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Roxbury, CT Homes for Sale

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  • 47 South St, Roxbury, CT 06783
    47 South St, Roxbury, CT 06783
    47 South St, Roxbury, CT 06783
    /38

    $850,000

    • 3 Beds
    • 2 Baths
    • 2,489 Sq Ft

    47 South St, Roxbury, CT 06783

    Step back in time and 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

    Agent Photo

    Michelle Alvord

    Berkshire Hathaway NE Prop.

    47 South St, Roxbury, CT 06783
  • 2 Pickett Rd, Roxbury, CT 06783
    2 Pickett Rd, Roxbury, CT 06783
    2 Pickett Rd, Roxbury, CT 06783
    /39

    $1,799,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,326 Sq Ft

    2 Pickett Rd, Roxbury, CT 06783

    Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6" white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet

    Alan O'Doherty William Pitt Sotheby's Int'l

    2 Pickett Rd, Roxbury, CT 06783
  • 4 Judge Rd, Roxbury, CT 06783
    4 Judge Rd, Roxbury, CT 06783
    4 Judge Rd, Roxbury, CT 06783
    /37

    $3,200,000

    • 3 Beds
    • 2 Baths
    • 1,974 Sq Ft

    4 Judge Rd, Roxbury, CT 06783

    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,

    Pat Lahoud Lahoud William Pitt Sotheby's Int'l

    4 Judge Rd, Roxbury, CT 06783
  • 220 Painter Hill Rd, Roxbury, CT 06783
    220 Painter Hill Rd, Roxbury, CT 06783
    220 Painter Hill Rd, Roxbury, CT 06783
    /40

    $2,750,000

    $145K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,570 Sq Ft

    220 Painter Hill Rd, Roxbury, CT 06783

    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,

    Stacey Matthews W. Raveis Lifestyles Realty

    220 Painter Hill Rd, Roxbury, CT 06783
  • 24 Hickory Ln, Roxbury, CT 06783
    24 Hickory Ln, Roxbury, CT 06783
    24 Hickory Ln, Roxbury, CT 06783
    /38

    $1,099,000

    $56K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,340 Sq Ft

    24 Hickory Ln, Roxbury, CT 06783

    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

    Pat Lahoud Lahoud William Pitt Sotheby's Int'l

    24 Hickory Ln, Roxbury, CT 06783
  • 21 Hemlock Rd, Roxbury, CT 06783
    21 Hemlock Rd, Roxbury, CT 06783
    21 Hemlock Rd, Roxbury, CT 06783
    /24

    $1,525,000

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    21 Hemlock Rd, Roxbury, CT 06783

    This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas

    Stacey Matthews W. Raveis Lifestyles Realty

    21 Hemlock Rd, Roxbury, CT 06783
  • 137 Davenport Rd, Roxbury, CT 06783
    137 Davenport Rd, Roxbury, CT 06783
    137 Davenport Rd, Roxbury, CT 06783
    /5

    $950,000

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    137 Davenport Rd, Roxbury, CT 06783

    INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home will be a Complete REMODEL with Separate Driveway. . The septic was last pumped September 2025, and annual taxes are just $3,851. Renovation by Design Builders

    Lisa Provino The Provino Group LLC

    137 Davenport Rd, Roxbury, CT 06783
  • 200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    200 North St, Roxbury, CT 06783
    /20

    $499,000

    • Land
    • 8.64 Acres
    • $57,755 per Acre

    200 North St, Roxbury, CT 06783

    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

    Jill Sloane Brown Harris Stevens

    200 North St, Roxbury, CT 06783
  • 90 Mallory Rd, Roxbury, CT 06783
    90 Mallory Rd, Roxbury, CT 06783
    90 Mallory Rd, Roxbury, CT 06783
    /29

    $575,000

    Open Mon 11AM - 1:15PM
    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    90 Mallory Rd, Roxbury, CT 06783

    Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful

    Richard Pomerantz William Pitt Sotheby's Int'l

    90 Mallory Rd, Roxbury, CT 06783
  • 268 South St, Roxbury, CT 06783
    268 South St, Roxbury, CT 06783
    268 South St, Roxbury, CT 06783
    /39

    $3,600,000

    • 5 Beds
    • 4.5 Baths
    • 6,190 Sq Ft

    268 South St, Roxbury, CT 06783

    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

    Peter Klemm Klemm Real Estate Inc

    268 South St, Roxbury, CT 06783
  • 297 Painter Hill Rd, Roxbury, CT 06783
    297 Painter Hill Rd, Roxbury, CT 06783
    297 Painter Hill Rd, Roxbury, CT 06783
    /38

    $4,495,000

    • 4 Beds
    • 7 Baths
    • 6,139 Sq Ft

    297 Painter Hill Rd, Roxbury, CT 06783

    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.

    Peter Klemm Klemm Real Estate Inc

    297 Painter Hill Rd, Roxbury, CT 06783
  • Lot 1 Chalybes Rd W, Roxbury, CT 06783
    Lot 1 Chalybes Rd W, Roxbury, CT 06783
    Lot 1 Chalybes Rd W, Roxbury, CT 06783
    /10

    $399,000

    • Land
    • 4.01 Acres
    • $99,501 per Acre

    Lot 1 Chalybes Rd W, Roxbury, CT 06783

    Private, Rural setting within a short walk to Roxbury Tennis courts, library and the Roxbury Market.This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 1 Chalybes Rd W, Roxbury, CT 06783
  • 246 North St, Roxbury, CT 06783
    246 North St, Roxbury, CT 06783
    246 North St, Roxbury, CT 06783
    /22

    $1,095,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft

    246 North St, Roxbury, CT 06783

    Juniper Hill offers masterfully upgraded one level living in Roxbury, Connecticut. Called a "Little Gem on the Hill" in Country Home, this unassuming ranch has been elevated with chic, yet family friendly styling. Modern comforts combine with country character in a home situated on compelling terrain. Large, level yard and play area that is difficult to find at this price point in the Litchfield

    Fred Bond William Pitt Sotheby's Int'l

    246 North St, Roxbury, CT 06783
  • 50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    /31

    $725,000

    • 5 Beds
    • 3 Baths
    • 1,365 Sq Ft

    50 Southbury Rd, Roxbury, CT 06783

    Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. At its

    Jeff Phillips William Pitt Sotheby's Int'l

    50 Southbury Rd, Roxbury, CT 06783
  • 307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    307 North St, Roxbury, CT 06783
    /8

    $250,000

    • Land
    • 3 Acres
    • $83,333 per Acre

    307 North St, Roxbury, CT 06783

    Approved Building lot with DOT approval for the driveway. Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Peaceful wooded lot to build your weekend or forever home! Close to Washington and Roxbury centers

    Sindy Butkus Klemm Real Estate Inc

    307 North St, Roxbury, CT 06783
  • 11 Evergreen Dr, Roxbury, CT 06783
    11 Evergreen Dr, Roxbury, CT 06783
    /2

    $1,200,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft

    11 Evergreen Dr, Roxbury, CT 06783

    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. There will be 9' ceiling height on the main level and 8' on the upper level. Both levels will 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

    Sharon McGuire William Pitt Sotheby's Int'l

    11 Evergreen Dr, Roxbury, CT 06783
  • 77 Judds Bridge Rd, Roxbury, CT 06783
    77 Judds Bridge Rd, Roxbury, CT 06783
    77 Judds Bridge Rd, Roxbury, CT 06783
    /39

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 2,901 Sq Ft

    77 Judds Bridge Rd, Roxbury, CT 06783

    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

    Joseph Lorino Klemm Real Estate Inc

    77 Judds Bridge Rd, Roxbury, CT 06783
  • 23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    /25

    $999,000

    $96K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    23 Painter Hill Rd, Roxbury, CT 06783

    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!

    Peter Klemm Klemm Real Estate Inc

    23 Painter Hill Rd, Roxbury, CT 06783
  • 69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, Roxbury, CT 06783
    /13

    $490,000

    $59K PRICE DROP
    • Land
    • 24.84 Acres
    • $19,726 per Acre

    69 Moosehorn Rd, Roxbury, CT 06783

    Build your dream on this designated "Scenic Road" abutting spectacular land trust trails. The lot consists of 24.8+/- acres, with a 9+/- acre building envelop. The building site is to be accessed from a future driveway running at the South border, along the Land Trust access point. The lightly wooded property rises to an 820-foot elevation and is resplendent with mature trees, ferns, moss and

    Stacey Matthews W. Raveis Lifestyles Realty

    69 Moosehorn Rd, Roxbury, CT 06783
  • 22 E Woods Rd, Roxbury, CT 06783
    22 E Woods Rd, Roxbury, CT 06783
    22 E Woods Rd, Roxbury, CT 06783
    /40

    $1,235,000

    • 4 Beds
    • 2.5 Baths
    • 3,476 Sq Ft

    22 E Woods Rd, Roxbury, CT 06783

    Completely reimagined from top to bottom, 22 E. Woods Rd. is a home where elevated design meets everyday comfort. From the moment you step inside, gleaming hardwood floors, abundant natural light, and an inviting open floor plan create a warm and welcoming atmosphere that feels equally suited to quiet mornings and lively gatherings. At the heart of the home is a stunning custom kitchen featuring

    Andy Sachs Compass Connecticut, LLC

    22 E Woods Rd, Roxbury, CT 06783
  • 1030 Washington Woodbury Rd, Roxbury, CT 06783
    1030 Washington Woodbury Rd, Roxbury, CT 06783
    1030 Washington Woodbury Rd, Roxbury, CT 06783
    /40

    $1,920,000

    $555K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,874 Sq Ft

    1030 Washington Woodbury Rd, Roxbury, CT 06783

    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

    Judith Auchincloss Klemm Real Estate Inc

    1030 Washington Woodbury Rd, Roxbury, CT 06783
  • 55 Ranney Hill Rd, Roxbury, CT 06783
    55 Ranney Hill Rd, Roxbury, CT 06783
    55 Ranney Hill Rd, Roxbury, CT 06783
    /12

    $2,000,000

    • Land
    • 26.48 Acres
    • $75,529 per Acre

    55 Ranney Hill Rd, Roxbury, CT 06783

    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!

    Sharon McGuire William Pitt Sotheby's Int'l

    55 Ranney Hill Rd, Roxbury, CT 06783
  • 99 Carriage Ln, Roxbury, CT 06783
    99 Carriage Ln, Roxbury, CT 06783
    99 Carriage Ln, Roxbury, CT 06783
    /38

    $1,495,000

    $240K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 6,395 Sq Ft

    99 Carriage Ln, Roxbury, CT 06783

    Welcome to 99 Carriage Lane, a private Roxbury estate offering over 6,000 square feet of refined living space, exceptional privacy on nearly four acres, and the opportunity to create a true resort-style outdoor retreat with approved pool plans. Set at the end of a quiet cul-de-sac, this beautifully renovated residence blends timeless architectural details with modern amenities and sophisticated

    Debra Tricarico Houlihan Lawrence

    99 Carriage Ln, Roxbury, CT 06783
  • 47 Squire Rd, Roxbury, CT 06783
    47 Squire Rd, Roxbury, CT 06783
    47 Squire Rd, Roxbury, CT 06783
    /27

    $3,995,000

    • 5 Beds
    • 5.5 Baths
    • 7,121 Sq Ft

    47 Squire Rd, Roxbury, CT 06783

    A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms

    Maria Taylor Klemm Real Estate Inc

    47 Squire Rd, Roxbury, CT 06783
  • 380 Southbury Rd, Roxbury, CT 06783
    380 Southbury Rd, Roxbury, CT 06783
    380 Southbury Rd, Roxbury, CT 06783
    /40

    $1,495,000

    $105K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,452 Sq Ft

    380 Southbury Rd, Roxbury, CT 06783

    Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

    ROSEANN BLANTON Berkshire Hathaway NE Prop.

    380 Southbury Rd, Roxbury, CT 06783
  • 85 Good Hill Rd, Roxbury, CT 06783
    85 Good Hill Rd, Roxbury, CT 06783
    85 Good Hill Rd, Roxbury, CT 06783
    /20

    $1,269,000

    $31K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft

    85 Good Hill Rd, Roxbury, CT 06783

    Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and

    Jason Saphire www.HomeZu.com

    85 Good Hill Rd, Roxbury, CT 06783
  • 179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    /13

    $985,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    179 South St, Roxbury, CT 06783

    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

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • 18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    18 Tunnel Rd, Roxbury, CT 06783
    /29

    $995,000

    $104K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    18 Tunnel Rd, Roxbury, CT 06783

    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

    Peter Klemm Klemm Real Estate Inc

    18 Tunnel Rd, Roxbury, CT 06783
  • 21 Carriage Ln, Roxbury, CT 06783
    21 Carriage Ln, Roxbury, CT 06783
    21 Carriage Ln, Roxbury, CT 06783
    /29

    $589,990

    Open House 8/23 Coming Soon
    • 3 Beds
    • 3 Baths
    • 1,248 Sq Ft

    21 Carriage Ln, Roxbury, CT 06783

    Coming Soon! 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

    Frank Durante William Raveis Real Estate

    21 Carriage Ln, Roxbury, CT 06783
  • 188 Bacon Rd, Roxbury, CT 06783
    188 Bacon Rd, Roxbury, CT 06783
    188 Bacon Rd, Roxbury, CT 06783
    /33

    $618,000

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft

    188 Bacon Rd, Roxbury, CT 06783

    Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. Main floor layout with separate spaces set up well for

    William Bolls Compass Connecticut, LLC

    188 Bacon Rd, Roxbury, CT 06783
  • 0 Southbury Rd, Roxbury, CT 06783
    0 Southbury Rd, Roxbury, CT 06783
    0 Southbury Rd, Roxbury, CT 06783
    /3

    $425,000

    • Land
    • 6.71 Acres
    • $63,338 per Acre

    0 Southbury Rd, Roxbury, CT 06783

    Rare in the Litchfield Hills-a flat, lightly wooded 6.71-acre buildable lot with a stream and stone walls. Perc'd for a spacious 4 bedroom custom home, and potential for a long private driveway. Perc's are 20 years old may have to be redone based on your plan.

    Jeff Phillips William Pitt Sotheby's Int'l

    0 Southbury Rd, Roxbury, CT 06783
  • 0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    0 Booth Rd, Roxbury, CT 06783
    /7

    $269,500

    $6K PRICE DROP
    • Land
    • 3.02 Acres
    • $89,238 per Acre

    0 Booth Rd, Roxbury, CT 06783

    Get away to the Country! Such a peaceful location to build your dream home. Lightly traveled road. All of nature loves the location, so will you!

    Sindy Butkus Klemm Real Estate Inc

    0 Booth Rd, Roxbury, CT 06783
  • 33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    /27

    $1,499,000

    $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    33 Sentry Hill Rd, Roxbury, CT 06783

    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,

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
  • 204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    204 North St Unit Lot 3, Roxbury, CT 06783
    /16

    $775,000

    • Land
    • 26.68 Acres
    • $29,048 per Acre

    204 North St Unit Lot 3, Roxbury, CT 06783

    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

    Jill Sloane Brown Harris Stevens

    204 North St Unit Lot 3, Roxbury, CT 06783
  • 25 Highmeadow Ln, Roxbury, CT 06783
    25 Highmeadow Ln, Roxbury, CT 06783
    25 Highmeadow Ln, Roxbury, CT 06783
    /38

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 4,310 Sq Ft

    25 Highmeadow Ln, Roxbury, CT 06783

    Imagine yourself at this private Litchfield County estate where open land, views, and timeless New England charm come together. Set on over 17 acres, this exceptional property offers the rare combination of privacy, recreation, and versatility, featuring a beautifully appointed Colonial, classic barn with apartment, heated gunite saltwater pool, and expansive grounds just 90 minutes from

    William Bolls Compass Connecticut, LLC

    25 Highmeadow Ln, Roxbury, CT 06783
  • 18 Ranney Hill Rd, Roxbury, CT 06783
    18 Ranney Hill Rd, Roxbury, CT 06783
    18 Ranney Hill Rd, Roxbury, CT 06783
    /35

    $1,795,000

    $205K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,198 Sq Ft

    18 Ranney Hill Rd, Roxbury, CT 06783

    Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble

    Sharon McGuire William Pitt Sotheby's Int'l

    18 Ranney Hill Rd, Roxbury, CT 06783
  • 20 Wellers Bridge Rd, Roxbury, CT 06783
    20 Wellers Bridge Rd, Roxbury, CT 06783
    20 Wellers Bridge Rd, Roxbury, CT 06783
    /20

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    20 Wellers Bridge Rd, Roxbury, CT 06783

    This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover

    WAYNE PISKURA Klemm Real Estate Inc

    20 Wellers Bridge Rd, Roxbury, CT 06783
  • 233 Southbury Rd, Roxbury, CT 06783
    233 Southbury Rd, Roxbury, CT 06783
    233 Southbury Rd, Roxbury, CT 06783
    /35

    $1,795,000

    • 5 Beds
    • 6 Baths
    • 5,447 Sq Ft

    233 Southbury Rd, Roxbury, CT 06783

    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

    Kathryn Clair William Pitt Sotheby's Int'l

    233 Southbury Rd, Roxbury, CT 06783
  • 216 Baker Rd, Roxbury, CT 06783
    216 Baker Rd, Roxbury, CT 06783
    216 Baker Rd, Roxbury, CT 06783
    /33

    $679,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,008 Sq Ft

    216 Baker Rd, Roxbury, CT 06783

    Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a

    David Landau RE/MAX Right Choice

    216 Baker Rd, Roxbury, CT 06783
  • 325 New Milford Rd E, Bridgewater, CT 06752
    325 New Milford Rd E, Bridgewater, CT 06752
    325 New Milford Rd E, Bridgewater, CT 06752
    /30

    $544,900

    $55K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,120 Sq Ft

    325 New Milford Rd E, Bridgewater, CT 06752

    Move right into this bright and well-maintained 4-bedroom, 2-bath split-level home set on a private, wooded 3-acre lot in desirable Bridgewater with low taxes. Recent updates include all new windows (2022), new gutters (2023), freshly painted kitchen cabinet doors (2026), and freshly painted bathrooms. The main level offers an open floor plan with hardwood floors, a spacious kitchen, and a

    Doug Collins Coldwell Banker Realty

    325 New Milford Rd E, Bridgewater, CT 06752

Showing Results 1 - 40, Page 1 of 2

Connecticut Litchfield County

Real Estate & Homes for Sale in Roxbury, CT

Why Live in Roxbury

Roxbury, CT, located in the Litchfield Hills just east of Bridgeport, offers a rural lifestyle with nearby urban amenities. Spanning 27 square miles with a population of over 2,000, Roxbury is known for its quiet, undeveloped landscape. Residents enjoy outdoor attractions like Hurlburt Park, which hosts the annual Roxbury Pickin’ and Fiddlin’ Contest, and River Road Preserve, ideal for hiking and fly-fishing. History enthusiasts can explore Mine Hill Preserve, featuring remnants of a 19th-century iron-making complex and extensive hiking trails. Adjacent to Mine Hill is the Kelsey Museum and Sculpture Garden, showcasing works by Sterett-Gittings Kelsey, and the Mine Hill Distillery, where visitors can sample locally distilled spirits. Homes in Roxbury range from raised ranch-style houses to historic Colonial homes, often situated on large lots with mature trees. The town is served by Regional School District Number 12, with highly rated Booth Free School and Shepaug Valley School, along with the nearby Kent School. While Roxbury lacks extensive commercial activity, residents can visit the Roxbury Market & Deli for groceries and meals, or travel 20 miles to Waterbury for more shopping options. For a broader shopping experience, New York City is accessible by train from Danbury, less than 20 miles south.

Learn more about living in Roxbury

Frequently Asked Questions

What is the average home price in Roxbury, CT?
Homes for sale in Roxbury, CT have an average home price of $1,633,872.
How many homes have sold over the last 12 months in Roxbury, CT?
31 homes have sold in Roxbury, CT over the last 12 months.
What is the average household income in Roxbury, CT?
The average household income in Roxbury, CT is $147K.
What are the most popular zip codes in Roxbury, CT?
The most popular zip codes in Roxbury, CT include 06783, 06752, 06798, 06793 and 06776.
How much do you need to make to afford a house in Roxbury?
The median home price in Roxbury is $1,495,000. If you put a 20% down payment of $299,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $7,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $330K a year to afford the median home price in Roxbury. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Roxbury is $147K.
How are the schools in Roxbury, CT?
Roxbury, CT has highly rated public and private schools. Some of the best schools in Roxbury based on Niche Grades are The Frederick Gunn School, Booth Free School and Pomperaug Regional High School. Browse all the schools in Roxbury, CT to learn more.

Home Prices in Roxbury, CT

The median home sale price in Roxbury, CT is $1,400,000, up 13% year-over-year. Homes in Roxbury sell in 128 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$1,400,000
Median Single Family Sale Price
$1,400,000
Median Townhouse Sale Price
$1,322,500
Median 2 Bedroom Sale Price
$1,009,000
Median 1 Bedroom Sale Price
$808,000
Average Price Per Sq Ft
$489
Number of Homes for Sale
31
Last 12 months Home Sales
31
Months of Supply
12.00
Median List Price
$1,495,000
Median Change From 1st List Price
12%
Median Home Sale Price YoY Change
13%
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