25

Roxbury, CT Homes for Sale

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  • /22

    $2,099,000

    • 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
  • /21

    $1,699,000

    • 2 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, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch. Dine or relax on the flagstone terrace next to the heated gunite pool. Mature gardens with

    Peter Klemm Klemm Real Estate Inc

    247 Painter Hill Rd, Roxbury, CT 06783
  • /34

    $1,699,000

    • 4 Beds
    • 3.5 Baths
    • 2,437 Sq Ft

    253 Tophet Rd, Roxbury, CT 06783

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

    Peter Klemm Klemm Real Estate Inc

    253 Tophet Rd, Roxbury, CT 06783
  • /39

    $2,500,000

    • 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
  • /40

    $1,899,000

    • 3 Beds
    • 3.5 Baths
    • 3,450 Sq Ft

    44 South St, Roxbury, CT 06783

    Set on South Street 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

    Lenore Mallett William Pitt Sotheby's Int'l

    44 South St, Roxbury, CT 06783
  • /26

    $1,784,000

    • 5 Beds
    • 3.5 Baths
    • 3,220 Sq Ft

    2 Pickett Rd, Roxbury, CT 06783

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

    Michael Lissack The Virtual Realty Group

    2 Pickett Rd, Roxbury, CT 06783
  • /33

    $2,245,000

    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    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
  • /40

    $2,650,000

    • 4 Beds
    • 3.5 Baths
    • 4,528 Sq Ft

    116 Squire Rd, Roxbury, CT 06783

    Utterly Private Country Estate. Expansive 4+ bedroom meticulously maintained, classically-designed house set high up a long tree-lined driveway w/distant southern & western/sunset views on 24+ secluded acres of verdant lawn, beautiful perennial gardens, ancient trees and a serene pond. Grand room dimensions, high ceilings, solid wide-board pine floors & windows designed to maximize the stunning

    Carolyn Klemm Klemm Real Estate Inc

    116 Squire Rd, Roxbury, CT 06783
  • /29

    $2,995,000

    • 3 Beds
    • 3.5 Baths
    • 3,384 Sq Ft

    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
  • /11

    $399,000

    • Land
    • 4.03 Acres
    • $99,032 per Acre

    Lot 3 Chalybes Rd, Roxbury, CT 06783

    Discover Your 4 acre Dream Homesite in Prime Roxbury Location. Nestled off a picturesque classic country lane, flanked by distinguished residences and just minutes from the vibrant heart of Roxbury Center, awaits an exceptional opportunity. This approved building parcel is primed for complete development, offering a level to gently sloping terrain within a private and serene setting. Imagine

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 3 Chalybes Rd, Roxbury, CT 06783
  • /11

    $599,000

    • Land
    • 16 Acres
    • $37,438 per Acre

    Lot 4 Chalybes Rd W, Roxbury, CT 06783

    Prime Roxbury Location. Nestled off a picturesque classic country lane, flanked by distinguished residences and just minutes from the vibrant heart of Roxbury Center, awaits an exceptional opportunity. This approved building parcel is primed for complete development, offering a level to gently sloping terrain within a private and serene setting. Imagine crafting your ideal retreat amidst the

    Kathryn Clair William Pitt Sotheby's Int'l

    Lot 4 Chalybes Rd W, Roxbury, CT 06783
  • /24

    $1,599,000

    • 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
  • /31

    $1,195,000

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    18 Tunnel Rd, Roxbury, CT 06783

    MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open

    Peter Klemm Klemm Real Estate Inc

    18 Tunnel Rd, Roxbury, CT 06783
  • /25

    $1,149,000

    • 4 Beds
    • 3 Baths
    • 1,782 Sq Ft

    23 Painter Hill Rd, Roxbury, CT 06783

    Mint / Move-in Condition! Pristine hilltop home with views on 3 +/- acres. Gorgeous, chic, mint renovation. Open floor plan kitchen/family room with wood-burning fireplace and French doors to a private flagstone patio. Bright and airy living room and dining room. Primary bedroom with vaulted ceilings, balcony and large ensuite renovated bath. Three more bedrooms, 1 full and 1 half bath. Only a

    Peter Klemm Klemm Real Estate Inc

    23 Painter Hill Rd, Roxbury, CT 06783
  • /30

    $1,295,000

    • 4 Beds
    • 3 Baths
    • 2,982 Sq Ft

    11 Hodge Rd, Roxbury, CT 06783

    This Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100's of acres of the Roxbury Land trust and enjoys valley views of the Shepaug River. Over time it became a really charming home in a very private and pretty setting

    Karen Casey William Pitt Sotheby's Int'l

    11 Hodge Rd, Roxbury, CT 06783
  • /38

    $1,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,167 Sq Ft

    55 Garnet Rd, Roxbury, CT 06783

    Welcome Home to this beautiful Estate in the charming Land of Roxbury!! Sprawling kitchen with high end appliances (Wolfe, Sub Zero) cabinets and countertops inluding wine bar with separate sink. Plenty of space for all your family holidays and well planned cocktail parties. This home has two Primary suites. Excellent for weekend guests and possible in laws. Custom built in 2017. 9 Ft ceilings.

    Joe Chemero Coldwell Banker Realty

    55 Garnet Rd, Roxbury, CT 06783
  • /12

    $999,000

    • Land
    • 20 Acres
    • $49,627 per Acre

    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783

    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

    Ryan Bollard William Pitt Sotheby's Int'l

    Lot 7 & Lot 8 Willow Brook Dr, Roxbury, CT 06783
  • /22

    $479,000

    • Land
    • 7 Acres
    • $70,545 per Acre

    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

    Jill Sloane Brown Harris Stevens

    238 North St, Roxbury, CT 06783
  • /6

    $245,000

    • Land
    • 3.00 Acres
    • $81,667 per Acre

    307 North St, Roxbury, CT 06783

    Peaceful wooded lot to build your weekend or forever home! Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Close to Washington and Roxbury centers makes this the perfect place to call home.90 minutes to NYC

    Sindy Butkus Klemm Real Estate Inc

    307 North St, Roxbury, CT 06783
  • /38

    $1,280,000 Open Sun 11AM - 1PM

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

    67 Transylvania Rd, Roxbury, CT 06783

    This much-admired residence is privately located on a quiet country road, with 3-plus acres of lawn and light woods lined by old stone walls. The flat, sweeping driveway curves past the house to the 3-car attached garage and circular driveway. The welcoming open foyer steps down to a living area with cathedral ceilings, Palladian window, gas fireplace, and wet bar, flowing into the dining area

    Cathy Masi Flagpole Realty Inc

    67 Transylvania Rd, Roxbury, CT 06783
  • /10

    $1,275,000

    • Land
    • 13 Acres
    • $100,078 per Acre

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! This exceptional 12.7-acre property boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. 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

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • /36

    $4,750,000

    • 4 Beds
    • 5.5 Baths
    • 7,063 Sq Ft

    11 Ravenrock, Roxbury, CT 06783

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

    Maria Taylor Klemm Real Estate Inc

    11 Ravenrock, Roxbury, CT 06783
  • /20

    $495,000

    • Land
    • 9 Acres
    • $57,292 per Acre

    200 North St, Roxbury, CT 06783

    THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE CHERISHED. This 8.64 acre lot features

    Jill Sloane Brown Harris Stevens

    200 North St, Roxbury, CT 06783
  • /40

    $775,000

    • 6 Beds
    • 5 Baths
    • 4,260 Sq Ft

    118 Chalybes Rd W, Roxbury, CT 06783

    Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide plank flooring bring warmth and style. This tranquil home embodies classic Connecticut living with its antique patina

    Catherine Aaron Berkshire Hathaway NE Prop.

    118 Chalybes Rd W, Roxbury, CT 06783
  • /21

    $464,000

    • Land
    • 25 Acres
    • $18,553 per Acre

    0 Wellers Bridge Rd, Roxbury, CT 06783

    Approved building lot with a completed survey and site plans, including wetland delineation and a forthcoming report. This 25.01-acre wooded oasis in Roxbury, located just half a mile from scenic Route 67, offers a tranquil and private retreat in the heart of historic Roxbury. With 250 feet of road frontage on Wellers Bridge Rd, this property is a prime opportunity for those looking to build a

    David Hughes Century 21 AllPoints Realty

    0 Wellers Bridge Rd, Roxbury, CT 06783

About Roxbury

Just a few miles east of Bridgeport, in western Connecticut's Litchfield Hills, sits the town of Roxbury, a rural area spread over 27 square miles with a population just over 2,000. That low population density means that residents here can appear somewhat isolated from the creature comforts associated with urban living, but that’s exactly how they like it. “People move to Roxbury because it’s quiet,” says local Realtor Stephanie Blake of Realty ONE Group Connect. “The rural nature of the town is its real appeal. At the same time, though, it’s c ...

Frequently Asked Questions

What is the average home price in Roxbury, CT?
Homes for sale in Roxbury, CT have an average home price of $1,644,588.
How many homes have sold over the last 12 months in Roxbury, CT?
44 homes have sold in Roxbury, CT over the last 12 months.
What are the most popular zip codes in Roxbury, CT?
The most popular zip codes in Roxbury, CT include 06488, 06484, 06776, 06810 and 06511.
How much do you need to make to afford a house in Roxbury?
The median home price in Roxbury is $1,337,000. If you put a 20% down payment of $267,400 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $6,990 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $300K a year to afford the median home price in Roxbury.
How are the schools in Roxbury, CT?
Roxbury, CT has highly rated public and private schools. Some of the best schools in Roxbury based on Niche Grades are Booth Free School, Pomperaug Regional High School and Shepaug Valley School. Browse all the schools in Roxbury, CT to learn more.

Home Trends in Roxbury, CT

Home Trends

Median Price (12 Mo)
$1,117,500
Median Single Family Price
$1,275,000
Average Price Per Sq Ft
$486
Number of Homes for Sale
16
Last 12 months Home Sales
44
Months of Supply
4.40
Median List Price
$1,337,000
Median Discount From 1st List Price
11%
Median Home Sale Price YoY Change
-11%
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