Refine Search
Map
Sort by
35 Raven Rock Rd, Roxbury
$12,995,000
5 Beds ⋅ 8 Baths ⋅ 24216276 MLS
Privately set at the crest of a hill beyond a gated drive, 35 Raven Rock Road commands breathtaking views across miles of bucolic Litchfield County countryside and the Shepaug River Valley. Spanning over 114 acres, this exceptional country compound offers extraordinary privacy, with 20+ acres of cultivated lawns, extensive gardens, sculptures, pond and specimen trees creating a remarkable estate setting. Built in 2002, the approximately 13,600 SF stone and slate residence pairs gracious proportions with exquisite finishes, superb custom millwork, marble floors, and 8 fireplaces. A marble entry hall leads to an elegant living room opening onto an expansive stone terrace overlooking the grounds and countryside. A formal dining room, paneled library and inviting family room adjoining a heated porch provide beautiful settings for entertaining and everyday living. The chef's kitchen features a professional range, Traulsen refrigeration and a separate cooking room with charbroilers and a stone pizza oven. The main-level primary suite offers a fireplace, dual walk-in closets, separate water closets and a marble bath. Four additional bedrooms feature en suite baths, complemented by an upstairs media/rec room. The finished lower level includes a gym, steam room, cedar closets and wine cellar. A heated pool, pool house, Har-Tru tennis court, 4-car garage with guest quarters and heated barn enrich the estate. Major infrastructure upgrade includes newly installed additional well system.

35 Raven Rock Rd, Roxbury
297 Painter Hill Rd, Roxbury
$3,950,000
4 Beds ⋅ 7 Baths ⋅ 24192621 MLS
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury
268 South St, Roxbury
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 24183686 MLS
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury
35 Schoolhouse Rd, Roxbury
$3,250,000
4 Beds ⋅ 5 Baths ⋅ 24201025 MLS
Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

35 Schoolhouse Rd, Roxbury
124 Botsford Hill Rd, Roxbury
$2,900,000
3 Beds ⋅ 2 Baths ⋅ 24186522 MLS
Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage, boarder tack lockers, laundry area, and full bath. Safety is enhanced by a commercial sprinkler system. Owned pole-mounted solar panels are installed but are not currently operational. Outside, expansive grass paddocks and a large sand/stone dust outdoor arena provide ample space for training and turnout. Bordering Land Trust property with a river and miles of trails, you can horseback ride or hike directly from your back door. "The Shepaug is one of those rivers that looks like it was painted by someone who had too much talent and not enough canvas." written by Charles Hayes. The Cape-style home features 3 bedrooms and 2 full baths, blending classic New England character with modern comfort. A 2-car attached garage is complemented by a detached 4-car garage, plus an additional detached 3-car garage with a second-floor apartment-ideal for guests, staff, rental income, or a home office.

124 Botsford Hill Rd, Roxbury
220 Painter Hill Rd, Roxbury
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 24167130 MLS
Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

220 Painter Hill Rd, Roxbury
55 Ranney Hill Rd, Roxbury
$2,000,000
24170752 MLS
If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

55 Ranney Hill Rd, Roxbury
51 Rocky Mountain Rd, Roxbury
$1,895,000
4 Beds ⋅ 5 Baths ⋅ 24210985 MLS
Charming Country Home with Exceptional Barn-Inspired Great Room Located on a quiet dead end road in central Roxbury, this charming home is enhanced by a spectacular great room addition crafted by master barn builder Ed Cady, creating a warm & distinctive gathering space with extraordinary character. The great room features an enormous walk-in stone fireplace w/ propane starter, soaring ceilings w/ hand-hewn beams, & beautiful wide-board floors. The inviting kitchen opens to a cozy sitting room & addl dining area, creating an easy flow for everyday living & entertaining. Upstairs, the spacious primary suite is a private retreat, complete with vaulted ceilings, a generous walk-in closet, & a beautifully appointed bath. A Juliet walkway overlooks the great room seating area, adding architectural interest & a wonderful sense of connection between the spaces. On the opposite side of the home are 3 additional bedrooms one with ensuite and 2 sharing a hall bath, offering comfortable accommodations for family & guests. The lower level offers abundant potential for a playroom or recreation space, complete w/ a convenient half bath. A 3 car garage provides plenty of parking & storage and connects directly to a practical mudroom w/ sink. With its exceptional craftsmanship, thoughtful floor plan, and inviting blend of rustic character and comfortable living spaces, this is a truly special country home. Walk to the town park w/ playground, baseball, soccer, basketball running traca

51 Rocky Mountain Rd, Roxbury
1030 Washington Woodbury Rd, Roxbury
$1,875,000
4 Beds ⋅ 5 Baths ⋅ 24146457 MLS
NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong indoor-outdoor flow, the property offers immediate enjoyment and the flexibility to personalize over time. Now offered at a compelling new price, this is an exceptional opportunity to acquire a significant Roxbury estate with outstanding value in today's market.

1030 Washington Woodbury Rd, Roxbury
233 Southbury Rd, Roxbury
$1,745,000
5 Beds ⋅ 6 Baths ⋅ 24189301 MLS
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 brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

233 Southbury Rd, Roxbury
25 Highmeadow Ln, Roxbury
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 24210448 MLS
Classic Colonial Set on 17+ High Pastoral Acres in Southern Roxbury CT. New Heated Gunite Pool Expertly Sighted Amongst Flowing Pasture & Attractive Outbuildings. 4 Bedroom, 2 Full + 2 Partial Bath Main Residence & Large Multi-Stall Horse Barn with 1 Bed/1 Bath Apt Above. Separate Large 3-Bay Utility Garage Plus Multiple Other Storage Sheds. Wonderful Floorplan Includes Private Living Room with Fireplace; a Welcoming Eat-in Kitchen, Dining Room & an Inviting Family Room with Beamed Ceiling & Access to Large Deck. Several Bonus Rooms Include: a Main Level Study, Lower Level Offices, Gym & Rec Room. An Attached 2-Car Garage Makes for Practical Country Living. Several Fenced Paddocks are Dotted throughout Groomed Pasture Lands. Easy Access to Numerous Villages including: Woodbury, Southbury, Washington, New Milford & South Britain.

25 Highmeadow Ln, Roxbury
33 Sentry Hill Rd, Roxbury
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 24163570 MLS
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 Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury
11 Evergreen Dr, Roxbury
$1,300,000
4 Beds ⋅ 4 Baths ⋅ 24154135 MLS
This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. The ceiling height on the main level 9'and 8' on the upper level. Both levels have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The kitchen is open to the family room which has a bank of 3 sets of sliders to the back deck area and a fireplace on the end wall. The main level includes a formal dining room, formal living room and a main level laundry/mud room. The upper level includes 3 additional bedrooms and 2 full baths. There is a study area as well as a rec room over the garage. The large 2 car garage will have an electric car charger. Roxbury is a lovely small town with bucolic farms and farmers markets. It is very sought after for weekend and summer homes. There are many land trust areas for hiking and exploring. The Shepard river is great for fishing and tubing. Litchfield County has many lakes for out door recreation. There are ski areas close by and lots of summer fairs. The area is known for art galleries, antique shops and great restaurants. Taxes TBD

11 Evergreen Dr, Roxbury
77 Judds Bridge Rd, Roxbury
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24193455 MLS
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry cabinetry, double oven, cook top, peninsula with seating, pantry, powder and laundry room, and a spacious den with vaulted ceilings, antique beams and centered around a soaring Rumford fireplace. The primary suite features a tray ceiling, en-suite bath with double sink, generous walk-in closet, while three additional bedrooms share a full bath. Out the French doors onto Ipe deck provides a refined setting for outdoor living and your private back yard. Additional highlights include a three-car garage, an unfinished bonus room over the garage that offers excellent expansion potential, new UV paned deck doors, updated mechanicals, architectural roof shingles, and a portable generator. Quintessential New England living at it's best!

77 Judds Bridge Rd, Roxbury
22 E Woods Rd, Roxbury
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 24192986 MLS
*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

22 E Woods Rd, Roxbury
336 South St, Roxbury
$998,000
4 Beds ⋅ 3 Baths ⋅ 24196812 MLS
Set on a picturesque, park-like property in desirable southern Roxbury, this beautiful 4-bedroom, 2.5-bath Colonial blends timeless charm, thoughtful updates, and inviting indoor-outdoor living. A dramatic two-story foyer opens to a formal dining room, spacious living room with custom built-in bookshelves, and impressive family room with a floor-to-ceiling fireplace and custom built-ins. The well-appointed kitchen features granite countertops, center island, Sub-Zero refrigerator, and French doors leading to an expansive deck and terrace-ideal for entertaining. Beautifully landscaped grounds create a private retreat with an in-ground pool, with double fencing, mature gardens, and lush plantings.Hundreds of thousand spend on improvements like new kitchen, expanded driveway/asphalt and charming stone steps and walkway. The home is partially furnished, with new furniture included. A professionally built chicken coop adds a touch of homestead living, perfect for raising chickens and enjoying fresh eggs. Also whole house Generac generator. Peaceful and private yet just 90 minutes from NYC, this exceptional Roxbury property offers space, comfort, and a lifestyle to enjoy.

336 South St, Roxbury
23 Painter Hill Rd, Roxbury
$969,000
4 Beds ⋅ 3 Baths ⋅ 24167690 MLS
Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

23 Painter Hill Rd, Roxbury
18 Tunnel Rd, Roxbury
$969,000
3 Beds ⋅ 3 Baths ⋅ 24163273 MLS
MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa 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 to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round, heated pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock outcroppings. Attached 2-car garage. Mint Condition! Move Right In!

18 Tunnel Rd, Roxbury
50 Southbury Rd, Roxbury
$950,000
5 Beds ⋅ 3 Baths ⋅ 24209875 MLS
* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also build the 4-bedroom estate of your dreams on this approved building lot, with its own driveway and road access. Or use the mostly flat lot as an orchard or garden, or hold the separate parcel as an investment to sell in the future. The lot abuts preserved land. Located in southern Roxbury, just 90 minutes from New York City, the main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. A brand-new standing-seam metal roof carries a lifetime guarantee. At the heart of the house is a spacious eat-in kitchen. On one side are a formal dining room and a library, and on the other is a sunlit double living room wrapped in windows. The 658-square-foot guest house overlooks a spring-fed pond and Little Jacks Brook. It has a generous living room, two bedrooms, and a full bath, and it runs on its own well and septic system. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and a gently rolling lawn.

50 Southbury Rd, Roxbury
2 Moosehorn Rd, Roxbury
$937,500
3 Beds ⋅ 2 Baths ⋅ 24210827 MLS
Moosehorn Rd in Roxbury was voted one of the most scenic Roads in town. Must see! Well-appointed and maintained, first time on the market, original owner, charming 1,456 sqft ranch, 3 bathrooms and 2 bedrooms, kitchen, dining, living room with fireplace, C/A, central vacuum, Generac generator connected. Walkout finished basement with entrance from garage is an in-law apartment with kitchen gas stove and full bath. The main house water comes from two sources a well and from a spring fed well. Detached barn offering heat and A/C with 950 sqfr four car garage and 600sqft attic; A two-car garage in the back with 600 sqft and 500sqft attic; many possibilities shop, studio/ in-law appt or garage/storage income. Your own Spring in your own property; close to Westchester, Fairfield and NYC. Great hiking, restaurants, and art abound within minutes. "As is Condition" See attached list of all recent maintenance service and repairs.

2 Moosehorn Rd, Roxbury
24 Hickory Ln, Roxbury
$925,000
4 Beds ⋅ 4 Baths ⋅ 24164547 MLS
Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

24 Hickory Ln, Roxbury
47 South St, Roxbury
$785,000
3 Beds ⋅ 2 Baths ⋅ 24180161 MLS
Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury
204 North St Unit Lot 3, Roxbury
$775,000
24139288 MLS
1st Time LISTED! LOT 3 at 204 North Street has ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. This 25 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently sloping tree-covered hills and an abundance of ferns, pine trees, oaks and maples as your canvas. The home site is absolutely private and perfect! This masterpiece lot is ideal to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the Woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. Shown by Owner/Agent.

204 North St Unit Lot 3, Roxbury
43 Baker Rd, Roxbury
$749,000
24197942 MLS
Stunning 15 acre parcel with many fresh improvements. New Steal bridge over rushing brook with waterfalls leads to brand new winding driveway to high, flat and cleared building site. Extensive stone walls. Fully engineered and ready to go! Septic quote is $15,000. Conduit quote to site is $14,700. do not enter property without an appt. Driveway is still being completed and we need to give notice.

43 Baker Rd, Roxbury
Painter Hill Rd, Roxbury
$599,000
24213504 MLS
Large 14 ac wooded parcel in AAA location with estate potential. Land rises from road with view potential at the top. Raw land with enough frontage and acreage for subdividing into a frontage and an interior lot. Or better yet enjoy it all. Or best of all: adjacent property is also available. Together would make 29 acres! Easy topo for driveway. Beautiful area abutting huge farmland. Just the best! Assessment and tax reflect PA 490 designation.

Painter Hill Rd, Roxbury
Painter Hill Rd, Roxbury
$599,000
24213535 MLS
Large wooded parcel in AAA location with estate potential. Land rises from road with view potential at the top. Raw land with enough frontage and acreage for subdividing into a frontage and an interior lot. Or better yet enjoy it all. Or best of all: adjacent twin property is also available. Together would make 29 acres! Easy topo for driveway. Beautiful area abutting huge farmland. Just the best!

Painter Hill Rd, Roxbury
21 Carriage Ln, Roxbury
$569,990
3 Beds ⋅ 3 Baths ⋅ 24197040 MLS
A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is primed for your entertaining desires or if you prefer, curl up to a book or a cocktail on the patio, deck or porch. Opportunity is knocking...call for an appointment.

21 Carriage Ln, Roxbury
Painter Hill Rd, Roxbury
$499,000
24213602 MLS
Note: LOCATION IS DOROTHY DIEBOLD LANE!! SYSTEM GLITCH!! Picturesque 11 acre parcel in super-prime location with estate potential, fronting on quiet town-maintained gravel road in Roxbury's sought-after high country. Rugged, characterful land with mature trees and options for potential homesites. Parklike area with spreading farm fields and Land Trust parcels just a short walk away. Adjacent parcel also available.(See Listing #24213585) Buyer to do all due diligence. Assessment and taxes reflect PA 490 Designation.

Painter Hill Rd, Roxbury
Dorothy Diebold Lane, Roxbury
$499,000
24213585 MLS
Large Historic Characterful parcel in uber-prime location with estate potential, fronting on two town-maintained gravel roads in Roxbury's sought-after high country. Locals remember buildings but all are long gone. Rugged, ledgy land with several options for potential homesites. Plenty of frontage and acreage for subdividing, but no surveys or studies have been done. Buyer to do all due diligence. Adjacent 11 ac approved lot also available (see Listing # 24213602). Assessment and taxes reflect PA 490 Designation.

Dorothy Diebold Lane, Roxbury
200 North St, Roxbury
$499,000
24189150 MLS
ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE CHERISHED. This 8.64 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently sloping tree-covered hills and an abundance of ferns, pine trees, oaks and maples as your canvas. The home site is absolutely flat and perfect! This masterpiece lot is ideal to build your dream home and to connect with what is important in life. Whether a weekender or full-time resident, the Woods will offer you ultimate privacy with endless possibilities for a simpler place and way of life. Our wonderful architectural team is available to design your one of a kind home or you can bring your own. Shown by Owner/Agent.

200 North St, Roxbury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!