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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39 Terrell Woodbury CT 06798

Price$649,900

Est. Mortgage: $/month

MLS Number 170195563

  • Single Family
  • Property Style Cape Cod, Ranch
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3.5

Truly one of the most amazing properties you will ever find! The picturesque location and phenomenal views surrounding the house will make every morning and evening memorable! Located in the historic town of Woodbury, this home is perfect for multi-generational living, artists and car enthusiasts to name just a few. The main level features 3 bedrooms, 2.5 bathrooms, an open floor plan kitchen and great room with large windows to capture the stunning views. There are 2 three season rooms with the one at the rear off the formal dining room large enough for entertaining and adjacent to the patio. Upstairs you will find a glorious loft perfect for artist studio or home office and a full one bedroom accessory apartment complete with fireplace and private rear deck. The lower level contains a large family room with fieldstone fireplace along with workshop and storage areas. There are 2 large detached garages on opposite sides of the house. One is an oversized 3 car with bonus room and the second can house 4 cars along with having a finished office space and a third level that is sheetrocked and large enough for a possible second apartment. 2nd level has a rear garage door entrance suitable for tractors, motorcycles etc. This building is heated and has it's own well and a working cesspool. Additional acreage is available. Imagine sitting in the Adirondack chairs and just relaxing and enjoying this spectacular location!

Listing Courtesy of Joseph Bette REALTORS Inc

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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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557 Upper Grassy Hill Woodbury CT 06798

MLS Number 170139389

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Acreage 2.73
  • Square Feet 3,791

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. Please take shoes off when inside. (Owner gave sq. footage to include finished basement)

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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89 Quail Run Woodbury CT 06798

Price$635,000

Est. Mortgage: $/month

MLS Number 170185636

  • Single Family
  • Property Style Cape Cod, Colonial
  • Bedrooms 3
  • Bathroom 4
  • Acreage 1.13

Quality to-be-built custom Eyebrow Colonial by HOBI award winning builder Connecticut Residential on lot with breathtaking VIEWS for miles! This exceptional ENERGY STAR CERTIFIED home on a quiet cul-de-sac boasts a spacious open floor plan with a wall of windows to drink in the incredible VIEWS! Gorgeous kitchen with granite or quartz countertops, stainless steel appliances, sliders to deck, dining area, bonus 1st floor study/office/bedroom, elegant first floor master bedroom suite with walk-in closet and bath with double vanity, shower, and soaking tub, wood floors throughout, FR featuring CATHEDRAL CEILING AND gas fp, tiled mudroom off garage, tons of storage, powder room, and large 3 CAR attached garage. Second floor has two additional bedrooms a bath AND A LOFT . Additional floorplans and lots available! Can build to suit and CUSTOMIZE to your lifestyle! Ask for additional building plans! All photos are from builder's portfolio of previously constructed homes and are not from this property.

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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101 Old Grassy Hill Woodbury CT 06798

MLS Number 170188467

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 5.17
  • Square Feet 5,794

Living in a world of Nature's Art! The entire property, both inside and out is truly emotionally stirring. A breathtaking statuesque quarry of stone lines one side balanced on the other by the most soothing body of water. Five lush professionally landscaped acres protect your privacy, level yard with industrial catch basins-drainage, low maintenance milled crushed stone driveway, double tiered decking, and an outdoor shower. All of the beauty flows in through enormous windows highlighting the builder's attention to detail and fine millwork....coffered ceilings, oversized crown and baseboard molding, solid large raised panels, and wider board hardwood floors. Additional features include separate entrance living quarters, 5 car garage, and top of the line mechanicals. This home could be comfortable hosting an event for 200 and still feel intimate. Grab your kayak, canoe and ice skates. Dare to be happy!

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/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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109 Flanders Woodbury CT 06798

Price$620,000

Est. Mortgage: $/month

MLS Number 170163890

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 2
  • Acreage 4.72

LOOK NO MORE! This stunning 3-4 bedroom colonial sits on over 4.5 acres. While it is minutes away from all the wonderful amenities that the center of Woodbury has to offer, it feels like it is a private retreat nestled in nature with all the bells and whistles. The home has comfortable room sizes and fabulous interior flow, great for entertaining. Like to cook? You are in luck with this state of the art chef's kitchen finished off with top of the line appliances and beautiful granite. Are you looking for a home that is as beautiful and comfortable on the outside as it is on the inside? Relax and fish in your own private pond, soak in the hot tub under the stars, enjoy a meal outside or have a fire. The house also has a whole house generator and a detached garage with 2 bays and a bonus room upstairs. This house is the best of both worlds- the charm of New England mixed with updated modern conveniences that is difficult to find.

Listing Courtesy of Regency Real Estate, LLC

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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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547 Flanders Woodbury CT 06798

Price$600,000

Est. Mortgage: $/month

MLS Number 170188887

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 5.64

The perfect antique home! Classic and updated, very well cared for 4 BR antique home on 5.6 park-like acres with two ponds. Original floors and windows (all windows reglazed and insulated with modern storm windows). Generator, new furnace, freshly painted exterior, Artist's Studio with fireplace and loft, had been used as an antique business by prior owner, could easily become an in-law suite or main floor master. Studio wing also has separate kitchen and additional separate bedroom. Eat-in kitchen has soapstone counters, six burner DCS range, farmhouse sink and pantry with plenty of storage. Walk up attic with plenty of headroom just waiting to be converted into additional living space. Property also features a fenced in garden and two outbuildings. Detached 3 car garage/barn with unfinished space above, and separate small outbuilding also usable as a small studio or workshop. With the studio, walk-up attic and the garage/barn there are a multitude of possible ways to enjoy this property.

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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44 Old Meadow Woodbury CT 06798

Price$599,900

Est. Mortgage: $/month

MLS Number 170198784

  • Single Family
  • Property Style Cape Cod, Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.69

Stunning & stately 4000+ sq./ft. home in The Village at Old Meadow, one of Woodbury's most beautiful & desirable subdivisions. Sited majestically on a gentle rise, the home is of unmatched quality, evidenced by its wood shingle roofs, copper gutters, sdl windows, & stone walls flanking the crushed stone drive. Inside, the welcoming two story foyer introduces one to the wide board knotty wood floors that run through out the home. To the left, glass filled French doors to the parlor, perfect for that baby grand piano. To the right, the oversized formal dining room. Straight ahead is the eat-in kitchen, completely open to the Great Room. The kitchen offers an L-shaped island with beverage cooler & prep sink, custom cabinets, granite counters & Viking stainless steel appliances. The Great Room features vaulted ceilings, stacked stone fireplace & wonderful natural light. From here step to the sunny deck over looking the exceptionally private back yard with plenty of room for a pool. The first floor master is incredibly spacious w/ walk-in closet & designer bath. Upstairs are 2 bedrooms sharing a full bath with double sinks & stylish tile & fixtures. The 4th bedroom has its own private full bath. There is also a den/game room here. Over the 3 car garage is a perfect home office or theater room-separate from the rest of the home and large enough to offer a variety of uses. The unfinished basement offers additional potential. Affordable luxury just a few miles from exit 14 of I-84.

Listing Courtesy of Joseph Bette REALTORS 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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132 Stone Pit Woodbury CT 06798

Price$599,000

Est. Mortgage: $/month

MLS Number 170115681

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 4
  • Bathroom 3
  • Acreage 5

Custom designed Ranch on private lot has elegant open floor plan with oversized rooms and vaulted ceilings! Spacious master suite has luxurious bath, bamboo floors, sitting room, and exercise room. Convenient central vacuum system, even in the garage. Music/intercom system throughout with hookups for all your modern devices. Soaring vaulted ceilings in kitchen and family room. Four-zone hydro-air system with electrostatic filters and all systems of the highest quality. Potential fourth bedroom in main floor office space. This home is secluded yet convenient to town, shops and restaurants. Just 15 minutes to I-84. A must see!

Listing Courtesy of Global Real Estate Network

$
$
%
$/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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419 Weekeepeemee Woodbury CT 06798

Price$599,000

Est. Mortgage: $/month

MLS Number 170191914

  • Single Family
  • Property Style Barn, Farm House
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.3

Charm, form & function best describe the uniqueness of this home! This classic Americana converted barn is right out of yesteryear from its reclaimed wood beams to its fieldstone fireplace and wide plank floors. It has been preserved and restored to allow its original character to shine through. The wrap around covered porch invites you into the main living level that includes the family room with fireplace, kitchen with a center island, propane stove & corian countertops, sitting room with built ins and french door to the deck, a master bedroom suite and another large bedroom with cedar closet. The second level is an entire floor of another master suite with a french doors to a balcony, and a large game room. It also has a third level cupola that offers views of the extraordinary property. As an added feature,the lower level is an expansive heated and air conditioned garage that runs full length of home. Built to accommodate any type of collection... cars, boats, tractors, furniture, antiques, or whatever you may collect. The bucolic outdoor setting displays beautiful perennial plantings, bluestone patios, natural stone walls and abuts the Flanders land trust. A truly unique offering!

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

43 Birchwood Woodbury CT 06798

Price$599,000

Est. Mortgage: $/month

MLS Number 170207109

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 2.61

Homeowners are drawn to Woodbury by its marvelous blend of gentle country living, quality shopping and dining, balanced by easy access to regional destinations. This handsome, brick-faced colonial offers a private and quiet location, yet is close to all. From the moment you enter the driveway and throughout this spacious and comfortable home it is clear that this property enjoys an exceptional level of care and brings a package of amenities to the table that is rare at this price point. The circular main level flow tours you from a grand two-story entry foyer past an office followed by a first floor en suite bedroom. Next is a generously sized living room with a fireplace overlooked from the balcony above. Expansive kitchen/casual dining area features stainless steel appliances, granite counters and a breakfast bar with french doors leading to a large deck for outdoor grilling & dining. The main level is anchored by staircases in the foyer and living room that meet at a landing on their way to the upper level. Master suite has his & her walk-in closets either side of a spa sized bathroom w/ double vanities, a jet tub & stall shower. One en suite guest bedroom. Two more guest bedrooms share Jack and Jill tub/shower with separate vanities. Finished, heated basement w/ french doors leading to fenced yard. Large workshop/mechanical room too! Plentiful level lawn surrounds the home which is bounded at rear by a Beaver pond that is part of 31+ acre conserved open space.

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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158 Scuppo Woodbury CT 06798

Price$595,645

Est. Mortgage: $/month

MLS Number 170155788

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 3
  • Acreage 9.13

Privacy, views, views, location, location!! Convenience to highway and completely private on 9.13 acres with magnificent views,property abuts 14 acres of natural preserves.Custom built colonial features gourmet kitchen with large pantry,opens to light and bright fam.Rm with custom woodwork and spectacular fireplace. 1st floor office,master bedrm suite w/dressing room, 2nd office and covered balcony. Additional 650 sq ft finished in basement

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/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

64 Silver Brook Woodbury CT 06798

Price$579,900

Est. Mortgage: $/month

MLS Number 170188912

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 4
  • Acreage 3

MOVE IN CONDITION! Beautiful custom cape with first floor master suite. Too many upgrades to mention them all! Located in premier community on a large private lot at the end of cul-de-sac and bordered by Flanders Nature Center! Beautiful chef's kitchen with island, breakfast bar, breakfast nook, granite counters, stainless appliances including a convection/microwave oven. The kitchen is open to the great room with great flow for entertaining. Hardwood floors are through out the main level as well as upstairs bedrooms and hall. Great room has a vaulted ceiling, fireplace and inside balcony overlooking from above. The main floor master suite is lovely with a sitting area, 2 walk in closets and a luxurious master bathroom with a hydro tub, dual sinks and a steam shower. The formal dining room, office, laundry room, mud room and half bath complete the main level. The upper level includes 2 additional bedrooms, 1 en suite and the other shares a hall bath with the large game room which could be used as a 4th bedroom. The house has an inviting covered front porch to sit and watch the sunset. There is a covered rear porch and blue stone patio to relax and have a cookout. Located under 2 hours from NYC makes this a wonderful weekend home as well as a full time home. This wonderful country home has been extremely well maintained and is ready for you to move right in!

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

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.