Connecticut Realtor with experience and knowledge of residential and commercial property in Roxbury

2/11/2026 9:55:07 PM
Under Contract
22 Woods Road Roxbury CT
22 Woods Road

Roxbury, Connecticut 06783

$685,000 | Under Contract

4 Beds | 3 Baths | 3476 Sqft | 6.89 Acres | 34 Days on Market

Property Type: Single Family For Sale

Sunsets beyond compare await you at the end of the curved driveway, up to your secluded 6.89-acre lot. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large c...

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2/7/2026 8:40:52 PM
Under Contract CTS
55 Mallory Road Roxbury CT
55 Mallory Road

Roxbury, Connecticut 06783

$599,000 | Under Contract - Continue

4 Beds | 3 Baths | 2682 Sqft | 3.23 Acres | 167 Days on Market

Property Type: Single Family For Sale

If privacy in the Litchfield Hills is your aspiration, this is the place for you! Gated entrance to this rustic Country Cape w/ covered porch set back off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owne...

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1/22/2026 6:56:20 PM
Under Contract
143 Tophet Road Roxbury CT
143 Tophet Road

Roxbury, Connecticut 06783

$2,295,000 | Under Contract

4 Beds | 6 Baths | 5848 Sqft | 4.01 Acres | 239 Days on Market

Property Type: Single Family For Sale

Located along one of Roxburys most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the...

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1/22/2026 12:18:10 AM
Under Contract CTS
178 Baker Road Roxbury CT
178 Baker Road

Roxbury, Connecticut 06783

$750,000 | Under Contract - Continue

1 Beds | 2 Baths | 1449 Sqft | 11.36 Acres | 29 Days on Market

Property Type: Single Family For Sale

Welcome to the Truman Judson Historical Property. 2 homes on 11.36 private hillside acres overlooking the Shepaug River. House 1 is a beautifully restored 1,449 sq ft converted barn offering 1 bedroom, 1.5 baths, living room plus a large den. Rich in character, it features stone ...

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1/7/2026 5:19:07 PM
Active
22 Woods Road Roxbury CT
22 Woods Road

Roxbury, Connecticut 06783

$685,000 | Active

4 Beds | 3 Baths | 3476 Sqft | 6.89 Acres | 1 Days on Market

Property Type: Single Family For Sale

Sunsets beyond compare await you at the end of the curved driveway, up to your secluded 6.89-acre lot. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large c...

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1/6/2026 6:20:00 PM
Active
242 Tophet Road Roxbury CT
242 Tophet Road

Roxbury, Connecticut 06783

$849,000 | Active

3 Beds | 2 Baths | 1862 Sqft | 6.07 Acres | 4 Days on Market

Property Type: Single Family For Sale

Nestled within one of Roxbury, Connecticuts most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to pe...

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1/5/2026 2:55:31 PM
Active
1030 Washington Woodbury Road Roxbury CT
1030 Washington Woodbury Road

Roxbury, Connecticut 06783

$2,475,000 | Active

4 Beds | 5 Baths | 4874 Sqft | 18.62 Acres | 3 Days on Market

Property Type: Single Family For Sale

Good Hope Estate. Transport yourself to this stunning European-style home with all the bells and whistles! The well thought out 4 bedroom, 4.5 bath home with seasonal views sits on 18 acres of privacy and nature! The eat-in kitchen is a chefs dream complete with Sub-Zero, Dacor r...

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1/2/2026 7:28:38 PM
Active
18 Tunnel Road Roxbury CT
18 Tunnel Road

Roxbury, Connecticut 06783

$1,075,000 | Active

3 Beds | 3 Baths | 2080 Sqft | 3.1 Acres | 279 Days on Market

Property Type: Single Family For Sale

MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes t...

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1/1/2026 3:40:09 PM
Active
8 Bayberry Hill Roxbury CT
8 Bayberry Hill

Roxbury, Connecticut 06783

$3,995,000 | Active

5 Beds | 6 Baths | 5940 Sqft | 31.77 Acres | 268 Days on Market

Property Type: Single Family For Sale

Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Librar...

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12/31/2025 3:59:44 PM
Active
233 Southbury Road Roxbury CT
233 Southbury Road

Roxbury, Connecticut 06783

$1,795,000 | Active

5 Beds | 6 Baths | 5447 Sqft | 14.82 Acres | 9 Days on Market

Property Type: Single Family For Sale

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected ...

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12/30/2025 3:45:28 PM
Active
50 Southbury Road Roxbury CT
50 Southbury Road

Roxbury, Connecticut 06783

$950,000 | Active

5 Beds | 3 Baths | 2000 Sqft | 8.71 Acres | 153 Days on Market

Property Type: Single Family For Sale

Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, a...

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12/8/2025 7:08:08 PM
Active
216 Baker Road Roxbury CT
216 Baker Road

Roxbury, Connecticut 06783

$699,900 | Active

4 Beds | 2 Baths | 2008 Sqft | 0.85 Acres | 31 Days on Market

Property Type: Single Family For Sale

Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached r...

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12/8/2025 5:00:39 PM
Active
55 Mallory Road Roxbury CT
55 Mallory Road

Roxbury, Connecticut 06783

$689,000 | Active

4 Beds | 3 Baths | 2682 Sqft | 3.23 Acres | 129 Days on Market

Property Type: Single Family For Sale

If privacy in the Litchfield Hills is your aspiration, this is the place for you! Pass through the gated entrance to this rustic Country Cape w/ covered front porch set back 500 ft off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighbo...

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11/21/2025 4:03:31 PM
Active
286 South Street Roxbury CT
286 South Street

Roxbury, Connecticut 06783

$1,095,000 | Active

5 Beds | 5 Baths | 2804 Sqft | 8.4 Acres | 233 Days on Market

Property Type: Single Family For Sale

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main...

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11/5/2025 12:14:35 AM
Active
47 South Street Roxbury CT
47 South Street

Roxbury, Connecticut 06783

$875,000 | Active

3 Beds | 2 Baths | 2489 Sqft | 4.47 Acres | 99 Days on Market

Property Type: Single Family For Sale

A antique home on a level scenic lot in sought-after Litchfield County. As you enter through the front door, youre welcomed by an original staircase & hickory wood floors. The living room features an exposed wood beam, a fireplace & hickory flooring. A formal dining room with cla...

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10/29/2025 11:37:46 PM
Active
11 Ravenrock Road Roxbury CT
11 Ravenrock Road

Roxbury, Connecticut 06783

$3,998,000 | Active

4 Beds | 6 Baths | 7063 Sqft | 20.11 Acres | 425 Days on Market

Property Type: Single Family For Sale

A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis co...

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10/18/2025 4:05:04 AM
Active
31 Hickory Lane Roxbury CT
31 Hickory Lane

Roxbury, Connecticut 06783

$1,795,000 | Active

4 Beds | 5 Baths | 6169 Sqft | 8.84 Acres | 82 Days on Market

Property Type: Single Family For Sale

Beautiful property in highly desirable Roxbury neighborhood. Traditional colonial with double story portico set back from quiet lane in park like setting with mature trees and gardens, huge pool, fruit trees, plenty of space for animals, stable, paddock. Detached garage in additi...

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10/17/2025 4:05:03 AM
Active
24 Hickory Lane Roxbury CT
24 Hickory Lane

Roxbury, Connecticut 06783

$1,155,000 | Active

4 Beds | 3 Baths | 3340 Sqft | 3.01 Acres | 83 Days on Market

Property Type: Single Family For Sale

This beautifully updated Post & Beam residence offers exceptional craftsmanship and modern amenities throughout. Over the past five years, the home has received numerous enhancements, including a new roof, remodeled kitchen with tile flooring, all-new Pella windows and doors, a...

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10/10/2025 1:05:10 PM
Active
38 Mountain Lane Roxbury CT
38 Mountain Lane

Roxbury, Connecticut 06783

$795,000 | Active

3 Beds | 3 Baths | 2336 Sqft | 4.96 Acres | 90 Days on Market

Property Type: Single Family For Sale

Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceili...

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10/2/2025 4:05:00 AM
Active
4 Judge Road Roxbury CT
4 Judge Road

Roxbury, Connecticut 06783

$3,200,000 | Active

3 Beds | 2 Baths | 1974 Sqft | 23 Acres | 98 Days on Market

Property Type: Single Family For Sale

Complete Equestrian Facility with Cape Cod Style Home. An ideal property for horse enthusiasts, trainers, or those seeking a turn-key boarding operation. This thoughtfully designed equestrian facility offers 16 matted stalls, a spacious indoor riding arena, and an elevated viewin...

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8/31/2025 3:33:07 PM
Active
179 South Street Roxbury CT
179 South Street

Roxbury, Connecticut 06783

$1,275,000 | Active

3 Beds | 2 Baths | 1772 Sqft | 12.74 Acres | 131 Days on Market

Property Type: Single Family For Sale

Own a Piece of Roxbury History! One of Roxburys three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangib...

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8/27/2025 1:14:05 PM
Active
85 Good Hill Road Roxbury CT
85 Good Hill Road

Roxbury, Connecticut 06783

$1,630,000 | Active

3 Beds | 3 Baths | 2440 Sqft | 2 Acres | 192 Days on Market

Property Type: Single Family For Sale

At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or...

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7/18/2025 4:36:40 PM
Active
L7&L8 Willow Brook Drive Roxbury CT
L7&L8 Willow Brook Drive

Roxbury, Connecticut 06783

$5,499,000 | Active

5 Beds | 4 Baths | 6729 Sqft | 20.13 Acres | 174 Days on Market

Property Type: Single Family For Sale

New Construction Opportunity - Custom Estate on 20+ Acres in Roxbury, CT - Designed and to be built by Havens Fine Homes and ARK Design Studio. Introducing a rare and extraordinary opportunity to own a fully custom, to-be-built estate on Lots 7 & 8 Willow Brook Drive in the hea...

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6/20/2025 2:31:43 PM
Active
88 Rucum Road Roxbury CT
88 Rucum Road

Roxbury, Connecticut 06783

$2,195,000 | Active

5 Beds | 6 Baths | 5113 Sqft | 8.04 Acres | 236 Days on Market

Property Type: Single Family For Sale

Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beaut...

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