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$1,225,000

This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

4 Beds ⋅ 4 Baths ⋅ 24130861 MLS

This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

68 Whittlesey Rd, Woodbury

$975,000

Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options for multigenerational living or working from home. The heart of the home is a generously sized kitchen with a sunny eat-in area, center sitting island, and easy access to a formal dining room-ideal for hosting gatherings and family meals.The open floor plan flows effortlessly into the vaulted living room with fireplace, creating a warm, inviting space perfect for everyday living. A large laundry room and attached garage add to the home's convenience. Upstairs, you'll find additional bedrooms, a dedicated home office, and a playroom-providing space for everyone to work, relax, and play.Step outside to your own private resort-style retreat, complete with a sparkling in-ground pool, fully equipped outdoor kitchen, and lower-level pool dressing area. Whether you're entertaining or simply unwinding, the outdoor space is a true showstopper.Enjoy year-round comfort with high-efficiency baseboard heating and central air conditioning. Finished with beautiful moldings, hardwood floors throughout, and set in a serene nature-filled setting just minutes to town-this home truly has it all.

5 Beds ⋅ 3 Baths ⋅ 24115189 MLS

Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options for multigenerational living or working from home. The heart of the home is a generously sized kitchen with a sunny eat-in area, center sitting island, and easy access to a formal dining room-ideal for hosting gatherings and family meals.The open floor plan flows effortlessly into the vaulted living room with fireplace, creating a warm, inviting space perfect for everyday living. A large laundry room and attached garage add to the home's convenience. Upstairs, you'll find additional bedrooms, a dedicated home office, and a playroom-providing space for everyone to work, relax, and play.Step outside to your own private resort-style retreat, complete with a sparkling in-ground pool, fully equipped outdoor kitchen, and lower-level pool dressing area. Whether you're entertaining or simply unwinding, the outdoor space is a true showstopper.Enjoy year-round comfort with high-efficiency baseboard heating and central air conditioning. Finished with beautiful moldings, hardwood floors throughout, and set in a serene nature-filled setting just minutes to town-this home truly has it all.

364 Hoop Pole Hill Rd, Woodbury

$959,000

Privacy and space galore at this renovated Colonial, which is ready for its next residents. 4 bedrooms and 3 1/2 baths, PLUS 2 additional rooms on the 3rd floor, offering office/rec/studio space, or additional bedroom space. NEW bathrooms. NEW carpet. NEW interior paint. Refinished oak floors. Refreshed kitchen. Exterior has been power washed, and the garage doors have been refurbished. Huge basement for storage. Beautiful yard in which to enjoy each season. Bask in the quiet life that beautiful Roxbury offers, with the convenience of shopping and dining in nearby Southbury, New Milford, and Woodbury.

4 Beds ⋅ 4 Baths ⋅ 24163402 MLS

Privacy and space galore at this renovated Colonial, which is ready for its next residents. 4 bedrooms and 3 1/2 baths, PLUS 2 additional rooms on the 3rd floor, offering office/rec/studio space, or additional bedroom space. NEW bathrooms. NEW carpet. NEW interior paint. Refinished oak floors. Refreshed kitchen. Exterior has been power washed, and the garage doors have been refurbished. Huge basement for storage. Beautiful yard in which to enjoy each season. Bask in the quiet life that beautiful Roxbury offers, with the convenience of shopping and dining in nearby Southbury, New Milford, and Woodbury.

34 Bacon Rd, Roxbury

$817,000

Large parcel of raw land offering a unique opportunity. This 66 acre parcel fronts two well connected roads, ensuring ease of access and flexibility in planning. With some clearing it offers easterly views of the rolling landscape and morning sunrises, making the parcel perfect for a large estate or residential compound. Roxbury is in southern Litchfield County with a population of less than 3,000 people, it is the epitome of a small New England town. Only 65 miles to New York City, this land's unique features and untapped potential await your vision.

24103219 MLS

Large parcel of raw land offering a unique opportunity. This 66 acre parcel fronts two well connected roads, ensuring ease of access and flexibility in planning. With some clearing it offers easterly views of the rolling landscape and morning sunrises, making the parcel perfect for a large estate or residential compound. Roxbury is in southern Litchfield County with a population of less than 3,000 people, it is the epitome of a small New England town. Only 65 miles to New York City, this land's unique features and untapped potential await your vision.

Good Hill Road, Roxbury

$750,000

Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

4 Beds ⋅ 3 Baths ⋅ 24132227 MLS

Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

118 Good Hill Rd, Woodbury

$710,000

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

3 Beds ⋅ 4 Baths ⋅ 24155513 MLS

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

58 Good Hill Rd, Woodbury

$580,000

Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to the 14x8 rear deck, ideal for outdoor entertaining or relaxing while enjoying the peaceful surroundings. The kitchen includes an island, LVP flooring and ample workspace. Hardwood floors throughout most of the home. Additional highlights include a newer propane heating system with on demand hot water, full basement with interior and garage access, Generator-ready wired for peace of mind and 2 car under house garage with auto door openers. Outside you'll find a 10x10 storage shed and recently paved driveway. Just minutes from Woodbury's vibrant Main Street is easy access to enjoy shopping, dining, the library, post office, parks and scenic land preserves for outdoor activities. Whether you're seeking full-time residence or a weekend getaway, this property offers a great opportunity in one of Connecticut's picturesque communities and "Antique Capitol". Ideally situated roughly 80 miles from NYC approximately 140 miles from Boston.

4 Beds ⋅ 2 Baths ⋅ 24179676 MLS

Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to the 14x8 rear deck, ideal for outdoor entertaining or relaxing while enjoying the peaceful surroundings. The kitchen includes an island, LVP flooring and ample workspace. Hardwood floors throughout most of the home. Additional highlights include a newer propane heating system with on demand hot water, full basement with interior and garage access, Generator-ready wired for peace of mind and 2 car under house garage with auto door openers. Outside you'll find a 10x10 storage shed and recently paved driveway. Just minutes from Woodbury's vibrant Main Street is easy access to enjoy shopping, dining, the library, post office, parks and scenic land preserves for outdoor activities. Whether you're seeking full-time residence or a weekend getaway, this property offers a great opportunity in one of Connecticut's picturesque communities and "Antique Capitol". Ideally situated roughly 80 miles from NYC approximately 140 miles from Boston.

338 Good Hill Rd, Woodbury

$450,000

Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields offer easy building sites and 360 views of nature. If seclusion in the forest is more up your alley, this plentiful land will accommodate for that too. Let your imagination run wild. These approved building lots are ready to develop! Multiple flat & cleared building sites. Underground power and utilities, running up Willow Brook Dr. Feasibility map available upon request with original percolation/soil data.

24168082 MLS

Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields offer easy building sites and 360 views of nature. If seclusion in the forest is more up your alley, this plentiful land will accommodate for that too. Let your imagination run wild. These approved building lots are ready to develop! Multiple flat & cleared building sites. Underground power and utilities, running up Willow Brook Dr. Feasibility map available upon request with original percolation/soil data.

Lot 7 & Lot 8 & Dr, Roxbury