Homes for Sale near Booth Free School

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  /11

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  22 Standish Rd, New Milford, CT 06776

  Location, location, location!! Great opportunity to buy this well maintained 4-Bedroom 2.5-Bathrooms in the heart of New Milford, CT. Features one acre lot with privacy fence, 2 fireplaces, central A/C, hardwood floors, MBR Bath. Book your appointment before it's gone.

  

  Santiago Jaraba

  Whitestone Real Estate Group

  (860) 579-6206

  22 Standish Rd, New Milford, CT 06776
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  Explore Booth Free School

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  /28

  $1,700,000

  • 3 Beds
  • 3 Baths
  • 2,312 Sq Ft

  95 Shinar Mountain Rd, Washington Depot, CT 06794

  Chic Mid-Century Modern Retreat with Sunset Views and Ultimate Privacy! Tucked away in the heart of nature and bordered by the protected Steep Rock Preserve, this stylish single-level Mid-Century Modern home is the perfect weekend getaway. Designed for effortless living and entertaining, the spacious, light-filled layout includes 3 bedrooms and 3 full baths. A wall of floor-to-ceiling windows

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 730-1696

  95 Shinar Mountain Rd, Washington Depot, CT 06794
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  /39

  $1,149,000

  • 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
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  /40

  $875,000 Open Sat 12PM - 2PM

  • 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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  /33

  $524,999

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  13 South St, Washington, CT 06793

  This beautifully updated 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience-ideal as a weekend retreat or a year-round home. Located just minutes from the renowned Mayflower Inn & Spa and the Frederick Gunn School, and only two hours from NYC, the location is unbeatable. Enjoy a brand-new kitchen featuring quartz countertops, custom cabinetry, and stainless steel

  

  Gary Crawford

  RE/MAX RISE

  (860) 784-7785

  13 South St, Washington, CT 06793
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  /39

  $2,572,500 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,559 Sq Ft

  277 Painter Hill Rd, Roxbury, CT 06783

  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

  Stacey Matthews W. Raveis Lifestyles Realty

  277 Painter Hill Rd, Roxbury, CT 06783
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  /40

  $1,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,324 Sq Ft

  55 Good Hill Rd, Woodbury, CT 06798

  Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

  Stacey Matthews W. Raveis Lifestyles Realty

  55 Good Hill Rd, Woodbury, CT 06798
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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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  /40

  $1,155,000

  • 4 Beds
  • 2.5 Baths
  • 3,340 Sq Ft

  24 Hickory Ln, Roxbury, CT 06783

  This beautifully updated Post & Beam residence offers exceptional craftsmanship and modern amenities throughout. Over the past five years, the home has received numerous enhancements, including a new roof, remodeled kitchen with tile flooring, all-new Pella windows and doors, asphalt driveway, 5-zone LP boiler, central A/C unit, and more. The inviting interior centers around a dramatic two-story

  Sidney Nazario Coldwell Banker Realty

  24 Hickory Ln, Roxbury, CT 06783
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  /40

  $1,399,000

  • 4 Beds
  • 3.5 Baths
  • 3,077 Sq Ft

  96 Squire Rd, Roxbury, CT 06783

  A distinguished equestrian estate of rare beauty, this property unites timeless New England architecture with the serenity of country living. Approached by a gated, tree-lined drive, the residence evokes an air of grace and permanence, set amidst sweeping pastures and centuries-old trees. The main residence exudes historic character and refinement, where wide-plank floors, hand-hewn beams, and

  Nikki Defrancesco Coldwell Banker Realty

  96 Squire Rd, Roxbury, CT 06783
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  /25

  $1,195,000

  • 2 Beds
  • 3.5 Baths
  • 3,285 Sq Ft

  49 South St, Washington, CT 06793

  Located near the prestigious Mayflower Inn and just minutes from the Washington Green in an area of many fine estates, this 1890's Barn style home with it's silo and 1970's additions, offers a unique opportunity for full renovation and customization. The land has been cleared for a western view with great sunsets and is ready to create your dream estate. While the property retains its historic

  Kathryn Clair William Pitt Sotheby's Int'l

  49 South St, Washington, CT 06793
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  /25

  $1,275,000

  • 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
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  /38

  $1,625,000

  • 4 Beds
  • 3.5 Baths
  • 3,597 Sq Ft

  62 Tepi Dr, Southbury, CT 06488

  Enjoy breathtaking sunsets from your fully renovated contemporary waterfront retreat! Set on the shores of Lake Lillinonah, Connecticut's second-largest recreational lake, this multi-level home was extensively renovated in 2023 to blend modern comfort with dramatic design and unforgettable views. Updates include new oak hardwood floors throughout, sisal wall-to-wall carpeting in guest spaces,

  Richard Pomerantz William Pitt Sotheby's Int'l

  62 Tepi Dr, Southbury, CT 06488
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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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  /36

  $1,195,000

  • 5 Beds
  • 5 Baths
  • 2,804 Sq Ft

  286 South St, Roxbury, CT 06783

  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

  286 South St, 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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  /40

  $1,275,000

  • 3 Beds
  • 5 Baths
  • 4,059 Sq Ft

  373 Transylvania Rd, Woodbury, CT 06798

  Custom-built. This unique home is made for entertaining. 4000 ft.2 home with 3 bedroom suites each containing its own full bath. 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, bow window w/bench seat & walk out to deck. Formal dining room has tray ceiling. Great room with fireplace and full bar. Den/library has fireplace. Bright piano room/sunroom/office also walks

  Beatriz Conroy William Raveis Real Estate

  373 Transylvania Rd, Woodbury, CT 06798
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  /40

  $919,000

  • 4 Beds
  • 4 Baths
  • 3,624 Sq Ft

  67 Transylvania Rd, Roxbury, CT 06783

  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

  67 Transylvania Rd, Roxbury, CT 06783
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  /23

  $879,000

  • 3 Beds
  • 2 Baths
  • 2,444 Sq Ft

  52 Curtis Rd, Bridgewater, CT 06752

  Tucked within the gentle hills and rolling farmland of Bridgewater, this fully remodeled custom farmhouse split redefines modern country living. Every inch of this residence has been thoughtfully redesigned and completely transformed, delivering a truly turnkey experience. The versatile open-concept design showcases a showstopping chef's kitchen with a waterfall quartz island, two-tone custom

  Lisa Brown-McDonald The Brokerage of New England

  52 Curtis Rd, Bridgewater, CT 06752
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  /40

  $3,975,000

  • 5 Beds
  • 4 Baths
  • 4,371 Sq Ft

  67 Squire Rd, Roxbury, CT 06783

  67 Squire Road blends striking modern architecture with timeless New England character on nearly 11 private acres in Roxbury. Thoughtfully designed and beautifully executed, this contemporary retreat offers 4,371 sq ft of light-filled living space with 5 bedrooms and 3 spa-quality baths. Radiant-heated white oak floors and walls of glass frame the surrounding landscape, bringing nature into the

  Omar Cruz Compass Connecticut, LLC

  67 Squire Rd, Roxbury, CT 06783
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  /24

  $339,000

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft

  13 Tamarack Ln Unit 13, Woodbury, CT 06798

  Beautiful end unit at Woodlake Community in Woodbury! Kitchen with stainless steel appliances and granite countertops plus tile floors. Hardwood floors on first level in Dining and living area with sliders to a deck overlooking the wooded back area and lake. This unit features upgraded 2 full plus 1 half bathrooms plus 2 bedrooms with plenty of closets. Laundry closet with shelving is on the

  Lynn Platania William Raveis Real Estate

  13 Tamarack Ln Unit 13, Woodbury, CT 06798
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  /8

  $390,000

  • 2 Beds
  • 1 Bath
  • 1,421 Sq Ft

  43 Hoop Pole Hill Rd, Woodbury, CT 06798

  Nestled in one of Woodbury's most desirable areas, this nearly 9-acre property offers a rare opportunity for visionaries, developers, or those looking to create their own private retreat. The house and barn are in need of significant renovation - or start fresh and build your dream home surrounded by rolling hills, a meandering stream, mature trees, and the serene charm that defines Litchfield

  Laura Rose RE/MAX RISE

  43 Hoop Pole Hill Rd, Woodbury, CT 06798
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  /40

  $519,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  14 Cambridge Cir, New Milford, CT 06776

  All good things! If you have been waiting for a home with the right combination of setting & location, design, size & amenities, one worth an investment, this is it! This remarkable Colonial features the most wanted style & amenities, and, it is located in Southern New Milford's most desired Meadowbrook neighborhood. Here is the rare & perfect opportunity for the buyer who prefers to make their

  Carole Sansone William Raveis Real Estate

  14 Cambridge Cir, New Milford, CT 06776
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  /40

  $377,750 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft

  2 South Meadows Unit 107B, Woodbury, CT 06798

  Take another look! Seller Contingency removed! Welcome Home to your new dream home! This beautiful, peaceful, calm upscale residence, offers 3 Levels of quiet elegance. Move in & enjoy the vacation at home..."Woodlake Life Style". Each room is thoughtfully purposed and decorated with a classy style. The kitchen spacious "open" concept, with Corian countertops. Cherry toned flooring adds a warm

  Terry Lee Adams Adams & Adams Real Estate

  2 South Meadows Unit 107B, Woodbury, CT 06798
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  /3

  $250,000

  • Land
  • 2.11 Acres
  • $118,483 per Acre

  7 Candace Ct, New Milford, CT 06776

  Beautiful Western Views on this 2.11 approved building lot. Level to sloping. Past septic and lot design available but probably needs to updated.

  Ed Cavallo Hegarty & Co Real Estate

  7 Candace Ct, New Milford, CT 06776
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  /22

  $479,000

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  12 Round Table Rd, New Milford, CT 06776

  Nestled on just under half an acre, this home is truly turn-key. Custom kitchen and baths all-new flooring, separate living and family rooms, a laundry center, and tasteful design throughout. The open floor plan has great flow and is perfect for entertaining and comfortable, casual living. The main floor includes the living room, dining room, kitchen, the primary bedroom and ensuite bathroom, 2

  Jorge Zea Blue Lighthouse Realty, Inc

  12 Round Table Rd, New Milford, CT 06776
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  /4

  $250,000

  • Land
  • 1.97 Acres
  • $126,904 per Acre

  7 Kiara Ct, New Milford, CT 06776

  WESTERN VIEWS AS FAR AS THE EYE CAN SEE! Build your dream home on this Beautiful 1.974 acre building lot located on a Cul de sac. Level to slightly sloping meadow with some mature trees. Past deep hole and perk test available that will probably need to be updated.

  Ed Cavallo Hegarty & Co Real Estate

  7 Kiara Ct, New Milford, CT 06776
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  /17

  $499,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  34 Transylvania Rd, Woodbury, CT 06798

  Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan kitchen/dining/livingroom. The lower

  Betsy Rosa Berkshire Hathaway NE Prop.

  34 Transylvania Rd, Woodbury, CT 06798
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  /26

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  38 W Mountain Ln, Roxbury, CT 06783

  Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of

  Maria Taylor Klemm Real Estate Inc

  38 W Mountain Ln, Roxbury, CT 06783
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  /13

  $549,000

  • Land
  • 24.84 Acres
  • $22,101 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
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  /40

  $675,000

  • 4 Beds
  • 3 Baths
  • 3,064 Sq Ft

  174 Weekeepeemee Rd, Woodbury, CT 06798

  Nestled on approximately 5.38 acres of lush, mature landscaping, this captivating house offers an abundance of space and tranquility. The property features four bedrooms and three bathrooms, spanning approximately 3,064 square feet of thoughtfully designed living space. The expansive, spacious lot is complemented by a serene outdoor space, boasting a paved patio, a spacious deck, and a sprawling,

  Laureen Kennedy Coldwell Banker Realty

  174 Weekeepeemee Rd, Woodbury, CT 06798
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  /40

  $3,200,000

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

  4 Judge Rd, Roxbury, CT 06783

  Complete Equestrian Facility with Cape Cod Style Home. An ideal property for horse enthusiasts, trainers, or those seeking a turn-key boarding operation. This thoughtfully designed equestrian facility offers 16 matted stalls, a spacious indoor riding arena, and an elevated viewing area with a kitchen-perfect for hosting clinics, lessons, or simply watching rides in comfort. The barn also includes

  Heather Crabtree Coldwell Banker Realty

  4 Judge Rd, Roxbury, CT 06783
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  /21

  $355,000

  • 2 Beds
  • 2 Baths
  • 2,118 Sq Ft

  8 Tamarack Ln Unit 8, Woodbury, CT 06798

  Low Taxes & Low HOA . Unique opportunity! This spacious end-unit condo offers 2118 ft of comfort, style, and a peaceful setting. Inside, the updated kitchen shines, complimented by gleaming hardwood floors upstairs and newer laminate flooring on the lower level. The end-unit location provides a serene view of the trees, giving the home a tranquil backdrop. Enjoy the outdoors from your deck ( with

  Jennifer Mayo William Raveis Real Estate

  8 Tamarack Ln Unit 8, Woodbury, CT 06798
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  /40

  $790,000

  • 5 Beds
  • 3.5 Baths
  • 2,870 Sq Ft

  50 Beardsley Rd, New Milford, CT 06776

  This spacious 5 bedroom, 3.5 bath colonial sits on a private interior lot of nearly 5 acres in the Sun Pond Woods development. The kitchen with its quartz counter tops, double oven, island and pantry make for great entertaining as it opens up to the large family room with fireplace. Also off of the kitchen is the sun room which has ac/electric heat and leads to the deck and the gas grill.

  Jim Stewart W. Raveis Lifestyles Realty

  50 Beardsley Rd, New Milford, CT 06776
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  /39

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  336 South St, Roxbury, CT 06783

  Quintessential Roxbury retreat, an updated classic 4-bedroom Colonial with open floor plan and separate office, nestled on over 4.5 picturesque park-like acres. This property offers the perfect blend of tranquil country living with the convenience of a great commuting location, just 90 minutes to NYC. Step inside to discover a home that has been freshly painted both inside and out, exuding a

  Kathryn Clair William Pitt Sotheby's Int'l

  336 South St, Roxbury, CT 06783
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  /34

  $739,000

  • 4 Beds
  • 3 Baths
  • 2,682 Sq Ft

  55 Mallory Rd, Roxbury, CT 06783

  If privacy in the Litchfield Hills is your aspiration, this is the residence for you! Pass through the gated entrance to this rustic Country Cape with covered front porch set back 500 feet off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owner constructed this quality built home with lasting craftsmanship. To say it has

  Gina Jacobs Gina Jacobs Real Estate

  55 Mallory Rd, Roxbury, CT 06783
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  /40

  $570,000

  • 6 Beds
  • 3 Baths
  • 4,487 Sq Ft

  5 Old Grassy Hill Rd, Woodbury, CT 06798

  Welcome to a rare find in scenic Woodbury, CT! A spacious and adaptable 6-bedroom, 3 full bathroom home perfectly suited for multigenerational living. Nestled on over 2 private, park-like acres with a peaceful pond, this property offers a unique combination of comfort, functionality, and natural beauty. Thoughtfully designed for flexible living, the home features separate living quarters,

  Shawna Mucherino Coldwell Banker Realty

  5 Old Grassy Hill Rd, Woodbury, CT 06798
• 

  

  /10

  $450,000

  • Land
  • 8.21 Acres
  • $54,811 per Acre

  31 Holmes Rd, Roxbury, CT 06783

  Peaceful 8.2-acre parcel located on a scenic, quiet road in Roxbury. Enveloped by mature hardwood forest with pockets of dappled sunlight and native fern understory, this magical setting offers both beauty and privacy. Set near the tri-town border of Roxbury, Washington, and Woodbury, the location offers easy access to all the amenities and charm of each town, including farmers markets, hiking

  Kathryn Bassett William Pitt Sotheby's Int'l

  31 Holmes Rd, Roxbury, CT 06783
• 

  

  /40

  $5,995,000

  • 5 Beds
  • 5.5 Baths
  • 6,884 Sq Ft

  84 Roxbury Rd, Washington, CT 06793

  Iconic and authentic, Shagbark Farm in central Washington represents the quintessential Connecticut country escape. Set on 3 separate parcels totaling over 85 acres and sited down a long private driveway this is the property of dreams. Classic white renovated 1930's colonial with 5 bedrooms, 5.5 bathrooms and incredible entertaining spaces inside and out. Oversized eat in gourmet kitchen with

  Pels Matthews W. Raveis Lifestyles Realty

  84 Roxbury Rd, Washington, CT 06793
• 

  

  /31

  $950,000

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  50 Southbury Rd, Roxbury, CT 06783

  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

  50 Southbury Rd, Roxbury, CT 06783

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