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

11/11/2025 2:52:22 PM
Under Contract CTS
32 Grassy Hill Road Roxbury CT
32 Grassy Hill Road

Roxbury, Connecticut 06783

$2,150,000 | Under Contract - Continue

4 Beds | 5 Baths | 4728 Sqft | 7.92 Acres | 220 Days on Market

Property Type: Single Family For Sale

Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbu...

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

Roxbury, Connecticut 06783

$875,000 | Active

3 Beds | 2 Baths | 2489 Sqft | 4.47 Acres | 43 Days on Market

Property Type: Single Family For Sale

Step back in time w/ this 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 for...

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11/3/2025 9:43:30 PM
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242 Tophet Road Roxbury CT
242 Tophet Road

Roxbury, Connecticut 06783

$849,000 | Active

3 Beds | 2 Baths | 1862 Sqft | 6.07 Acres | 113 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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10/31/2025 9:40:16 PM
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23 Painter Hill Road Roxbury CT
23 Painter Hill Road

Roxbury, Connecticut 06783

$999,000 | Active

4 Beds | 3 Baths | 1782 Sqft | 3 Acres | 223 Days on Market

Property Type: Single Family For Sale

Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and French doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom ...

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10/31/2025 9:39:43 PM
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18 Tunnel Road Roxbury CT
18 Tunnel Road

Roxbury, Connecticut 06783

$1,025,000 | Active

3 Beds | 3 Baths | 2080 Sqft | 3.1 Acres | 223 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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10/31/2025 4:39:14 PM
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67 Squire Road Roxbury CT
67 Squire Road

Roxbury, Connecticut 06783

$3,975,000 | Active

5 Beds | 4 Baths | 4371 Sqft | 10.64 Acres | 13 Days on Market

Property Type: Single Family For Sale

67 Squire Road blends striking modern architecture with timeless New England character on nearly 11 private acres in Roxbury. Thoughtfully designed and beautifully executed, this contemporary retreat offers 4,371 sq ft of light-filled living space with 5 bedrooms and 3 spa-qualit...

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

Roxbury, Connecticut 06783

$3,998,000 | Active

4 Beds | 6 Baths | 7063 Sqft | 20.11 Acres | 369 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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10/24/2025 12:00:02 AM
Under Contract CTS
35 Bronson Mountain Road Roxbury CT
35 Bronson Mountain Road

Roxbury, Connecticut 06783

$2,495,000 | Under Contract - Continue

5 Beds | 6 Baths | 8091 Sqft | 42 Acres | 80 Days on Market

Property Type: Single Family For Sale

Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you...

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

Roxbury, Connecticut 06783

$1,795,000 | Active

4 Beds | 5 Baths | 6169 Sqft | 8.84 Acres | 26 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
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24 Hickory Lane Roxbury CT
24 Hickory Lane

Roxbury, Connecticut 06783

$1,155,000 | Active

4 Beds | 3 Baths | 3340 Sqft | 3.01 Acres | 27 Days on Market

Property Type: Single Family For Sale

Stunning Post & Beam Home with Extensive Upgrades. 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 wi...

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10/15/2025 11:20:29 PM
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67 Transylvania Road Roxbury CT
67 Transylvania Road

Roxbury, Connecticut 06783

$919,000 | Active

4 Beds | 4 Baths | 3624 Sqft | 3.13 Acres | 146 Days on Market

Property Type: Single Family For Sale

This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. Its set on over three gorgeous acres with beautiful stone walls and a private usable yard thats perfect for a pool. Extensive stonework is present on side steps, patio...

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10/14/2025 2:52:58 PM
Under Contract CTS
253 Tophet Road Roxbury CT
253 Tophet Road

Roxbury, Connecticut 06783

$1,549,000 | Under Contract - Continue

4 Beds | 4 Baths | 2437 Sqft | 3 Acres | 223 Days on Market

Property Type: Single Family For Sale

Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year....

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

Roxbury, Connecticut 06783

$795,000 | Active

3 Beds | 3 Baths | 2336 Sqft | 4.96 Acres | 34 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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10/9/2025 10:21:23 PM
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96 Squire Road Roxbury CT
96 Squire Road

Roxbury, Connecticut 06783

$1,399,000 | Active

4 Beds | 4 Baths | 3077 Sqft | 9.2 Acres | 35 Days on Market

Property Type: Single Family For Sale

A distinguished equestrian estate of rare beauty, this property unites timeless New England architecture with the serenity of country living. Approached by a gated, tree-lined drive, the residence evokes an air of grace and permanence, set amidst sweeping pastures and centuries-o...

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

Roxbury, Connecticut 06783

$3,200,000 | Active

3 Beds | 2 Baths | 1974 Sqft | 23 Acres | 42 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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9/29/2025 3:52:36 PM
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45 Moosehorn Road Roxbury CT
45 Moosehorn Road

Roxbury, Connecticut 06783

$1,949,000 | Active

4 Beds | 4 Baths | 4517 Sqft | 8.04 Acres | 223 Days on Market

Property Type: Single Family For Sale

Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12...

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9/24/2025 3:52:20 PM
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55 Mallory Road Roxbury CT
55 Mallory Road

Roxbury, Connecticut 06783

$739,000 | Active

4 Beds | 3 Baths | 2682 Sqft | 3.23 Acres | 73 Days on Market

Property Type: Single Family For Sale

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

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9/23/2025 5:13:42 PM
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33 Sentry Hill Road Roxbury CT
33 Sentry Hill Road

Roxbury, Connecticut 06783

$1,495,000 | Active

4 Beds | 4 Baths | 2716 Sqft | 3.01 Acres | 223 Days on Market

Property Type: Single Family For Sale

Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Mooseho...

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9/23/2025 5:10:06 PM
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247 Painter Hill Road Roxbury CT
247 Painter Hill Road

Roxbury, Connecticut 06783

$1,595,000 | Active

3 Beds | 4 Baths | 2396 Sqft | 3.19 Acres | 223 Days on Market

Property Type: Single Family For Sale

Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxburys best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaul...

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9/19/2025 7:04:35 PM
Under Contract
16 Sentry Hill Road Roxbury CT
16 Sentry Hill Road

Roxbury, Connecticut 06783

$2,995,000 | Under Contract

5 Beds | 6 Baths | 5455 Sqft | 16.71 Acres | 134 Days on Market

Property Type: Single Family For Sale

Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious me...

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9/12/2025 2:10:58 AM
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143 Tophet Road Roxbury CT
143 Tophet Road

Roxbury, Connecticut 06783

$2,295,000 | Active

4 Beds | 6 Baths | 5848 Sqft | 4.01 Acres | 189 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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9/9/2025 1:12:42 PM
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336 South Street Roxbury CT
336 South Street

Roxbury, Connecticut 06783

$995,000 | Active

3 Beds | 3 Baths | 2556 Sqft | 4.53 Acres | 71 Days on Market

Property Type: Single Family For Sale

Quintessential Roxbury retreat, an updated classic 3-bedroom Colonial with open floor plan and separate office, nestled on over 4.5 picturesque park-like acres. This property offers the perfect blend of tranquil country living with the convenience of a great commuting location, j...

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9/8/2025 5:17:57 PM
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8 Bayberry Hill Roxbury CT
8 Bayberry Hill

Roxbury, Connecticut 06783

$3,995,000 | Active

5 Beds | 6 Baths | 5940 Sqft | 31.77 Acres | 213 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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9/2/2025 6:26:17 PM
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103B Chalybes Road Roxbury CT
103B West Chalybes Road

Roxbury, Connecticut 06783

$3,050,000 | Active

4 Beds | 3 Baths | 4071 Sqft | 16.71 Acres | 139 Days on Market

Property Type: Single Family For Sale

TO BE BUILT - A Home by CORBO! A rare opportunity to build your dream home on approximately 16 private acres in Roxbury, CT-one of lower Litchfield Countys most sought-after towns. This award-winning Colonial reproduction pairs timeless architecture with modern craftsmanship and ...

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

Roxbury, Connecticut 06783

$1,275,000 | Active

3 Beds | 2 Baths | 1772 Sqft | 12.74 Acres | 75 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
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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 | 136 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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8/25/2025 2:33:13 PM
Under Contract CTS
118 Chalybes Road Roxbury CT
118 West Chalybes Road

Roxbury, Connecticut 06783

$775,000 | Under Contract - Continue

6 Beds | 5 Baths | 4260 Sqft | 5.18 Acres | 473 Days on Market

Property Type: Single Family For Sale

Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide...

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8/18/2025 12:23:41 PM
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2 Pickett Road Roxbury CT
2 Pickett Road

Roxbury, Connecticut 06783

$1,784,000 | Active

5 Beds | 4 Baths | 3096 Sqft | 8.35 Acres | 87 Days on Market

Property Type: Single Family For Sale

NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open...

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8/9/2025 2:56:10 PM
Under Contract
11 Hodge Road Roxbury CT
11 Hodge Road

Roxbury, Connecticut 06783

$975,000 | Under Contract

4 Beds | 3 Baths | 2982 Sqft | 6 Acres | 140 Days on Market

Property Type: Single Family For Sale

This Circa 1851 Historic house known as Mine and Quarry House in Roxbury, Ct Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100s of acres of the Roxbury Land trust and enjoys ...

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8/7/2025 5:56:33 PM
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50 Southbury Road Roxbury CT
50 Southbury Road

Roxbury, Connecticut 06783

$950,000 | Active

5 Beds | 3 Baths | 2000 Sqft | 8.71 Acres | 98 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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8/7/2025 4:14:47 PM
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99 Carriage Lane Roxbury CT
99 Carriage Lane

Roxbury, Connecticut 06783

$1,675,000 | Active

4 Beds | 3 Baths | 6395 Sqft | 3.79 Acres | 122 Days on Market

Property Type: Single Family For Sale

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and peaceful location-perfect for those seeking comfort and tranquility. Step inside to a spacious open-concept living and dining area, ideal for hosting gatherings and entertaining with ease. Th...

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8/7/2025 3:38:37 PM
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97 Chalybes Road Roxbury CT
97 West Chalybes Road

Roxbury, Connecticut 06783

$2,480,000 | Active

4 Beds | 4 Baths | 4266 Sqft | 4.029 Acres | 112 Days on Market

Property Type: Single Family For Sale

TO BE BUILT - A New Classic by Connecticut Residential. A rare opportunity to bring your dream home to life in scenic Roxbury, CT-this timeless Farm House Colonial-inspired residence is thoughtfully designed for both elegance and ease. Sited on a private 4-acre parcel, the propos...

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7/18/2025 4:36:40 PM
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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 | 118 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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7/13/2025 4:05:02 AM
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22 Woods Road Roxbury CT
22 Woods Road

Roxbury, Connecticut 06783

$735,000 | Active

4 Beds | 3 Baths | 3476 Sqft | 6.89 Acres | 123 Days on Market

Property Type: Single Family For Sale

Meander up the curved driveway to your secluded 6.89-acre lot with sunsets beyond compare. 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 closets. Prim...

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7/3/2025 12:44:01 PM
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81 Chalybes Road Roxbury CT
81 West Chalybes Road

Roxbury, Connecticut 06783

$2,200,000 | Active

4 Beds | 5 Baths | 3677 Sqft | 4.01 Acres | 133 Days on Market

Property Type: Single Family For Sale

TO BE BUILT - A New Classic by Connecticut Residential. Heres your chance to create something truly special in the heart of lower Litchfield County. Tucked away on over 4 private acres in picturesque Roxbury, this proposed home by Connecticut Residential blends timeless Colonial ...

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

Roxbury, Connecticut 06783

$2,195,000 | Active

5 Beds | 6 Baths | 5113 Sqft | 8.04 Acres | 180 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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6/18/2025 1:44:13 PM
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103A Chalybes Road Roxbury CT
103A West Chalybes Road

Roxbury, Connecticut 06783

$2,850,000 | Active

5 Beds | 7 Baths | 4777 Sqft | 16.71 Acres | 149 Days on Market

Property Type: Single Family For Sale

TO BE BUILT - A Home by CORBO! Tranquil luxury on 16 private acres in Roxbury, CT-an exceptional opportunity to bring your dream home to life in the heart of lower Litchfield County. Set well back from the road and oriented for western exposure, this stunning property offers swee...

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5/22/2025 10:35:11 PM
Active
286 South Street Roxbury CT
286 South Street

Roxbury, Connecticut 06783

$1,195,000 | Active

5 Beds | 5 Baths | 2804 Sqft | 8.4 Acres | 177 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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