Woodbury CT Real Estate

Located approximately 85 miles north of New York City and referred to as Connecticut’s “Antique Capital” is Woodbury. Woodbury 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.

>> Learn more about the town of Woodbury, CT

Properties in Woodbury

Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

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105 Old Grassy Hill Woodbury CT 06798

Price$2,800,000

Est. Mortgage: $/month

MLS Number 170010438

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 57.87

This outstanding private retreat is set on 57+ acres at the end of a cul-de-sac and is bordered by a large pond and the Flanders Nature Center, The property offers beautiful views, hiking trails through the woods and a secluded setting. Custom designed by the architect Moisan, the home features quality details, a gourmet kitchen, and grand entertainment spaces. Something special!

Listing Courtesy of Coldwell Banker Res Brokerage

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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59 Hillside Woodbury CT 06798

Price$1,749,000

Est. Mortgage: $/month

MLS Number 170207963

  • Single Family
  • Property Style European
  • Bedrooms 5
  • Bathroom 7
  • Acreage 3.49

Amazing views and gorgeous surroundings adorn this luxury villa situated on a hillside in historic Woodbury. Enjoy serenity in your remarkable outdoor living space while taking in the miles of rolling hills. Fine details in the construction and finish can be admired throughout the over 9,000 ft of this dream dwelling "Masterfully" designed by noted Architect Rick Moisan of Moisan Architects. Incredible architectural lighting throughout, as well as French doors leading to the balconies and pool's terrace, heated herringbone hardwood floors and five fireplaces that will warm you on a cold winter's day. Arched central foyer leading to all of the main floor rooms including a beautiful sunroom adjacent to your infinity pool. The kitchen with professional modern appliances, including Wolf gas cooktop, double oven and butler's pantry. The master suite with luxurious spa-like bath and walk-in closet has its own laundry facilities. The guest suite with separate entrance is housed above the heated 3-car garage and additional apartment housed on the main floor has full kitchen, bath, bedroom and two-story great room that opens to the beautiful outdoor terrace. Enjoy summer nights dining under the two turreted loggias or simply enjoy some tea and take in the breathtaking views. Convenient to Historic Arts and Antiques District and immersed in nature at its finest, this spectacular abode is located just minutes from major thruways. Property borders the Trolley Bed Land Preserve.

Listing Courtesy of Global Real Estate Network

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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Woodbury CT 06798

Price$1,200,000

Est. Mortgage: $/month

MLS Number 170110604

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 9.18

Set back on 9+ acres, this property offers privacy in a choice location. As visitors ease down its circular stone drive the New England Colonial charm of this exceptional estate welcomes them. Upon entering the formal foyer the homes texture and character are made obvious by the wooden wall cladding, a detail that is carried throughout much of the home. The space on the main level is arranged in such a way that there is a sense of ease in movement. Wide, open doorways carry you from one room to the next, while the warmth of the wood paneling creates a sense of intimacy in each individual space. The formal living room and kitchen are open to the homes expansive four-season porch, overlooking the breathtaking views of the Litchfield hills. A large open dining/living area with built-in custom cabinetry abuts the L -shaped kitchen workspace. Adjoining is a formal library/office that extends into the illuminated den. On the upper floor there are two bedrooms and two bathrooms. The current (original) owners personalized this living level by converting the third bedroom into an opulent bath & dressing room. Luxurious living extends to the exterior of the home as well, where both sport and relaxation can be found in the homes gunite pool and tennis court. With mature plantings throughout and expansive views the properties landscape rings true to the title of country estate.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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Chohees Woodbury CT 06798

Price$995,000

Est. Mortgage: $/month

MLS Number 170190382

  • Land
  • Acreage 105.7

Expansive track of rolling acres in rural Woodbury. Subdivide for residential, farming, gun range, dirt bikes, hunting. Many possible uses. Adjoining 4 acre lot on Flanders Rd can also be purchased for a total of 109 contiguous acres.

Listing Courtesy of Gina Jacobs Real Estate & Property Management

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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283 Saw Pit Hill Woodbury CT 06798

Price$899,900

Est. Mortgage: $/month

MLS Number 170196322

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 6
  • Acreage 9.27

Incredible value! An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces & designed with every luxurious amenity imaginable. Gorgeous wrap around mahogany covered porch (with hot tub). Stunning two-story entry. A chef's kitchen offering the most discriminating buyer a large center isle, custom cherry cabinets, granite counters, handmade copper sink, Subzero, Viking stove, two dishwashers, convection oven & large dining area. Open concept seen and 9+ft ceilings throughout. Formal dining rm (w/custom cabinetry & limestone counters) living rm w/wet bar, gas fireplace & superb piano rm. Brazilian cherry flooring. An abundant use of windows & French doors blend the interior & outdoor spaces. Private office, full bath & powder rm complete main lvl. Impressive master suite w/octagonal ceiling, Brazilian cherry floors, gas fireplace, walk-in closet (organizers) & elegant bath (claw foot tub, antique vanity & tiled shower with jets/body sprays). Three additional guest rms (two share a bath, one an en-suite), & media rm w/vaulted ceiling & entertainment center. The finished lower level (possible in-law space) offers a recreation area, full bath, game rm, den & transitions easily to the exterior to enjoy the salt water sports pool w/water fall & deck jets, patio area & outdoor kitchen. Whole house audio system. Energy Star Rated Home. Look no further...this truly is a spectacular home set in an idyllic setting!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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32 & 40 Peter Woodbury CT 06798

Price$895,000

Est. Mortgage: $/month

MLS Number 170212725

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 5
  • Bathroom 7
  • Acreage 5.36

If you are looking for an exceptional home with quality craftsmanship and style, look no further. This brilliantly designed home includes 2 lots #32 and #40 on 5 stately acres in Woodbury, CT. Grace and sophistication is brought to life yet is relaxed enough to call a family retreat. The main home is impeccably well kept offering single level living on 3 acres with a versatile open floor plan, tennis court and a pool house. You enter your property from a lovely tree-lined driveway boasting gorgeous perennial flower gardens that evoke beauty and peacefulness. Thru the entryway foyer, there is a splendid living room complete with oversized fireplace and impressive panoramic view of a gorgeous landscaped courtyard and bluestone patio. The large scale comprehensive kitchen boasts a walk in pantry with auto lighting, two SubZero refrigerators, Wolf dual-fuel range with griddle, KitchenAid dishwasher, eat in dining area and a family room with an oversized brick fireplace and built in two speaker sound system. The library is magnificently crafted with walnut raised paneling, bookcases, a double closet and cabinets. There are three generous sized bedrooms including a welcoming master with a fireplace, walkout and en suite bathroom. Enjoy summer soirees in your beautiful bluestone wrapped Gunite pool and professionally lit hard surface tennis court. Great commuter location just 90 minutes from NYC. Perfect for multi-family, weekenders or rental. To see it is to fall in love with it!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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1 The Estate on Meadowbrook Farm Woodbury CT 06798

MLS Number 170209891

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3

Fall in love with this breath taking property in one of the most charming corners of Connecticut. Exquisite custom built estate surrounded by 400 acres of natural paradise. This fabulous estate is built with state of the art quality components, superior materials and craftsmanship. You simply can not find another property like this so close to Manhattan. This is your ultimate dream home. Built in 2008 with nothing spared. Exceptional features including extremely efficient geothermal heating and cooling, as well as smart home technology. The gourmet kitchen features antique granite counters, marble backsplash, SubZero &Wolf appliances. Kitchen and eating area are open to the family room with fireplace and a wall of glass doors leading to a wrap-around porch making it ideal for entertaining. Master bedroom is enhanced by a gas fireplace, master bath features crema marfil marble. The highly efficient geothermal heating and cooling system is secured with 4 inches of foam plus fiberglass insulation throughout for maximum performance. This exceptional home is everything you've been waiting for. To rebuild this unique estate with all the exceptional quality and attention to detail would cost nearly 2 million or more. Don't miss this special opportunity. Call your agent for a private showing!

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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466 Main Woodbury CT 06798

MLS Number 170047103

  • Commercial
  • Acreage 3.28
  • Square Feet 8,000

To be built - 8000 to 10000 metal building. Five 12' doors, level lot with many possibilities. Rent to multiple tenants or run your own business out of one of Woodbury's last industrial sites. Great exposure and minutes to all major routes.

Listing Courtesy of Drakeley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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270 Main Woodbury CT 06798

MLS Number 170158464

  • Commercial
  • Acreage 1.09
  • Square Feet 4,302

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. The incredibly well maintained property and multiple buildings have tremendous potential for a variety of commercial and mixed use occupancy (Professional office, retail, home business, residential rental etc. ) Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. The property is high visibility with ample public parking adjacent to the property boundaries. Interior features include wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage. Perfect for in-home business and professional uses.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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270 Main Woodbury CT 06798

Price$699,000

Est. Mortgage: $/month

MLS Number 170156120

  • Single Family
  • Property Style Antique
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1.09

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. Wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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100 Cat Swamp Woodbury CT 06798

Price$649,000

Est. Mortgage: $/month

MLS Number 170140365

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 3
  • Acreage 4.62

Gorgeous Reproduction Cape by Rick Moisan Architects, combining the elegance of the past with all the conveniences of new. Located on treasured Cat Swamp Road, set privately on 4.5 acres with spring fed pond, stone patio, screened porch and main floor master bedroom and beautiful old Barn, this New "Old" home is sited to maximize views of the property, including the graceful pond and charming two story horse barn with fencing, Meditation Gardens with water feature. The home offers high ceilings and open floor plan with four fireplaces, Central Air and Central Vac, AD wide board pine floors and generous public spaces. A true escape but just minutes from town for great dining, shopping and hiking, this gracious home is surrounded by gorgeous level land, mature plantings, stone walls, stone patios and English boxwood gardens. In ground sprinkler system for lawn and canine fencing.. This home truly has it all!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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130 Quassuk Woodbury CT 06798

Price$639,900

Est. Mortgage: $/month

Pending

MLS Number 170192126

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 6.64

Private gated entry, 6+ acres, with a must-see Pool Paradise! Just 90 mins to NYC, this beautiful 4 bedroom Colonial on over 6 acres of land provides plenty of space for living and playing. The majestic entryway leads to the kitchen featuring stainless appliances and granite countertops. Enjoy a meal at the enormous island, or move to the eat-in area for additional seating. The kitchen flows into the formal dining and living room, as well, so you can see your guests and family members from each area. The living room has a cozy fireplace and hardwood floors throughout. First floor also features an office. Upstairs, you will find 4 bedrooms and a bonus room with plenty of space to work out, watch a movie, or just relax. The lower level stands out with an amazing game/media room complete with a wet bar, half bath, and so much more! There is additional storage on this level and all utilities are hidden so your entertainment setup is seamless.Step outside and enjoy the gorgeous in-ground pool complete with concert-style lighting and a separate pool house, as well as the stone patio and fire pit off the back of the house. The pool area features an 11-speaker stereo system for amazing sound, as well as cable and WiFi hookups at the pool house. There is an automated gate at the property entrance and additional safety features such as a whole-house alarm system, automated garage doors controlled by an app, setup for 5 outdoor cameras, and a whole house generator. This is a must-see!

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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.

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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.