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
23 Senexet Rd Woodstock, CT Welcome to this stunning 2022-built Colonial set on 2.42 private acres in desirable Woodst...	3 beds \| 2 baths \| 2,626 sq.ft.	$674,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.02% Airbnb Rental Income: $2288 Traditional Rental Income: $4133 Airbnb ROI: 0.18% Traditional ROI: 4.02%
60 Indian Spring Rd Woodstock, CT This lakefront year-round property is available on the desirable Witches Woods Lake, a 70-...	2 beds \| 2 baths \| 1,855 sq.ft.	$699,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.47% Airbnb Rental Income: $1451 Traditional Rental Income: $2898 Airbnb ROI: -0.41% Traditional ROI: 2.47%
101 Child Hill Rd Woodstock, CT Welcome to this beautiful & idyllic colonial, sitting off of Woodstock Hill! The views are...	4 beds \| 3 baths \| 2,150 sq.ft.	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 2.19%
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: 2.06% Traditional cash on cash: 3.68% Airbnb Rental Income: $2288 Traditional Rental Income: $2311 Airbnb ROI: 2.06% Traditional ROI: 3.68%
20 Loyola Rd Woodstock, CT Enjoy lake-house living in the Quiet Corner of Woodstock CT on Quasset Lake! Walk directly...	2 beds \| 2 baths \| 2,216 sq.ft.	$698,900	Airbnb cash on cash: -1.81% Traditional cash on cash: 1.4% Airbnb Rental Income: $1451 Traditional Rental Income: $3114 Airbnb ROI: -1.81% Traditional ROI: 1.4%
4 Loyola Rd Extension Woodstock, CT This lakeside escape was completely redone in 2023. This beautifully updated 1-bedroom, 1-...	1 beds \| 1 baths \| 961 sq.ft.	$625,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.87% Airbnb Rental Income: $1062 Traditional Rental Income: $1995 Airbnb ROI: -1.36% Traditional ROI: 0.87%
36 Olde Meadow Rd Woodstock, CT 36 Olde Meadow Rd, Woodstock, CT 06281 \| Single Family Residential	4 beds \| 2 baths \| 2,900 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.19% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: -0.19%
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: 2.36% Traditional cash on cash: 5.47% Airbnb Rental Income: $2288 Traditional Rental Income: $3143 Airbnb ROI: 2.36% Traditional ROI: 5.47%
00 Ide Perrin Rd Woodstock, CT 00 Ide Perrin Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$299,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.43% Airbnb Rental Income: $843 Traditional Rental Income: $1094 Airbnb ROI: -1.62% Traditional ROI: 0.43%
Aplin Hill Ln Woodstock, CT Aplin Hill Ln, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 9.08% Airbnb Rental Income: $843 Traditional Rental Income: $1105 Airbnb ROI: 1.98% Traditional ROI: 9.08%
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: 1.31% Traditional cash on cash: 5.74% Airbnb Rental Income: $2288 Traditional Rental Income: $3581 Airbnb ROI: 1.31% Traditional ROI: 5.74%
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: 0.63% Traditional cash on cash: 4.46% Airbnb Rental Income: $2288 Traditional Rental Income: $3826 Airbnb ROI: 0.63% Traditional ROI: 4.46%
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: 2.76% Traditional cash on cash: 8.96% Airbnb Rental Income: $1451 Traditional Rental Income: $2196 Airbnb ROI: 2.76% Traditional ROI: 8.96%
186 Brickyard Rd 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: 0.83% Traditional cash on cash: 3.69% Airbnb Rental Income: $2288 Traditional Rental Income: $3262 Airbnb ROI: 0.83% Traditional ROI: 3.69%
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: 7.34% Airbnb Rental Income: $null Traditional Rental Income: $4131 Airbnb ROI: N/A Traditional ROI: 7.34%
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.	$329,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 6.58% Airbnb Rental Income: $1451 Traditional Rental Income: $2826 Airbnb ROI: 0.74% Traditional ROI: 6.58%
158 W Quasset Rd 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: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $6671 Airbnb ROI: N/A Traditional ROI: 0.98%
586 English Neighborhood Road Woodstock, CT IF YOU'VE BEEN DREAMING OF OWNING A LOG HOME YOUR WAIT MAY BE OVER! THIS COMFY CABIN IS RU...	3 beds \| 1 baths \| 1,220 sq.ft.	$365,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 4.11% Airbnb Rental Income: $2288 Traditional Rental Income: $2300 Airbnb ROI: 2.41% Traditional ROI: 4.11%
48 Grey Fox Lndg 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: 6.94% Airbnb Rental Income: $null Traditional Rental Income: $7592 Airbnb ROI: N/A Traditional ROI: 6.94%
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: 1.27% Traditional cash on cash: 4.17% Airbnb Rental Income: $2288 Traditional Rental Income: $3074 Airbnb ROI: 1.27% Traditional ROI: 4.17%
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: 1.43% Traditional cash on cash: 3.13% Airbnb Rental Income: $2288 Traditional Rental Income: $2553 Airbnb ROI: 1.43% Traditional ROI: 3.13%
16 Walnut Rd. Woodstock, CT Immaculate, young cape cod style offering 6 rooms, 3 bedrooms and two full baths in a desi...	3 beds \| 2 baths \| 1,554 sq.ft.	$399,900	Airbnb cash on cash: 2.04% Traditional cash on cash: 5.27% Airbnb Rental Income: $2288 Traditional Rental Income: $2927 Airbnb ROI: 2.04% Traditional ROI: 5.27%
349 Route 197 Woodstock, CT Bring your vision to this 3-bedroom, 2-bath Cape set on a 2.5-acre corner lot in Woodstock...	3 beds \| 2 baths \| 1,229 sq.ft.	$299,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 7.01% Airbnb Rental Income: $2288 Traditional Rental Income: $2740 Airbnb ROI: 3.39% Traditional ROI: 7.01%
12 Loyola Rd Extension Woodstock, CT This cottage in Woodstock is a quintessential charming retreat located on Quasset Lake. It...	1 beds \| 1 baths \| 711 sq.ft.	$439,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2% Airbnb Rental Income: $1062 Traditional Rental Income: $1810 Airbnb ROI: -0.71% Traditional ROI: 2%
511 Perrin Rd Woodstock, CT 511 Perrin Rd, Woodstock, CT 06281 \| Single Family Residential	2 beds \| 2 baths \| 2,393 sq.ft.	$650,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -0.54% Airbnb Rental Income: $1451 Traditional Rental Income: $1662 Airbnb ROI: -1.6% Traditional ROI: -0.54%
21 Fairfield Dr Woodstock, CT 21 Fairfield Dr, Woodstock, CT 06281 \| Single Family Residential	3 beds \| 1 baths \| 2,014 sq.ft.	$500,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 1.23% Airbnb Rental Income: $2288 Traditional Rental Income: $2130 Airbnb ROI: 0.35% Traditional ROI: 1.23%
1210 Route 169 Woodstock, CT 1210 Route 169, Woodstock, CT 06281 \| Single Family Residential	4 beds \| 1 baths \| 3,070 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $2643 Airbnb ROI: N/A Traditional ROI: 4.13%
429 New Sweden Rd Woodstock, CT 429 New Sweden Rd, Woodstock, CT 06281 \| Single Family Residential	3 beds \| 2 baths \| 2,478 sq.ft.	$625,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.49% Airbnb Rental Income: $2288 Traditional Rental Income: $2786 Airbnb ROI: -0.34% Traditional ROI: 1.49%
25 Rte 197 #70 Woodstock, CT 25 Rte 197 #70, Woodstock, CT 06281 \| Manufactured Home	2 beds \| 1 baths \| 450 sq.ft.	$75,000	Airbnb cash on cash: -14.53% Traditional cash on cash: -5.87% Airbnb Rental Income: $1451 Traditional Rental Income: $1662 Airbnb ROI: -14.53% Traditional ROI: -5.87%
95 Pole Bridge Rd Woodstock, CT 95 Pole Bridge Rd, Woodstock, CT 06281 \| Single Family Residential	4 beds \| 3 baths \| 3,868 sq.ft.	$1,275,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.24% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: -1.24%
Route 197 Rte Woodstock, CT Route 197 Rte, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.47% Airbnb Rental Income: $843 Traditional Rental Income: $1105 Airbnb ROI: -1.62% Traditional ROI: 0.47%
Child Dome Rd Woodstock, CT Child Dome Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$179,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.78% Airbnb Rental Income: $843 Traditional Rental Income: $1094 Airbnb ROI: -0.63% Traditional ROI: 2.78%
182 Baxter Rd Woodstock, CT 182 Baxter Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$74,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 10.62% Airbnb Rental Income: $843 Traditional Rental Income: $1105 Airbnb ROI: 2.63% Traditional ROI: 10.62%
259 Quarry Rd Woodstock, CT 259 Quarry Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$595,000	Airbnb cash on cash: -2.37% Traditional cash on cash: -1.55% Airbnb Rental Income: $843 Traditional Rental Income: $967 Airbnb ROI: -2.37% Traditional ROI: -1.55%
Baxter Rd Woodstock, CT Baxter Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$74,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 10.62% Airbnb Rental Income: $843 Traditional Rental Income: $1105 Airbnb ROI: 2.63% Traditional ROI: 10.62%
Lot 03-2 New Sweden Rd Woodstock, CT Lot 03-2 New Sweden Rd, Woodstock, CT 06281 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 7.44% Airbnb Rental Income: $843 Traditional Rental Income: $1105 Airbnb ROI: 1.29% Traditional ROI: 7.44%

Real Estate investment in Woodstock, CT

There are 38 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 $201. In August 2026, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $2,337.

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

There are 38 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 $2,337.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, CT

23 Senexet Rd

Woodstock, CT

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

$674,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $2288

Traditional Rental Income: $4133

Airbnb ROI: 0.18%

Traditional ROI: 4.02%

60 Indian Spring Rd

Woodstock, CT

2 beds | 2 baths | 1,855 sq.ft.

$699,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1451

Traditional Rental Income: $2898

Airbnb ROI: -0.41%

Traditional ROI: 2.47%

101 Child Hill Rd

Woodstock, CT

4 beds | 3 baths | 2,150 sq.ft.

$520,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2053

Airbnb ROI: N/A

Traditional ROI: 2.19%

70 Red Cedar Road

Woodstock, CT

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

$390,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $2288

Traditional Rental Income: $2311

Airbnb ROI: 2.06%

Traditional ROI: 3.68%

20 Loyola Rd

Woodstock, CT

2 beds | 2 baths | 2,216 sq.ft.

$698,900

Airbnb cash on cash: -1.81%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $1451

Traditional Rental Income: $3114

Airbnb ROI: -1.81%

Traditional ROI: 1.4%

4 Loyola Rd Extension

Woodstock, CT

1 beds | 1 baths | 961 sq.ft.

$625,000

Airbnb cash on cash: -1.36%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $1062

Traditional Rental Income: $1995

Airbnb ROI: -1.36%

Traditional ROI: 0.87%

36 Olde Meadow Rd

Woodstock, CT

4 beds | 2 baths | 2,900 sq.ft.

$799,900

Airbnb cash on cash: N/A

Traditional cash on cash: -0.19%

Airbnb Rental Income: $null

Traditional Rental Income: $2337

Airbnb ROI: N/A

Traditional ROI: -0.19%

Center Road

Woodstock, CT

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

$489,900

Airbnb cash on cash: 2.36%

Traditional cash on cash: 5.47%

Airbnb Rental Income: $2288

Traditional Rental Income: $3143

Airbnb ROI: 2.36%