Roxbury, CT Homes

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  /40

  $1,195,000

  • 3 Beds
  • 2.5 Baths
  • 4,012 Sq Ft

  24 Roxbury Rd, Woodbury, CT 06798

  Tucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury/Roxbury line, this stunning Colonial-Contemporary residence offers an unparalleled blend of privacy, natural beauty, and modern comfort on nearly 10 acres of pristine land. Surrounded by mature trees, vibrant plantings, and lush greenery, the property is enhanced by the gentle sounds of Transylvania Brook

  

  Shaylene Neumann

  Houlihan Lawrence

  (475) 265-6372

  24 Roxbury Rd, Woodbury, CT 06798
• Explore Roxbury

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  /14

  $2,500 total monthly price

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft
  • Apartment for Rent

  160 North St, Roxbury, CT 06783

  FURNISHED RENTAL AVAILABLE SEPT 2, 2025- MAY 2026 @ $2,500/MONTH. Spacious one bedroom apartment above garage on large, private estate. Clean, updated and comfortable. Bright living room with built ins and mini bar. Dining room and kitchen. Stackable washer/dryer in unit. Excellent credit, references and application required. Electricity included. Oil heat paid for by tenant.

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 750-8200

  160 North St, Roxbury, CT 06783
• 

  $407,500 Sold Oct 29, 2025

  • Land
  • 6.79 Acres
  • $60,015 per Acre

  • 227 Days On Market

  238 North St, Roxbury, CT 06783

  DRIVEWAY NOW UNDER Construction! Engineering APPROVED-Permit on File. Rarely available Lot in Roxbury! Magical 6.79 acre lot featuring a majestic stream and spring house, un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. This masterpiece lot is perfect to build your dream home and to connect with what is important in

  Jill Sloane Brown Harris Stevens

  238 North St, Roxbury, CT 06783
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  Not Listed For Sale

  00 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783
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  /40

  $875,000

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

  47 South St, Roxbury, CT 06783

  Step back in time w/ this antique home on a level scenic lot in sought-after Litchfield County. As you enter through the front door, you're welcomed by an original staircase & hickory wood floors. The living room features an exposed wood beam, a fireplace & hickory flooring. A formal dining room with classic pine floors & french doors that lead to a 4 season room. The 4 season room features a

  

  Michelle Alvord

  Berkshire Hathaway NE Prop.

  (860) 390-4127

  47 South St, Roxbury, CT 06783
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  /8

  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783

  Available May 2026: $2,200 plus utilities per month. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 1 bedroom/1 bath apartment, is located beneath the main house and may be rented with the main house(Upstairs 3-bedroom) or completely

  Melinda Dubow Klemm Real Estate Inc

  10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783
• 

  $1,650,000 Sold Oct 23, 2025

  • 3,302 Sq Ft
  • $500/SF
  • 23 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1991

  78 Garnet Rd, Roxbury, CT 06783

  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

  78 Garnet Rd, Roxbury, CT 06783
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  Not Listed For Sale

  00 Chalybes Rd W, Roxbury, CT 06783

  00 Chalybes Rd W, Roxbury, CT 06783
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  /37

  $1,795,000

  • 4 Beds
  • 5 Baths
  • 6,169 Sq Ft

  31 Hickory Ln, Roxbury, CT 06783

  Beautiful property in highly desirable Roxbury neighborhood. Traditional colonial with double story portico set back from quiet lane in park like setting with mature trees and gardens, huge pool, fruit trees, plenty of space for animals, stable, paddock. Detached garage in addition to under house garage with plenty of possibilities for guest house, studio, office. Large woodshed and enclosed

  Philippa Malkin W. Raveis Lifestyles Realty

  31 Hickory Ln, Roxbury, CT 06783
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  /28

  $6,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 1,260 Sq Ft
  • House for Rent

  10 Sentry Hill Rd, Roxbury, CT 06783

  Now available from January 2026. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 4-bedroom, 3 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with all new appliances including a wine

  Melinda Dubow Klemm Real Estate Inc

  10 Sentry Hill Rd, Roxbury, CT 06783
• 

  $1,200,000 Sold Oct 17, 2025

  • 3,920 Sq Ft
  • $306/SF
  • 150 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  53 Transylvania Rd, Roxbury, CT 06783

  Fantastic Colonial in Roxbury down long private drive featuring low maintenance salt water spa pooL. The house is surrounded by nature, with multiple entertaining spaces and gardens. Amazing bird life is a natural symphony while relaxing outdoors. The home has a lovely gracious layout all with detailed millwork and a vaulted great room with almost floor to ceiling windows on three sides creating

  Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania Rd, Roxbury, CT 06783
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  Est $1,485,659 Not Listed For Sale

  • 3 Beds

  18 Brandy Wine Crossing, Roxbury, CT 06783

  18 Brandy Wine Crossing, Roxbury, CT 06783
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  /40

  $1,675,000

  • 4 Beds
  • 2.5 Baths
  • 6,395 Sq Ft

  99 Carriage Ln, Roxbury, CT 06783

  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

  99 Carriage Ln, Roxbury, CT 06783
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  /39

  $25,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 2,762 Sq Ft
  • House for Rent

  24 Old Roxbury Rd, Roxbury, CT 06783

  Available SUMMER 2026 at 75,000 total. Also, school year 2025/2026 at $15,000/mo. Perched high on a scenic Roxbury hillside, this brand new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing

  Stacey Matthews W. Raveis Lifestyles Realty

  24 Old Roxbury Rd, Roxbury, CT 06783
• 

  $1,050,000 Sold Oct 15, 2025

  • 1,571 Sq Ft
  • $668/SF
  • 147 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1966

  19 Spargo Rd, Roxbury, CT 06783

  Step into timeless style and serene privacy with this beautifully maintained 1966 mid-century modern home. Set on almost 5 acres of lush, private land, this 3-bedroom, 2.5-bath residence blends classic design with modern upgrades. The just-renovated bathrooms feature high-end, spa-like finishes, while the expansive deck provides the perfect setting for outdoor entertaining or peaceful relaxation.

  Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo Rd, Roxbury, CT 06783
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  Est $175,025 Not Listed For Sale

  • 5 Beds

  268 Southbury Rd, Roxbury, CT 06783

  268 Southbury Rd, Roxbury, CT 06783
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  /33

  $1,630,000

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  85 Good Hill Rd, Roxbury, CT 06783

  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

  85 Good Hill Rd, Roxbury, CT 06783
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  /37

  $5,500 total monthly price

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • House for Rent

  28 Old Ln, Roxbury, CT 06783

  Tucked into the hills of Roxbury, this 4,000 sq ft Mid-Century Modern home is a private architectural retreat surrounded by wildflower clearings, forest, and dramatic granite outcroppings. The property exudes rustic country charm, favoring natural beauty over manicured formality. Inside, cathedral ceilings with numerous skylights create an airy, light-filled space that blurs the line between

  Robert Barker Houlihan Lawrence WD

  28 Old Ln, Roxbury, CT 06783
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  $1,837,500 Sold Sep 16, 2025

  • 2,640 Sq Ft
  • $696/SF
  • 357 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1815

  27 Wakelee Rd, Roxbury, CT 06783

  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

  Stacey Matthews W. Raveis Lifestyles Realty

  27 Wakelee Rd, Roxbury, CT 06783
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  Est $1,245,589 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft

  82 Squire Rd, Roxbury, CT 06783

  82 Squire Rd, Roxbury, CT 06783
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  /35

  $2,195,000

  • 5 Beds
  • 6 Baths
  • 5,113 Sq Ft

  88 Rucum Rd, Roxbury, CT 06783

  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

  88 Rucum Rd, Roxbury, CT 06783
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  /28

  $20,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 3,089 Sq Ft
  • House for Rent

  5 North St, Roxbury, CT 06783

  Summer 2026: July and/or August at $20,000 per month. Inquire for alternate dates. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room

  Melinda Dubow Klemm Real Estate Inc

  5 North St, Roxbury, CT 06783
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  $500,000 Sold Sep 05, 2025

  • 1,397 Sq Ft
  • $358/SF
  • 84 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  322 North St, Roxbury, CT 06783

  An artists custom retreat can now be your blank slate. 5.48 acres, straddles the towns of Roxbury (3.36 acres) and Washington (2.12 acres) Best of both worlds! Tucked back into the lightly treed lot bounded by old stonewalls, this unique home offers vaulted ceilings, hardwood flooring on both levels, bright sunroom off the kitchen, dining room or den on main level. Cozy woodstove in LR. The

  Mary Ann Bennett Drakeley Real Estate, Inc.

  322 North St, Roxbury, CT 06783
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  Est $672,368 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,696 Sq Ft

  29 Apple Ridge, Roxbury, CT 06783

  29 Apple Ridge, Roxbury, CT 06783
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  /40

  $2,295,000

  • 4 Beds
  • 5.5 Baths
  • 5,848 Sq Ft

  143 Tophet Rd, Roxbury, CT 06783

  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

  143 Tophet Rd, Roxbury, CT 06783
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  /25

  $7,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 3,236 Sq Ft
  • House for Rent

  116 Wellers Bridge Rd, Roxbury, CT 06783

  Mid-Century single-level in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The home has multiple versatile rooms giving a choice of layout to fit your needs. The

  Claudine McHugh Klemm Real Estate Inc

  116 Wellers Bridge Rd, Roxbury, CT 06783
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  $2,575,000 Sold Aug 29, 2025

  • 3,384 Sq Ft
  • $761/SF
  • 53 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1750

  18 Mallory Rd, Roxbury, CT 06783

  Idyllic Period Colonial with Pool Set Along Tranquil Town Road. This c1750 Colonial Has been Tastefully Updated & Expanded. 3 Bedrooms, 3.5 Baths. Central AC. Striking Gunite Pool Set Privately & Surrounded by Lush Landscape & Stone Terracing. Beautifully Proportioned Public Rooms Include: Living Room with Fireplace; Formal Dining Room; Library with Fireplace; Large Eat-in Kitchen with Fireplace

  Graham Klemm Klemm Real Estate Inc

  18 Mallory Rd, Roxbury, CT 06783
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  Est $1,440,682 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  310 North St, Roxbury, CT 06783

  310 North St, Roxbury, CT 06783
• 

  

  /39

  $2,150,000

  • 4 Beds
  • 5 Baths
  • 4,728 Sq Ft

  32 Grassy Hill Rd, Roxbury, CT 06783

  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

  32 Grassy Hill Rd, Roxbury, CT 06783
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  /27

  $15,000 total monthly price

  • 4 Beds
  • 6 Baths
  • 3,996 Sq Ft
  • House for Rent

  34 Old Roxbury Rd, Roxbury, CT 06783

  Available for $15,000/mo for April and May, 2026 and $75,000 for Summer 2026. Enjoy Modern Luxury in Connecticut's Countryside. The meticulously renovated 4-bedroom residence seamlessly blends the original mid century architecture with contemporary sophistication. Enter on the main level with 2 bedrooms and 2 full baths, sauna, foyer, powder room and media room with large screen tv and bar.

  Stacey Matthews W. Raveis Lifestyles Realty

  34 Old Roxbury Rd, Roxbury, CT 06783
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  $1,800,000 Sold Aug 28, 2025

  • 4,800 Sq Ft
  • $375/SF
  • 116 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  67 Botsford Hill Rd, Roxbury, CT 06783

  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

  Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,816 Sq Ft

  6 Painter Hill Rd, Roxbury, CT 06783

  6 Painter Hill Rd, Roxbury, CT 06783
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  /22

  $1,949,000

  • 4 Beds
  • 3.5 Baths
  • 4,517 Sq Ft

  45 Moosehorn Rd, Roxbury, CT 06783

  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

  45 Moosehorn Rd, Roxbury, CT 06783
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  /17

  $7,500 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 3,026 Sq Ft
  • House for Rent

  18 Bear Burrow Rd, Roxbury, CT 06783

  Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90

  Maria Taylor Klemm Real Estate Inc

  18 Bear Burrow Rd, Roxbury, CT 06783
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  $1,465,000 Sold Aug 22, 2025

  • 3,022 Sq Ft
  • $485/SF
  • 41 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  19 Good Hill Terrace, Roxbury, CT 06783

  Welcome to this enchanting Roxbury home that feels like a private oasis. This stunning property sits on over 7 acres and features a heated saltwater pool, a chef's kitchen with an open concept that overlooks the great room with vault ceilings, and radiant heated floors that leads to the patio, gardens, and pool. A custom built heated 2 story post and beam barn that offers a 3-car garage was built

  Tanya Uhelsky RE/MAX RISE

  19 Good Hill Terrace, Roxbury, CT 06783
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  Est $1,833,115 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  49 Garnet Rd, Roxbury, CT 06783

  49 Garnet Rd, Roxbury, CT 06783
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  /21

  $1,595,000

  • 3 Beds
  • 4 Baths
  • 2,396 Sq Ft

  247 Painter Hill Rd, Roxbury, CT 06783

  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

  247 Painter Hill Rd, Roxbury, CT 06783
• 

  $1,400,000 Sold Aug 22, 2025

  • 3,389 Sq Ft
  • $413/SF
  • 60 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  88 Hemlock Rd, Roxbury, CT 06783

  Exquisite Barn House with Heated Pool. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated Retreat. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; A Library which Envelopes you with an Antique Board Ceiling, Fireplace & French Doors; Formal Dining Room & A Timeless Eat-in Kitchen which Speaks to Family Room that

  Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
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  Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,341 Sq Ft

  24 Baker Rd, Roxbury, CT 06783

  24 Baker Rd, Roxbury, CT 06783
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  /27

  $1,495,000

  • 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

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