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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

168 Upper Grassy Hill Road Woodbury CT 06798

MLS Number 170480181

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,354
  • Acreage 7.08

Fly in for the weekend! Gorgeous cape home abutting a local AIRSTRIP offering the possibility of flying home with the appropriate permission. Recently built with security in mind, you will love this pristine cape with all the measures taken for security and living off the grid. Nestled up against the Roxbury/Woodbury line this home abuts the old Roxbury airport, a 38x60 clear-span heated barn for all your toys, and is an incredibly efficient home with state-of-the-art heating, electrical, and engineering. Some of these mechanical upgrades include a 45 KW diesel generator plumbed to the oil tank, a solar array that makes more power than the property can use including heating and AC, electric gates with automatic watering systems on the walls and plantings, a casino grade security camera system, a 400 amp split service to operate the generator and solar in synchrony, and extensive underground and outdoor lighting to light up every inch of the 7 plus acres. Let's not forget the house, which has a welcoming open floor plan with lots of light, a gorgeous kitchen/great room with a cathedral ceiling, the main level master bedroom, and plenty of room for expansion. Built to last this contemporary cape provides all foam insulation, a 60-year roof, copper gutters, cedar shake siding with azek trim, and garage space for 16 or more vehicles. There is plenty of outdoor space including a ground-level deck with retractable awning, and a glass solarium with electricity and cable.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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43 Old Meadow Road Woodbury CT 06798

MLS Number 170496468

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,385
  • Acreage 1.97

This impeccably maintained reproduction farmhouse sits atop a quiet cul de sac in the historic town of Woodbury. As you drive down the quiet road, you are greeted by the home's friendly front porch, a place where you can sit and rock as you listen to the sounds of Radey Pond. The landscape has been embraced, with each area being utilized to its highest potential. The long stretch of level land has been left clear for an expanse of grass, while the sloped backyard has been carved out to create an oasis with the gunite pool, hot tub, and waterfall, all enclosed by a 10-foot cedar privacy fence. All plantings have been recently refreshed with minimal maintenance in mind, connecting the theme of simplistic living that sellers have accomplished within the home. The interior has a pleasing color palette of cream and gray, lending itself to a variety of furnishing tastes and styles. Features such as oak floors, crown molding, and eight over eight windows add a degree of intimacy to this spacious home. Whether you seek to house an au pair, grandparents, or friends, there are private areas to accommodate them all. The home's layout allows for everyone to be independent while remaining together with two complete kitchens and one kitchenette, three living rooms, and many other multi-functional areas. Inviting, well-designed, and spacious - 43 Old Meadow.

Listed by Michael Caporizzo of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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156 Weekeepeemee Road Woodbury CT 06798

Woodbury, CT156 Weekeepeemee Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 170470182

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,194
  • Acreage 2.66

This sunny 5-bedroom French country home was built by an architect for himself, and offers superior craftmanship, stunning millwork, secret doors, and an enormous gourmet kitchen. Enjoy gathering in the expansive kitchen area with multiple dishwashers, Subzero refrigerators, wine cooler, Wolf Industrial 6-burner stove with dual ovens, wall oven, warming drawer and microwave. The oversized island is filled with bookcases, baskets, and drawer storage. The beautiful eat-in kitchen has table seating for 8+. The dining room, family room, home office, library, and sunroom are full of architectural details making each one unique and inviting. This home features 9' ceilings, French doors, 4 fireplaces, wide chestnut board flooring and cozy nooks throughout. The outdoor hot tub is sheltered in small barn that sits off the master bedroom at the end of the oversized stone patio that runs the length of the house and is surrounded by stone walls and English gardens. The master bedroom suite is simple amazing with a foyer, 2 walk-in closets, floor to ceiling bookcases and fireplace, 6x8 shower, jacuzzi tub and a secret door to the private gym. Additional house amenities include attached 2-car garage, detached 1-car garage w/ firewood storage, whole-house generator, alarm system, 220 AMP electric, zoned air conditioning/hydro air heating systems. The additional movie room, art studio and kids' playroom make this an amazing home or weekend retreat for friends and family.

Listed by Kate K Willoughby of Gina Jacobs Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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87 Coach Light Drive Woodbury CT 06798

MLS Number 170493340

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,904
  • Acreage 4.63

Come home to the privacy of this exquisitely detailed country home on 4.63 acres in pristine move in condition with an in-ground pool and pool house completing the amenity package. The home features 10 rooms, 4 bedrooms, 4 full and 2 half baths. The Main Floor offers a state-of-the-art kitchen with dining area, walk-in pantry, stainless appliances, double oven, refrigerator, dishwasher gas cooktop stove, granite counters and 8-foot center island. The kitchen opens to a large family room with fireplace, detailed built-ins, sunroom with mahogany flooring, with direct access to a mahogany deck, pool, pool patio and pool house. Formal dining room, living room and laundry room are also featured. The upper level offers the primary bedroom suite with fireplace, luxurious full bath, whirlpool tub, walk-in shower and two walk-in closets with dressing area. Two-bedroom suites each with full bathroom accommodation. French doors lead to a large sitting room designed for relaxation and comfort accessible from each bedroom suite. An additional bedroom with access to a full hall bath is also available, all can be directly accessed by private entrance.

Listed by Peter Filous of Coldwell Banker Realty

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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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8 Stone Hollow Road Woodbury CT 06798
Under Agreement

MLS Number 170484979

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,050
  • Acreage 1.82

Stunning New England Colonial with superior craftsmanship and the protected land of Flanders Preserve abutting, make this home the perfect place to be. It's raised bed gardens with stone surround, stonewalls, circular driveway, gorgeous gardens and level lawn set it apart. The fully heated and cooled sun room overlooks the perennial gardens, stone terrace and mature trees. The interior spaces include high-end trim & finishing work along with coffered and vaulted ceilings, wideboard oak floors, marble baths and french doors, all which create a rich and sumptuous interior. The Chef's kitchen offers granite counters and stainless Wolf and Miele appliances, a prep island, breakfast nook and opens on to spacious vaulted ceiling family room with fireplace. The main level master is complete with luxurious marble bath, steam shower, raised hearth fireplace and 2 walk in closets. Additionally, 3 fireplaces and a fully heated and cooled sun room which can be used in all seasons round out the first floor. The second level has and easy flow with three bedrooms, one en suite and office/loft space. An attached over sized garage leads to a Mud Room with built-ins and laundry room. A private and magical location, just a few minutes from Historic Woodbury Center and 90 minutes from NYC. Perfection!

Listed by Kathryn Clair and Kathryn Clair Bassett of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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452 Middle Road Turnpike Woodbury CT 06798

Woodbury, CT452 Middle Road Turnpike

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170497866

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,325
  • Acreage 11.27

Private story book stone and shingle home on over 11 acres. Eleven Rooms include two primary bedrooms on the main level. Spacious living room and family room overlook the park-like grounds. Cozy sitting room with fireplace has French door that leads to stone patio. Kitchen has been remodeled and includes stainless steel appliances. There are five fireplaces, oak pegged floors and oodles of charm. In ground heated pool, rolling lawn, specimen trees and early stone walls. Detached two bay garage/barn with finish space above and multiple sheds. Many updates and improvements include cedar shake roof, irrigation system, bathrooms, landscaping, pergola, pool heater, heated studio above garage - to many improvements to list, call for complete list. 2 hours from NYC.

Listed by Maria Taylor and Claudine McHugh of Klemm Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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137 Minortown Road Woodbury CT 06798
Pending Continue to Show

MLS Number 170494374

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,674
  • Acreage 10.18

As you pass the gated entrance and tall trees that line the drive approaching this private country getaway, you'll think you're on vacation. Whether entertaining guests or just relaxing, the 1000 sq ft Great Room with 16' Cathedral Ceiling and soaring riverstone fireplace make every day special. Sunlight streams through the arched windows facing the back of the home with a 50' deck that leads to the outstanding heated gunite pool. The first floor primary bedroom suite with fireplace and sliders to the deck adjoins a full bath with heated floor, jetted tub & walk-in shower. Adjoining the Great Room is the spacious kitchen with granite counter, double-oven, heated tile floor and stainless steel appliances. A full bath & separate laundry room are close by and lead to the attached two-car garage. There's plenty of room for guests in the three bedrooms with full bath on the upper level. A finished walk-out lower level with fireplace adds 540 sq ft to the home & is adjacent to an unfinished space with wine closet & mechanicals including a hydro-air heating system. Car enthusiasts & hobbyists will appreciate the detached 24 x 40 garage/barn with 12' insulated doors & 2x6 construction. The private 10+ acre parcel includes a large, level lawn with playscape and a path leading through the forest to 1000' of river frontage for fishing or just getting close to nature. Private and pristine, this stay-cation paradise is just a few minutes from shopping & Woodbury's acclaimed restaurants.

Listed by Tom Greto of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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27 Peter Road Woodbury CT 06798

Woodbury, CT27 Peter Road

Price$999,999

Est. Mortgage: $/month

MLS Number 170346864

  • Land
  • Acreage 46.4
  • Zoning OS100

Build your dream home here!!! Level building site. Most of the 46 acres is fenced. Barn with small apartment and two outbuildings. Come live in beautiful Litchfield County and enjoy the sunsets! Cows not included.

Listed by Sindy Butkus of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 2,000
  • Acreage 87.5

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.

Listed by John Sniffen of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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$999,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170463012

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 6,965
  • Acreage 4.42

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 5 full baths plus 1 bath in cabana. 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!

Listed by Jodi Langford of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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17 Birchwood Lane Woodbury CT 06798

MLS Number 170493815

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,230
  • Acreage 3.37

NYC MOMA-Inspired Home, located in country quaint Woodbury CT One of the last modern designs of the late Architect Richard Merrell. A Home by CORBO build & winner of the 2010 CT HOBI Best Custom Home Award. Designed with a love for nature & art, this Prairie style home truly integrates with its exterior surroundings, hidden amongst the trees, softly laid against its prominent stone ledges and overlooking a private pond. Each window is designed to be its own “painting” looking out over the landscape. The Bauhaus minimalist interior removes any unnecessary projections into the living space, allowing the home to fall away and expand from your eyes wherever possible. This home is a beautiful example of Architecture as Art. Offering 2 primary suites and an additional guest room. This 3 bed, 3 bath, 3 car garage home sits atop 3.37acres and features an artist loft / office with lookout, white modern Interior, pizza oven, expansive stone patios, private deck, front porch, wine cellar, whole house generator and hi-end european fixtures throughout. When you arrive at this incredible home you feel like you are entering the museum of modern art where exquisite architecture and design come together. This sophisticated modern home seamlessly blends form, function and efficiency. This stylish home offers an abundance of decadent amenities throughout, a perfect getaway from the city. Enjoy the tranquility and relaxing living in Litchfield county.

Listed by Magda Ballaro of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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

Under Agreement

MLS Number 170457136

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,900
  • Acreage 0.92

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

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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