Real Estate Investment Properties for Sale in Roxbury, CT

Looking for investment property in Roxbury, CT with high ROI ?

Explore a variety of short-term homes & houses in Roxbury, CT. Invest wisely with VRBO & Roxbury, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Roxbury, CT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
179 South Street Roxbury, CT Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been ch...	3 beds \| 2 baths \| 1,772 sq.ft.	$1,275,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.23% Airbnb Rental Income: $593 Traditional Rental Income: $3139 Airbnb ROI: -1.16% Traditional ROI: 1.23%
23 Painter Hill Road Roxbury, CT Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic,...	4 beds \| 3 baths \| 1,782 sq.ft.	$999,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.06% Airbnb Rental Income: $1924 Traditional Rental Income: $3446 Airbnb ROI: -0.12% Traditional ROI: 2.06%
247 Painter Hill Road Roxbury, CT Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by R...	3 beds \| 4 baths \| 2,396 sq.ft.	$1,575,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.96% Airbnb Rental Income: $593 Traditional Rental Income: $3692 Airbnb ROI: -1.36% Traditional ROI: 0.96%
18 Tunnel Road Roxbury, CT MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and ha...	3 beds \| 3 baths \| 2,080 sq.ft.	$999,000	Airbnb cash on cash: -2.9% Traditional cash on cash: 0.51% Airbnb Rental Income: $593 Traditional Rental Income: $3472 Airbnb ROI: -2.9% Traditional ROI: 0.51%
33 Sentry Hill Road Roxbury, CT Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dir...	4 beds \| 4 baths \| 2,716 sq.ft.	$1,475,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 0.13% Airbnb Rental Income: $1924 Traditional Rental Income: $4564 Airbnb ROI: -2.17% Traditional ROI: 0.13%
45 Moosehorn Road Roxbury, CT Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for...	4 beds \| 4 baths \| 4,517 sq.ft.	$1,949,000	Airbnb cash on cash: -2.4% Traditional cash on cash: -0.46% Airbnb Rental Income: $1924 Traditional Rental Income: $4929 Airbnb ROI: -2.4% Traditional ROI: -0.46%
11 Ravenrock Road Roxbury, CT A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in t...	4 beds \| 6 baths \| 7,063 sq.ft.	$3,998,000	Airbnb cash on cash: -2.78% Traditional cash on cash: -0.55% Airbnb Rental Income: $1924 Traditional Rental Income: $9650 Airbnb ROI: -2.78% Traditional ROI: -0.55%
286 South Street Roxbury, CT Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt...	5 beds \| 5 baths \| 2,804 sq.ft.	$1,095,000	Airbnb cash on cash: -3.22% Traditional cash on cash: 4.43% Airbnb Rental Income: $232 Traditional Rental Income: $7791 Airbnb ROI: -3.22% Traditional ROI: 4.43%
8 Bayberry Hill Roxbury, CT Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft...	5 beds \| 6 baths \| 5,940 sq.ft.	$3,995,000	Airbnb cash on cash: -3.16% Traditional cash on cash: -0.44% Airbnb Rental Income: $232 Traditional Rental Income: $10054 Airbnb ROI: -3.16% Traditional ROI: -0.44%
103A Chalybes Road West Roxbury, CT TO BE BUILT - A Home by CORBO! Tranquil luxury on 16 private acres in Roxbury, CT-an excep...	5 beds \| 7 baths \| 4,777 sq.ft.	$2,850,000	Airbnb cash on cash: -3.17% Traditional cash on cash: 0.51% Airbnb Rental Income: $232 Traditional Rental Income: $9716 Airbnb ROI: -3.17% Traditional ROI: 0.51%
103B Chalybes Road West Roxbury, CT TO BE BUILT - A Home by CORBO! A rare opportunity to build your dream home on approximatel...	4 beds \| 3 baths \| 4,071 sq.ft.	$3,050,000	Airbnb cash on cash: -2.67% Traditional cash on cash: -1.51% Airbnb Rental Income: $1924 Traditional Rental Income: $4689 Airbnb ROI: -2.67% Traditional ROI: -1.51%
85 Good Hill Road Roxbury, CT At the end of a long, winding private driveway, this exceptional Roxbury estate offers tot...	3 beds \| 3 baths \| 2,440 sq.ft.	$1,630,000	Airbnb cash on cash: -2.99% Traditional cash on cash: -0.45% Airbnb Rental Income: $593 Traditional Rental Income: $4147 Airbnb ROI: -2.99% Traditional ROI: -0.45%
81 Chalybes Road West Roxbury, CT TO BE BUILT - A New Classic by Connecticut Residential. Here's your chance to create somet...	4 beds \| 5 baths \| 3,677 sq.ft.	$2,200,000	Airbnb cash on cash: -2.48% Traditional cash on cash: 0.67% Airbnb Rental Income: $1924 Traditional Rental Income: $7859 Airbnb ROI: -2.48% Traditional ROI: 0.67%
L7&L8 Willow Brook Drive Roxbury, CT New Construction Opportunity - Custom Estate on 20+ Acres in Roxbury, CT - Designed and to...	5 beds \| 4 baths \| 6,729 sq.ft.	$5,499,000	Airbnb cash on cash: -3.15% Traditional cash on cash: -1.97% Airbnb Rental Income: $232 Traditional Rental Income: $6048 Airbnb ROI: -3.15% Traditional ROI: -1.97%
242 Tophet Road Roxbury, CT Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this cha...	3 beds \| 2 baths \| 1,862 sq.ft.	$849,000	Airbnb cash on cash: -2.86% Traditional cash on cash: 1.28% Airbnb Rental Income: $593 Traditional Rental Income: $3579 Airbnb ROI: -2.86% Traditional ROI: 1.28%
97 Chalybes Road West Roxbury, CT TO BE BUILT - A New Classic by Connecticut Residential. A rare opportunity to bring your d...	4 beds \| 4 baths \| 4,266 sq.ft.	$2,480,000	Airbnb cash on cash: -2.56% Traditional cash on cash: -0.53% Airbnb Rental Income: $1924 Traditional Rental Income: $6080 Airbnb ROI: -2.56% Traditional ROI: -0.53%
50 Southbury Road Roxbury, CT Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern R...	5 beds \| 3 baths \| 2,000 sq.ft.	$950,000	Airbnb cash on cash: -3.23% Traditional cash on cash: 1.45% Airbnb Rental Income: $232 Traditional Rental Income: $4143 Airbnb ROI: -3.23% Traditional ROI: 1.45%
38 West Mountain Lane Roxbury, CT Tucked away on a long private road, this light and bright Roxbury retreat combines timeles...	3 beds \| 3 baths \| 2,336 sq.ft.	$795,000	Airbnb cash on cash: -2.84% Traditional cash on cash: 1.67% Airbnb Rental Income: $593 Traditional Rental Income: $3648 Airbnb ROI: -2.84% Traditional ROI: 1.67%

Your search for investment property begins and ends here

Single Family Homes for Sale in Roxbury, CT

179 South Street

Roxbury, CT

3 beds | 2 baths | 1,772 sq.ft.

$1,275,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $593

Traditional Rental Income: $3139

Airbnb ROI: -1.16%

Traditional ROI: 1.23%

23 Painter Hill Road

Roxbury, CT

4 beds | 3 baths | 1,782 sq.ft.

$999,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $1924

Traditional Rental Income: $3446

Airbnb ROI: -0.12%

Traditional ROI: 2.06%

247 Painter Hill Road

Roxbury, CT

3 beds | 4 baths | 2,396 sq.ft.

$1,575,000

Airbnb cash on cash: -1.36%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $593

Traditional Rental Income: $3692

Airbnb ROI: -1.36%

Traditional ROI: 0.96%

18 Tunnel Road

Roxbury, CT

3 beds | 3 baths | 2,080 sq.ft.

$999,000

Airbnb cash on cash: -2.9%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $593

Traditional Rental Income: $3472

Airbnb ROI: -2.9%

Traditional ROI: 0.51%

33 Sentry Hill Road

Roxbury, CT

4 beds | 4 baths | 2,716 sq.ft.

$1,475,000

Airbnb cash on cash: -2.17%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $1924

Traditional Rental Income: $4564

Airbnb ROI: -2.17%

Traditional ROI: 0.13%

45 Moosehorn Road

Roxbury, CT

4 beds | 4 baths | 4,517 sq.ft.

$1,949,000

Airbnb cash on cash: -2.4%

Traditional cash on cash: -0.46%

Airbnb Rental Income: $1924

Traditional Rental Income: $4929

Airbnb ROI: -2.4%

Traditional ROI: -0.46%

11 Ravenrock Road

Roxbury, CT

4 beds | 6 baths | 7,063 sq.ft.

$3,998,000

Airbnb cash on cash: -2.78%

Traditional cash on cash: -0.55%

Airbnb Rental Income: $1924

Traditional Rental Income: $9650

Airbnb ROI: -2.78%

Traditional ROI: -0.55%

286 South Street

Roxbury, CT

5 beds | 5 baths | 2,804 sq.ft.

$1,095,000

Airbnb cash on cash: -3.22%

Traditional cash on cash: 4.43%

Airbnb Rental Income: $232

Traditional Rental Income: $7791

Airbnb ROI: -3.22%