Woodbury CT Real Estate

Located approximately 85 miles north of New York City and referred to as Connecticut’s “Antique Capital” is Woodbury. Woodbury 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.

Properties in Woodbury

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Search by Property Type: Luxury Homes | Single Family HomesCondos | Land

59 Hillside Woodbury CT 06798

Woodbury, CT59 Hillside Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number 170207963

  • Single Family
  • Property Style European
  • Bedrooms 5
  • Bathroom 7
  • Acreage 3.49

Amazing views and gorgeous surroundings adorn this luxury villa situated on a hillside in historic Woodbury. Enjoy serenity in your remarkable outdoor living space while taking in the miles of rolling hills. Fine details in the construction and finish can be admired throughout the over 9,000 ft of this dream dwelling "Masterfully" designed by noted Architect Rick Moisan of Moisan Architects. Incredible architectural lighting throughout, as well as French doors leading to the balconies and pool's terrace, heated herringbone hardwood floors and five fireplaces that will warm you on a cold winter's day. Arched central foyer leading to all of the main floor rooms including a beautiful sunroom adjacent to your infinity pool. The kitchen with professional modern appliances, including Wolf gas cooktop, double oven and butler's pantry. The master suite with luxurious spa-like bath and walk-in closet has its own laundry facilities. The guest suite with separate entrance is housed above the heated 3-car garage and additional apartment housed on the main floor has full kitchen, bath, bedroom and two-story great room that opens to the beautiful outdoor terrace. Enjoy summer nights dining under the two turreted loggias or simply enjoy some tea and take in the breathtaking views. Convenient to Historic Arts and Antiques District and immersed in nature at its finest, this spectacular abode is located just minutes from major thruways. Property borders the Trolley Bed Land Preserve.

Listing Courtesy of Global Real Estate Network

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$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Woodbury CT 06798

Woodbury, CT

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170110604

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 9.18

Set back on 9+ acres, this property offers privacy in a choice location. As visitors ease down its circular stone drive the New England Colonial charm of this exceptional estate welcomes them. Upon entering the formal foyer the homes texture and character are made obvious by the wooden wall cladding, a detail that is carried throughout much of the home. The space on the main level is arranged in such a way that there is a sense of ease in movement. Wide, open doorways carry you from one room to the next, while the warmth of the wood paneling creates a sense of intimacy in each individual space. The formal living room and kitchen are open to the homes expansive four-season porch, overlooking the breathtaking views of the Litchfield hills. A large open dining/living area with built-in custom cabinetry abuts the L -shaped kitchen workspace. Adjoining is a formal library/office that extends into the illuminated den. On the upper floor there are two bedrooms and two bathrooms. The current (original) owners personalized this living level by converting the third bedroom into an opulent bath & dressing room. Luxurious living extends to the exterior of the home as well, where both sport and relaxation can be found in the homes gunite pool and tennis court. With mature plantings throughout and expansive views the properties landscape rings true to the title of country estate.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Chohees Woodbury CT 06798

Woodbury, CTChohees Trail

Price$925,000

Est. Mortgage: $/month

MLS Number 170190382

  • Land
  • Acreage 105.7

Expansive track of rolling acres in rural Woodbury. Subdivide for residential, traditional farming, solar farm, hemp farm, gun range, dirt bikes, or hunting. Many possible uses. Adjoining 4 acre lot on Flanders Rd can also be purchased for a total of 109 contiguous acres.

Listing Courtesy of Gina Jacobs Real Estate & Property Management

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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283 Saw Pit Hill Woodbury CT 06798

Woodbury, CT283 Saw Pit Hill Road

Price$899,900

Est. Mortgage: $/month

Pending

MLS Number 170196322

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 6
  • Acreage 9.27

Incredible value! An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces & designed with every luxurious amenity imaginable. Gorgeous wrap around mahogany covered porch (with hot tub). Stunning two-story entry. A chef's kitchen offering the most discriminating buyer a large center isle, custom cherry cabinets, granite counters, handmade copper sink, Subzero, Viking stove, two dishwashers, convection oven & large dining area. Open concept seen and 9+ft ceilings throughout. Formal dining rm (w/custom cabinetry & limestone counters) living rm w/wet bar, gas fireplace & superb piano rm. Brazilian cherry flooring. An abundant use of windows & French doors blend the interior & outdoor spaces. Private office, full bath & powder rm complete main lvl. Impressive master suite w/octagonal ceiling, Brazilian cherry floors, gas fireplace, walk-in closet (organizers) & elegant bath (claw foot tub, antique vanity & tiled shower with jets/body sprays). Three additional guest rms (two share a bath, one an en-suite), & media rm w/vaulted ceiling & entertainment center. The finished lower level (possible in-law space) offers a recreation area, full bath, game rm, den & transitions easily to the exterior to enjoy the salt water sports pool w/water fall & deck jets, patio area & outdoor kitchen. Whole house audio system. Energy Star Rated Home. Look no further...this truly is a spectacular home set in an idyllic setting!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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40 Peter Woodbury CT 06798

Woodbury, CT40 Peter Road

Price$800,000

Est. Mortgage: $/month

MLS Number 170229526

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 3
  • Bathroom 4
  • Acreage 2.86

EXTRAORDINARY VALUE AND QUALITY! Sophistication and Stylish Country Elegance awaits you at this quiet piece of paradise in sought after Litchfield county. This brilliantly designed home is set back on 3 private acres with gorgeous perennial flower gardens that evoke beauty and peacefulness. The main home is impeccably well kept featuring single level living with a versatile open floor plan, a professionally lit hard surface tennis court, built in pool and a pool house/studio. Thru the lovely entryway foyer, there is a splendid living room complete with oversized fireplace and impressive panoramic view of the lovely courtyard and new bluestone patio. The large scale comprehensive kitchen boasts a walk in pantry with auto lighting, two SubZero refrigerators, Wolf dual-fuel range with griddle, KitchenAid dishwasher, eat in dining area and a family room with an oversized brick fireplace and built in two speaker sound system. The library is magnificently crafted with walnut raised paneling, bookcases, a double closet and cabinets. There are three generous sized bedrooms including a welcoming master suite with a walk-in closet, fireplace, sitting area, full bath and a walkout to the patio. The pool house/studio offers one bedroom, a kitchen area complete with sink, stove and refrigerator, a full bath and a 2 car garage. Incredible value loaded with charm and character. Pristine condition. Very well maintained and neat as a pin - shows real pride of ownership. A must see!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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466 Main Woodbury CT 06798

MLS Number 170047103

  • Commercial
  • Acreage 3.28
  • Square Feet 8,000

To be built - 8000 to 10000 metal building. Five 12' doors, level lot with many possibilities. Rent to multiple tenants or run your own business out of one of Woodbury's last industrial sites. Great exposure and minutes to all major routes.

Listing Courtesy of Drakeley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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270 Main Woodbury CT 06798

Woodbury, CT270 Main Street South

Price$675,000

Est. Mortgage: $/month

MLS Number 170156120

  • Single Family
  • Property Style Antique
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1.09

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. Wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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270 Main Woodbury CT 06798

MLS Number 170158464

  • Commercial
  • Acreage 1.09
  • Square Feet 4,302

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. The incredibly well maintained property and multiple buildings have tremendous potential for a variety of commercial and mixed use occupancy (Professional office, retail, home business, residential rental etc. ) Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. The property is high visibility with ample public parking adjacent to the property boundaries. Interior features include wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage. Perfect for in-home business and professional uses.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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79 Nettleton Hollow Woodbury CT 06798
Pending

MLS Number 170220603

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 29.7

Recently renovated antique home nestled in bucolic bliss within estate area close to Mayflower Auberge, the historic town of Washington, and ninety minutes from Manhattan. Beautifully sited on 30± acres off a quiet scenic road, the 4,600± square foot house is lovingly maintained with loads of character and many period details throughout. The main level interior boasts several spacious gathering rooms with hardwood flooring throughout, exposed antique beams, newly updated and open kitchen with marble counters and windowed dining area that opens to rear western-facing deck, a huge rustic family room with large stone fireplace and deck access, a combined living/dining room with fireplace, and an office/playroom/spare. Upstairs there's four bedrooms comprising a master suite with new marble bath, and three separately situated guest bedrooms serviced by two updated marble baths. There's also a walk-up attic that can serve as an office or additional. A large unfinished basement offers massive storage area, workshop, laundry, and easy walk-out to grounds. Outside is a sensory treat with charming gardens, stone walls, cedar-scented breezes through towering trees, mature specimen plantings, and cleared trails that lead to your own whispering brook. Other highlights include a heated Gunite pool with bluestone patio, red clay tennis court, 2-car/2-level garage with lower workshop space. This quintessential New England country home is one-of-a-kind and move-in ready.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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 Transylvania Woodbury CT 06798

Woodbury, CT17 Transylvania Road

Price$629,000

Est. Mortgage: $/month

Pending

MLS Number 170194259

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2

Enjoy pure privacy in this turnkey colonial, beautifully sited on 2 acres in Woodbury. Set back down a winding driveway, this immaculate 3 bedroom/2.5 bath home sits among soaring white pines and lush, mature gardens. Soaked in natural light, the open floor plan home features expansive living spaces with rich finishes including a kitchen with eating island, granite counter-tops and full pantry that opens to a great room and patio. On the second floor you'll find two generous bedrooms and a serene master suite that features dual stone vanities, glass shower and large jetted tub. Entertain in style with an upper level recreation room (or potential 4th bedroom) and over-sized patio that flows naturally into the indoor living spaces via French doors. Other highlights include laundry room, office, as well as sizable three car garage. Conveniently located, the home sits less than 5 minutes away from Hollow Park, New Morning Market, Glebe House & Gardens as well as many of Woodbury's best restaurants!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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557 Upper Grassy Hill Woodbury CT 06798

MLS Number 170232058

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.73
  • Square Feet 3,791

Spectacular Colonial with attention to details throughout triple levels. Stunning special features including marble entrance with vaulted ceilings, beautiful open floor plan, custom trim and moldings, surround sound, magnificent high end finishes and capacious size rooms. Quality custom built home is perfect for enjoying entertaining guests with the breathtaking patio, deck and spa. Completely updated home, main level boasts elegant foyer, formal living and dining rooms, spacious family room, main level office with built ins and more. Eat in gourmet kitchen hosts granite counters, newer stainless steel appliances with wine fridge, dining area, gleaming hardwood floors and walkout to private deck. Sunk in living room features palladium windows and gas fireplace. Formal living/ dining rooms with hardwood floors, open floor plan, pillars and custom draperies. Magnificent upper level with master bedroom en-suite, generous walk-in closet, trey ceiling, hardwood and master luxury marble full bath. Additional bedrooms with lush wall to wall carpeting & great closet space. Lower level has in-law set up complete with dining area, kitchen, bonus room w/ exquisite gas fireplace surrounded by glass tile. Large bedroom area with high quality Murphy bed, striking hardwood floors, French doors with walk-out to impressive stone patio complete with fenced in spa pool. Belgium block lined driveway, appealing distant views, central ac, triple zone efficient heat , full house generator and more!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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419 Weekeepeemee Woodbury CT 06798

Woodbury, CT419 Weekeepeemee Road

Price$574,900

Est. Mortgage: $/month

MLS Number 170191914

  • Single Family
  • Property Style Barn, Farm House
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.3

Charm, form & function best describe the uniqueness of this home! This classic Americana converted barn is right out of yesteryear from its reclaimed wood beams to its fieldstone fireplace and wide plank floors. It has been preserved and restored to allow its original character to shine through. The wrap around covered porch invites you into the main living level that includes the family room with fireplace, kitchen with a center island, propane stove & corian countertops, sitting room with built ins and french door to the deck, a master bedroom suite and another large bedroom with cedar closet. The second level is an entire floor of another master suite with a french doors to a balcony, and a large game room. It also has a third level cupola that offers views of the extraordinary property. As an added feature,the lower level is an expansive heated and air conditioned garage that runs full length of home. Built to accommodate any type of collection... cars, boats, tractors, furniture, antiques, or whatever you may collect. The bucolic outdoor setting displays beautiful perennial plantings, bluestone patios, natural stone walls and abuts the Flanders land trust. A truly unique offering!

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 2019
* 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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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.