46 Roxbury, CT Real Estate Listings

Sort by:
$1,150,000Est. Payment
4 Beds | 4 Baths | 3,500 Sqft
Lot Squire Road, Roxbury, CT 06783
House For Sale

Would you like to escape for the weekend to one of the most beautiful Towns in Litchfield county,let me introduce this unique opportunity to build your dream weekend home in Roxbury Ct,own this exquisite energy eficient new construction with high end finishes ,state of art first floor master bedroom suite with luxurious bath,gourmet kitchen open floor plan ,this is a perfect blend of modern and traditional architecture and style. designed for modern life style .Home Built By Corbo,call for floor plans and detail info.

$289,900Est. Payment
3.05 Acres
Lot 1 Squire Road, Roxbury, CT 06783
Lots Land For Sale

Escape the city and return to natural paradise at this beautiful 3 acre parcel of privacy Only 90 minutes from Manhattan but a world away. Located on one of the most lovely country roads in Litchfield County with discrete neighbors .Just across from lovely trails for morning walks.The property feels like it fell out of a dream with its splendid wooded areas and expansive fields around. Build your ultimate dream house , this is the place to go to unwind, be reminded of the beauty of nature, and recharge from your busy life.

$2,750,000Est. Payment
5 Beds | 4 Baths | 3,428 Sqft
238 Painter Hill Road, Roxbury, CT 06783
House For Sale

Picture-perfect essence of NE. c.1872. 5 BR main residence, guest house, gunite pool, screened porches, brick dining patio w/ pergola. Fully renovated in 2015 while maintaining all of its charm. Quiet setting w/ western exposure at the top of Painter Hill. Ideally sited on 12+/- AC of level lawn w/ antique canopied trees, flowering perennials, rebuilt stone walls, pond, bocci court & orchard. Interior w/ period details. Oak flooring & exposed hand-hewn beams. Country kitchen w/ glass-faced cabinetry, soapstone counters & designer appliances - Subzero refrigerator, Wolf stove + walk-in pantry, butler closet. Formal dining room w/ 8-over-8 windows, sunset views & direct access to outdoor dining patio. Adjacent are the formal LR w/ views of the grounds, FP & cozy family room/media nook. Main floor master suite, private screened porch, walk-in closet/dressing room, marble BA, dbl sinks, soaking tub & separate shower. Also on main floor, office, laundry rm w/ dbl set of Miele washer/dryers. On 2nd floor, 4 guest BRs, 2 w/ sleeping coves & built-in storage, 2 full baths. Partially finished lower level w/ temperature-controlled wine cellar & pantry. Guesthouse/ home office w/ full eat-in kit w/ the quality of the main house. Main level en-suite BR & 1/2 BA. Upper level w/ media room & sleeping alcoves. Full house generator & irrigation system. Plans are avail for barns/garage. Orig antique barnwood avail for construction - inquire on pricing. 90 minutes from NYC. Further History: Information from a survey of Roxbury by Rachel Carley. This 19th-century farmstead is significant as one of few Roxbury properties remaining in the family of the original owners. An Irish immigrant, Thomas OBrien (b. 1845) came to America in 1848 as a child and became a citizen in 1872. In 1924 he deeded his home lot to his son Edward J. OBrien, who then owned the property at 277 Painter Hill. In 1970, this property at 238 Painter Hill Road was distributed from Edwards estate to his son Joseph O

$775,000Est. Payment
2 Beds | 3 Baths | 2,955 Sqft
24 Sentry Hill Road, Roxbury, CT 06783
House For Sale

Unique one of a kind custom built home is a must see. Perfect getaway or full time home infused with custom beams, vaulted ceilings, crown molding, custom built ins and so much more. The homes attention to detail has the perfect blend of Modern Style and Old World Charm that brings this home to be Elegant. The home is sitting on 6.94 acres located in the Judds Bridge area of Roxbury. The main level has a beautiful kitchen, an open concept great room with fireplace that opens to the dining room which is equipped with its own wet bar, multiple wine chillers, refrigerator and dishwasher which makes this open combination perfect for entertaining. As you stroll up the the custom built glass panel staircase you will find a master bedroom suite with vaulted ceilings massive beams and super deep walk in closets. There is a second master suite located at ground level with its own living space, fireplace,recessed lighting and full bathroom. Private setting extra large eco plank built deck has sunken hot tub with nothing but nature surrounding you. There are possibilities to expand this home with the 4 bedroom septic and possibilities to build another home for extended family and friends on the upper ridge with beautiful views of Roxbury

$775,000Est. Payment
4 Beds | 3 Baths | 3,264 Sqft
12 East Woods Road, Roxbury, CT 06783
House For Sale

Hillside Sanctuary is your own personal retreat. Set on 6.58 private acres the property is magnificent. The multi-terraced gardens include stonewalls, staircases, fountain, arbors, box and yew hedges, shrubs, roses, perennials and bulbs with multiple sitting spots. Quiet, cozy and tucked in among the gardens is the cottage style clapboard home. Throughout are French doors, large windows, built-ins and there are three fireplaces. Designed for easy living, the main floor includes the formal living room and dining room, spacious kitchen, library, master bedroom with full bath and dressing room, second bedroom with full bath and laundry. The above grade lower level includes the third and fourth bedrooms with French doors to the exterior and full bath. There is a 54' upper level deck that can be reach from the living room, library and master bedroom. Extra special is the wrap around pergola with stone patio. Property is two parcels. If one were to merge the two lots there would be a property tax savings of approximately $1,500. Buyer to verify with tax assessor. 90 minutes from NYC.

$497,500Est. Payment
3 Beds | 3 Baths | 1,810 Sqft
91 North Street, Roxbury, CT 06783
House For Sale

Custom Gambrel Colonial. PRIVATELY SET FAMILY ROOM w many built ins and desk area is PERFECT FOR A QUIET WORK FROM HOME/SCHOOL SITUATION. Charming home with built ins, wainscoting, hardwood flooring thru out. The kitchen is a delight - white, bright, granite, farm sink, built in bench, island, and sliders to private back deck, dine el fresco to the sound of the babbling little brook! Formal dining room, spacious enough for holiday gatherings or every day meals. Living room is welcoming with paneled fireplace and built in book shelf. Sunny Master suite and two additional bedrooms three steps up from the family room. Checks all the box's with quaint small town, privacy, charm, character, space to work from home, potential pool site, low taxes & under two hours to Manhattan. Check out Shepaug Schools new Vo-Ag program! Home has oil/FHA heat, but was originally built w electric heat - thermostat in every room so easy to just take the chill off in the rooms your using for these brisk mornings! Maintained w pride by original owners, newly sided, easy add for CAIR if desired, duct work is in. Generator hook up, work shop in basement. Walk to Roxbury Market for your morning coffee or deli lunch, grab your mail, play a game of tennis and then stop at the library for a good read on your way back home. Not enough? Try the numerous amazing hiking trails, local history, take an easy jaunt to Lake Waramaug or Bantam Lake for boating/ kayaking or lazy day fishing.

$1,695,000Est. Payment
4 Beds | 4 Baths | 3,663 Sqft
45 Ranney Hill Road, Roxbury, CT 06783
House For Sale

Sophisticated country home. Breath-taking grounds complete with stonewalls, apple trees, vegetable gardens, creek and in-ground, heated saltwater gunite pool. Renovated home features a spacious and inviting great room with stone fireplace and French doors that open to views of mature gardens, pergola covered porch and stunning views provide a wonderful setting. A gem. Sun-filled two+ acres set bucolically amidst horse and sheep pastures yet within walking distance of coffee at the General Store and iconic Maple Bank Farm stand. Gorgeous and mature gardens. Light-filled spaces include wainscoted rooms, custom cabinetry, office with fireplace, claw-footed tub among other architectural details. A special property worth visiting. Less than 2 hours from Brooklyn/Manhattan.

$725,000Est. Payment
3 Beds | 2 Baths | 1,768 Sqft
17 Jonathan Drive, Roxbury, CT 06783
House For Sale

Single level 3 bedroom home with gorgeous Western views. Cozy stone fireplace, open floor plan, brand new central air, new gas range. 2 car garage under and plenty of storage. Large basement could be finished for more livable space. 1.5 hours to NYC. 5 minutes to Washington.

$1,500,000Est. Payment
3 Beds | 3 Baths | 2,495 Sqft
92 Botsford Hill Road, Roxbury, CT 06783
House For Sale

Fully renovated in 2020 by a locally renowned architect, character, charm, convenience, and romance continue to define this stunning property, located in a whisper-quiet setting on an elevated position with mountain vistas along one of the most scenic country roads in Litchfield County. The white clapboard antique "modern" is beautifully sited on 6 cleared acres of rolling meadow bordered by stone walls and accented with canopied shade trees, a babbling brook, a spring-fed pond alive with life, and abundant birdsong this is the picture-perfect essence of New England just 90 minutes from NYC. The offering includes a 34-bedroom main house, 1-bedroom guest cottage, 4-stall horse barn, and detached garage/outbuilding. The core of the home is the historical farmhouse which has since been expanded and fully modernized into a family home or turnkey key away property The 2,495 square-foot c.1794 main house was designed for low maintenance and built to optimize live-work-play purposes with two separate home offices, pre-wired CAT-5, and an array of top-of-the-line features to satisfy those who enjoy combining work and leisure activities and blurring the boundaries between interior and exterior. Throughout the house are new Marvin windows with custom Hunter Douglas wood blinds, 8-inch live sawn oak flooring, custom millwork, stonework, lighting, and fixtures. Completely new central AC, plumbing and electrical wiring with 200AMP service, and new top-of-the-line mechanicals. A heated/cooled enclosed walkway with stone floor and mahogany ceiling allows optional entry for guests or direct access from the attached garage. The main floor features a comfortable "great room" style open layout with vaulted ceiling and a well-appointed sky-lit kitchen at its heart. Among its features are exposed aged beams, custom maple wood cabinets for ample storage and utility, quartzite counters with marble backsplash, an apron sink, 6-burner Viking gas range/oven, Bosch refrigeration and dishwasher, and quartzite center island with an induction cooktop and Bosch oven. The kitchen is designed for daily use but large enough to prepare gourmet melas for entertaining. A stone fireplace creates an inviting focal point for the airy great room composed of vaulted ceilings with triptych of windows providing ample natural eastern lighting and one of the best views of the property. Glass sliders provide direct access to the Mahogany deck -- best suited for al fresco dining, entertaining, lounging, or indulging in the serenity of the surrounding countryside. The adjoining room with a second wood-burning fireplace can serve as a media room or a more intimate space for gathering, with French doors and custom blackout shades that offer added privacy. Quietly located apart from the common spaces is the exquisite first-floor owners suite that echoes the same sense of scale with a vaulted ceiling, oversized windows also affording eastern views, and a generous walk-in closet with built-in shelving and drawers. The ensuite bath features counters and marble tiling, a huge walk-in glass shower with a double shower, and a soaking tub, also with a marble decking. There's also custom blackout shades installed in the bedroom for those who relish sleeping in. Completing the main floor is an office/nursery/playroom off the owners' suite and, separated by a powder room, a second office/study that can serve as a flexible fourth bedroom. Two bedrooms with a shared full bath with combo shower/tub comprise the upper level. The partially finished lower level with walkout to pergola-covered patio contains a laundry room and additional dry space for storage. The finished area is included in total square feet. The grandfathered guest cottage can be accessed via its separate driveway or walking bridge crossing the brook. It was updated to the same quality level as the main house and features an eat-in kitchen with slider access to a deck overlooking the grounds, a combined living/dining space with fireplace, one bedroom, and a full bath with combo shower/tub. The lower level was recently converted into a gym with 1/4" high-impact rubber floor and wiring for a wall-mounted TV and two separate storage spaces. The 6-acre property has been fully cleared and has an active brook running through it that runs to the pond. The grounds are as stunning as they are romantic, accented by mature shade trees, privacy screening plantings, recently planted maples and oaks for the next generation, and 40 newly planted spruces to provide impressive visual depth over time. The land is predominantly flat, with some gentle sloping around the perimeter. The pond has been cared for and stocked with trout and carp to mitigate algae growth over summer. In keeping with the neighborhood, the land is conducive to horses or planting gardens. There is plenty of room for a pool, and either of the existing outbuildings can serve as a future pool house. About the town of Roxbury, Connecticut The unspoiled and scenic town of Roxbury, located in beautiful Litchfield County, was incorporated in 1796. Roxbury was long known as a mining town, as silver was mined here as well as iron for steel making and granite used to construct, among other landmarks, the Brooklyn Bridge and Grand Central Station. Roxbury is also known as a picturesque farming town with its beautiful rolling hills and open fields, and its location within the watershed of the Shepaug River. The area is as diverse as its residents, which include actors, artists, writers and local tradesmen who help to keep the ambulance and fire department a volunteer service. Nearly 3,000 acres, or about 15 percent, of Roxbury's total area is conserved as open space under the stewardship of the Roxbury Land Trust. The Trust was established in 1970 and continues its mission to protect the natural beauty and rural character of the town, providing space for hiking, fishing, cross country skiing and biking. The commute to New York City is approximately 90 minutes.

$7,500,000Est. Payment
4 Beds | 7 Baths | 7,050 Sqft
848688 Good Hill Road, Roxbury, CT 06783
House For Sale

Opal House at Booth Hill is one of the finest properties in Litchfield County. Sited on 86 acres, with magnificent 20 mile views, enjoying complete privacy, you arrive at a private entrance flanked by a serene pond, cross a charming bridge and proceed up a long drive to the estate which includes a beautiful Georgian Colonial style Main House, set on sweeping lawns with mature trees and enhanced by spectacular professionally planned gardens. Two Guest Cottages, a Har-True tennis court, 25 x 50 heated gunite Swimming Pool, a 3 tee/ 2 hole golf course, several garages housing six car bays, and two storage barns complete the propertys amenities.The 12 room house, totally renovated in 1995, is designed for family comfort and entertaining and features classical architectural detailing, six fireplaces, a massive Living Room with a 12 window seat looking out to the Gardens and Views, and French doors leading to the flanking stone terraces and gardens. The open gourmet country kitchen, family room and breakfast area feature a large sitting area with fireplace, Viking Range, Subzero fridge, granite counter-tops, and other chefs features. There are four bedrooms, all with full baths en suite. The Master has numerous closets and 10 ceilings. There is a large playroom, easily converted to an exercise room, and full bathroom in the finished basement. A generator completely services the main house and guest cottages.

$79,900Est. Payment
8 Acres
Lot 14 Pickett Road, Roxbury, CT 06783
Lots Land For Sale

8.35 Acre parcel close to Washington Town Line. Short distance to Shepaug High School.Some wetlands on property and easment for Eversource. Home site would be closer to the Davenport / Pickett Rd. intersection. All available maps and parcel details in attachments online.

$149,000Est. Payment
3.43 Acres
0 Mallory Road, Roxbury, CT 06783
Lots Land For Sale

Wonderful lot on Roxbury's Mallory Road. A chance to build your dream house in Roxbury, Region 12 Schools, build what you would like! Stream, Wood road. Be in by the fall. Minutes from shopping in Washington Depot, Southbury, Woodbury or New Milford. Centrally located. 1.5 hours from Manhattan

$195,000Est. Payment
5 Acres
74 Chalybes Road West, Roxbury, CT 06783
Lots Land For Sale

Secluded sloping 5 acre approved building lot. Three bedroom Septic Approval with great perks! Should be the last house on the road (Town has no plans to connect one end of the road to the other). Town will extend the road to your driveway entrance. Perks and Deep hole test may have to be redone! Regional 12 School District, Affordable Property taxes, Easy access to Brookfield and Danbury shopping. Country Living at its best!

$2,900,000Est. Payment
5 Beds | 5 Baths | 6,494 Sqft
36 Bronson Mountain, Roxbury, CT 06783
House For Sale

One of a kind custom built property with celebrity appeal! Sitting on 14 Acres with Wonderful Mountain views the property is located on a gated private road that offers complete privacy from the press and unwanted 3rd party visitors. The home has been meticulously designed both inside and out. The finest details were incorporated in the design from top to bottom. With over 6400 square feet of living space, 5 beds, 4.1 baths, first floor home theater room, open concept kitchen and living room, formal dining room, first floor office, and a finished basement (with an additional 3400 square feet) that offers space for 10 cars this property offers plenty of size flexibility. Located just 90 minutes from NYC this estate is a rare find! Pre approval or proof of funds required before showing and listing agent must be present.

$325,000Est. Payment
3 Beds | 3 Baths | 2,930 Sqft
386 South Street, Roxbury, CT 06783
House For Sale

Country Contemporary Cape located in secluded Evergreen Woods; Extremely open floor plan kitchen with beautiful beamed ceiling; lots of light open and bright; vaulted ceiling, kitchen island, laundry room on first floor; fully finished lower level for studio or family room has high ceilings and tons of light and brick walls, interesting touches throughout including the master bedroom with built-ins, ceiling fans and vaulted wood ceilings say country but cozy too; Not too far from Roxbury Falls, Roxbury Boat ramp and Nature Preserve.

$1,549,000Est. Payment
5 Beds | 9 Baths | 6,600 Sqft
20 Grassy Hill Road, Roxbury, CT 06783
House For Sale

Set on a Gorgeous Scenic Country Equestrian road. Contemporary with high ceilings, Open Floor Plan and Light everywhere from the grand window! Lush lawn and pasture with Horse Barn. Impeccably maintained grounds. The front entrance opens to a grand staircase with colossal ceilings, Hardwood floors and enormous picture windows with an exceptional view from every room The open kitchen offers gorgeous stone countertops and backsplash with island for easy entertaining. From the impeccable flagstone patio, to the sprawling 3-acre lawn. An enormous master suite includes beautiful en suite, large walk-in closet with built-ins & giant soaking tub! The lower level is complete with an abundance of space that could be used as an additional living space, home entertainment room or home based business! Other amenities..Horse Barn, gorgeous & mature landscaping, home office/art studio(separate structure), in-law suite, three-car garage, freshly painted inside and out, close proximity to town, & much more!

$1,800,000Est. Payment
36 Acres
110 Town Line Road, Roxbury, CT 06010
Lots Land For Sale

Rare opportunity to build on one of the most beautiful elevated sunny parcels in Roxbury with dramatic vistas of the Shepaug River Valley and 240-degree views. Seller is in the process of having the property surveyed and perc tested. Will be delivered shovel ready.

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >