Refine Search
Sort by
$5,250,000
4 Beds 6 Baths 24043841 MLS
White Tail Farm, located in Roxbury, CT, just 90 miles from Manhattan, is an 86-acre estate offering the best of New England living. Centered around a restored c.1790s farmhouse, the property was substantially renovated and expanded in 2003, resulting in a spacious residence that artfully combines historical elements with modern amenities--ideal for discerning individuals seeking a private sanctuary or a multi-generational compound. With a combined total of 9042 sqft of space, 6 bedrooms, 6 bathrooms comprised of a guest house, in-law and main house, this property has room for everyone. The main residence features oak flooring, beamed ceilings, and six fireplaces. The upper level has two primary suites with en-suite baths and walk-in closets, plus two additional bedrooms and a guest room. The lower level comprises a Great Room for recreation. Outdoor amenities include a heated gunite pool, tennis court, sports court, and a 4-acre meadow with surrounding woods which are perfect for hiking and snowshoeing. The guest house provides a spacious flexible living space with two fireplaces, a recreation room, bedroom, full bath, and a kitchenette. The estate's 86 acres include a spring-fed pond, Battle Swamp Brook, curated landscaping by Robin Key, and walking trails. Additional features include a 3-car garage, a 4-stall barn, solar panels, and recent upgrades like a new well pump, cedar roof, garage doors, and smart ho

62 Davenport Rd, Roxbury

$4,360,000
5 Beds 6 Baths 24021983 MLS
Set on 14 private and fully fenced acres, this truly spectacular property, once owned by Walter Matthau and his wife Carol Grace, is surrounded by the Matthau Land Trust. The newly built main house was conceived by Geoff Fairbairn, a well-known Litchfield builder, with the current owners adding more features and square footage to the compound, with an eye for detail and enchanting style. The two original cottages have been updated, keeping the historic touches, and are currently used as a guest house and an extensive gym and office area. Among the many things that make this property so special are an attached five-car garage, a pool with spa and sun deck, radiant heat floors, a magnificent 18-foot stone chimney designed by Jorge Criollo and a three-season screened-in porch complete with a Malm fireplace. Roxbury is a renown artists community, home to such former and current notables as Richard Widmark, Walter Matthau, Marilyn Monroe, Arthur Miller, the illustrator Barry Blitt, the authors Frank & Ellen McCourt, Daniel Day Lewis, James Taylor and the stunning Alexander Calder Estate with its many sculptures. Roxbury's proximity to the city has made it possible for the current owners to easily film in the city and return in just over an hour and a half! Property consists of 2 separate lots - the compound sits on one lot (6+/- acres) and the other lot (7+/- acres) is unencumbered and can be gifted, sold or used as a building lot.

130 Tophet Rd, Roxbury

$3,500,000
4 Beds 7 Baths 24057344 MLS
Tucked Down a Long Private Driveway Less than 1-Min to the Village is this Chic Renovated Colonial with Heated Pool. This Elegant 4+ Bedroom, 6.5 Bath Home Is Very Finely Detailed. Sophisticated Floor-plan Features 2 Main Level Bedrooms including Luxurious Primary Suite with 2 Full Baths, Large Walk-in Closets & a Fireplace. 3 Other en-Suite Bedrooms. Large Country Kitchen with Vaulted Ceiling & Fireplace. Come Nestle by the Fire in the Inviting Library. Dramatic Formal Living Room with Vaulted Ceiling & Fireplace. Separate Dining Room Wrapped in Glass. Convenient In-House 2-Car Garage. Easy Access to Roxbury Village & Town Tennis Courts. Less than 12 Min to Washington, Woodbury, New Milford & Southbury. 1.5 Hours NYC. A Very Chic Country Retreat.

44 Chalybes Rd, Roxbury

$3,340,000
5 Beds 6 Baths 24088086 MLS
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 Fireplace, ModernLuxury Bath, and Dressing Room. A Separate 1-Bedroom Guest Suite Adds Versatility. Outdoors, Discover A Heated Gunite Pool Surrounded by Mature Award-Winning Gardens. Large Stone Terraces & a Meandering Garden Path Add a Texture to this Layered Property. 3-Car Over-sized Attached Garage. Only Minutes from Roxbury, Washington Depot, and Historic Woodbury CT. First Time on the Market in Over 35 Years

8 Bayberry Hl, Roxbury

$3,000,000
4 Beds 7 Baths 170590440 MLS
Exceptional Private Country Home with Heated Pool. This Luxurious 4 Bedroom, 6.5 Bath Home is Privately Set In the Midst of 12-Manicured Acres with Subtle Views & Serenity. Finely Detailed & Thoughtfully Appointed Including a Private Main Level Primary Suite with 2 En Suite Baths, Fireplace & Large Closets. 3 Other En-Suite Bedrooms. Generous Eat-in Country Kitchen with Vaulted Ceiling & Fireplace. Separate Formal Dining Room. Large Living Room with Beamed Cathedral Ceiling, Fireplace & Access to Stone Terrace. Quaint Library for Quiet reflection. Partially Finished Lower Level with Walk-out & Full Bath. Tucked Quietly Away Yet within Easy Access to Roxbury, Washington, Woodbury - a Mere 90-Miles to NYC. Cell Coverage. High Speed Internet. Choice.

44 Chalybes Rd, Roxbury

$2,775,000
4 Beds 6 Baths 170560982 MLS
Perched at one of Roxbury's highest elevations, with hypnotizing views, lies the Golden Harvest homestead of master builder Ed Cady. The compound sits on a 26 acre parcel personally selected for its privacy, elevation and direct adjacency to the Roxbury Land Trust's 450 acre preserve. Using antique timber barn frames from upstate New York, he constructed the buildings that stand today. The main house exudes casual comfort, with hand-hewn beams blending seamlessly with modern finishes. There are five fireplaces in the main home, antique wide-board floors, native Roxbury granite and endless bespoke details that are so distinctively Cady. The spacious kitchen has a separate eating area, pantry and sun-filled greenhouse. The public wing of the home houses the great room, with soaring ceilings, never-ending views and room for both intimate and large-scale entertaining. The upper level houses two primary bedroom suites plus an office that is easily converted to an additional BR. The lower level includes a recreation room and full bath. The 1BR/1.5BA guest house - well separated from the main house - is a jewel with all the same Cady detailing and a deck overlooking the entire Shepaug River Valley. The barn has parking for 3+ additional vehicles and an in-law apartment above. Additional outbuildings give the property a rich historic texture. The craftsmanship and quality here is at the highest level, and the opportunity to own the "King’s Castle" comes up only once in a generation.

19 Golden Harvest Rd, Roxbury

$2,700,000
5 Beds 6 Baths 24093019 MLS
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 guest room on the main level, perfect for nursery or in-laws.3 bedrooms/2 baths on the second level. Lower level game room has full bath and can be used as a 6th bedroom. Gunite heated pool with stone terraces incorporates room for relaxing and dining pool side. 3 car garage has unfinished space above which could be finished to an apartment or studio. Multi zone stereo system. Just 5 minutes to Washington with chic shops, farmer's market and

Roxbury

$2,547,500
3 Beds 3 Baths 24138574 MLS
This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.

277 Painter Hill Rd, Roxbury

$2,501,000
5 Beds 6 Baths 24122044 MLS
Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you'll know you have arrived at your forever home. Designed for both grand entertaining and intimate daily life, the home's beautiful open spaces are bathed in natural light. Every detail has been meticulously crafted to create an atmosphere of refined elegance and comfort. This residence features five spacious bedrooms, six luxurious baths, and four fireplaces, each adding a touch of warmth and classic charm. Outdoor living is elevated to an art form here. The award-winning infinity pool and spa appear to spill into the professionally designed landscape, which seamlessly blends with the natural wooded surroundings, ensuring complete privacy. A grand stone terrace with a fireplace and a sprawling covered porch provide the perfect settings for memorable outdoor gatherings, dining, and relaxation. This estate truly offers the best of both worlds-it feels a world away from the hustle and bustle yet is conveniently located close to everything. The property consists of three separate parcels and benefits from low Roxbury taxes, adding to its appeal. This is more than just a home; it's a lifestyle. We invite you to plan extra time for your private showing to fully appreciate the except

Roxbury

$2,300,000
4 Beds 5 Baths 24167123 MLS
Roxbury Shingle-Style Gem with Sparkling Pool! This grand residence sits off one of Litchfield County's most treasured and bucolic roads amidst boldfaced names - past and present - and backing up to a 60-acre parcel of Roxbury Land Trust. Prepare to be "wowed" by the sun-flooded double height living room, gorgeous eat-in-kitchen, formal dining room, four-season sunroom, wood-paneled library/den, and well-executed rec room. Four oversized bedrooms with ensuite baths, including primary suite options on both the main floor and upstairs. A large outdoor deck which spills onto a native stone terrace with grill and pizza oven; perfect for entertaining friends and family. Partially finished basement with gym and tons of storage. Pristine 20x40 gunite pool and spa added in 2022. Cagenio-wired smart home with mega-speed internet, Wifi covering the interior and exterior patio and pool areas, whole house generator. Many "hidden money" upgrades inside and out, including roof in 2021 (w/ 50-yr transferable warranty), five zone HVAC system with all units replaced 2021-2024, pool and spa in 2022, whole-house generator, mini-splits in the sunroom and gym area, and a comprehensive automation system. In the heart of Litchfield County, convenient to Lake Waramaug, fine dining, farmers markets, town tennis courts and thousands of acres of land trust to explore. 90 minutes to NYC but a world away.

77 Tophet Rd, Roxbury

$1,966,500
4 Beds 5 Baths 24085777 MLS
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 color, was purchased by the current owner in 2021 and underwent an exquisite glow-up by a noted local designer who transformed the residence into something formal, yet intimate; a place that feels so right with rooms that serve purpose. The masterfully appointed chef's kitchen will delight with abundant prep space, oversized range, and a refrigeration wall with dedicated cooling, freezer and wine storage. A sun-filled gathering space is adjacent as well as an informal dining area. A butler's pantry connects the kitchen and the formal dining room. The formal LR is across the foyer, a serene space with one of the home's 3 fireplaces. A den and a media lounge complete the main floor. Upstairs, the primary suite has been reimagined into a luxury space with dressing room and a spa bath. 2 guest BRs and a full bath complete this level. Above the 2 car garage is a guest apartment with living area/gym, BR and BA. Immaculate grounds with mature gardens and multiple outdoor dining spaces. Ready for new memories, this is a gem of a home within a dream of a town.

32 Grassy Hill Rd, Roxbury

$1,925,000
4 Beds 6 Baths 24093575 MLS
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. There is also a formal living room with wrap around deck which takes in the views. Interiors are newly updated with designer wallpapers, custom window treatments, and luxury lighting. The second floor hosts 3 generously sized en-suite bedrooms which surround a central gathering space with built-in desks. The attic level is fully finished with a full bath for 4th bedroom, game room, gym, home office and/or studio. The salt water heated pool and spa take in the rolling ridge line views across a vast tract of protected land. Newly cleared lawns with fire pit. Excellent mechanical systems, including a 27K generator and Buderus furnace. Peaceful and private, yet just 10 minutes to Washington or Woodbury for farm stands, organic groceries, restaurants and boutiques. 1.5 hours from NYC and 30 minutes to the train station.

143 Tophet Rd, Roxbury

$1,837,500
4 Beds 3 Baths 24034591 MLS
Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could be used as a shared play room with 3 bedrooms circulating it. Antique floors and hand hewn beams throughout. The large cooking fireplace has been revived to its former glory and the 2 smaller fireplaces have had propane inserts added. Recent upgrades include: Generator, new heating, interior and exterior paint, wood shingle roof, built ins, curtains etc. Tennis court was partially removed, foundation still in place. Buyers can rebuild it or scrape concrete and create additional lawn or gardens.

27 Wakelee Rd, Roxbury

$1,825,000
3 Beds 4 Baths 24043497 MLS
PETITE ESTATE:South St in the heart of Roxbury, FoxCroft is a classic 1792 Colonial farmhouse on a generous parcel of land. The property includes a heated pool, guest house, studio, 3 car garage with hayloft, and a pond, as well as remnants of its history: an old ice house and a well house. Inside, original fireplaces anchor each of the main rooms, including a large central fireplace with a bread oven. The sunroom opens to views of the surrounding trees and offers a quiet spot to read or work. Built-in shelves and exposed beams appear throughout, balancing simplicity with style.The kitchen has been updated with a six-burner Viking stove, Bosch dishwasher, and SubZero refrigerator, and connects to a butler's pantry for storage and utility. Front and back staircases lead upstairs to 3 ensuite bedrooms with lots of closet space. The primary suite includes a fireplace, walk-in closet, and a bonus room that could serve as a study or dressing room. The guest cottage, once a schoolhouse with cubbies, offers its own living space with a bedroom, sitting area, and full bath. The studio nearby includes a half bath, separate laundry, and flexible open space under high ceilings, ideal for creative, remote work or a play space. Outdoors, the land invites exploration. There are perennial gardens, a meadow, a pond that used to be Roxbury's town skating pond, and shaded paths among old trees and stone walls.FoxCroft is a place to settle in, or to get away. It's ready for its next chapter

44 South St, Roxbury

$1,800,000
4 Beds 6 Baths 24064600 MLS
This is the perfect country getaway estate property, a vintage home that has been totally renovated in the 21st century. This 4BR home, 2BR guest house, heated in-ground pool with cabana and modern barn are privately sited on over 6 beautifully landscaped acres in the heart of charming Roxbury in the beautiful hills of Litchfield County. Take in the view of the property from your covered deck, or move through the French doors inside to the living room with a fire in the fireplace, steps from the kitchen. This is a great house for entertaining as the floor plan flows easily from the living room into the den and dining room, or retreat further into the office with it's separate entrance to a private patio. The main floor Primary Suite has another fireplace (of the four found throughout the house) and a lovely ensuite bathroom. Upstairs are three bedrooms, each ensuite. The lower level has a media room that could also easily be a gym or game room. Near the pool across the lawn is the 2BR guest house with an open floor plan and a screen porch overlooking the pool. Sited nicely away from the houses is the 5600 sf barn which can accommodate a significant car collection, equipment storage or the hobby of your dreams! If you have been looking for a classic country escape, comfortable yet elegant and beautifully appointed, yet 90 minutes to Manhattan, look no further!

108 Davenport Rd, Roxbury

$1,800,000
4 Beds 3 Baths 24091368 MLS
Discover the appeal of this Swedish inspired shingle-style beauty with light and modern finishes throughout. It's nestled into 41+ ultra-private acres on a picturesque country road. Enter the front door into the two-story foyer which flows into the vaulted ceiling living room with lots of glass, adobe fireplace and easy access to the tucked away library with floor to ceiling bookshelves. The newly renovated kitchen with seating area and fireplace is a natural gathering space. The elegant kitchen has soft colored custom cabinetry, white marble countertops, new appliances and brass hardware. The powder room and laundry complete this floor. A set of glass doors lead to the exterior entertaining space with large stone terrace and in ground heated gunite pool. The spacious and private primary suite is conveniently located on the main level and boasts a brand-new bathroom. The light-colored hardwood floors throughout the main level public spaces and staircase add to the elegance of this house. The upper level offers three additional bedrooms with vaulted ceilings and a full bath. The park-like grounds are breathtaking with a mix of rolling meadows, fenced pastures and forestry. Once a stable, the barn is currently being used as a 3-season recreation room. 4.9 acre front lot is in Roxbury and the rear lot with the house is 36.4 acres located in Bridgewater.

67 Botsford Hill Rd, Roxbury

$1,764,000
4 Beds 5 Baths 24176141 MLS
Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

176 Apple Ln, Roxbury

$1,725,000
4 Beds 5 Baths 24046861 MLS
Meander over a small bridge and through tall pines to reach this distinctive 4 bedroom home on 6 very private acres. A gracious wood paneled central foyer directs you into the living room, dining room, or through to a thoughtfully designed great room. The kitchen features a wrap-around island with bar stools, high-end appliances walk-in pantry/laundry. It also opens to the breakfast nook and sitting areas with stunning stone fireplace and large windows. French doors open to a blue stone terrace with newly installed outdoor kitchen and pizza oven. The new Gunite heated pool has automatic cover and plentiful blue stone terracing for relaxing. Enjoy the built-in Jacuzzi which seats 6 comfortably. The main floor is completed by the spacious primary bedroom, huge walk in closet, office nook and luxury bath. Upstairs are 2 ensuite bedrooms. The large finished lower level is walk out. It has been expanded to include; media/game room, bedroom/bath, gym, and storage rooms. Impressive high ceilings, the finest stone and woodwork, and exacting attention to detail. There is a full staircase in the garage which leads to an unfinished space which might make an excellent in-law apt or studio.

381 South St, Roxbury

$1,670,000
3 Beds 4 Baths 24101659 MLS
A split rail fence along the meandering drive leads you to this beautiful and sophisticated farmhouse on 15.29 acres of peaceful countryside. Storybook wrap-around porch, new Gunite heated saltwater pool, separate guest apartment, enormous barn, apple trees, perennial gardens and pond are highlights. The pristine house has recessed wood paneling and floors, window seats, built-ins and crown molding. It's warm and inviting with 9' ceilings and an abundance of windows. The formal living/dining room combination is nicely sized with exposed beams, fireplace, built-ins and glass door to deck. The Chef's kitchen boasts Dacor, Viking and Subzero appliances, polished granite countertops and deck access. Open to the kitchen is the cozy family room with fireplace. A library/study or office on main level includes window seat, recessed paneling, beams, built-ins and bookshelves. A powder room is located just off the floor to ceiling recessed paneled foyer. The dreamy primary bedroom has two baths, two walk-in closets, built-ins, bookshelves and window seat. Two additional bedrooms (one used as office) full bath and laundry are on this floor. The lower level has a finished space perfect for rec or exercise room. The separate one-bedroom apt sits above the two-car garage and enjoys its own deck. The barn is heated, cooled and is ready to be finished for party barn, studio, office or pool house. Litchfield Hills has so much to offer. Come take a look!

78 Garnet Rd, Roxbury

$1,650,000
4 Beds 5 Baths 170549073 MLS
Located in beautiful Litchfield County in the picturesque town of Roxbury, this modern stylish 4 bedroom, 4.5 bathroom home is situated on 5 private, quiet acres, This property offers a fabulous great room with soaring beamed ceiling, an amazing floor to ceiling stone fireplace that is flanked w/2 story windows, walls that are completely lined with glass and French doors that lead to large outdoor entertaining area with wonderful outdoor stone fireplace and beautiful sunsets. Inviting living/dining area w/vaulted ceilings, large stone gas fireplace and opens to the modern high-end kitchen w/cathedral wood lined ceiling, large quartz center island and state of the art appliances. First floor primary bedroom w/Italian stone bath. Upper level has a 2nd primary bedroom suite with stone bath and washer & dryer unit, two additional quest bedrooms, both en-suite with stone baths, Lower level has a large finished area, a great family/rec room. There is also a professionally installed home business grade Ubiquiti UniFi wired and wireless network. All fireplaces are piped for propane. Invisible fencing has also been installed on the property. Only 90 minutes to Manhattan. Totally done and ready to move in!!

49 Garnet Rd, Roxbury

$1,650,000
3 Beds 4 Baths 24122582 MLS
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 studio, gym or party space right in front of the beautiful saltwater pool. Inside you'll find 9' ceilings in the formal living/dining room with incredible natural light. Cozy up by the fire and continue to admire the beautiful grounds through the large doors to the porch. You'll find recessed paneling in the library along with a window seat and built-in's. Continued artisan millwork is found throughout the home. The kitchen has Dacor, Viking and Subzero appliances along with granite countertops, dual sinks and a large pantry with additional access to the porch in addition to a large family room with another fireplace. Up the dramatic open staircase to the second floor you'll find two generous sized bedrooms, a dedicated laundry room and full bathroom. In the tranquil primary suite you'll find more peaceful views of the grounds, vaulted ceilings, two walk-in closets, two baths, built-in's and another window seat to admire the property.

78 Garnet Rd, Roxbury

$1,650,000
3 Beds 3 Baths 24010430 MLS
One of early Roxbury's fabulous beauties! This well-preserved, late nineteenth-century Victorian Farmhouse has been lovingly maintained over the years, featuring modern renovations with appreciation and sensitivity to original detail. Huge, bright country kitchen, made for easy entertaining, is the central gathering place. Marble center island open to four directional views of the gardens, stone patio & walls, large blue stone screened porch and in-ground gunite pool. Adjoining, relaxed, yet formal, dining room has original Italianate bay windows and doors. Welcoming front and back parlor rooms feature wrap-around veranda and screened bluestone porch. Three period fireplaces. Three generous sized bedrooms on the second floor; main suite has a large closet room and a two room bath. Three story Country Carpenters Bank Barn with 4+ parking places. Also included, #8 Painter Hill. a four-room cottage, at a distance, planted out and private to main house with its own driveway. An income producing property since 1986. Stunning and private setting. The six acre protected property is adjacent, on two sides, to Roxbury's historic farms. Other two sides border major estates. Features a brook, land dotted with stately old growth Sugar Maples, conifers and open land. Walk to Maple Bank farm stand, Roxbury Market and houses of worship. A very special country estate 90 minutes from NYC. Q

6 Painter Hill Rd, Roxbury

$1,600,000
4 Beds 5 Baths 24133274 MLS
This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room bedroom suite - perfect for guests, in-laws, or live-in help. This wing could easily be converted to a main floor primary if desired. Upstairs hosts the current primary bedroom w/ frpl & updated bath, as well as 2 addl bedrooms w/ a shared hallway bath. The updated, eat-in kitchen walks out to an airy screened porch w/ ample space to accommodate both lounging & dining. It is lightly shaded by mature trees and overlooks fieldstone terraces, established gardens & fruit trees. This property offers a uniquely flat and expansive lawn in a truly 'park-like' setting. The previous owner was a master gardener who meticulously cultivated specimen Rhododendrons throughout the lightly wooded surrounds. The mature plantings combine w/ native Mountain Laurel to create a spectacular display in early Summer. The exterior is completed by a 22 x 45 salt water, Gunite pool w/ integrated 6 x 8 Jacuzzi. It is 10' deep & boasts a diving board, retractable cover, & automated chemistry system allowing for hassle free ownership.

31 Hickory Ln, 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.