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 |
|---|---|---|---|
1030 Washington Woodbury RdRoxbury, CTGood 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%
|
88 Rucum RdRoxbury, CTSpectacularly 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%
|
24 Hickory LnRoxbury, CTFabulous 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%
|
11 Ravenrock RdRoxbury, CTA 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%
|
286 South StRoxbury, CTDiscover 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%
|
8 Bayberry HlRoxbury, CTPrivately 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%
|
85 Good Hill RdRoxbury, CTAt 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%
|
99 Carriage LnRoxbury, CTLooking 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%
|
L7&L8 Willow Brook DrRoxbury, CTNew 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%
|
242 Tophet RdRoxbury, CTNestled 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%
|
50 Southbury RdRoxbury, 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: -1.61%
|
38 W Mountain LnRoxbury, CTTucked 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%
|
216 Baker RdRoxbury, CTStep 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%
|
233 Southbury RdRoxbury, 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: -2.09%
|
22 E Woods RdRoxbury, CT22 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%
|
47 South StRoxbury, CT47 South St, Roxbury, CT 06783 | Single Family Residential |
3 beds | 2 baths | 2,489 sq.ft. |
$875,000 |
Airbnb cash on cash: -2.87%
|
55 Mallory RdRoxbury, CT55 Mallory Rd, Roxbury, CT 06783 | Single Family Residential |
4 beds | 3 baths | 2,682 sq.ft. |
$599,000 |
Airbnb cash on cash: -0.76%
|
31 Hickory LnRoxbury, CT31 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%
|
4 Judge RdRoxbury, CT4 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%
|
69 Moosehorn RdRoxbury, CT69 Moosehorn Rd, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$549,000 |
Airbnb cash on cash: N/A
|
Lot 1 Chalybes Rd WRoxbury, CTLot 1 Chalybes Rd W, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
200 North StRoxbury, CT200 North St, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$499,000 |
Airbnb cash on cash: N/A
|
Lot 4 Chalybes Rd WRoxbury, CTLot 4 Chalybes Rd W, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$599,000 |
Airbnb cash on cash: N/A
|
Booth RdRoxbury, CTBooth Rd, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$275,000 |
Airbnb cash on cash: N/A
|
31 Holmes RdRoxbury, CT31 Holmes Rd, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$450,000 |
Airbnb cash on cash: N/A
|
Lot 7 & Lot 8 Willow Brook DrRoxbury, CTLot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | N/A |
$999,000 |
Airbnb cash on cash: N/A
|
204 North St Lot 3Roxbury, CT204 North St Lot 3, Roxbury, CT 06783 | Other |
N/A beds | N/A baths | N/A |
$775,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Roxbury, CT
There are 27 properties for sale in the city of Roxbury . The median list price in Roxbury is $950,000 and the average price per square foot is $316. In February 2026, the average monthly cash on cash return in Roxbury is 1.00%. The average monthly rental income in Roxbury is $3,579.