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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
176 Apple Lane Roxbury, CT Your 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: -1.09% Traditional cash on cash: 2.77% Airbnb Rental Income: $1641 Traditional Rental Income: $8323 Airbnb ROI: -1.09% Traditional ROI: 2.77%
1030 Washington Woodbury Road Roxbury, CT NEW 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: -0.9% Traditional cash on cash: 2.96% Airbnb Rental Income: $1641 Traditional Rental Income: $8326 Airbnb ROI: -0.9% Traditional ROI: 2.96%
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.	$985,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.85% Airbnb Rental Income: $1274 Traditional Rental Income: $3139 Airbnb ROI: -0.62% Traditional ROI: 1.85%
23 Painter Hill Road Roxbury, CT Mint 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: -0.42% Traditional cash on cash: 1.8% Airbnb Rental Income: $1641 Traditional Rental Income: $3446 Airbnb ROI: -0.42% Traditional ROI: 1.8%
24 Hickory Lane Roxbury, CT Tucked away in one of Roxbury's most desirable neighborhoods, this 4-bedroom, 2.5-bath Col...	4 beds \| 3 baths \| 3,340 sq.ft.	$1,155,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.57% Airbnb Rental Income: $1641 Traditional Rental Income: $3425 Airbnb ROI: -0.52% Traditional ROI: 1.57%
45 Chalybes Road Roxbury, CT Light-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: -0.75% Traditional cash on cash: 5.81% Airbnb Rental Income: $1274 Traditional Rental Income: $6948 Airbnb ROI: -0.75% Traditional ROI: 5.81%
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.	$1,099,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.78% Airbnb Rental Income: $1274 Traditional Rental Income: $3472 Airbnb ROI: -0.76% Traditional ROI: 1.78%
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.	$1,649,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 1.36% Airbnb Rental Income: $1641 Traditional Rental Income: $4564 Airbnb ROI: -0.85% Traditional ROI: 1.36%
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.	$1,049,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 6.22% Airbnb Rental Income: $903 Traditional Rental Income: $7791 Airbnb ROI: -1.18% Traditional ROI: 6.22%
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: -1.56% Traditional cash on cash: 1.01% Airbnb Rental Income: $903 Traditional Rental Income: $10054 Airbnb ROI: -1.56% Traditional ROI: 1.01%
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: -0.86% Traditional cash on cash: 1.3% Airbnb Rental Income: $1274 Traditional Rental Income: $4147 Airbnb ROI: -0.86% Traditional ROI: 1.3%
99 Carriage Lane Roxbury, CT Looking 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: -1.01% Traditional cash on cash: 1.29% Airbnb Rental Income: $1641 Traditional Rental Income: $4372 Airbnb ROI: -1.01% Traditional ROI: 1.29%
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.	$799,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.98% Airbnb Rental Income: $1274 Traditional Rental Income: $3579 Airbnb ROI: -0.66% Traditional ROI: 2.98%
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: -0.98% Traditional cash on cash: 3.07% Airbnb Rental Income: $903 Traditional Rental Income: $4143 Airbnb ROI: -0.98% Traditional ROI: 3.07%
38 W 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: -0.73% Traditional cash on cash: 3.01% Airbnb Rental Income: $1274 Traditional Rental Income: $3648 Airbnb ROI: -0.73% Traditional ROI: 3.01%
216 Baker Road 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.	$689,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.72% Airbnb Rental Income: $1641 Traditional Rental Income: $3354 Airbnb ROI: 0.34% Traditional ROI: 3.72%
233 Southbury Road 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: -1.75% Traditional cash on cash: 4.35% Airbnb Rental Income: $903 Traditional Rental Income: $10743 Airbnb ROI: -1.75% Traditional ROI: 4.35%
11 Evergreen Drive Roxbury, CT This 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: -0.32% Traditional cash on cash: 3.97% Airbnb Rental Income: $1641 Traditional Rental Income: $5966 Airbnb ROI: -0.32% Traditional ROI: 3.97%
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.	$3,595,000	Airbnb cash on cash: -1.73% Traditional cash on cash: 0.87% Airbnb Rental Income: $1641 Traditional Rental Income: $9858 Airbnb ROI: -1.73% Traditional ROI: 0.87%
56 Goldmine Road Roxbury, CT This 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: -0.87% Traditional cash on cash: 0.58% Airbnb Rental Income: $1274 Traditional Rental Income: $2725 Airbnb ROI: -0.87% Traditional ROI: 0.58%
28 Garnet Road Roxbury, CT Discover modern serenity in this secluded contemporary retreat nestled on 3.44 private acr...	3 beds \| 4 baths \| 3,696 sq.ft.	$1,050,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 4.02% Airbnb Rental Income: $1274 Traditional Rental Income: $5508 Airbnb ROI: -0.72% Traditional ROI: 4.02%
246 North Street Roxbury, CT Juniper Hill offers masterfully updated one level living in Roxbury, Connecticut. Dubbed a...	3 beds \| 2 baths \| 2,031 sq.ft.	$1,195,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.56% Airbnb Rental Income: $1274 Traditional Rental Income: $3389 Airbnb ROI: -0.7% Traditional ROI: 1.56%

Real Estate investment in Roxbury, CT

There are 23 properties for sale in the city of Roxbury . The median list price in Roxbury is $1,195,000 and the average price per square foot is $363. In May 2026, the average monthly cash on cash return in Roxbury is 3.00%. The average monthly rental income in Roxbury is $4,372.

Roxbury, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 23 investment properties available for sale in Roxbury.

In 2026, the best neighborhood to buy investment property is Roxbury.

The ROI for Long-Term is higher than the Short-Term in Roxbury with average rental income of $4,372.

Your search for investment property begins and ends here

Investment Property for Sale in Roxbury, CT

176 Apple Lane

Roxbury, CT

4 beds | 5 baths | 3,566 sq.ft.

$1,995,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $1641

Traditional Rental Income: $8323

Airbnb ROI: -1.09%

Traditional ROI: 2.77%

1030 Washington Woodbury Road

Roxbury, CT

4 beds | 5 baths | 4,874 sq.ft.

$1,995,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $1641

Traditional Rental Income: $8326

Airbnb ROI: -0.9%

Traditional ROI: 2.96%

179 South Street

Roxbury, CT

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

$985,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $1274

Traditional Rental Income: $3139

Airbnb ROI: -0.62%

Traditional ROI: 1.85%

23 Painter Hill Road

Roxbury, CT

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

$1,095,000

Airbnb cash on cash: -0.42%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $1641

Traditional Rental Income: $3446

Airbnb ROI: -0.42%

Traditional ROI: 1.8%

24 Hickory Lane

Roxbury, CT

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

$1,155,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $1641

Traditional Rental Income: $3425

Airbnb ROI: -0.52%

Traditional ROI: 1.57%

45 Chalybes Road

Roxbury, CT

3 beds | 4 baths | 2,725 sq.ft.

$995,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 5.81%

Airbnb Rental Income: $1274

Traditional Rental Income: $6948

Airbnb ROI: -0.75%

Traditional ROI: 5.81%

18 Tunnel Road

Roxbury, CT

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

$1,099,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $1274

Traditional Rental Income: $3472

Airbnb ROI: -0.76%

Traditional ROI: 1.78%

33 Sentry Hill Road

Roxbury, CT

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

$1,649,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $1641

Traditional Rental Income: $4564

Airbnb ROI: -0.85%