The Matthews TeamWilliam Raveis

The Matthews Team

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

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Search by Property Type: Luxury Homes | Homes with LandSingle Family HomesCondos | Land

401 Hoop Pole Hill Road Woodbury CT 06798

Woodbury, CT401 Hoop Pole Hill Road

Price$2,150,000

Est. Mortgage: $/month

MLS Number 170405026

  • Single Family
  • Square Feet 6,216
  • Bedrooms 6
  • Bathroom 6
  • Year Built 2003

Stately Colonial with magnificent eastern views of the Litchfield Hills located on 27 peaceful secluded acres. A sweeping driveway through a 10 acre meadow leads you to the hilltop perch of this distinctive residence, a 20'x60' gunite heated pool, a full basketball court and a 1.5 story barn. Upon entry the foyer is flanked by the formal living room with a fireplace and the formal dining room with raised panels and chair rail. Cross the center hall to the informal great room with a coffered ceiling, a wall of windows, floor to ceiling fieldstone fireplace, built-in bookcases and French doors to the flagstone patio. The grand chef's kitchen features marble counters, abundant cabinets to the ceiling, 2 dishwashers, Wolf range and wall ovens and Subzero refrigerator, an island, a raised river-stone fireplace and slider to the patio. First floor has an ensuite bedroom and a screen porch overlooking the pool and the spectacular views. On the second floor all 4 bedrooms are ensuite. The master suite focal point is the stone wall with a raised propane fireplace. There is a dressing room and walk in closet. Laundry is on the second floor. The basement has 3 finished rooms suitable for a variety of uses and a home gym outfitted with Technogym equipment. The large ensuite room over the garage is perfect for guests or home office. Whole house generator. New windows. New in-ground internet cable with 1GB speed. Property abuts Roxbury Land Trust.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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49 Pond Valley Road Woodbury CT 06798

Woodbury, CT49 Pond Valley Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 170396419

  • Single Family
  • Square Feet 6,014
  • Property Style Colonial
  • Bathroom 5
  • Year Built 1994

MINT! MINT! MINT! Gorgeous 16 acre gated property with park like grounds and amazing water views. Totally private yet minutes from town. Explore the grounds or relax by the pool with built in hot tub. The house is move in condition and the current owners have upgraded just about everything. Wood floors on both levels with 9' ceilings. The large chef's kitchen is open to the family room, both having access to the blue stone patio and in ground pool. There is a sun room with stone floor off the family room also with access to the pool. The other main floor rooms include an office, formal living and dining rooms, a mud room, butlers pantry and 2 half baths. The upstairs includes an amazing master suite with its own sitting room, large walk in closet with a built in safe and a master bath with dual sinks, and whirlpool tub. 3 additional large bedrooms with walk in closets share 2 full baths, 1 jack & jill. There is an upstairs laundry on this level also. Some of the many upgrades include a state of the art alarm system, which includes opening & closing the gate from your phone. There are 2 driveway sensors, a trigger to turn light posts on at night all the way up the driveway, 24 zone sprinkler system you can operate remotely, Sonos speaker system for kitchen, office and patio area. See addendum for additional features. 2 state of the art Furnaces with Whole house humidifier's built in and Filters that include UV lights to kill any bacteria in the air.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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64 Hillside Road Woodbury CT 06798

Woodbury, CT64 Hillside Road

Price$1,199,000

Est. Mortgage: $/month

MLS Number 170463012

  • Single Family
  • Square Feet 6,965
  • Year Built 1987
  • Bathroom 4
  • Bedrooms 4

Luxurious, secluded country estate w/pool. You will fall in love with this custom built colonial that leaves nothing to be desired. Set back on a quiet country road in historic Woodbury, CT this home is on 4.42 verdant acres and offers privacy and a beautiful New England landscape. The first floor offers plenty of space for entertaining with an oversized family room with stone fireplace, sun room, den with fireplace, game parlor, LR and formal DR with fireplace. This home features large open kitchen with island, granite counters, Viking cooktop, double ovens and custom cabinetry. On the second floor are 4BRs and 3 full baths. The huge master suite has a formal fireplace, window seats, walk-in closets, and balcony. Suite also includes a sophisticated 14x15 wood paneled room with bookshelves and center island that could double as a study and closet. Enjoy sunset views in rear of house from multi level decks, outdoor fireplace. The spectacular in ground pool has granite deck and is set amongst trees, gardens, waterfall and spa. Cabana has full bath, cabinets, refrigerator and sink for food prep. Fully finished basement, 7 car garage w/in-law/staff quarters, kitchen & wood stove, approx 1200 sq ft not included in total sq ft. This home has been host to many gatherings with plenty of room for family and friends. If you are looking for a private retreat to call home, you've just found it. You will never want to leave!

Listing Courtesy of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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575 Weekeepeemee Road Woodbury CT 06798

MLS Number 170433479

  • Single Family
  • Square Feet 2,000
  • Year Built 1795
  • Bedrooms 3
  • Property Style Colonial

Unique opportunity to own approximately 87 acres with Antique home in need of T L C and Barnes. There are four lots that make up the 87 acres . One lot in Bethlehem and Three in Woodbury. Lot 1- 7.00 acres Located in Bethlehem, Ct. Lot 2 - 7.22 acres. Lot 3 with house and barns is -11.59 Acres and Lot 4 with 61.76 acres. Sold all together will not divide. Property is currently a operating horse boarding facility. Main Barn with a 60 x 120 indoor riding ring plus 20 stalls. Feed room and tack room. Offices on second floor. Two additional post and beam barns with stalls and loads of storage space and potential. Out door riding ring. The 1795 Colonial needs to be completely redone. It's down to the studs and awaiting to be remodel. Over all this property offers a loads of possibilities.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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198 Plumb Brook Road Woodbury CT 06798

Woodbury, CT198 Plumb Brook Road

Price$990,800

Est. Mortgage: $/month

MLS Number 170406410

  • Single Family
  • Square Feet 5,411
  • Property Style Colonial
  • Bedrooms 4
  • Year Built 2001

This magnificent 5,411 sq ft home which offers a perfect balance of elegance, livable refinement & classic appeal is situation on 3.84 private, park like acres adjacent to Flander's Nature Center. The property is beautifully landscaped & has an exquisite gunite heated pool & spa, custom stone work & gardens, a perfect outdoor retreat. This 11-room colonial welcomes you with a grand entrance and striking chandelier. The first floor has an expansive open floor plan which includes a formal living room & dining room, office, a large eat in kitchen that overlooks the pool & gardens, a family room with hard wood floors, 9-foot ceilings & a gas fireplace and one full and one-half bath. The second floor includes a lovely master bedroom suit with walk-in closet and a spa tub, three additional bedrooms & another full bath. The walk out lower level is another glorious living area with floor to ceiling windows, custom mahogany wine cellar, full bath & large entertainment area. French doors lead out to the stunning pool area with outdoor granite bar equipped with refrigerator & storage. This property also has two waterproof AZEK decks with lighting & a 2-story barn with cupola equipped with heat, air conditioning & electrical. There is a security system, sound system, underground propane tank & generator that services the entire house including the heated pool. This country estate has been meticulously maintained and is truly one of a kind. Floor Plan https://www.planomatic.com/mls64918

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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41 Steeple View Lane Woodbury CT 06798
Pending Continue to Show

MLS Number 170426776

  • Single Family
  • Square Feet 5,983
  • Property Style Colonial
  • Bathroom 5
  • Bedrooms 5

Fabulous design and style are evident throughout this 5200 square foot colonial in one of Woodbury's most desirable subdivisions! Located just two-minutes from the town center, this meticulously maintained and updated home provides generous room sizes, several different gathering areas, two fireplaces, extensive moldings, high ceilings, a two-story foyer, an expansive deck & patio, and a gunite pool. The main level includes a front to back formal living room with built-ins, fireplace & game area, a cozy office, a formal dining room just off the kitchen, a family room with a stone fireplace and back staircase, and finally a beautiful kitchen with a large center island and eat-in area overlooking the pool and yard. The upper level offers four guest bedrooms, one of two laundry areas, three full baths, and a luxurious master suite and master bath. A walkout lower level could make an ideal in-law apartment as it provides another gathering room, a second laundry area, a full bath, and your very own movie theater with eight comfy seats. This finished ground-level area conveniently walks out onto the patio surrounding the pool and provides easy access to changing areas and the full bath during picnics and gatherings. Other outdoor space includes gorgeous walkways, stone walls, level yard areas, a circular driveway, mature landscaping, and a three-car garage. Beautifully maintained, designed, and furnished!

Listing Courtesy of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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7 Strong Field Road Woodbury CT 06798

Woodbury, CT7 Strong Field Road

Price$899,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170457136

  • Single Family
  • Square Feet 2,900
  • Bedrooms 4
  • Year Built 2022
  • Property Style Cape Cod

New cape in Woodbury's in town subdivision. Walk to town, schools and restaurants!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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88 Curtiss Meadows Woodbury CT 06798

Woodbury, CT88 Curtiss Meadows

Price$799,900

Est. Mortgage: $/month

MLS Number 170433422

  • Single Family
  • Square Feet 5,744
  • Bathroom 5
  • Property Style Colonial
  • Year Built 2006

Space for everyone! Impeccably maintained and cared for home with close to 6000 square feet of living space and room to comfortably fit all generations under one roof! Nestled on a four-acre parcel in a quiet cul de sac at the southernmost end of Woodbury, this four-bedroom home provides generous room sizes, tons of closet space, two porches, and wood flooring throughout the first and second floor. Over 1500 square feet in the finished walk-out lower level with three rooms, a half bath, and a beautiful four-season sun porch that overlooks the grounds, mature landscaping, and abutting open space owned by Flanders Nature Center. The upper floor provides all good-sized bedrooms with newer wide pine floors, several walk-in closets with built-ins, and three full baths. The main level offers a two-story foyer, formal dining and living rooms with plenty of natural light, an eat-in kitchen overlooking a family room with a fireplace. Don't miss this home with its privacy, access to walking trails & acres of nature preserve, level lot, room for a pool, and plenty of area for outdoor activities. Just 2 minutes from downtown Woodbury, 5 minutes to 84 and 90 minutes to NYC!

Listing Courtesy of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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
Pending Continue to Show

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: 3.56% last updated on Jan 20, 2022
* 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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623 Upper Grassy Hill Road Woodbury CT 06798
Pending Continue to Show

MLS Number 170460842

  • Single Family
  • Square Feet 2,559
  • Bathroom 3
  • Year Built 1975
  • Bedrooms 3

Quintessential CT retreat designed by notable historic restorer Ed Cady. One of Woodbury's last original post and beam homes, this 3 bed, 2.5 bath is the ultimate country escape. Located on one of the most sought-after streets, this hilltop modern farmhouse has spanning eastern and western views from every vantage point. Relocated in 1975, this charming home provides all the old world amenities including wide plank flooring, 4 brick fireplaces, and exposed hand hewn beams, yet still providing a desirable open floor plan. Upon entry, the original brick encased stairwell with a 4'x4' skylight leads to a sitting room with sliding barn doors, and a master bedroom suite with cathedral ceiling, many built ins, plaster coated walls and one of the four gorgeous brick fireplaces. The kitchen was renovated in 2021 and boasts custom cabinets with antique brass fixtures, Carrara marble kitchen island, quartz countertops, 8 burner Italian gas stove, commercial grade Viking hood and state-of-the-art stainless appliances.The upper deck was expanded in 2018 to accommodate an outdoor dining area and the lower deck, which leads to two additional bedrooms, family room & laundry, have floor to ceiling sliders which allow for year round enjoyment. Many exterior features including granite stone veneer around the foundation, antique stone steps. blue stone walls and a country landscape design. A custom Bocce Ball court and hilltop Adirondack lookout round out this truly special country retreat.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 Cowles Road Woodbury CT 06798

MLS Number 170405763

  • Land
  • MLS Status Active
  • Acreage 25
  • Other Amenities Waterfront
  • Subdividable

Seclusion and privacy abutting one of the biggest land preserves in all of Litchfield County. 25 acres of rolling and level woodland back up to Flanders Nature center and other large undeveloped tracts of land providing the ultimate getaway location. Only 90 minutes from NYC, this subdividable tract of land is protected to the North by Flanders and to the west by wetland soils on the neighboring 50 acre lot. Build your own estate on the entire 25 acres, take a one time split and create two 12.5 acre parcels, or subdivide into 4 or more lots. There is so much potential on this unrestricted lightly wooded parcel. Located on a little traveled gravel road this property has easy access to many walking trails, two Christmas tree farms, and is only a short drive to three town centers. Lots of possibilities if you want to getaway!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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$649,000

Est. Mortgage: $/month

MLS Number 170461821

  • Single Family
  • Square Feet 3,470
  • Bedrooms 4
  • Year Built 1998
  • Property Style Colonial

294 Railtree Hill is a beautiful 4-bedroom colonial on 3.02 acres designed for typical indoor-outdoor living. The main floor boasts, a huge size living room with oversized windows, a cooling ceiling fan, and brick fireplace, dining room, family room, and updated kitchen with new granite countertop, new backsplash, and new Stainless-Steel Appliances, as well as a the eat-in kitchen with access to the back deck! The laundry room can be found conveniently in the main floor along with a half bath. Upstairs offers 4 good size bedrooms with plenty of closet space and full bath. The master bedroom suite has large walk-in closet and a bonus closet. The master bathroom comes with a Jacuzzi to soak away the day's stress, double sink vanity, and walk in tiled shower. The walk out basement is finished, giving you options for an exercise room, playroom, or storage space, half bath, and access to the garage. Some other features: long private driveway, two cars garage, hardwood floor throughout the house, Fresh paint inside, Central Air, recessed light. Amongst many other unique amenities. This home is a truly spectacular. Schedule a private tour today!

Listing Courtesy of KW Legacy Partners

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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