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The Matthews Group

Recently Listed Homes in Woodbury CT

Browse recently listed homes for sale in Woodbury, CT below. You may also be interested in viewing all available homes in Woodbury.

Newly Listed Homes for Sale Woodbury

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

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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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6 Fawn Meadow Lane Woodbury CT 06798

MLS Number 170455411

  • Single Family
  • Square Feet 2,467
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2022

TO BE BUILT! Welcome to Fawn Meadow Estates, Lot #20. 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 Cape with beautiful views to enjoy from your welcoming front porch. Inside the home you have vaulted ceilings, a combination kitchen, dining area, and great room! The first floor is complete with an office just off the foyer, and a MAIN LEVEL, MASTER SUITE, with enough room for a sitting area, overlooking the rear porch with complete privacy from the OPEN SPACE that this specific lot offers! The second level offers two bedrooms, a jack-and-jill bathroom, and your laundry 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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13 Washington Road Woodbury CT 06798

Woodbury, CT13 Washington Road

Price$259,000

Est. Mortgage: $/month

MLS Number 170445999

  • Single Family
  • Square Feet 2,085
  • Bathroom 2
  • Year Built 1829
  • Property Style Colonial

This vintage home includes 4 bedrooms with one on the third floor that is spacious and has plenty of storage. The wide board floors throughout the home together with some oversized windows makes it sunny and bright. Enjoy the covered porch and extra large patio looking out onto the long deep lot with an "as is" vinyl pool. This home is located seconds from Main Street and walking distance to the library, stores, community theater, community center, schools and playgrounds. Enjoy the parks and hiking trails and keep in mind that Woodbury was featured in the May, 2021 New York Times as "peace, quaint beauty and a sense of history." The Reader's Digest named it "Best Small Town in Ct." Located 1 1/2 hr by car to NYC and 1/2 hr by train. Major routes are close by as are private schools, golf courses, country clubs and great restaurants. Enjoy concerts in the park and hiking trails to a tower overlooking the town!! This home needs much work and is being sold "as is."

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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97 Main Street South Woodbury CT 06798

Woodbury, CT97 Main Street South

Price$495,000

Est. Mortgage: $/month

MLS Number 170361509

  • Single Family
  • Square Feet 3,000
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1823

This 1823 Colonial makes a statement! Five fireplaces, wide board flooring, exposed beams, original paneling, hardware and large welcoming rooms. Remodeled eat in kitchen, extensive custom reproduction cabinetry, center island w under counter bar, room for full size dining table - French door out to enclosed porch & one of two stone patios. Entertain in the large living room boasting the main fireplace with bee hive oven and surrounded by warmth w original paneling, cubbies and exposed beams. Work from home in the amazing front room, all set up as an office with walls of custom built ins & desk top area designed to look like authentic built ins when all closed up-A huge bonus in these times! Formal dining room with fireplace, currently being used as a first floor bedroom. Four generous sized bedrooms upstairs all have wide board flooring, two with cozy fireplaces. Fifth, smallest bedroom could make a perfect master bath. All rooms are light filled. Front and back stairs. So many beautiful original features, ready for your own personal changes and to carry on the history. Historic Main Street Woodbury, named "Best Small Town in CT" by Readers Digest. 1/2 hour to train station or 1.5 hrs to NYC. Subject to easement for shop (adjacent building) parking and septic.

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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4 Main Street South Woodbury CT 06798

Woodbury, CT4 Main Street South

Price$289,900

Est. Mortgage: $/month

MLS Number 170454163

  • Single Family
  • Square Feet 2,976
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1920

Opportunity is knocking! Many possibilities for this long-time mixed-use property including the possibility of an in-home business, a commercial first floor use, and a second-floor apartment or, two residential rentals each with over 1800 square feet. This post and beam structure provides large spans allowing for many different floor plans. Most recently used as the home of the Powder Room, this 1800 first floor area has been tastefully renovated and could be used as a single-level home with no steps! All upgraded mechanicals, beautiful wide Chesnut wood flooring, large rooms, a private office and don't forget that gorgeous front porch to take in all the action of Main Street. The upper level has been completely gutted to the beams and is ready for one's imagination. A wide-open area with a full third floor/attic that could be easily vaulted and finished, exposing all those hand hewn-beams. The current owner has run all the necessary electrical and heating ducts to the second floor making conversion easy for the next owner. Located right smack between Main Street South and North this home doesn't miss a beat!

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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294 Railtree Hill Road Woodbury CT 06798

Woodbury, CT294 Railtree Hill Road

Price$384,900

Est. Mortgage: $/month

MLS Number 170447084

  • Single Family
  • Square Feet 2,770
  • Year Built 1998
  • Bathroom 4
  • Property Style Colonial

Rare find. 3 acres, 10 Rooms 2 car garage. Colonial with Formal Living room and Dining room, eat in kitchen with large windowed breakfast nook, huge bonus room with vaulted ceilings and fireplace. Main bedroom with walk-in closet and full bath. 3 more bedrooms all located in a private serene setting. Perfectly located for easy access to Parks, Museums, Shopping, and near Good Hill Farm Airport for the occasional or regular elite aeronautical commuter. Don't let this one get away. Will require some personal touches but will qualify for conventional financing.

Listing Courtesy of New England Realty Assoc 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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5 Westwood Road Woodbury CT 06798

Woodbury, CT5 Westwood Road

Price$419,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170452826

  • Single Family
  • Square Feet 1,961
  • Bedrooms 3
  • Year Built 1907
  • Bathroom 2

This immaculate early 1900s Colonial has been perfectly restored to "like new" condition inside & out. The perfect combination of old and new situated on a peaceful tree lined street overlooking a beautiful pond and open fields. Just minutes to the center of town, shopping, highways and everything Woodbury has to offer. A bright & airy layout with hardwood floors throughout both levels is perfect for today's lifestyle. Tastefully renovated open concept kitchen w/granite counter tops, custom soft close cabinetry, stainless steel appliances & tiles back splash flows into the dining area and fireplaced living room. THIS HOME HAS IT ALL-whole house generator, new roof, new well tank, vinyl siding, LED lighting, new appliances and a 2 car garage with a seperate heated workshop. Don't miss out on this turn key opportunity!

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

12 Hard Hill Road Woodbury CT 06798

Woodbury, CT12 Hard Hill Road

Price$409,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170414302

  • Single Family
  • Square Feet 2,570
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1977

Welcome home to 12 Hard Hill Road, Woodbury, Come see what one-level living is really like, you will love the openness of this beautiful updated kitchen and dining room with a floor-to-ceiling brick fireplace.Over 2,500 sq/ft. Gleaming Hardwood floors thru-out the first floor, including the 4 large Bedrooms !! The lower level has a Large Family room with another floor-to-ceiling brick fireplace, and a slider out to the rear yard. The lower level also has a bonus room great for the kids or office space and a 2-Car garage, Nice professionally landscaped level grounds. A home to be proud of in beautiful Woodbury.

Listing Courtesy of Showcase Realty,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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178 Quassapaug Road Woodbury CT 06798

Woodbury, CT178 Quassapaug Road

Price$449,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170450829

  • Single Family
  • Square Feet 2,033
  • Property Style Cape Cod
  • Year Built 1979
  • Bedrooms 3

Welcome Home!! This beautifully maintained and updated Cape is the perfect place to call home. At first sight, this dormered oversized Cape offers lovely curb appeal. Once inside you will find a spacious front to back Living room and Dining room combo with a cozy fireplace. The eat in kitchen offers newer stainless steel appliances, granite counters, a large reach-in pantry, laundry closet and a back door to the grilling deck. The 1st floor master bedroom suite has a full bath and 3 double door closets for plenty of storage. There is also an update half bath on the first floor. Upstairs you will find 2 enormous bedrooms and another updated full bath. Gleaming hardwood floors are though-out most of this beautiful home and the newer windows, roof and boiler will give you years of low maintenance comfort. The finish-able lower level has high ceilings, loads of storage room and another laundry hookup if you would like. There is an awesome oversized shed with a heated workshop for those who like to tinker and the private back yard is a great place to unwind after a long day. Situated in a charming country setting but still close to shopping and entertainment. You can enjoy some of Woodbury's wonderful fine dining, antiquing, brewery, wine trail or a flea market. You won't want to miss this one!

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

96 Stagecoach Road Woodbury CT 06798

Woodbury, CT96 Stagecoach Road

Price$450,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170450333

  • Single Family
  • Square Feet 2,330
  • Year Built 1994
  • Property Style Cape Cod, Colonial
  • Bathroom 3

Perfectly situated near the end of a neighborhood cul-de-sac in a desirable setting-this classic Connecticut colonial/cape style home welcomes all victors with a charming front porch and nicely landscaped grounds. Upon entry one immediately notices the gleaming hardwood floors that traverse the main level and guide you to the formal yet relaxed living and dining rooms. The open concept kitchen and family room with cozy fireplace and vaulted ceilings create a wonderful space to entertain family and friends alike. The main level owner's suite with well-appointed full bathroom, walk-in closet and sitting area is the perfect respite at the end of a long day. Three generously sized bedrooms with large closets and another light and bright full bathroom await on the upper level. The walk-out lower level await your finishing touches. Large rear deck looks out upon the gently sloping and private backyard. Wonderful location, great pride of ownership and ready for its next owner!

Listing Courtesy of Keller Williams Realty

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

107 Sprain Brook Road Woodbury CT 06798

Woodbury, CT107 Sprain Brook Road

Price$499,000

Est. Mortgage: $/month

MLS Number 170448145

  • Single Family
  • Square Feet 2,760
  • Bedrooms 3
  • Bathroom 3
  • Property Style Ranch

A sprawling, single level home in Connecticut's "most charming" town. Located a short drive from the town centers of historic Woodbury, Roxbury and Washington, this home provides a convenience to area private schools, award-winning restaurants, hiking trails, and wineries. Sit on the flagstone front landing or the back and side decks to enjoy the peaceful sounds of Sprain Brook. Plenty of room to play and entertain on this property's 3+ acres. There is much to see here with 2,700 sqft separated into two wings, this home includes ten rooms, three bedrooms, 2.5 baths, formal living and dining rooms, family room, study, and home office. The kitchen and baths will need your own creativity, but good bones exist here with newer hot water heater, roof, gutters, HVAC, well pump and generator hookup! Very generously sized rooms and a huge amount of basement and garage storage space for your toys and power equipment. Excellent opportunity for one-level living or a weekender's retreat just 90 minutes from New York City. Come make this home your own and enjoy everything this quintessential New England town has to offer before the first snow falls!

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

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.