Roxbury Real Estate

Roxbury Real Estate

Welcome to Roxbury, Connecticut, a hidden gem nestled in the heart of Litchfield County. Known for its picturesque landscapes and rich history, Roxbury offers a unique blend of rural charm and modern conveniences that make it an ideal place to call home.

With its rolling hills, lush forests, and serene lakes, Roxbury is a haven for nature lovers and outdoor enthusiasts. The town is surrounded by stunning natural beauty, providing ample opportunities for hiking, biking, and exploring the great outdoors. The nearby Roxbury Land Trust boasts miles of scenic trails, perfect for a leisurely stroll or an invigorating hike.

Roxbury's quaint village center features a delightful mix of local shops, artisanal eateries, and community events that foster a strong sense of belonging. Residents enjoy a tight-knit community atmosphere, where neighbors become friends and local gatherings are cherished traditions. The town's commitment to preserving its historic character is evident in its charming colonial architecture and well-maintained public spaces.

Education is a priority in Roxbury, with access to excellent schools that emphasize academic achievement and personal growth. Families will appreciate the safe, welcoming environment that Roxbury provides, making it an ideal place to raise children.

With its combination of natural beauty, community spirit, and rich history, Roxbury, CT, is more than just a place to live; it’s a lifestyle. Whether you’re looking to settle down in a cozy cottage or a sprawling estate, Roxbury has something for everyone. Discover the magic of Roxbury and find your dream home in this enchanting town today!

Newest Listings in Roxbury

179 South St, Roxbury
$889,000
ACTIVE Status ⋅ 24216868 MLS
Stunning Private Setting ready to Build Your Dream Home up top!-- Beautiful East Facing Views from this Piece of Roxbury History! Land ready to build with one of Roxbury's three oldest homes on the site which 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 tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust land, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

179 South St, Roxbury
179 South St, Roxbury
$2,450,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24216864 MLS
TO BE BUILT HOME, ALONG WITH ANTIQUE AND HISTORIC BARN--- Own a Piece of Roxbury History! One of Roxbury's 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 tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Antique Home is uninhabitable at this time. A full rebuild and renovation is required.

179 South St, Roxbury
35 Raven Rock Rd, Roxbury
$12,995,000
5 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 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
137 Davenport Rd, Roxbury
$895,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216151 MLS
Discover turnkey living in Litchfield County at this thoughtfully updated Roxbury home, just over the Washington-Roxbury line and close to everything. A redesigned open floor plan on a single level creates an effortless connection between the kitchen and gathering spaces, offering a welcoming setting for everyday living and entertaining. Recent improvements include a new kitchen, new wood flooring throughout, updated baths, new windows, gutters and a new HVAC system. Extensive landscaping clean up completes the refresh, creating an inviting outdoor setting. With substantial updates already complete, this move-in-ready home offers a fresh start in Litchfield county. Low taxes! Owner is licensed Real Estate Broker.

137 Davenport Rd, Roxbury
Painter Hill Rd, Roxbury
$599,000
ACTIVE Status ⋅ 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
ACTIVE Status ⋅ 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
Painter Hill Rd, Roxbury
$499,000
ACTIVE Status ⋅ 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
ACTIVE Status ⋅ 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
2 Moosehorn Rd, Roxbury
$937,500
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
51 Rocky Mountain Rd, Roxbury
$1,895,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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
25 Highmeadow Ln, Roxbury
$1,595,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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
50 Southbury Rd, Roxbury
$950,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
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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.

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