Roxbury, CT Homes for Sale

/38
$785,000

$65K PRICE DROP
- 3 Beds
- 2 Baths
- 2,489 Sq Ft
47 South St, Roxbury, CT 06783

Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your

Michelle Alvord

Berkshire Hathaway NE Prop.

47 South St, Roxbury, CT 06783
Explore Roxbury
/40
$998,000
- 4 Beds
- 2.5 Baths
- 2,556 Sq Ft
336 South St, Roxbury, CT 06783

Set on a picturesque, park-like property in desirable southern Roxbury, this beautiful 4-bedroom, 2.5-bath Colonial blends timeless charm, thoughtful updates, and inviting indoor-outdoor living. A dramatic two-story foyer opens to a formal dining room, spacious living room with custom built-in bookshelves, and impressive family room with a floor-to-ceiling fireplace and custom built-ins. The

Karen Gilmore Redfin Corporation

336 South St, Roxbury, CT 06783
/39
$1,799,000

New Construction
- 5 Beds
- 4.5 Baths
- 3,326 Sq Ft
2 Pickett Rd, Roxbury, CT 06783

Presenting a truly rare opportunity for BRAND NEW CONSTRUCTION in Roxbury, CT, this luxury residence offers approximately 3,300+ SF of meticulously designed living space, including a spacious finished basement & attached double garage. Enjoy exquisite finishes throughout, highlighted by 6" white oak hardwood flooring, custom architectural millwork and decorative shiplap details. The gourmet

Alan O'Doherty William Pitt Sotheby's Int'l

2 Pickett Rd, Roxbury, CT 06783
/18
$749,000
- Land
- 15.73 Acres
- $47,616 per Acre
43 Baker Rd, Roxbury, CT 06783

Stunning 15 acre parcel with many fresh improvements. New Steal bridge over rushing brook with waterfalls leads to brand new winding driveway to high, flat and cleared building site. Extensive stone walls. Fully engineered and ready to go! Septic quote is $15,000. Conduit quote to site is $14,700. do not enter property without an appt. Driveway is still being completed and we need to give notice.

Stacey Matthews W. Raveis Lifestyles Realty

43 Baker Rd, Roxbury, CT 06783
/37
$2,900,000

$300K PRICE DROP
- 3 Beds
- 2 Baths
- 1,974 Sq Ft
124 Botsford Hill Rd, Roxbury, CT 06783

Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage,

Pat Lahoud William Pitt Sotheby's Int'l

124 Botsford Hill Rd, Roxbury, CT 06783
/40
$2,750,000

$145K PRICE DROP
- 4 Beds
- 4.5 Baths
- 4,570 Sq Ft
220 Painter Hill Rd, Roxbury, CT 06783

Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece,

Stacey Matthews W. Raveis Lifestyles Realty

220 Painter Hill Rd, Roxbury, CT 06783
/38
$925,000

$230K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,340 Sq Ft
24 Hickory Ln, Roxbury, CT 06783

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and

Pat Lahoud William Pitt Sotheby's Int'l

24 Hickory Ln, Roxbury, CT 06783
/20
$499,000
- Land
- 8.64 Acres
- $57,755 per Acre
200 North St, Roxbury, CT 06783

ENGINEERING and DRIVEWAY APPROVED! 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

Jill Sloane Brown Harris Stevens

200 North St, Roxbury, CT 06783
/39
$3,600,000
- 5 Beds
- 4.5 Baths
- 6,190 Sq Ft
268 South St, Roxbury, CT 06783

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite

Peter Klemm Klemm Real Estate Inc

268 South St, Roxbury, CT 06783
/38
$3,950,000

$545K PRICE DROP
- 4 Beds
- 7 Baths
- 6,139 Sq Ft
297 Painter Hill Rd, Roxbury, CT 06783

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room.

Peter Klemm Klemm Real Estate Inc

297 Painter Hill Rd, Roxbury, CT 06783
/6
$485,000
- Land
- 10 Acres
- $48,500 per Acre
Lot 8 Willow Brook Dr, Roxbury, CT 06783

Welcome to Lot 8 Willow Brook Drive! If your dream has been to build your custom home on a picturesque canvas of classic New England countryside, this property is ready to bring your vision to life. Offering 10 sprawling acres of peaceful, former cattle pasture, Lot 8 provides a gentle, easy-to-build landscape framed by open meadows and surrounding natural woodland. The lot benefits from lovely

Ryan Bollard William Pitt Sotheby's Int'l

Lot 8 Willow Brook Dr, Roxbury, CT 06783
/10
$399,000
- Land
- 4.01 Acres
- $99,501 per Acre
Lot 1 Chalybes Rd W, Roxbury, CT 06783

Private, Rural setting within a short walk to Roxbury Tennis courts, library and the Roxbury Market.This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best

Kathryn Clair William Pitt Sotheby's Int'l

Lot 1 Chalybes Rd W, Roxbury, CT 06783
/29
$950,000
- 5 Beds
- 3 Baths
- 1,959 Sq Ft
50 Southbury Rd, Roxbury, CT 06783

* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also

Jeff Phillips William Pitt Sotheby's Int'l

50 Southbury Rd, Roxbury, CT 06783
/9
$1,200,000

New Construction
- 4 Beds
- 3.5 Baths
- 3,800 Sq Ft
11 Evergreen Dr, Roxbury, CT 06783

This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. There will be 9' ceiling height on the main level and 8' on the upper level. Both levels will have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The

Sharon McGuire William Pitt Sotheby's Int'l

11 Evergreen Dr, Roxbury, CT 06783
/39
$1,295,000
- 4 Beds
- 2.5 Baths
- 2,901 Sq Ft
77 Judds Bridge Rd, Roxbury, CT 06783

A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry

Joseph Lorino Klemm Real Estate Inc

77 Judds Bridge Rd, Roxbury, CT 06783
/25
$969,000

$126K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,782 Sq Ft
23 Painter Hill Rd, Roxbury, CT 06783

Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

Peter Klemm Klemm Real Estate Inc

23 Painter Hill Rd, Roxbury, CT 06783
/13
$490,000

$59K PRICE DROP
- Land
- 24.84 Acres
- $19,726 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
/40
$1,195,000

$40K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,476 Sq Ft
22 E Woods Rd, Roxbury, CT 06783

*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light

Andy Sachs Compass Connecticut, LLC

22 E Woods Rd, Roxbury, CT 06783
/40
$1,875,000

$600K PRICE DROP
- 4 Beds
- 4.5 Baths
- 4,874 Sq Ft
1030 Washington Woodbury Rd, Roxbury, CT 06783

NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong

Judith Auchincloss Klemm Real Estate Inc

1030 Washington Woodbury Rd, Roxbury, CT 06783
/12
$2,000,000
- Land
- 26.48 Acres
- $75,529 per Acre
55 Ranney Hill Rd, Roxbury, CT 06783

If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS!

Sharon McGuire William Pitt Sotheby's Int'l

55 Ranney Hill Rd, Roxbury, CT 06783
/27
$3,995,000
- 5 Beds
- 5.5 Baths
- 7,121 Sq Ft
47 Squire Rd, Roxbury, CT 06783

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms

Maria Taylor Klemm Real Estate Inc

47 Squire Rd, Roxbury, CT 06783
/40
$1,495,000

$105K PRICE DROP
- 4 Beds
- 4.5 Baths
- 4,452 Sq Ft
380 Southbury Rd, Roxbury, CT 06783

Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

ROSEANN BLANTON Berkshire Hathaway NE Prop.

380 Southbury Rd, Roxbury, CT 06783
/20
$1,269,000

$31K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,440 Sq Ft
85 Good Hill Rd, Roxbury, CT 06783

Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and

Jason Saphire www.HomeZu.com

85 Good Hill Rd, Roxbury, CT 06783
/29
$969,000

$130K PRICE DROP
- 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 Spa 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
/36
$2,995,000
- 4 Beds
- 5.5 Baths
- 7,063 Sq Ft
11 Ravenrock, Roxbury, CT 06783

Thoughtfully designer-refreshed, the property is looking especially beautiful and polished, with fresh paint throughout, a new cedar roof over the guest house, and the main residence's cedar roof freshly washed and oiled, bringing out its natural beauty. The grounds have also been freshly manicured, enhancing the estate's exceptional setting. A private gated road leads to this elegant

Maria Taylor Klemm Real Estate Inc

11 Ravenrock, Roxbury, CT 06783
/29
$585,000

$5K PRICE DROP
- 3 Beds
- 3 Baths
- 1,248 Sq Ft
21 Carriage Ln, Roxbury, CT 06783

A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is primed for

Frank Durante William Raveis Real Estate

21 Carriage Ln, Roxbury, CT 06783
/40
$3,495,000
- 4 Beds
- 4.5 Baths
- 4,456 Sq Ft
35 Schoolhouse Rd, Roxbury, CT 06783

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room

Pels Matthews W. Raveis Lifestyles Realty

35 Schoolhouse Rd, Roxbury, CT 06783
/40
$998,000
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
16 Jonathan Dr, Roxbury, CT 06783

Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a

Ginny Gordon-O’Neill William Raveis Real Estate

16 Jonathan Dr, Roxbury, CT 06783
/27
$1,469,000

$180K PRICE DROP
- 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
/16
$775,000
- Land
- 26.68 Acres
- $29,048 per Acre
204 North St Unit Lot 3, Roxbury, CT 06783

1st Time LISTED! LOT 3 at 204 North Street has ENGINEERING and DRIVEWAY APPROVED! 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 25 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently

Jill Sloane Brown Harris Stevens

204 North St Unit Lot 3, Roxbury, CT 06783
/35
$1,795,000
- 5 Beds
- 6 Baths
- 5,447 Sq Ft
233 Southbury Rd, Roxbury, CT 06783

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand

Kathryn Clair William Pitt Sotheby's Int'l

233 Southbury Rd, Roxbury, CT 06783
/30
$544,900

$55K PRICE DROP
- 4 Beds
- 2 Baths
- 2,120 Sq Ft
325 New Milford Rd E, Bridgewater, CT 06752

Move right into this bright and well-maintained 4-bedroom, 2-bath split-level home set on a private, wooded 3-acre lot in desirable Bridgewater with low taxes. Recent updates include all new windows (2022), new gutters (2023), freshly painted kitchen cabinet doors (2026), and freshly painted bathrooms. The main level offers an open floor plan with hardwood floors, a spacious kitchen, and a

Doug Collins Coldwell Banker Realty

325 New Milford Rd E, Bridgewater, CT 06752
/8
$395,000
- Land
- 2.53 Acres
- $156,126 per Acre
133 Painter Hill Rd, Woodbury, CT 06798

Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic

Judith Auchincloss Klemm Real Estate Inc

133 Painter Hill Rd, Woodbury, CT 06798

Connecticut Litchfield County

Why Live in Roxbury

Roxbury, CT, located in the Litchfield Hills just east of Bridgeport, offers a rural lifestyle with nearby urban amenities. Spanning 27 square miles with a population of over 2,000, Roxbury is known for its quiet, undeveloped landscape. Residents enjoy outdoor attractions like Hurlburt Park, which hosts the annual Roxbury Pickin’ and Fiddlin’ Contest, and River Road Preserve, ideal for hiking and fly-fishing. History enthusiasts can explore Mine Hill Preserve, featuring remnants of a 19th-century iron-making complex and extensive hiking trails. Adjacent to Mine Hill is the Kelsey Museum and Sculpture Garden, showcasing works by Sterett-Gittings Kelsey, and the Mine Hill Distillery, where visitors can sample locally distilled spirits. Homes in Roxbury range from raised ranch-style houses to historic Colonial homes, often situated on large lots with mature trees. The town is served by Regional School District Number 12, with highly rated Booth Free School and Shepaug Valley School, along with the nearby Kent School. While Roxbury lacks extensive commercial activity, residents can visit the Roxbury Market & Deli for groceries and meals, or travel 20 miles to Waterbury for more shopping options. For a broader shopping experience, New York City is accessible by train from Danbury, less than 20 miles south.

Learn more about living in Roxbury

Roxbury, CT Home Prices

	Roxbury, CT
Median Home Price	$1,297,500
Median Sale Price	$1,195,000 -9% YoY
Avg. Price per Square Foot	$484
Median Single Family Price	$1,282,000
Median Townhouse Price	$1,412,500
Total Active Listings	33 listings
Market Conditions	9 Months of Supply Buyer's Market

Frequently Asked Questions

What is the average home price in Roxbury, CT?

Homes for sale in Roxbury, CT have an average home price of $1,721,687.

Are home prices dropping in Roxbury?

Yes, home prices in Roxbury are down 7% in the last 12 months.

How many homes have sold over the last 12 months in Roxbury, CT?

31 homes have sold in Roxbury, CT over the last 12 months.

What is the average household income in Roxbury, CT?

The average household income in Roxbury, CT is $147K.

What are the most popular zip codes in Roxbury, CT?

The most popular zip codes in Roxbury, CT include 06783, 06752, 06798, 06776 and 06793.

How much do you need to make to afford a house in Roxbury?

The median home price in Roxbury is $1,297,500. If you put a 20% down payment of $259,500 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $6,930 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $297K a year to afford the median home price in Roxbury. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Roxbury is $147K.

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 The Frederick Gunn School, Booth Free School and Pomperaug Regional High School. Browse all the schools in Roxbury, CT to learn more.

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