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.

Condos for Sale in Woodstock, CT

Search for Condos for Sale in Woodstock, Connecticut. Browse all of Mashvisor’s Condos listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 18 Condos listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1026 Route 171 Woodstock, CT Stunning 3-bedroom, 2-bath Colonial in picturesque Woodstock, CT, situated on 2 serene acr...	3 beds \| 2 baths \| 1,728 sq.ft.	$449,999	Airbnb cash on cash: 8.11% Traditional cash on cash: 0.61% Airbnb Rental Income: $6015 Traditional Rental Income: $1665 Airbnb ROI: 8.11% Traditional ROI: 0.61%
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%
37 Pulpit Rock Road Woodstock, CT Location, location, location! Tucked away on a quiet scenic road just steps from historic ...	4 beds \| 3 baths \| 2,682 sq.ft.	$649,900	Airbnb cash on cash: 0.72% Traditional cash on cash: 4.24% Airbnb Rental Income: $3137 Traditional Rental Income: $4558 Airbnb ROI: 0.72% Traditional ROI: 4.24%
72 Lake View Drive Woodstock, CT *MOTIVATED SELLER*Welcome to your summer getaway or year-round oasis. This 2-bedroom 2...	2 beds \| 2 baths \| 1,338 sq.ft.	$649,000	Airbnb cash on cash: -1.6% Traditional cash on cash: 1.21% Airbnb Rental Income: $1588 Traditional Rental Income: $2838 Airbnb ROI: -1.6% Traditional ROI: 1.21%
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: -0.8% Traditional cash on cash: 2.06% Airbnb Rental Income: $3137 Traditional Rental Income: $5083 Airbnb ROI: -0.8% 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: -2.23% 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 Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers o...	5 beds \| 4 baths \| 4,172 sq.ft.	$565,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 8.33% Airbnb Rental Income: $4090 Traditional Rental Income: $6137 Airbnb ROI: 2.8% Traditional ROI: 8.33%
47 Little Bungee Hill Road Woodstock, CT Welcome home to this charming 1,412 sq ft ranch just a stone's throw from sparkling Lake B...	4 beds \| 2 baths \| 1,412 sq.ft.	$450,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 3.85% Airbnb Rental Income: $3137 Traditional Rental Income: $3096 Airbnb ROI: 2.25% Traditional ROI: 3.85%
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.	$450,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.4% Airbnb Rental Income: $3137 Traditional Rental Income: $2465 Airbnb ROI: 2.31% Traditional ROI: 2.4%
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%
25 Barlow Cemetery Road Woodstock, CT Set on a private 1.64-acre lot in West Woodstock, this beautifully maintained 3-bedroom, 2...	3 beds \| 2 baths \| 1,728 sq.ft.	$485,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 3.36% Airbnb Rental Income: $6015 Traditional Rental Income: $3034 Airbnb ROI: 7.31% Traditional ROI: 3.36%
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.	$190,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 6.8% Airbnb Rental Income: $1588 Traditional Rental Income: $1881 Airbnb ROI: 2.67% Traditional ROI: 6.8%
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%

Your search for investment property begins and ends here

Condos for Sale in Woodstock, CT

1026 Route 171

Woodstock, CT

3 beds | 2 baths | 1,728 sq.ft.

$449,999

Airbnb cash on cash: 8.11%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $6015

Traditional Rental Income: $1665

Airbnb ROI: 8.11%

Traditional ROI: 0.61%

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%

37 Pulpit Rock Road

Woodstock, CT

4 beds | 3 baths | 2,682 sq.ft.

$649,900

Airbnb cash on cash: 0.72%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $3137

Traditional Rental Income: $4558

Airbnb ROI: 0.72%

Traditional ROI: 4.24%

72 Lake View Drive

Woodstock, CT

2 beds | 2 baths | 1,338 sq.ft.

$649,000

Airbnb cash on cash: -1.6%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $1588

Traditional Rental Income: $2838

Airbnb ROI: -1.6%

Traditional ROI: 1.21%

19 Hiawatha Heights

Woodstock, CT

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

$999,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $3137

Traditional Rental Income: $5083

Airbnb ROI: -0.8%

Traditional ROI: 2.06%

1669 Route 169

Woodstock, CT

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

$1,250,000

Airbnb cash on cash: -2.23%

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%