Woodbury CT Real Estate

Located approximately 85 miles north of New York City and referred to as Connecticut’s “Antique Capital” is Woodbury. 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 old world 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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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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505 Upper Grassy Hill Woodbury CT 06798

Price$1,485,000

Est. Mortgage: $/month

MLS Number 170056391

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 6.62

Award-winning sunsets and serene living await you on this spacious estate known as Cardinal Hill. Graced with a beautiful heated in ground swimming pool, tennis court, and barn, this 1940's Colonial was solidly built in this lovely section of Litchfield County. Discover all the wonderful shops in this antique district and come home to relax on a warm sunny day as you take in the extraordinary views for miles, available because the property is located in one of the highest elevations in Woodbury. Enjoy outstanding entertainment opportunities on picturesque grounds lined with stonewalls and stone terraces. Extra building on property houses a two-bay garage with attic and large gym with half bath. Additionally, the one-bedroom 1066 square ft. guesthouse with kitchen and living room is the perfect in-law apartment. Abutting guest house is a 480 square foot home-office with cathedral ceiling and separate heating and cooling. Total square footage (including unfinished basement) equals 7267 sqft. Located just minutes from I-84, this dream house is calling you home!

Listing Courtesy of Global Real Estate Network

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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: 3.82% last updated on Jun 13, 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$1,175,000

Est. Mortgage: $/month

MLS Number 170180381

  • Multi Family Multi-Family For Sale
  • Property Style Other
  • Acreage 1.5
  • Square Feet 11,020

Offered as a 9 Unit Portfolio consisting of three, 3-Unit properties located in Woodbury CT. Amazing and rare opportunity for qualified investors to add these income producing assets and squeeze into this tight market. These are Turn-Key properties that are well maintained, and fully rented with many updates done in the last 12-18 Months. Don't miss this opportunity to add these quality assets to your investment portfolio in highly sought after area where rents are consistently rising year over year. See MLS# 170180372, MLS# 170175757, MLS# 170175756

Listing Courtesy of Consolidated Realty Services

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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$1,100,000

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: 3.82% last updated on Jun 13, 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$999,000

Est. Mortgage: $/month

MLS Number 170196322

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

An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces and 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 room. Brazilian cherry flooring. An abundant use of windows & French doors blend the interior & outdoor spaces. Private office, full bath & powder rm complete main level. Impressive master suite w/octagonal ceiling, Brazilian cherry floors, gas fireplace, walk-in closet (w/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 room, den & transitions easily to the exterior to enjoy the salt water sports pool w/water fall & deck jets, patio area & outdoor kitchen. Russound 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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226 Scuppo Woodbury CT 06798

Price$995,000

Est. Mortgage: $/month

MLS Number 170199403

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 3.96

This classic Georgian Colonial style home has been beautifully maintained and offers a private 3.96 acre setting. The charm is enhanced by the vintage NYC brick exterior. The ceiling height is generous, the rooms are spacious and comfortable, and the hardwood floors, some with in-laid details, establish the character. A two-story foyer leads to a den with gas fireplace, a sun room with abundant windows and a formal dining room with tray ceiling and gas fireplace. The chef's kitchen features a large center island with 6 burner gas cook top, granite counters, double ovens and a butler's pantry. There is a dining area with French doors to the patio and a family room with gas fireplace The house has 5 BR and 3 full and 2 half baths.The master suite has 2 walk in closets and a master bath with 2 vanities, an over-sized shower and a whirlpool tub.Two guest bedrooms share a Jack and Jill full bath with double sinks. The remaining bedrooms have access to a full bath and there is a large office area with built in desks. For those who appreciate a mudroom this one is functional with laundry room, half bath, back staircase, and access to the attached 3 car garage. The spacious back patio with built in gas grill is private and perfect for entertaining. On the opposite side of the quiet gravel road there are 248 acres of town owned land convenient for long walks with your dog. This gracious home has been beautifully maintained and offers a private setting in a convenient location.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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$700,000

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: 3.82% last updated on Jun 13, 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: 3.82% last updated on Jun 13, 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: 3.82% last updated on Jun 13, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

130 Quassuk Woodbury CT 06798

Price$689,000

Est. Mortgage: $/month

MLS Number 170192126

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

Welcome to your entertainment oasis. 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 really 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 in 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: 3.82% last updated on Jun 13, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.