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 |
|---|---|---|---|
176 Apple LaneRoxbury, CTYour turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manic... |
4 beds | 5 baths | 3,566 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -1.06%
|
1030 Washington Woodbury RoadRoxbury, CTNEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers s... |
4 beds | 5 baths | 4,874 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -0.88%
|
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. |
$985,000 |
Airbnb cash on cash: -0.44%
|
18 Ranney Hill RoadRoxbury, CTPerfect Country Home! Located close to town on a quiet country road. Built is 2018, the ne... |
4 beds | 4 baths | 3,198 sq.ft. |
$2,000,000 |
Airbnb cash on cash: -0.91%
|
20 Wellers Bridge RoadRoxbury, CTThis handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Gre... |
3 beds | 3 baths | 2,059 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.27%
|
23 Painter Hill RoadRoxbury, CTMint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm... |
4 beds | 3 baths | 1,782 sq.ft. |
$1,095,000 |
Airbnb cash on cash: -0.38%
|
24 Hickory LaneRoxbury, CTTucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborho... |
4 beds | 4 baths | 3,340 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.45%
|
45 Chalybes RoadRoxbury, CTLight-filled, modern living on a private nearly 3-acre corner lot - with room to grow. Set... |
3 beds | 4 baths | 2,725 sq.ft. |
$995,000 |
Airbnb cash on cash: -0.56%
|
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: -0.57%
|
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. |
$1,595,000 |
Airbnb cash on cash: -0.81%
|
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. |
$995,000 |
Airbnb cash on cash: -1.02%
|
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. |
$1,500,000 |
Airbnb cash on cash: -0.72%
|
99 Carriage LaneRoxbury, CTLooking to escape the hectic pace of city life? Welcome to this peaceful, beautifully reno... |
4 beds | 3 baths | 6,395 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -0.98%
|
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. |
$799,000 |
Airbnb cash on cash: -0.42%
|
50 Southbury RoadRoxbury, CTCottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York ... |
5 beds | 3 baths | 1,365 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.73%
|
38 W 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: -0.5%
|
216 Baker RoadRoxbury, CTStep back in time with this historic 1800s Colonial that retains its original character an... |
4 beds | 2 baths | 2,008 sq.ft. |
$679,000 |
Airbnb cash on cash: 0.43%
|
233 Southbury RoadRoxbury, CTPerched 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: -1.66%
|
4 Judge RoadRoxbury, CTExceptional equestrian estate featuring a fully equipped horse facility and charming Cape-... |
3 beds | 2 baths | 1,974 sq.ft. |
$3,200,000 |
Airbnb cash on cash: -0.87%
|
11 Evergreen DriveRoxbury, CTThis is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a clas... |
4 beds | 4 baths | 3,800 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.27%
|
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. |
$3,395,000 |
Airbnb cash on cash: -1.76%
|
2 Pickett RoadRoxbury, CTPresenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury... |
5 beds | 5 baths | 3,326 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -0.69%
|
56 Goldmine RoadRoxbury, CTThis cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding up... |
3 beds | 3 baths | 2,620 sq.ft. |
$1,375,000 |
Airbnb cash on cash: -0.73%
|
28 Garnet RoadRoxbury, CTDiscover modern serenity in this private contemporary retreat nestled on 3.44 private acre... |
3 beds | 4 baths | 3,696 sq.ft. |
$1,000,000 |
Airbnb cash on cash: -0.53%
|
246 North StreetRoxbury, CTJuniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed a... |
3 beds | 2 baths | 2,031 sq.ft. |
$1,095,000 |
Airbnb cash on cash: -0.51%
|
47 Squire RoadRoxbury, CTA breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boa... |
5 beds | 6 baths | 7,121 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -1.42%
|
Real Estate investment in Roxbury, CT
There are 27 properties for sale in the city of Roxbury . The median list price in Roxbury is $1,200,000 and the average price per square foot is $359. In June 2026, the average monthly cash on cash return in Roxbury is 2.00%. The average monthly rental income in Roxbury is $4,372.