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.
Investment Property for Sale in Roxbury, CT
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
78 Garnet RoadRoxbury, CTLooking for a calming and peaceful property? You'll find total peace and quiet on this 15.... |
3 beds | 4 baths | 3,302 sq.ft. |
$1,675,000 |
Airbnb cash on cash: -0.46%
|
179 South StreetRoxbury, CTOwn 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: 0.1%
|
23 Painter Hill RoadRoxbury, CTMint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic,... |
4 beds | 3 baths | 1,782 sq.ft. |
$1,025,000 |
Airbnb cash on cash: N/A
|
247 Painter Hill RoadRoxbury, CTPristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by R... |
3 beds | 4 baths | 2,396 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -0.34%
|
18 Tunnel RoadRoxbury, CTMUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and ha... |
3 beds | 3 baths | 2,080 sq.ft. |
$1,049,000 |
Airbnb cash on cash: -1.38%
|
33 Sentry Hill RoadRoxbury, CTMint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dir... |
4 beds | 4 baths | 2,716 sq.ft. |
$1,495,000 |
Airbnb cash on cash: N/A
|
336 South StreetRoxbury, CTQuintessential Roxbury retreat, an updated classic 3-bedroom Colonial with open floor plan... |
3 beds | 3 baths | 2,556 sq.ft. |
$995,000 |
Airbnb cash on cash: -1.28%
|
45 Moosehorn RoadRoxbury, CTPristine 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: N/A
|
11 Ravenrock RoadRoxbury, CTA private gated road leads to this elegant shingle-style estate on 20+ secluded acres in t... |
4 beds | 6 baths | 7,063 sq.ft. |
$4,450,000 |
Airbnb cash on cash: N/A
|
11 Hodge RoadRoxbury, CTThis Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic... |
4 beds | 3 baths | 2,982 sq.ft. |
$975,000 |
Airbnb cash on cash: N/A
|
286 South StreetRoxbury, CTDiscover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt... |
5 beds | 5 baths | 2,804 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -3.22%
|
8 Bayberry HillRoxbury, CTPrivately 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%
|
103A Chalybes Road WestRoxbury, CTTO 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%
|
103B Chalybes Road WestRoxbury, CTTO 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: N/A
|
85 Good Hill RoadRoxbury, CTAt 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%
|
81 Chalybes Road WestRoxbury, CTTO 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: N/A
|
99 Carriage LaneRoxbury, CTWelcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and p... |
4 beds | 3 baths | 6,395 sq.ft. |
$1,675,000 |
Airbnb cash on cash: N/A
|
L7&L8 Willow Brook DriveRoxbury, CTNew 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%
|
242 Tophet RoadRoxbury, CTNestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this cha... |
3 beds | 2 baths | 1,862 sq.ft. |
$895,000 |
Airbnb cash on cash: -1.08%
|
97 Chalybes Road WestRoxbury, CTTO 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: N/A
|
50 Southbury RoadRoxbury, CTCottage, 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: -3.24%
|
2 Old Turnpike RoadRoxbury, CTWelcome to 2 Old Turnpike Road, a classic 3-bedroom, 2-bath ranch nestled on 2.52 acres in... |
3 beds | 2 baths | 1,372 sq.ft. |
$585,900 |
Airbnb cash on cash: 0%
|
158 Painter Hill RoadRoxbury, CTGreat value, excellent location! Painter Hill is one of Roxbury's most scenic country road... |
3 beds | 3 baths | 2,793 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -1.59%
|
38 West Mountain LaneRoxbury, CTTucked 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: -0.82%
|
Real Estate investment in Roxbury, CT
There are 25 properties for sale in the city of Roxbury . The median list price in Roxbury is $1,549,000 and the average price per square foot is $455. In October 2025, the average monthly cash on cash return in Roxbury is 1.00%. The average monthly rental income in Roxbury is $4,372.