The Matthews Team

William Raveis Lifestyles Realty

Woodbury CT Real Estate

Located approximately 85 miles north of New York City and referred to as Connecticut’s “Antique Capital” is Woodbury. Woodbury Woodbury Connecticut has become a very popular spot for food, giving it the nickname “Foodberry”, as many great restaurants have recently opened or renovated their spaces. One of Litchfield County’s larger communities by population due to its easily commutable distance from the cities of Waterbury and Danbury, Woodbury has managed to retain its classic New England charm, with gorgeous sweeping landscapes, well restored Colonial, Greek Revival, and Victorian homes and simple cultural appeal.Curtis House in Woodbury

Properties in Woodbury

Contact the William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

Time Saving Tip: Sign up for a free account to save your favorite listings and get notified when new properties match your criteria.

Search by Property Type: Luxury Homes | Homes with LandSingle Family HomesCondos | Land

25 & 39 Quanopaug Trail Woodbury CT 06798

Woodbury, CT25 & 39 Quanopaug Trail

Price$2,495,000

Est. Mortgage: $/month

MLS Number 170495307

  • Single Family
  • Bedrooms 6
  • Bathroom 6
  • Square Feet 7,413
  • Acreage 8.94

This immaculate estate marries luxury with sustainability in a private oasis. Set atop nearly 9 acres of woods and open land, this meticulously renovated 6 bedroom 4.5 bathroom house is an absolute must see. The main floor features vaulted ceilings with exposed beams and an open floor plan that fills the rooms with natural light. The residence's many large windows provide gorgeous views of the expansive property, which includes a heated in-ground pool and a stone-lined swimming pond. A huge stone fireplace accents the living room while the loft area upstairs features gorgeous hardwood floors. The multi-purpose room above the garage has incredible 22-ft ceilings and a wall of windows to take in the scenery plus an indoor Trampoline! A newly refinished basement with two additional rooms is perfect for guests and boasts a fantastic Game Room.. Recent renovations include full house solar power, geothermal heating and cooling, two Tesla Power house batteries, and a totally revamped pool area, and outdoor trails. The energy efficient design of this home includes Greenblock Insulated Concrete Forms which provide protection from extreme weather conditions and are 70% more efficient to heat than a traditionally framed house! This is a sustainable dream home that is as eco-friendly as it is incredible. Set against a backdrop of the forests, rolling hills, and perfect sunsets, this is a house you'll immediately want to make your permanent home. Come take a look!

Listed by Dave Fairty of The Bella Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

168 Upper Grassy Hill Road Woodbury CT 06798

MLS Number 170480181

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,354
  • Acreage 7.08

Fly in for the weekend! Gorgeous cape home abutting a local AIRSTRIP offering the possibility of flying home with the appropriate permission. Recently built with security in mind, you will love this pristine cape with all the measures taken for security and living off the grid. Nestled up against the Roxbury/Woodbury line this home abuts the old Roxbury airport, a 38x60 clear-span heated barn for all your toys, and is an incredibly efficient home with state-of-the-art heating, electrical, and engineering. Some of these mechanical upgrades include a 45 KW diesel generator plumbed to the oil tank, a solar array that makes more power than the property can use including heating and AC, electric gates with automatic watering systems on the walls and plantings, a casino grade security camera system, a 400 amp split service to operate the generator and solar in synchrony, and extensive underground and outdoor lighting to light up every inch of the 7 plus acres. Let's not forget the house, which has a welcoming open floor plan with lots of light, a gorgeous kitchen/great room with a cathedral ceiling, the main level master bedroom, and plenty of room for expansion. Built to last this contemporary cape provides all foam insulation, a 60-year roof, copper gutters, cedar shake siding with azek trim, and garage space for 16 or more vehicles. There is plenty of outdoor space including a ground-level deck with retractable awning, and a glass solarium with electricity and cable.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

87 Coach Light Drive Woodbury CT 06798

MLS Number 170493340

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,904
  • Acreage 4.63

Come home to the privacy of this exquisitely detailed country home on 4.63 acres in pristine move in condition with an in-ground pool and pool house completing the amenity package. The home features 10 rooms, 4 bedrooms, 4 full and 2 half baths. The Main Floor offers a state-of-the-art kitchen with dining area, walk-in pantry, stainless appliances, double oven, refrigerator, dishwasher gas cooktop stove, granite counters and 8-foot center island. The kitchen opens to a large family room with fireplace, detailed built-ins, sunroom with mahogany flooring, with direct access to a mahogany deck, pool, pool patio and pool house. Formal dining room, living room and laundry room are also featured. The upper level offers the primary bedroom suite with fireplace, luxurious full bath, whirlpool tub, walk-in shower and two walk-in closets with dressing area. Two-bedroom suites each with full bathroom accommodation. French doors lead to a large sitting room designed for relaxation and comfort accessible from each bedroom suite. An additional bedroom with access to a full hall bath is also available, all can be directly accessed by private entrance.

Listed by Todd P Sargent and Joe Chemero of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

43 Old Meadow Road Woodbury CT 06798

MLS Number 170496468

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,385
  • Acreage 1.97

This impeccably maintained reproduction farmhouse sits atop a quiet cul de sac in the historic town of Woodbury. As you drive down the quiet road, you are greeted by the home's friendly front porch, a place where you can sit and rock as you listen to the sounds of Radey Pond. The landscape has been embraced, with each area being utilized to its highest potential. The long stretch of level land has been left clear for an expanse of grass, while the sloped backyard has been carved out to create an oasis with the gunite pool, hot tub, and waterfall, all enclosed by a 10-foot cedar privacy fence. All plantings have been recently refreshed with minimal maintenance in mind, connecting the theme of simplistic living that sellers have accomplished within the home. The interior has a pleasing color palette of cream and gray, lending itself to a variety of furnishing tastes and styles. Features such as oak floors, crown molding, and eight over eight windows add a degree of intimacy to this spacious home. Whether you seek to house an au pair, grandparents, or friends, there are private areas to accommodate them all. The home's layout allows for everyone to be independent while remaining together with two complete kitchens and one kitchenette, three living rooms, and many other multi-functional areas. Inviting, well-designed, and spacious - 43 Old Meadow.

Listed by Michael Caporizzo of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

156 Weekeepeemee Road Woodbury CT 06798

Woodbury, CT156 Weekeepeemee Road

Price$1,199,000

Est. Mortgage: $/month

MLS Number 170470182

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,194
  • Acreage 2.66

This sunny 5-bedroom French country home was built by an architect for himself, and offers superior craftmanship, stunning millwork, secret doors, and an enormous gourmet kitchen. Enjoy gathering in the expansive kitchen area with multiple dishwashers, Subzero refrigerators, wine cooler, Wolf Industrial 6-burner stove with dual ovens, wall oven, warming drawer and microwave. The oversized island is filled with bookcases, baskets, and drawer storage. The beautiful eat-in kitchen has table seating for 8+. The dining room, family room, home office, library, and sunroom are full of architectural details making each one unique and inviting. This home features 9' ceilings, French doors, 4 fireplaces, wide chestnut board flooring and cozy nooks throughout. The outdoor hot tub is sheltered in small barn that sits off the master bedroom at the end of the oversized stone patio that runs the length of the house and is surrounded by stone walls and English gardens. The master bedroom suite is simple amazing with a foyer, 2 walk-in closets, floor to ceiling bookcases and fireplace, 6x8 shower, jacuzzi tub and a secret door to the private gym. Additional house amenities include attached 2-car garage, detached 1-car garage w/ firewood storage, whole-house generator, alarm system, 220 AMP electric, zoned air conditioning/hydro air heating systems. The additional movie room, art studio and kids' playroom make this an amazing home or weekend retreat for friends and family.

Listed by Kate K Willoughby of Gina Jacobs Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

181 Joshua Hill Road Woodbury CT 06798

Woodbury, CT181 Joshua Hill Road

Price$1,195,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170505517

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,726
  • Acreage 26.16

The historic homestead of Andrew Tuttle sits on 26 acres, just outside of the town center. The home has been lovingly preserved, restored and updated. Ca 1780, the house boasts it's original antique features including horizontal and vertical board paneling, wide board wood floors, exposed beams, doors, built-ins and hardware. There are 3 original fireplaces, one with a bee-hive oven. A Charming corner cupboard adorns both the formal dining room and family room. The charming living room is great for entertaining and includes built-in bookshelves and fireplace. The first level primary bedroom offers french doors onto a stone terrace and an updated full bath. There are three additional bedrooms with a walk in cedar closet for great storage and an office/music room on the second floor, along with an update bath on the upper level. Picturesque grounds include a rolling lush lawn, stone terrace, stone walls, mature perennial gardens, fruit trees, flowering bushes, grape vines. The Studio Barn has is ideal for an artist studio or woodworker with insulation and flooring added to the studio space or can easily be reconverted to the original space as a garage. The "Summer House" is a fabulous dining area or bunkhouse which sits out just past the gardens. The Property includes a parcel across the street. Conservation easement to maintain its history and beauty. All this just 90 minutes from NYC, minutes from great dining, shopping and hiking in Award Winning Historical Woodbury!

Listed by Kathryn Clair and Kathryn C Bassett of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

452 Middle Road Turnpike Woodbury CT 06798

Woodbury, CT452 Middle Road Turnpike

Price$1,100,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170497866

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,325
  • Acreage 11.27

Private story book stone and shingle home on over 11 acres. Eleven Rooms include two primary bedrooms on the main level. Spacious living room and family room overlook the park-like grounds. Cozy sitting room with fireplace has French door that leads to stone patio. Kitchen has been remodeled and includes stainless steel appliances. There are five fireplaces, oak pegged floors and oodles of charm. In ground heated pool, rolling lawn, specimen trees and early stone walls. Detached two bay garage/barn with finish space above and multiple sheds. Many updates and improvements include cedar shake roof, irrigation system, bathrooms, landscaping, pergola, pool heater, heated studio - to many improvements to list, call for complete list. 2 hours from NYC.

Listed by Maria Taylor and Claudine McHugh of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

27 Peter Road Woodbury CT 06798

Woodbury, CT27 Peter Road

Price$999,999

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170346864

  • Land
  • Acreage 46.4
  • Zoning OS100

Build your dream home here!!! Level building site. Most of the 46 acres is fenced. Barn with small apartment and two outbuildings. Come live in beautiful Litchfield County and enjoy the sunsets! Cows not included.

Listed by Sindy Butkus of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

575 Weekeepeemee Road Woodbury CT 06798

MLS Number 170433479

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 2,000
  • Acreage 87.5

Unique opportunity to own approximately 87 acres with Antique home in need of T L C and Barnes. There are four lots that make up the 87 acres . One lot in Bethlehem and Three in Woodbury. Lot 1- 7.00 acres Located in Bethlehem, Ct. Lot 2 - 7.22 acres. Lot 3 with house and barns is -11.59 Acres and Lot 4 with 61.76 acres. Sold all together will not divide. Property is currently a operating horse boarding facility. Main Barn with a 60 x 120 indoor riding ring plus 20 stalls. Feed room and tack room. Offices on second floor. Two additional post and beam barns with stalls and loads of storage space and potential. Out door riding ring. The 1795 Colonial needs to be completely redone. It's down to the studs and awaiting to be remodel. Over all this property offers a loads of possibilities.

Listed by John Sniffen of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

23 Steeple View Lane Woodbury CT 06798

Woodbury, CT23 Steeple View Lane

Price$949,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170508998

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,541
  • Acreage 2.18

Stunning reproduction colonial in a storybook setting. Beautifully landscaped, private, and peaceful on a level lot backing up to open space. Located on a popular cul de sac this 5 bedroom home offers a versatile floor plan with excellent flow. The front to back living room has French doors leading out to an elegant stone patio that also connects with the kitchen for easy entertaining. The kitchen is open to a vaulted family room with exposed beams and is adjacent to the oversized dining room. Extra-wide wood plank floors can be found throughout the main level along with custom built ins and gorgeous molding and woodwork lending to the authenticity of the reproduction style. The upper level landing is open and flanked by 4 large bedrooms. The exceptional MB suite is up a staircase off the family room with ample closet space and a large full bath with steam shower and separate tub, 2 sinks, a dressing area and bright natural light. The lower level has French doors leading out to the phenomenal, landscaped yard and is being used as a rec room/exercise room, but can be used for anything you might need! This house has all the charm of an 18th century home but with modern conveniences, including a generator, newer wood shingle roof, newer central air handlers and more! Move right in and enjoy this beautiful home year round, or as a weekend getaway. Come see what you have been missing in this market. This is truly a one of a kind property that will make you feel right at home.

Listed by Kristen Stolfi of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

7 Strong Field Road Woodbury CT 06798

Woodbury, CT7 Strong Field Road

Price$899,900

Est. Mortgage: $/month

Under Agreement

MLS Number 170457136

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,900
  • Acreage 0.92

New cape in Woodbury's in town subdivision. Walk to town, schools and restaurants!

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

6 Mill Road Woodbury CT 06798

Woodbury, CT6 Mill Road

Price$849,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170493920

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,892
  • Acreage 1.95

Enjoy the sounds of the Nonnewaug River from this renovated 1870's saltbox. The perfect marriage of old and new, the home offers wide plank floors, horizontal board paneling, barn siding walls, thermopane windows, propane hot air and central air conditioning. The combined living/dining room is comfortable and cozy. Barn wood siding walls add character to the family room with picture windows overlooking pea stone terrace bordered by evergreens. Office, laundry room and full bath complete the main level. The second floor includes two bedrooms, marble and tile bath and the primary bedroom sitting room with exposed beams, closets and built-ins. The third level is dedicated to the spacious primary with vaulted ceiling, full marble and tile bath and walk-in closet. Beautiful stone walls and paths, specimen plantings, multiple sitting spaces and stone fountain are perfect for outdoor enjoyment.

Listed by Maria Taylor and Claudine McHugh of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2022 SmartMLS, Inc.