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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 us for more information and to schedule a showing for any real estate below. Save your favorite listings when you create an account with us, and you can get email updates when similar properties are posted.

 

105 Old Grassy Hill Road, Woodbury, CT 06798

InternalID N336832

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Acres 57.87
  • SqFt 7178

Private retreat set on 57+ acres at end of cul de sac, bordered by large pond & flanders nature center with views & hiking trails. Custom designed by architect moisan & featuring quality details, gourmet kitchen, grand entertainment spaces. Spectacular!

Listing Courtesy of Coldwell Banker Res Brokerage

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: 3.95% last updated on Apr 27, 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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, Woodbury, CT 06798

Price$2,800,000

Est. Mortgage: $/month

CMLS 99026760

  • Residential
  • Bedrooms 5
  • Acreage 57.87
  • Square Feet 7178

Private Retreat Set On 57+ Acres At End Of Cul-de-sac. Bordered By Large Pond & Flanders Nature Center With Views & Hiking Trails. This Moisan- Designed, Custom Home Features Quality Details And Workmanship, A Gorgeous Gourmet Kitchen, Grand Entertainment Spaces & Much More! Spectacular!

Listing Courtesy of Coldwell Banker Orange

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: 3.95% last updated on Apr 27, 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 St South, Woodbury, CT 06798

InternalID L10229171

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Acres 18.36
  • SqFt 4416

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 Realty

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: 3.95% last updated on Apr 27, 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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97a Owl Ridge Road, Woodbury, CT 06798

Price$1,890,000

Est. Mortgage: $/month

CMLS 99111364

  • Residential
  • Bedrooms 4
  • Acreage 3
  • Square Feet 5000

Enjoy This Wonderful Lifestyle On Owl Ridge, One Of The Most Exclusive Subdivisions In Woodbury Ct. Breath Taking Views In Private Setting Only Few Lots Left. This Distinguished Custom Home Is Built To Perfection By Corbo.

Listing Courtesy of William Raveis Southbury

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: 3.95% last updated on Apr 27, 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 St South, Woodbury, CT 06798

InternalID L10229193

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Acres 8.36
  • SqFt 4416

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 Realty

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: 3.95% last updated on Apr 27, 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

505 Upper Grassy Hill Rd, Woodbury, CT 06798

InternalID L10194813

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 6.62
  • SqFt 3848

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 Realty

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: 3.95% last updated on Apr 27, 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

505 Upper Grassy Hill Road, Woodbury, CT 06798

Price$1,749,000

Est. Mortgage: $/month

CMLS 99173099

  • Residential
  • Bedrooms 4
  • Acreage 6.62
  • Square Feet 3848

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

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: 3.95% last updated on Apr 27, 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

556 Flanders Rd, Woodbury, CT 06798

Price$1,695,000

Est. Mortgage: $/month

InternalID W10208924

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Acres 20
  • SqFt 5500

GEOTHERMAL five bedroom custom-built colonial bordered by 200 acres of Flanders Nature Center land trust and only 90 minutes from NYC. Built with state of the art quality components, superior materials and craftsmanship, this house features a maintenance-free exterior, all oak hardwood flooring (3, 5, 7 inch pattern) and tile throughout, wood moldings, trim and panels, french doors and Smarthome technology The gourmet kitchen features antiqued granite counters, marble backsplash, and professional Sub Zero and Wolf appliances. Kitchen and eating area are open to the family room with fireplace and 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 the home for maximum performance. Please call your agent to provide a more complete and detailed features list of all this custom home has to offer.

Listing Courtesy of William Raveis Real Estate

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: 3.95% last updated on Apr 27, 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

17 Gate Post Ln, Woodbury, CT 06798

Price$1,695,000

Est. Mortgage: $/month

InternalID L10141824

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 10.23
  • SqFt 6500

Stately Georgian Manor. Custom built by current owners. Pillared long alarmed driveway. Approach leads to circular drive front entrance. Stucco exterior. Large stone terrace overlooking lush landscaping contributes to the park-like setting.Meticulously maintained. Hip Roof, 23 ft. ceiling in dining and living room including a bank of 23 ft floor to ceiling rue palladium windows which grace the interior of the home allowing exceptional natural light. French doors, State of the art alarm system including 4 security cameras. Large stone terrace overlooking lush landscaping contributes to the park-like setting. Electro Static Air Filter provides a dust free environment. Full house water filtration system. Kitchen includes a double oven and built in "Crumb Vacuum" allowing for easy cleanup. All rooms are generous scale.Elegant details and woodwork are all hallmark throughout the gracious interior. Interior upper balcony also with true palladium window overlooking central living room and dining area lends to the open feel of the home. In ground propane tank...Above ground oil tank..Perfect house for entertaining. Rarely available exceptional glamour. Truly a pleasure to show and a MUST SEE!

Listing Courtesy of William Pitt Sotheby's Int'l Realty

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: 3.95% last updated on Apr 27, 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

17 Gate Post Lane, Woodbury, CT 06798

Price$1,695,000

Est. Mortgage: $/month

CMLS 99148659

  • Residential
  • Bedrooms 4
  • Acreage 10.23
  • Square Feet 6542

European Inspired Stately Home On 10 Private Acres W/long Circular Driveway, Fabulous Stone Terrace That Overlooks The Lush Landscaping & The Park-like Setting. Elegant Details & Woodwork Are Hallmarks Throughout The Gracious Interior. Amazing Palladian Windows, French Doors & 23 Ft Ceilings, Grace The Living & Dining Rms, Allowing Exceptional Natural Light. Living Rm Also Boasts Marble Fireplace. Interior Balcony Lends To The Open Feel Of The Home. Gourmet Kitchen, Family Rm W/stone Fireplace, Study W/coffered Ceiling & 1st Floor Master Suit. Upper Level Offers 2nd Master Suite & 2 Additional Bedrooms Both En-suite. State Of The Art Alarm System W/4 Security Cameras. This Is A Perfect Home For Entertaining W/exceptional Glamour. Must See!

Listing Courtesy of William Pitt Sotheby's

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: 3.95% last updated on Apr 27, 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

36 E Hill Rd, Woodbury, CT 06798

Price$1,595,000

Est. Mortgage: $/month

InternalID L10220555

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Acres 7.19
  • SqFt 6911

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 The Matthews Group

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: 3.95% last updated on Apr 27, 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

32 & 40 Peter Rd, Woodbury, CT 06798

Price$1,595,000

Est. Mortgage: $/month

InternalID W10198589

  • Residential
  • Bedrooms 5
  • Bathroom 7
  • Acres 5.36
  • SqFt 5087

Warm, Welcoming and Wonderful... Hold on to your heart, Welcome to the Quintessential Country Estate! Located on a quiet road between historic Woodbury and Washington, CT this is the perfect full time or weekend residence. Privacy, elegance and functionality abound in this entertainers paradise. Relax and unwind on 5 acres of tranquil lush gardens, stone outcroppings and terraces. The magnificent interior is enhanced by a remarkable high end kitchen complete with Wolf dual-fuel oven range, built-in KitchenAid dishwasher, hidden appliance garage, Sub zero fridge, granite counters and breakfast area with oversized picture windows which allow for great light and views from every room. Special features include a home security system, sound system, LED landscape lighting, lighted tennis court, inground pool, 1 bedroom pool house studio, 1 bedroom carriage house, a fountained pond and so much more. Close to town and all amenities. Easy commuter location - 90 mins from NYC.

Listing Courtesy of William Raveis Real Estate

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: 3.95% last updated on Apr 27, 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

  © 2017 Greater Fairfield County CMLS, Inc. All rights reserved.

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the Greater Fairfield County CMLS, Inc. Real estate listings held by brokerage firms other than The Matthews Group are marked with either the “IDX Detail Logo” or the "IDX Thumbnail Logo” (a little black house surrounding the letters “IDX”) and detailed information about them includes the name of the listing broker.