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.

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.

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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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36 East Hill Road, Woodbury, CT 06798

Price$1,595,000

Est. Mortgage: $/month

CMLS 99185462

  • Residential
  • Bedrooms 5
  • Acreage 7.19
  • Square Feet 5651

Absolutely Spectacular Mosian Designed Home With Many Recents 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 Washington

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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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.

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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.

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132 Stone Pit Road, Woodbury, CT 06798

Price$849,000

Est. Mortgage: $/month

CMLS 99141591

  • Residential
  • Bedrooms 4
  • Acreage 5
  • Square Feet 5148

Very Private Custom Designed Ranch. Elegant Open Floorpan W/very Large Rooms And Soaring Ceilings. Bamboo Flooring, Gourmet Kitchen, Gas Fireplace, High Ceilings, And Full Unfinished Basement. Huge Master Br Has Bamboo Floors, A Luxurious Bath, Sitting Room, And An Exercise Room. There Is A Central Vacuum System Even In The Garage To Clean Your Cars. Music/intercom System With A Hookup For Your I-pod, Mp3 Player, Or Laptop. Vaulted Ceilings Range From 10' To 25' In The Family Room And Kitchen. 4 Zone Hydro-air With Electrostatic Filters, All Systems Are Of The Highest Quality. The Office On The Main Level Can Be A 4th Bedroom. Private Yet Convenient To Town. Must See To Appreciate!!

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

556 Flanders Rd, Woodbury, CT 06798

InternalID W10204622

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Acres 3
  • SqFt 5600

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 inquire 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

40 Peter Road, Woodbury, CT 06798

Price$1,595,000

Est. Mortgage: $/month

CMLS 99177067

  • Residential
  • Bedrooms 5
  • Acreage 2.86
  • Square Feet 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. Impeccably Well Kept. Grace, Style And Perfection.

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.

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

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

138 Scuppo Road, Woodbury, CT 06798

Price$895,000

Est. Mortgage: $/month

CMLS 99170692

  • Residential
  • Bedrooms 4
  • Acreage 24.57
  • Square Feet 2660

24 Acres, 4 Br Custom Home, Parking For 8 Vehicles Comfortably! Det 38x38 Metal Garage W 3 Overhead Dooors. 2- 10x12, 1- 10x14. Bring The Rv! Plus Heated Office, Bath And Loft. Home & Garage Built To Withstand Any Weather Condition, Self Sustaining W Full Auto Generators For Both, Cisterns For Water Reserve, Land To Garden-farm And Hunt! Professionally Landscaped W Fruit Trees & Berry Patches. Amazing Chicken Coop, 2 Addtn'l Out Buildings. Secluded, Yet On The Cusp Of 3 Towns. 2-3 Miles Of Cut Trails Traverse The Property, Perfectly Tamped 120x90 Area, Potential For Tennis, Basketball Court Or Riding Ring. Additional Open Paddock Area. Brook & 2 Small Ponds. Inground Heated Gunite Pool.

Listing Courtesy of Joyce Drakeley 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

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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.