The Matthews GroupWilliam Raveis

The Matthews Group

Woodbury CT Real Estate

Located approximately 85 miles north of New York City and referred to as Connecticut’s “Antique Capital” is Woodbury. Woodbury Woodbury Connecticut has become a very popular spot for food, giving it the nickname “Foodberry”, as many great restaurants have recently opened or renovated their spaces. 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 classic New England charm, with gorgeous sweeping landscapes, well restored Colonial, Greek Revival, and Victorian homes and simple cultural appeal.Curtis House in Woodbury

Properties in Woodbury

Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

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1204 Main Street South Woodbury CT 06798
Pending Continue to Show

MLS Number 170362476

  • Single Family
  • Square Feet 5,415
  • Bedrooms 8
  • Bathroom 9
  • Year Built 1827

The Main House was built in 1827, an addition was added in the 1990's. The property is within "Woodbury Historic District No.2" Part of the history of Woodbury can be found out front on the stone wall facing the street - A Benjamin Franklin Mile Stone Marker. Previously was The Longwood Country Inn. Just recently it was The Olive Tree Restaurant - the dining room seats 50, in the Summer the patio can serve 40. The property is 4.34 acres which extends back to 240' of frontage on the Pomperaug River. This large Colonial has 8 Bedrooms - 6 have full bathrooms, 2 share a full bathroom, 6 Fireplaces and Hardwood Floors. A blue stone patio lies out back. Beautiful flowering shrubs and perennial flowers can be found around the property. Gorgeous sunsets year round! This property can be used for an Inn, a restaurant or a private home, or a gathering place for families and friends to spend Holidays or to just get together yet still have their own space!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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12 Strong Field Road Woodbury CT 06798

Woodbury, CT12 Strong Field Road

Price$632,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170449690

  • Single Family
  • Square Feet 1,400
  • Year Built 2022
  • Bathroom 2
  • Property Style Ranch

In town single level home in a small cul de sac in the heart of historic Woodbury. Just a 5 minute walk to schools, shopping, and restaurants! Scale down into this cozy two bedroom home with a kitchen/great room with vaulted beamed ceiling and corner fireplace. Just 1 or 2 steps from the garage to the living area and room for additional sq ft in the bonus room or in the lower level.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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1917 Main Street North Woodbury CT 06798

MLS Number 170422373

  • Single Family
  • Square Feet 3,523
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 2

Live, work, and play on Main Street North, Woodbury. Over 3500 sq feet in this Italianate Antique home with high ceilings, a gorgeous newer kitchen with an eat-in area, pantry, granite counters, and stainless appliances. The main level office and artist room provide an ideal spot for an in-home business or an antique shop as it once was. All the amenities one would expect in a charming older home including substantial moldings and built-ins, two staircases, specialty stainless skylights, a cupola, and three fireplaces. This Main Street home is situated on a private yet open 6-acre lot with a beautiful 28x53 post and beam barn overlooking a pond, and a 21 x 45 workshop with heat. The barn would make an ideal guest house or just plenty of storage with driveway access and a full walkout lower level. The workshop is heated and perfect for those staying at home to work. Bring the dirtbikes & quads and really enjoy the six-acre parcel or bring the animals and run your own farm. This convenient location is only within 5 minutes to Woodbury, Watertown, and Bethlehem town centers as well as many golf courses and private schools.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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224 Railtree Hill Road Woodbury CT 06798

MLS Number 170443378

  • Single Family
  • Square Feet 2,400
  • Bathroom 3
  • Property Style Ranch, Modern
  • Bedrooms 3

This spacious MID-CENTURY MODERN 2 level home has been completely remodeled and is just 5 minutes from the center of Town. Sleep soundly knowing everything has been upgraded or replaced from the new propane-fired furnace, heated tile floors and hardwood, new windows, galvanized gutters, new bladder tank, a whole-home water filter, and painted in and out. The 1960's one-of-kind Dutch fireplace is the focal point in the living/dining area for additional coziness and ambiance. Nearby is the kitchen with quartz island and countertops, floating shelves, and a full pantry around the corner. The generous-sized, main-level master suite was designed with a custom closet and full bath with heated Italian porcelain tiled floor, frameless shower, and floating vanity. Enjoy the lower level family room with 2 bedrooms and a full bath with soaking tub and washer/dryer hookups. AND IF THAT'S not enough, how about a whole house 14kw generator w/auto transfer switch, SONOS speaker system w/individual amps for master bath, living room, and outdoor deck...also connect all your wireless devices to the Eero wireless WIFI system, cad 6 outlets, and accessible security camera system monitored via your phone. Storefront/glass garage doors w/app enabled door opener, newly paved driveway, large level lot. Short drive to NYC. Broker related to Seller.

Listing Courtesy of Town & Country Realty and Design,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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201 Orchard Avenue Woodbury CT 06798

MLS Number 170436576

  • Single Family
  • Square Feet 2,000
  • Year Built 2021
  • Property Style Colonial
  • Bathroom 3

TO BE BUILT! Welcome to Fawn Meadow Estates, Lot #22. Impressive NEW HOME to be built by Trofa Construction; a reputable builder with impeccable attention to custom details, who has been building high end homes in Fairfield and Litchfield counties for the last 36 years! A 3/4 Bedroom / 2.5 bathroom Modern Farmhouse home on a private, lot surrounded by nature. Inside the home you have a sought after open floor plan with combination kitchen, dining area, and great room! The second level offers a master suite with walk in closet and private bath, two bedrooms, a jack-and-jill bathroom, and a finished bonus space over the garage which could be used as a fourth bedroom/office/bonus room. Fawn Meadow offers a convenient commuter location within a lightly wooded neighborhood bordered by flowering meadows, with yearly views! Still time to make changes and pick out your finishes. Call for detailed home specs and set up a time and meet the builder! Interior renderings and home drawings are not house specific and include some optional details. Just 30 miles to Southeast Station, and less than 90 miles to NYC! No deed restrictions. (Fawn Meadow is not recognizable with GPS, type in 166 Orchard Ave, Woodbury - subdivision entrance is directly across the street!)

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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11 Knoll Road Woodbury CT 06798

Woodbury, CT11 Knoll Road

Price$599,000

Est. Mortgage: $/month

MLS Number 170441564

  • Single Family
  • Square Feet 3,556
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1981

Gorgeous 1980's high quality contemporary, set on just under 2 acres of open level and lightly wooded land. Modern design elements with soaring ceilings, grand glass sliders, walls of glass and native stone fireplace which bring the feeling of the outside in! Minutes to both Woodbury Center and Roxbury, this oasis is privately sited on a quiet lane with a long driveway.. Covered parking for 5 cars, with an attached 2 bay and an additional 3 bay garage. The gracious layout with grand public spaces, wraparound deck with access from each room, High Ceilings and a finished lower level with family room or gym are just some of the amenities which make it the perfect getaway. The Master suite is also on the first level with a nearby office/den to make one level living easy. This special home is a gem and just moments to Woodbury Center and Roxbury... and only 90 minutes from Manhattan!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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Town Line Road Woodbury CT 06798

MLS Number 170314046

  • Land
  • MLS Status Active
  • Acreage 33.71
  • Other Amenities Golf, Waterfront
  • Zoning OS100

Beautiful open farmland at the end of Town Line Road off of Main Street North. Nestled in the Woodbury, Watertown, and Bethlehem corner this secluded parcel offers easy access to everything. Three town centers, many restaurants, private schools, golf courses, and minutes to route 8. Most of the property abuts 50 acres of open space owned by the Town of Woodbury ensuring complete privacy and easy access to the Nonnewaug falls. A terrific opportunity to live off the grid!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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 Davids Hill Road Woodbury CT 06798
Open House

MLS Number 170452601

  • Single Family
  • Next Open House: Sun 12/12 11:00 am. to 1:00 pm.
  • Square Feet 2,475
  • Bedrooms 4
  • Bathroom 3

Welcome Home to 59 Davids Hill Road. This beautiful cedar shake colonial sits in a great location at the end of the cul-de-sac just off Flanders Rd in Litchfield County. There is great flow throughout this home with FIRST FLOOR LIVING if needed! This open concept layout offers living room with fireplace, dining and kitchen all open and available to entertain. The large en-suite Master bedroom has french doors to a new composite deck to enjoy your morning coffee. Formal dining and a nice large foyer lead up to the paneled staircase and the second floor. Three bedrooms, one with a window nook all have ample closet space and brand new carpeting. A gorgeous fully remodeled bathroom finishes off the second floor. The list of upgrades is long covering most of the large ticket items, i.e. roof, gutters, furnace and central air (2014) Water heater (2016) Siding and paint (2020) and much more. Woodbury has so much to offer and was just listed as one of the most quaint towns in the U.S. Enjoy shopping, award winning restaurants, close proximity to major highways and 1.5 hours to NYC.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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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100 Main Street North Woodbury CT 06798

Woodbury, CT100 Main Street North

Price$575,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170447315

  • Single Family
  • Square Feet 3,390
  • Year Built 1750
  • Bedrooms 4
  • Property Style Colonial

Settled in 1673, Woodbury is one of Connecticut's premier historic destinations with its Main Street lovingly referred to as the “Antiques Capitol of Connecticut”. Like many of the other registered homes, 100 Main Street North has been subtly modified to accommodate a modern use. From the road it is simply regarded as a lovely central chimney colonial, in keeping with its neighbors the exterior has been left unmodified from its original construction in 1750. Pull up the adjacent drive and you gain access to the four private dwellings as well as the three outdoor storage spaces. Each living area has an element that gives nod to the 270 year old construction, whether it be the wide plank hardwood floors or original exposed beams, the home's history peaks forth to its present residents. Currently the home is acting as an investment property, but if desired can be returned to a single family dwelling or used as a place of business. Sited at the end of the Main Street walking path and directly across from one of Connecticut's most notable organic markets, this property is ideally located. Woodbury was once a secret but more recently has been finding its name in large publications such as the New York Times, with its rustic charm and historical beauty both being admired as the place to be- this is certainly an opportunity to seize.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

100 Main Street North Woodbury CT 06798

Woodbury, CT100 Main Street North

Price$575,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170446829

  • Multi Family Multi-Family For Sale
  • Square Feet 3,390
  • Bathroom 4
  • Bedrooms 4
  • Year Built 1750

Settled in 1673, Woodbury is one of Connecticut's premier historic destinations with its Main Street lovingly referred to as the “Antiques Capitol of Connecticut”. Like many of the other registered homes, 100 Main Street North has been subtly modified to accommodate a modern use. From the road it is simply regarded as a lovely central chimney colonial, in keeping with its neighbors the exterior has been left unmodified from its original construction in 1750. Pull up the adjacent drive and you gain access to the four private dwellings as well as the three outdoor storage spaces. Each living area has an element that gives nod to the 270 year old construction, whether it be the wide plank hardwood floors or original exposed beams, the home's history peaks forth to its present residents. Currently the home is acting as an investment property, but if desired can be returned to a single family dwelling or used as a place of business. Sited at the end of the Main Street walking path and directly across from one of Connecticut's most notable organic markets, this property is ideally located. Woodbury was once a secret but more recently has been finding its name in large publications such as the New York Times, with its rustic charm and historical beauty both being admired as the place to be- this is certainly an opportunity to seize.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

225 Orchard Avenue Woodbury CT 06798

MLS Number 170436579

  • Single Family
  • Square Feet 1,800
  • Year Built 2021
  • Property Style Colonial
  • Bathroom 3

TO BE BUILT! Welcome to Fawn Meadow Estates, Lot #23. Impressive NEW HOME to be built by Trofa Construction; a reputable builder with impeccable attention to custom details, who has been building high end homes in Fairfield and Litchfield counties for the last 36 years! A 3 Bedroom / 2.5 bathroom Modern Farmhouse Colonial on a private, lot surrounded by nature. Inside the home you have a sought after open floor plan with combination kitchen, dining area, and great room! The first floor is complete with a laundry room, powder bath, and mudroom! The second level offers a master suite with walk in closet and private bath, two bedrooms, a jack-and-jill bathroom, and a bonus space over the garage which could be finished as a fourth bedroom/office/bonus room, or left unfinished! Finishing this space adds an additional aprox 300 square feet. This 2100 square foot option is offered at $619,000. Fawn Meadow offers a convenient commuter location within a lightly wooded neighborhood bordered by flowering meadows, with yearly views! Still time to make changes and pick out your finishes. Call for detailed home specs and set up a time and meet the builder! Interior renderings and home drawings are not house specific and include some optional details. Just 30 miles to Southeast Station, and less than 90 miles to NYC! No deed restrictions. (Fawn Meadow is not recognizable with GPS, type in 166 Orchard Ave, Woodbury - subdivision entrance is directly across the street!)

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

305 Main Street South Woodbury CT 06798

Woodbury, CT305 Main Street South

Price$504,900

Est. Mortgage: $/month

MLS Number 170424411

  • Single Family
  • Square Feet 2,015
  • Bathroom 3
  • Property Style Colonial
  • Year Built 1835

Soon to completed tastefully restored vintage in the heart of down town Main Street South. Walk to all the town's amenities within a few minutes from your home or take in the views and the beauty of historic Main Street from your brand new front porch. Taken down to the studs, this antique will feature wide board hardwood flooring, exposed beams, vaulted ceilings and a first floor master bedroom. All new mechanicals including plumbing, electrical, heating and central air. The main level will provide a brand kitchen with a vaulted ceiling, a first floor bedroom and a living room with a fireplace opening to a cozy front porch. The upper level offers a bedroom with a cathedral ceiling, a second bedroom, office, and two full baths. Move to the action and enjoy downtown Woodbury!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 2021
* 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 TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.