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.

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

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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: 3.92% last updated on Nov 2, 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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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: 3.92% last updated on Nov 2, 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: 3.92% last updated on Nov 2, 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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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: 3.92% last updated on Nov 2, 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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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

{$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: 3.92% last updated on Nov 2, 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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162 Middle Road, Woodbury, CT 06798

Price$1,990,000

Est. Mortgage: $/month

MLS Number L10234253

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

High above Woodbury's town center in Litchfield County is this beautiful custom home located on 82 acres. A current feasibility study shows a possible 20 lot subdivision or gifting opportunity with frontage and access from two roads. Caretaker apartment and meticulous three story barn. This energy efficient and well maintained property offers privacy and views. One of a kind opportunity!! Also, listed under land MLS#L10234828

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: 3.92% last updated on Nov 2, 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: 3.92% last updated on Nov 2, 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: 3.92% last updated on Nov 2, 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: 3.92% last updated on Nov 2, 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: 3.92% last updated on Nov 2, 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, Woodbury, CT 06798

Price$1,695,000

Est. Mortgage: $/month

MLS Number W10208924

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 20

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

{$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: 3.92% last updated on Nov 2, 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

40 Peter, Woodbury, CT 06798

Price$1,595,000

Est. Mortgage: $/month

MLS Number W10198589

  • Single Family
  • Property Style Ranch
  • Bedrooms 5
  • Bathroom 7
  • Acreage 5.36

A hidden gem in the Antique capital of CT! This one of a kind, owner remodeled, spectacular home will become a place of pride for you, your family and guests. Built in 1976, this 5,000+ sf. open concept, deluxe property seamlessly adapts to whatever your day might bring. Enjoy beautiful views of your gorgeous gardens, stone outcroppings & terraces. Every inch of this home speaks to the quality materials finishes and meticulous attention to detail. 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. Have a cocktail party, an evening tennis match on your professionally lighted tennis court, cookout on your built-in gas grill or a nighttime swim. There is plenty of room for entertaining large groups or just an intimate dinner party under the stars. Great rental opportunity for the guest or pool house and winter storage for multiple vehicles. Guest house has 1,147sf - 1 BR, 1 bath, 1 car garage. Pool house has a loft bedroom, 1 bath and 2 car garage. You won't stop discovering the treasures this custom built home has in store for you. What will you make of it? The ultimate luxurious hideaway? A gardeners paradise?

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: 3.92% last updated on Nov 2, 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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