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 19 Single Family Residential 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
1030 Washington Woodbury Rd Roxbury, CT Good Hope Estate. Transport yourself to this stunning European-style home with all the bel...	4 beds \| 4 baths \| 4,874 sq.ft.	$2,475,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.19% Airbnb Rental Income: $1924 Traditional Rental Income: $8326 Airbnb ROI: -0.82% Traditional ROI: 2.19%
88 Rucum Rd Roxbury, CT Spectacularly renovated barn with additions including fabulous Media Room. 11 Rooms includ...	5 beds \| 4 baths \| 5,113 sq.ft.	$2,195,000	Airbnb cash on cash: -1.76% Traditional cash on cash: 1.06% Airbnb Rental Income: $232 Traditional Rental Income: $5760 Airbnb ROI: -1.76% Traditional ROI: 1.06%
24 Hickory Ln Roxbury, CT Fabulous open Post & Beam home, loaded with recent upgrades over the past 3 years: New Roo...	4 beds \| 2 baths \| 3,340 sq.ft.	$1,155,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 1.56% Airbnb Rental Income: $1924 Traditional Rental Income: $3425 Airbnb ROI: -0.31% Traditional ROI: 1.56%
11 Ravenrock Rd Roxbury, CT A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in t...	4 beds \| 5 baths \| 7,063 sq.ft.	$3,595,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 0.81% Airbnb Rental Income: $1924 Traditional Rental Income: $9650 Airbnb ROI: -1.66% Traditional ROI: 0.81%
286 South St Roxbury, CT Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt...	5 beds \| 3 baths \| 2,804 sq.ft.	$1,095,000	Airbnb cash on cash: -1.72% Traditional cash on cash: 5.92% Airbnb Rental Income: $232 Traditional Rental Income: $7791 Airbnb ROI: -1.72% Traditional ROI: 5.92%
8 Bayberry Hl Roxbury, CT Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft...	5 beds \| 4 baths \| 5,940 sq.ft.	$3,995,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.01% Airbnb Rental Income: $232 Traditional Rental Income: $10054 Airbnb ROI: -1.71% Traditional ROI: 1.01%
85 Good Hill Rd Roxbury, CT At the end of a long, winding private driveway, this exceptional Roxbury estate offers tot...	3 beds \| 2 baths \| 2,440 sq.ft.	$1,630,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 1.3% Airbnb Rental Income: $593 Traditional Rental Income: $4147 Airbnb ROI: -1.23% Traditional ROI: 1.3%
99 Carriage Ln Roxbury, CT Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully reno...	4 beds \| 2 baths \| 6,395 sq.ft.	$1,599,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.14% Airbnb Rental Income: $1924 Traditional Rental Income: $4372 Airbnb ROI: -0.85% Traditional ROI: 1.14%
L7&L8 Willow Brook Dr Roxbury, CT New Construction Opportunity - Custom Estate on 20+ Acres in Roxbury, CT - Designed and to...	5 beds \| 3 baths \| 6,729 sq.ft.	$5,499,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 0% Airbnb Rental Income: $232 Traditional Rental Income: $6048 Airbnb ROI: -1.18% Traditional ROI: 0%
242 Tophet Rd 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: -1.39% Traditional cash on cash: 2.75% Airbnb Rental Income: $593 Traditional Rental Income: $3579 Airbnb ROI: -1.39% Traditional ROI: 2.75%
50 Southbury Rd 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: -1.61% Traditional cash on cash: 3.07% Airbnb Rental Income: $232 Traditional Rental Income: $4143 Airbnb ROI: -1.61% Traditional ROI: 3.07%
38 W Mountain Ln Roxbury, CT Tucked away on a long private road, this light and bright Roxbury retreat combines timeles...	3 beds \| 2 baths \| 2,336 sq.ft.	$795,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 3.01% Airbnb Rental Income: $593 Traditional Rental Income: $3648 Airbnb ROI: -1.5% Traditional ROI: 3.01%
216 Baker Rd Roxbury, CT Step back in time with this historic 1800s Colonial that retains its original character an...	4 beds \| 2 baths \| 2,008 sq.ft.	$699,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.65% Airbnb Rental Income: $1924 Traditional Rental Income: $3354 Airbnb ROI: 0.68% Traditional ROI: 3.65%
233 Southbury Rd Roxbury, CT Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain...	5 beds \| 6 baths \| 5,447 sq.ft.	$1,795,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 4.35% Airbnb Rental Income: $232 Traditional Rental Income: $10743 Airbnb ROI: -2.09% Traditional ROI: 4.35%
22 E Woods Rd Roxbury, CT 22 E Woods Rd, Roxbury, CT 06783 \| Single Family Residential	4 beds \| 2 baths \| 3,476 sq.ft.	$685,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.71% Airbnb Rental Income: $1924 Traditional Rental Income: $3183 Airbnb ROI: -1.06% Traditional ROI: 1.71%
47 South St Roxbury, CT 47 South St, Roxbury, CT 06783 \| Single Family Residential	3 beds \| 2 baths \| 2,489 sq.ft.	$875,000	Airbnb cash on cash: -2.87% Traditional cash on cash: 0.04% Airbnb Rental Income: $593 Traditional Rental Income: $2677 Airbnb ROI: -2.87% Traditional ROI: 0.04%
55 Mallory Rd Roxbury, CT 55 Mallory Rd, Roxbury, CT 06783 \| Single Family Residential	4 beds \| 3 baths \| 2,682 sq.ft.	$599,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 3.54% Airbnb Rental Income: $1924 Traditional Rental Income: $3817 Airbnb ROI: -0.76% Traditional ROI: 3.54%
31 Hickory Ln Roxbury, CT 31 Hickory Ln, Roxbury, CT 06783 \| Single Family Residential	4 beds \| 3 baths \| 6,169 sq.ft.	$1,795,000	Airbnb cash on cash: -2.34% Traditional cash on cash: 0.64% Airbnb Rental Income: $1924 Traditional Rental Income: $6384 Airbnb ROI: -2.34% Traditional ROI: 0.64%
4 Judge Rd Roxbury, CT 4 Judge Rd, Roxbury, CT 06783 \| Single Family Residential	3 beds \| 2 baths \| 1,974 sq.ft.	$3,200,000	Airbnb cash on cash: -3.06% Traditional cash on cash: -2.26% Airbnb Rental Income: $593 Traditional Rental Income: $2669 Airbnb ROI: -3.06% Traditional ROI: -2.26%

Your search for investment property begins and ends here

Single Family Homes for Sale in Roxbury, CT

1030 Washington Woodbury Rd

Roxbury, CT

4 beds | 4 baths | 4,874 sq.ft.

$2,475,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1924

Traditional Rental Income: $8326

Airbnb ROI: -0.82%

Traditional ROI: 2.19%

88 Rucum Rd

Roxbury, CT

5 beds | 4 baths | 5,113 sq.ft.

$2,195,000

Airbnb cash on cash: -1.76%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $232

Traditional Rental Income: $5760

Airbnb ROI: -1.76%

Traditional ROI: 1.06%

24 Hickory Ln

Roxbury, CT

4 beds | 2 baths | 3,340 sq.ft.

$1,155,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $1924

Traditional Rental Income: $3425

Airbnb ROI: -0.31%

Traditional ROI: 1.56%

11 Ravenrock Rd

Roxbury, CT

4 beds | 5 baths | 7,063 sq.ft.

$3,595,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: 0.81%

Airbnb Rental Income: $1924

Traditional Rental Income: $9650

Airbnb ROI: -1.66%

Traditional ROI: 0.81%

286 South St

Roxbury, CT

5 beds | 3 baths | 2,804 sq.ft.

$1,095,000

Airbnb cash on cash: -1.72%

Traditional cash on cash: 5.92%

Airbnb Rental Income: $232

Traditional Rental Income: $7791

Airbnb ROI: -1.72%

Traditional ROI: 5.92%

8 Bayberry Hl

Roxbury, CT

5 beds | 4 baths | 5,940 sq.ft.

$3,995,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $232

Traditional Rental Income: $10054

Airbnb ROI: -1.71%

Traditional ROI: 1.01%

85 Good Hill Rd

Roxbury, CT

3 beds | 2 baths | 2,440 sq.ft.

$1,630,000

Airbnb cash on cash: -1.23%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $593

Traditional Rental Income: $4147

Airbnb ROI: -1.23%

Traditional ROI: 1.3%

99 Carriage Ln

Roxbury, CT

4 beds | 2 baths | 6,395 sq.ft.

$1,599,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $1924

Traditional Rental Income: $4372

Airbnb ROI: -0.85%