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

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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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The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$2,495,000

Est. Mortgage: $/month

MLS Number 170032891

  • Single Family
  • Property Style European
  • Bedrooms 4
  • Bathroom 7
  • Acreage 3.49

Hillside Villa. Perched at one of Woodbury's highest elevations, this immaculate residence defines luxury living. Masterfully designed by Rick Moisan, the home was sited and built to take full advantage of the open and sweeping 180 degree views across the rolling Litchfield Hills. Offering over 9,000 square feet of interior living space, no expense was spared in the construction and finish. Interior details include 5 FPs, heated herringbone hardwood floors, tray ceilings with architectural lighting, and abundant French doors to balconies or to the pool terrace. Public rooms are accessed off the arched central foyer and include a formal DR, LR, den, FR, the kitchen and a breathtaking poolside sunroom. The kitchen couldn't be better equipped and offers full size SubZero refrigerator and freezer, Wolf gas cooktop and double oven, and a full butler pantry. Upstairs there are three spacious bedroom suites including a master wing with salon, bedroom with FP, a spa bathroom and dressing room complete with W/D. A guest studio with separate entrance and full bath spans the entire second level of the heated 3-car garage. The main floor also offers a guest apartment that has a full KIT, BA, BR, and two-story great room that opens onto the pool terrace. Outside features include the stone and stucco exterior, slate roof, the central terrace built around the gunite infinity pool, and two turreted loggias. More than simply a home for sale, this is a lifestyle upgrade that you deserve.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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920 Main, Woodbury, CT 06798

Price$2,195,000

Est. Mortgage: $/month

MLS Number L10229171

  • Single Family
  • Property Style Antique, Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 18.36

Magnificent...Widely Publicized and Nationally recognized, Gorgeous Antique Estate with Riverfront, Complete with Guest House, in ground pool, 6 stately barns and silo. gorgeous perennial gardens, outdoor kitchen with stone pizza oven, stone and brick terraces, screened porch, rolling pasture,.. 2 land parcels. Think farm to table, Country Inn, Wedding venue, Horse farm, antique business,.. many possibilities, all subject to town approvals, Encompasses all the richness of the Litchfield County area. Enjoy area lakes, Golf, Antiquing on Ct Antique Trail, skiing and amazing Parks, vineyard, 5 Bedroom, 4 full and 2 half in main house, 4 fireplaces, stone patio. Located in the heart of the County -- yet minutes from Rte. 84 and only a short drive from NYC...

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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920 Main, Woodbury, CT 06798

Price$1,849,000

Est. Mortgage: $/month

MLS Number L10229193

  • Single Family
  • Property Style Antique, Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 8.36

Magnificent...Widely Publicized and Nationally recognized, Gorgeous Antique Estate with Riverfront, Complete with Guest House, in ground pool, 6 stately barns and silo. gorgeous perennial gardens, outdoor kitchen with stone pizza oven, stone and brick terraces, screened porch, rolling pasture,.. 2 land parcels. Think Country Inn, Wedding venue, Horse farm, antique business,.. many possibilities, all subject to town approvals, Encompasses all the richness of the Litchfield County area. Enjoy area lakes, Golf, Antiquing on Ct Antique Trail, skiing and amazing Parks, vineyard, 5 Bedroom, 4 full and 2 half in main house, 4 fireplaces, stone patio. Located in the heart of the County -- yet minutes from Rte. 84 and only a short drive from NYC... See Additional Land available see MLS L10072456

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$1,749,000

Est. Mortgage: $/month

MLS Number L10194813

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

Views. Set on one of the beautiful back roads in Woodbury on the Roxbury Border, this elegant stone 1940's Colonial, complete with guest house, party barn, pool and tennis court offers all the amenities of a great estate. Manicured grounds and stone terraces - Guest house with kitchen, living room and one bedroom. Additional building with large space for office/ gym or party barn with half bath, two bay garage.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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97 A Owl Ridge, Woodbury, CT 06798

Price$1,490,000

Est. Mortgage: $/month

MLS Number W10234176

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3.5

New exciting model home to be built at The Owl Ridge Estates.One of the most beautiful subdivisions in Litchfield county,Woodbury Ct. Don't miss this opportunity ,only 2 lots left.This is exquisite energy eficient new construction with high end finishes ,State of art first floor master bedroom suite with luxurious bath,gourmet kitchen open floor plan ,this is a perfect blend of modern and traditional architecture and style. designed more modern life style Another quality Home Built By Corbo. Visit: https://www.theestatesatowlridge.com/

Listing Courtesy of William Raveis Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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36 East Hill, Woodbury, CT 06798

Price$1,395,000

Est. Mortgage: $/month

MLS Number L10220555

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 7.19

Absolutely Spectacular Mosian designed home with many recent upgrades. 5 bedrooms, 6.5 baths, 5 fireplaces. Open floor plan boasts a light sunny kitchen with sitting and breakfast nooks which opens to living room, family room and formal dining room. Main floor master with gorgeous bathroom and dressing area. Chic sunroom with chessboard floor walks out to boxwood garden. Wide board floors throughout, wood shingle roof, fantastic moldings and built ins. Lower level cabana room that walks out to pool area with changing rooms, kitchen and full bath. Whole house generator. Gated entry with peastone parking area, low maintenance gardens and large lawn. 2 minutes to organic market, 15 minutes to Washington Depot.

Listing Courtesy of William Raveis Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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97 Owl Ridge, Woodbury, CT 06798

Price$1,390,000

Est. Mortgage: $/month

MLS Number 170029138

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 3.66
  • Square Feet 4,000

Spectacular property in Woodbury, Ct. Quite possibly the most charming corner of Litchfield county. Exquisite and unique custom built estate surrounded by acres of natural paradise. This fabulous home is built with state of the art quality components, superior materials & craftsmanship! Come and fall in love with this breath-taking property in the Estates of Owl Ridge.Home Built By Corbo.Only 1h and 15 min. from Manhattan.This is the last building lot with magnificent views.You must come and see this most charming corner of Woodbury CT!

Listing Courtesy of William Raveis Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

283 Saw Pit Hill, Woodbury, CT 06798

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170031081

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

Charming custom built home on 9+acres, Very private setting with lovely wrap around mahogany porch, 9 ft ceilings, detailed crown moldings and trim throughout, Brazilian cherry hardwood floors, 2 story entry with sweeping stairwell. Living room with lovely bay window and gas fireplace, Dining room with wonderful tray ceiling and fabulous built in hutch with granite counter top. Oversized great room with french doors to balcony, built in wet bar with beverage refrigerator, ice maker and instant hot water, Gourmet country kitchen with large granite island, handmade copper sink, Sub Zero with separate refrigerator and freezer, Viking gas range, an additional convection oven, two Kitchen Aid dishwashers. Private office with built in hutch and full bath. The upper level boasts the master bedroom suite with gas fireplace, walkin closet with washer & dryer, wonderful stone master bath with double shower heads, wall jets and soaking tub, 3 additional bedrooms and two full baths, Media room/den with cathedral ceilings and built in entertainment center. Lower level is completley finished with an extra guest area with full bath, and laundry. French doors that lead to heated salt water pool area with fountains, terraces and fantastic outdoor kitchen. 3 car heated garage with hot/cold sink. This is a fabulous home with a wonderful setting and amazing details throughtout

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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766 Main, Woodbury, CT 06798

MLS Number W10231459

  • Commercial
  • Acreage 0.92
  • Square Feet 11,926

Location,Prime Location minutes away to I-84 and on the gate-way of the antiques capital of the wold Wood bury Ct. Commercial/Retail/office Building ground floor fully occupied, upper level 5,000Sf.+-is vacant 4 units. with great potential for more income. 1,520SF. end cap with drive-thru. New Roof was installed 3years ago , New pavement one year ago. New plaza built across the way. feel free to contact listing broker for more details and information.

Listing Courtesy of AL Dasilva Realty

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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79 Nettleton Hollow, Woodbury, CT 06798

MLS Number 170032536

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 29.7

Recently renovated historic home in estate area close to Mayflower Grace, historic town of Washington and ninety minutes from Manhattan. Beautifully sited on over 29 acres off a quiet scenic road with charming gardens, mature trees, red clay tennis court and heated Gunite pool. The house is lovingly maintained with many period details throughout. The interior boasts spacious rooms with lovely views, exposed antique beams, large stone fireplace, marble kitchens and baths, and hardwood floors throughout. This quintessential New England country home is one-of-a-kind and move-in ready. Owners have created trails throughout the property.

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

43 River Bend, Woodbury, CT 06798

Price$839,000

Est. Mortgage: $/month

MLS Number 170014237

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

Gorgeous Custom Reproduction Eyebrow Colonial set on 2+ acres. Top Quality finishes throughout and under 2 hrs to NYC, minutes to Woodbury Center for great hiking trails, gourmet dining and shopping the Connecticut Antique Trail. Easy entertaining awaits with the stone patios surrounded by stone sitting wall with views over the 10 acre Land preserve and Pomperaug River. High quality chef's kitchen and high end baths offer a feeling of luxury while a relaxed feel throughout the home. The open floor plan offers Living Room with Vaulted Ceiling, extensive moldings, three fireplaces and wood stove, maple floors, first and second Level options for Master Bedroom. Mature perennial gardens, level lawn for great play area and specimen plantings abound throughout the property. The finished lower level with gym, family room and bedroom. The home was custom built by Heritage homes of Woodbury and beautifully renovated in 2010 to include a new three car garage, 650 ft finished second level and circular driveway and many upgrades. The kitchen boasts a custom high end kitchen complete with 60” professional oven, center island, 2 sinks and an abundance of marble counter and cabinets. The fully fenced yard includes a blue stone patio and Beautifully landscaped front and rear yards. --

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.