Roxbury Houses for Sale

Looking for a calming and peaceful property? You'll find total peace and quiet on this 15.29 acre impeccably maintained property bordering Roxbury Land Trust land. With a beautiful wrap around porch to take in views of the beautiful fruit trees, mature gardens, pond and level grounds this farmhouse is perfect inside and out. The heated and cooled large barn is a perfect flex space for an art

Andrew Murphy E.J. Murphy Realty

This stunning property has undergone an extensive, down-to-the-studs renovation, creating a home that feels brand new. The redesigned layout features a spacious, open-concept great room, complemented by an elegant living room/sunroom with a striking stone fireplace that walks out to the back deck. The chef's kitchen is a showstopper, designed to impress even the most discerning culinary

Stacey Matthews W. Raveis Lifestyles Realty

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and peaceful location-perfect for those seeking comfort and tranquility. Step inside to a spacious open-concept living and dining area, ideal for hosting gatherings and entertaining with ease. The modern kitchen features state-of-the-art appliances, ample counter space, and generous storage-making it a dream for

Debra Tricarico Houlihan Lawrence

At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both

Pat Lahoud William Pitt Sotheby's Int'l

Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

Pels Matthews W. Raveis Lifestyles Realty

Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms.

Stacey Matthews W. Raveis Lifestyles Realty

Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl

Stacey Matthews W. Raveis Lifestyles Realty

Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12+, chef's kitchen, vaulted ceilings, hardwood floors and two gas fireplaces. Heated pool surrounded by endless summer

Peter Klemm Klemm Real Estate Inc

Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch and another bedroom in finished lower level. Dine or relax on the flagstone

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

Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages.

Peter Klemm Klemm Real Estate Inc

Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow

Rick Distel Compass Connecticut, LLC

NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel

Michael Lissack The Virtual Realty Group

If privacy in the Litchfield Hills is your aspiration, this is the house for you. Country Cape with covered front porch set back off the road. Custom built home that is being offered for the first time on the market. SOLID QUALTIY CONSTRUCTION. New owner needs to do cosmetic updates and flooring to make it their own. Expansive kitchen with angled island leads to the open 2 story great room with

Gina Jacobs Gina Jacobs Real Estate

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

Great value, excellent location! Painter Hill is one of Roxbury's most scenic country roads. Close to Toplands Farm with beautiful pastoral views, a short drive to Maple Bank Farm for local produce, and just steps to a quiet dirt road for long walks. This charming Cape, built by the reputable local builder/owner in 2005, has 3 BR, 2.5 baths, a free-form Gunite pool and amazing outdoor living

Bonnie Garguilo William Pitt Sotheby's Int'l

Welcome to 2 Old Turnpike Road, a classic 3-bedroom, 2-bath ranch nestled on 2.52 acres in the picturesque town of Roxbury, CT. Offering 1,372 sq. ft. of comfortable living space plus a full unfinished basement with garage access, this home provides both charm and potential. Step inside to find a bright and inviting layout with spacious living areas, ideal for both everyday living and

Mychelle Gilbert Showcase Realty, Inc.

Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway.

Jeff Phillips William Pitt Sotheby's Int'l

Approved 6.08 acre building Lot with income producing Cottage! Charming 2 level home with windowed kitchen and bath, living room with WBFP and 2 bedrooms upstairs. The perfect weekend or Full-time Getaway-a Hikers Dream! This magical 6-acre lot features un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. A masterpiece

Jill Sloane Brown Harris Stevens

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene

Kathryn Clair William Pitt Sotheby's Int'l

Meander up the curved driveway to your secluded 6.89-acre lot with sunsets beyond compare. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large closets. Primary suite has large walk-in shower stall & two walk-in closets. Many possibilities with the two large finished rooms

MaryAnne Betso Coldwell Banker Realty

This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway

Cathy Masi Flagpole Realty Inc

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

Kathryn Clair William Pitt Sotheby's Int'l

Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a

Graham Klemm Klemm Real Estate Inc

MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round 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! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and French doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom with vaulted ceilings, balcony and large ensuite renovated bath. Three more bedrooms, 1 full and 1 half bath. Only a

Peter Klemm Klemm Real Estate Inc

A private gated road leads to this elegant shingle-style estate on 20+ secluded acres in the beautiful Litchfield Hills with spectacular views that go on for miles. This property includes a four bedroom, five and a half bath main residence, in ground heated Gunite pool, tennis court, one-bedroom caretaker's apartment over a 3-bay garage, two bedroom guest apartment and greenhouse. This compound

Maria Taylor Klemm Real Estate Inc

TO BE BUILT - A New Classic by Connecticut Residential. A rare opportunity to bring your dream home to life in scenic Roxbury, CT-this timeless Farm House Colonial-inspired residence is thoughtfully designed for both elegance and ease. Sited on a private 4-acre parcel, the proposed 4,266 sq ft home offers antique wooden timbers, refined architectural details, enduring craftsmanship, and a layout

Christopher Haggerty Around Town Real Estate LLC

New Construction Opportunity - Custom Estate on 20+ Acres in Roxbury, CT - Designed and to be built by Havens Fine Homes and ARK Design Studio. Introducing a rare and extraordinary opportunity to own a fully custom, to-be-built estate on Lots 7 & 8 Willow Brook Drive in the heart of highly sought-after Roxbury, Connecticut. Perfectly sited at the edge of the wood line, this exquisite new

Ryan Bollard William Pitt Sotheby's Int'l

TO BE BUILT - A New Classic by Connecticut Residential. Here's your chance to create something truly special in the heart of lower Litchfield County. Tucked away on over 4 private acres in picturesque Roxbury, this proposed home by Connecticut Residential blends timeless Colonial charm with modern-day comfort-thoughtfully designed for today's lifestyle while honoring traditional New England

Christopher Haggerty Around Town Real Estate LLC

TO BE BUILT - A Home by CORBO! A rare opportunity to build your dream home on approximately 16 private acres in Roxbury, CT-one of lower Litchfield County's most sought-after towns. This award-winning Colonial reproduction pairs timeless architecture with modern craftsmanship and is ideally positioned for western exposure and unforgettable sunsets (subject to tree clearing and final siting).

Christopher Haggerty Around Town Real Estate LLC

TO BE BUILT - A Home by CORBO! Tranquil luxury on 16 private acres in Roxbury, CT-an exceptional opportunity to bring your dream home to life in the heart of lower Litchfield County. Set well back from the road and oriented for western exposure, this stunning property offers sweeping views (subject to tree clearing and final siting) and the ultimate in privacy. Choose this thoughtfully designed

Christopher Haggerty Around Town Real Estate LLC