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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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40 Peter Woodbury CT 06798

Price$925,000

Est. Mortgage: $/month

MLS Number 170088765

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 4
  • Acreage 3.13

A quiet piece of paradise awaits you in Historic Litchfield County. Surrounded by luxurious perennial gardens, breathtaking views, stone outcroppings and terraces, this peaceful estate brings grace and sophistication to life yet is relaxed enough to call a country retreat. Set back from the road with a circular driveway, the 3,400 square foot single level home is equipped with a formal dining room, spacious formal living room with one of five fireplaces and a wall of windows that allows a bright entertaining space.The large scale kitchen with sunny views boasts a walk-in pantry, Sub Zero and Wolf appliances, eat-in dining area, warm family room with brick fireplace, walk out to stone terrace and built-in grill area. Three generous sized bedrooms include a peaceful master bedroom with third fireplace and walk-out to garden, en suite bathroom with glass shower, and dressing room..a clothes lover's dream! Other interior highlights include a walnut-paneled library with fourth fireplace, laundry room, and full basement with fireplace and plenty of storage space. Outdoors you'll enjoy Woodbury summers in your beautiful bluestone-wrapped Gunite pool-one of the focal points of the 3+ acre lot with a tranquil serene patio, lighted professional tennis court, stone terrace, an abundance of perennial gardens and specimen plantings, and room for all of your entertaining events.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$799,000

Est. Mortgage: $/month

MLS Number 170140365

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

Moison Designed Estate, combining the elegance of the past with all the conveniences of new! Located on over 4.5 stunning acres, this New "Old" home is sited to maximize views of the property, including the graceful pond and charming two story horse barn. Set privately on one of the most treasured streets in Woodbury, this Cape offers an open floor plan with four fireplaces, wide board pine floors and generous public spaces. A true escape, this gracious home is surrounded by gorgeous grounds including stone walls, patios, boxwood gardens and features a screened porch. Just minutes from Main Street in Woodbury, this home truly has it all!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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43 River Bend Woodbury CT 06798

Price$779,000

Est. Mortgage: $/month

MLS Number 170170593

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.04

Sophisticated Colonial on 2 park like acres with mature landscaping of fruit trees, Japanese maples, hydrangeas, stone walls, privacy and exterior lighting that surround the home. The yard is fully fenced with views of over 10 acres of land preserve that includes the Pomperaug river. This home offers high end finishes and fabulous details throughout, hardwood floors, 4 bedrooms, (potential 5th) 3.5 baths and 4 fireplaces Enjoy the open floor plan, living room with vaulted ceilings, reclaimed wood wall feature, fireplace and wood beams. Updated bright kitchen with gorgeous light, 4'x10' center island with quartz counter, 2 sinks, professional stove, Caesar stone counters and custom cabinetry. The Kitchen opens to charming family room with Blue Stone Fireplace. The fabulous oversize sun filled dining room boasts a large fireplace and is lined with French doors that lead to a Blue Stone patio for outstanding outdoor entertaining. The main level also has one of two master bedrooms with vaulted ceilings, hardwood floors, fireplace and master bath with stone shower and and large soaking tub. The upper level consists of the second master bedroom with built in shelving and a full bath and 2 additional bedrooms. The lower level of the home is finished with a large media/play room, a second area for a gym and ample storage. The three-car garage has a finished upper level which could be a great game room. This home is fully renovated and ready for you just to unpack and enjoy!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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: 4.17% last updated on Apr 18, 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

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: 4.17% last updated on Apr 18, 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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138 Quanopaug Woodbury CT 06798

Price$679,900

Est. Mortgage: $/month

MLS Number 170119895

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.63
  • Square Feet 3,634

Cool brand new contemporary home on quiet cul de sac drive abutting acres of open space. Gorgeous open floor plan with 2 story cathedral ceiling, large spans and fabulous kitchen opening to great room. Kitchen features stone backsplash, room for three chairs at the center island, and granite counter-tops. Plenty of private outdoor entertaining space including a back patio out of the walkout lower level, upper deck off the great room and open wraparound front porch. The upper level offers a master suite with luxurious master bath and large closet/dressing area, 3 bedrooms with two full baths, a balcony overlooking great room and a laundry room. The lower level has plenty of headroom to make a play or game room and a french door opening to a large patio. Many extras including first-floor study with fireplace, cobblestone lined driveway and walkway, stone veneer and massive mahogany front door. Room for a pool on just over an acre and a half but hundreds of acres of open space out your back window!

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

557 Upper Grassy Hill Woodbury CT 06798

MLS Number 170139389

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 4
  • Acreage 2.73

Fabulous, meticulously cared for Contemporary with forever views. The quality, custom built home has open kitchen, all brand new appliances, eating area, that flows out to a deck, and family room. There is a formal dining room and living room and an office completes the first floor. En suite master - with fantastic views from the bath, dressing room, large closets, two additional bedrooms with a bath in between are on the second floor. The lower level consists of an wonderful kitchen area, an exercise area, banquets for entertaining, steam shower in the well appointed bath and even a Murphy Bed for additional guests. Around the corner outside is the spa pool making the lower level an adult paradise. Surround sound, brilliant hardwood floors and attention to detail make this house special. The grounds are open with an emphasis on the long reaching views. The driveway is edged in Belgian Stone. A perfect place to come home to.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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.