Woodbury CT Luxury Homes for Sale

Find the latest luxury homes for sale in Woodbury, CT. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. Contact us for more information and to schedule a showing.

32 & 40 Peter, Woodbury, CT 06798

Price$1,249,000

Est. Mortgage: $/month

MLS Number 170088765

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 4
  • Acreage 5.36

2 parcels with 2 houses beautifully sited in a pastoral setting complete with perennial gardens, stone walls, and lofty pines. Located on a quiet road between historic Woodbury and Washington, CT, this offering includes a 3-bed/2.2-bath primary residence w 2-car garage, gunite pool w 1-bed poolhouse, tennis court, and 1-bed guest house w its own address. The 3,400 sq/ft home includes a formal dining room, formal living room with 1 of 5 fireplaces. Large-scale kitchen boasts a walk-in pantry, Sub Zero & Wolf appliances, eat-in dining area, family room with brick fireplace, walk-out to stone terrace & built-in grill area. 3 generous sized bedrooms include a peaceful master with 3rd fireplace & walk-out, en suite bathroom with marble flooring, glass shower, & dressing room. Other interior highlights incl a warm, walnut-paneled library with 4th fireplace, laundry room, & full basement with fireplace. Outdoors you'll enjoy Woodbury summers in the beautiful bluestone-wrapped Gunite pool-the focal point of the 5+-acre lot w lighted tennis court, stone terrace, perennial gardens and specimen plantings, & room for many outdoor activities. Completing the main property is a pool house with 1-bed/1-bath, sitting area w 2 add'l garage spaces. The 1-bed/1.1-bath guest house includes full kitchen, living/dining room with fireplace, 2 walk-in closets & garage. Total privacy in the very heart of Woodbury Ct. Near town, shopping, skiing, golf and organic farm stands-90 mins from NYC.

Listing Courtesy of William Pitt Sotheby's Int'l

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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: 4.57% last updated on Jun 21, 2018
* 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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17 Gate Post, Woodbury, CT 06798

Price$1,445,000

Est. Mortgage: $/month

MLS Number 170088216

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 10.23

Stately Georgian Colonial with Celebrity appeal. This one owner master piece was custom built on a secluded lot at the end of a long security protected driveway. The dramatic curb appeal is apparent as you drive up to the property with stone walls, lush landscaping and a beautiful stucco exterior. As you enter the home the open floor plan creates a perfect environment for entertaining with 23 foot ceilings, marble floors, 23 foot floor to ceiling palladium windows, and a balcony that sits high above the family room. The attention to detail is one of a kind with fine trim work and moldings through out the home. The home features 2 master bedrooms one on the first floor and one on the second, both complete with large closets and full master baths. The other 2 bedrooms both have ensuite baths and great size and storage. With a gourmet kitchen, 3 car garage, mud room, dining room, and over 10 acres of land this home is truly a rare find. Everything is meticulously maintained and secured with a state of the art security system. Your search ends with one showing!

Listing Courtesy of Century 21 AllPoints Rlty

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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: 4.57% last updated on Jun 21, 2018
* 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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162 Middle Road, Woodbury, CT 06798

Price$1,300,000

Est. Mortgage: $/month

MLS Number 170081148

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 83.38

WOW!! WHAT A LOCATION AND VIEWS LIKE YOU ON ARE THE BIG SCREEN!! Absolutely majestic on a hilltop 83 acre piece of heaven! Views of the entire town of Woodbury from this gigantic Contemporary Colonial. Possible 20 lot subdivision with access and frontage on two roads. Seperate apartment above the garage along with a 3 story barn. Beautiful craftsmenship inside from the hand carved chimney to the immaculate granite countertops. Amazingly maintained and cared for by the owner who put a lot of love into this home and property.

Listing Courtesy of Century 21 AllPoints Rlty

{$office->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: 4.57% last updated on Jun 21, 2018
* 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, Woodbury, CT 06798

Price$1,799,999

Est. Mortgage: $/month

MLS Number 170076583

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

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 Real Estate

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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$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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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 A Main, Woodbury, CT 06798

Price$1,849,000

Est. Mortgage: $/month

MLS Number L10229193

  • Single Family
  • Property Style Colonial, Antique
  • 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

{$office->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: 4.57% last updated on Jun 21, 2018
* 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

920 Main, Woodbury, CT 06798

Price$2,195,000

Est. Mortgage: $/month

MLS Number L10229171

  • Single Family
  • Property Style Colonial, Antique
  • 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...Tax and assessment include 912 Main St.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->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: 4.57% last updated on Jun 21, 2018
* 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.