Newest Homes for Sale in Roxbury, CT

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

Pels Matthews W. Raveis Lifestyles Realty

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

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

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

Frank Durante William Raveis Real Estate

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck

Lisa Rollins Team Compass Connecticut, LLC

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

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

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

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

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

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

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.

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

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

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

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