $5083

Airbnb ROI: -1.62%

Traditional ROI: 2.06%

1669 Route 169

Woodstock, CT

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

$1,250,000

Airbnb cash on cash: -2.39%

Traditional cash on cash: -0.75%

Airbnb Rental Income: $1363

Traditional Rental Income: $2860

Airbnb ROI: -2.39%

Traditional ROI: -0.75%

70 Laurel Hill Drive

Woodstock, CT

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

$420,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $3238

Airbnb ROI: N/A

Traditional ROI: 4.87%

4 Perrin Road

Woodstock, CT

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

$535,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 8.97%

Airbnb Rental Income: $3040

Traditional Rental Income: $6137

Airbnb ROI: 1.38%

Traditional ROI: 8.97%

130 Tripp Road

Woodstock, CT

2 beds | 1 baths | 1,222 sq.ft.

$338,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $1363

Traditional Rental Income: $2197

Airbnb ROI: -0.43%