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

98 Owl Ridge Woodbury CT 06798

Woodbury, CT98 Owl Ridge Road

Price$1,899,000

Est. Mortgage: $/month

MLS Number 170322385

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 2.29
  • Square Feet 7,552

Welcome to your custom built estate, down a private wooded driveway that leads to paradise. As you enter the Owl Ridge Estates subdivision, your eyes will transfix on the unbelievable scenery. The rolling hills of Litchfield county and quaint charm of Woodbury will astound you and take your breath away. Surrounding this home is 90 acres of open space owned by Flanders Nature Preserve. Gaze upon the stone and shingle custom built home with no attention to detail spared. This smart home features an extensive array of features and technology such as a large pre-wired home office, security, irrigation, and more! The living spaces are complete with every beautiful high end touch such as coffered ceilings, wainscoating, crown mounding 10ft ceilings, 4 fireplaces, and custom built walnut cabinetry. The master bedroom boasts an incredible 12x15 walk in closet, fireplace, sitting area, rainfall shower and freestanding tub. There is simply too much meticulous detail in this home to fit into this description; it is an absolute MUST SEE with your own eyes. The backyard is straight out of a luxury resort with multiple covered and open living spaces, with a 20x40 heated pool with auto-cover, travertine deck, pavilion, waterfalls, gas fire pits, state of the art sound system, professional landscaping and customizable lighting. In addition, the 1,500 square foot basement comes complete with a wet bar, fireplace, gym, full bath, storage, and pool access.

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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

Pending Continue to Show

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: 2.8% last updated on Oct 22, 2020
* 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$1,150,000

Est. Mortgage: $/month

MLS Number 170344614

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

An elegant, English country estate expertly designed with unparalleled attention to detail. Designed to take full advantage of the natural beauty of the setting, such as tall rustling trees, meditation terrace, sun-dappled perennial rock gardens and meandering verdant paths providing not only beauty but also a tranquil feeling of retreat offering privacy and promoting rejuvenation making you feel right at home. Showcasing a built-in pool, tennis court, guest cottage and 2.86 professionally manicured acres highlighting flexible outdoor space and restorative feelings of wellness. The heart of the home is the kitchen/family room where you have a dream chef's kitchen that opens to an impressive family room surrounded by amazing views of the natural landscape. The open floor plan highlights single level living with 7 rooms and 5 fireplaces including a formal living room, walnut panel library and three rear bedrooms including a master bedroom suite complete with fireplace, sliders to private terrace, full bath and a walk in dressing room. The lower level hosts 3,200 sq ft of storage/recreational space perfect for a workout room, home theatre or soundproof studio. A fabulous weekend/vacation property or for year round enjoyment. Litchfield County is well known for its art galleries, unique boutiques, local theatre, great restaurants as well as many antique shops. 1.5 hrs from NYC. Make this property your home away from home!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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 River Bend Woodbury CT 06798

MLS Number 170337368

  • Single Family
  • Property Style Cape Cod, Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 1.84

"The River Runs Through It". Beautifully designed Rick Moisan home overlooking the Pomperaug River in the heart of historic Woodbury. Located in a small cul de sac on the west side of town, this custom home offers a gorgeous kitchen with Viking appliances, wet bar, pantry & center island, a family room with a fireplace, built-ins, and vaulted ceiling, and a main level master suite. There is room for everyone with three upper-level bedrooms, a bonus room with half bath above the attached garage, and a playroom in the partially finished lower level. Overlooking the river and abutting open space, this home provides fabulous outdoor space including a cozy deck off the kitchen for morning coffee, a large back patio bounded by stone walls accessed through the family and living rooms, a covered front porch, and a better barn for additional car storage. A well built and cared for home with many reproduction features such as simulated divided light windows, wood shingle roof, cedar clapboard siding, and a design that fits in Woodbury's historic character. An ideal location as you can walk to everything in town or stay home and enjoy nature while fishing or walking along the Pomperaug River that is a stones throw from your back patio.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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 Silver Brook Woodbury CT 06798

Woodbury, CT5 Silver Brook Lane

Price$995,000

Est. Mortgage: $/month

MLS Number 170334334

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.3

Gorgeous Reproduction Colonial privately sited on 2.3 acres just minutes to great restaurants, Flanders Nature Preserve for hiking trails and shopping. The home was custom-built with high end finishes throughout by Muratori Builders and lovingly tended by it original owners. In keeping with the character of a historic Connecticut colonial there are exposed beams, wood shingled roof, three fireplaces, 12 over 12 windows, custom cabinetry, beaded clapboard siding and stone terraces. The great room with it's cathedral ceiling and "bar room" leads out to a three season porch overlooking the sumptuous grounds. A top of the line, open concept kitchen with vaulted ceiling is complete with Subzero, DCS and Bosch appliances and opens to a cozy breakfast area and fireplace. Offering easy comfort and great capacity for entertaining weekend guests, the home has all the amenities for today's living including a three bay garage, whole house generator, irrigation system and walk up attic for expansion. It comprises all the character of a classic antique home, while creating a modern easy lifestyle -- all just 90 minutes from NYC!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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 Carmel Hill Woodbury CT 06798

MLS Number 170344829

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 2.38

This amazing home is 6020 square foot light and bright 5 bedroom colonial situated on a beautiful level landscaped 2.38 acre lot. This lovely home consists of the main house and a spacious in law home. The main house features sunken family room with hardwood floors and stone fireplace, large eat in kitchen, formal dining, transom windows, very open floor plan, first floor office, formal living room, 2 kitchens and 4 bedrooms hard wood floors throughout. The In law was built in 2004 and includes additional kitchen family room with gas fireplace, large bedroom opens to a beautiful sitting area with second gas fireplace. The in law boasts dual balconies and a separate private grill and patio area.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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190 Orchard Woodbury CT 06798

MLS Number 170317446

  • Single Family
  • Property Style Chateau, Tudor
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.33

This is a very unique and special house designed by a well known architect. Throughout this home you will find nothing short of breathtaking elegance and expert, exceptional craftsmanship. This chateau boasts an inviting floor plan that gives an ode to classic style, but is truly built for a modern lifestyle. Not a single detail in this home was spared, and each room is like it's very own suite for you to be able to retreat to. Grab your coffee and breathe in the fresh country air as you wake up every morning in your very private oasis surrounded by unparalleled natural beauty. You will find yourself surrounded by mature trees, a pristinely manicured garden, and the smell of freshly budding flowers. You are under the impression of complete seclusion yet surrounded by everything you need! Without a doubt, you will fall in love with this fabulous home and it's unbeatable location. Come and enjoy the country lifestyle away from the City in lovely Woodbury Connecticut, a town that is quaint, beautiful, and teeming with old world charm. Protected by privacy but only ten minutes away from grocery stores and all the exciting places downtown Woodbury has to offer such as antique shops, fabulous restaurants and grocery stores. Come experience what real living feels like in this immaculate home and schedule a showing today!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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339 Hoop Pole Hill Woodbury CT 06798

Woodbury, CT339 Hoop Pole Hill Road

Price$749,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170336078

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5

Views, Views, Views!! One of the highest points in all of Woodbury and by far the best views in Litchfield County. Long distant views from the hilltop off of Hoop Pole Hill Road. Enjoy the breezy summer nights on your stone terrace next to your vanishing edge gunite pool with jacuzzi. 5-acre plot with a level house site and privacy from your neighbors. Light and bright contemporary home with a wall of glass to take in those sweeping views far into the distance!. Amenities provide 4 to 5 bedrooms and three full baths, generous sized dining room overlooking the living room with 24' soaring cathedral ceiling and a wall of glass. Many recent upgrades over the past year, plenty of room for everyone, and an ideal spot for an in-law suite. Beautiful outdoor space with a spacious level yard, privacy from neighbors, and room for outbuildings or expansion. Million-dollar VIEWS for less!

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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495 Main Woodbury CT 06798

Woodbury, CT495 Main Street South

Price$699,999

Est. Mortgage: $/month

MLS Number 170294859

  • Multi Family Multi-Family For Sale
  • Bedrooms 5
  • Bathroom 7
  • Acreage 1.01
  • Square Feet 5,600

This 3 building compound works either as a weekend retreat from city life OR as rentals in a PRIME rental market. (Note: Main house now 2 separate apartments). TOTAL s.f. of 5600 includes: The Bull House (2700 s.f.; fully restored; two gorgeous, SEPARATE 2 BR residences; spacious rooms, period details!). A 2200 s.f. Retail bldg (2-stories + full basement) w/ attached 1 BR apt. (700 s.f). Also a 2-story, post & beam barn zoned commercial. Lush landscaping. Patios, fenced-in backyard, generous parking complete this highly-visible opportunity. Great Mechanicals and condition V.Good / Excellent. In heart of vibrant Historic District. Footsteps to award-winning restaurants, culture & retail. Sidewalks throughout town. Greens, parks, Sr. center, library, schools all close; hiking, fly-fishing, skiing, golf nearby. 90 miles from NYC, 11 fr Metro North, 4 fr Rt. 84. Woodbury benefiting from NY Metro demand surge in weekend and business opportunities. Property currently earns annual revenue of $79,000. Additional income avail via 800 s.f antique barn (full electric, separate septic, EZ access to water supply; ready for modest development into residence, office). A special property and once-in-a-lifetime chance to live, work and thrive in Litchfield Co.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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495 Main Woodbury CT 06798

Woodbury, CT495 Main Street South

Price$699,999

Est. Mortgage: $/month

MLS Number 170294325

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 6
  • Acreage 1.01

Historic and spacious antique home with separate, first floor In-Law. Located in the heart of Woodbury's town center and Historic District. Period details abound throughout the 1745 Bull House (main home), which offers approx. 1680 s.f., has 2 big, bright BR's, 2 ½ BA; 5 Rooms total. The ground level In-Law w/private patio offers 2 BR's, 1 ½ BA; 4 Rooms in approx. 1000 s.f. Walk across the rear patio and through the level, fenced in backyard to a charming retail shop (2200 s.f) with an attached, ADDITIONAL 1 BR, private cottage (fully refurbished in 2018). A 2-story, post & beam barn (zoned commercial) completes this compound. Generous parking. Meticulously maintained mechanicals. **Footsteps to award-winning restaurants, culture & retail. **Sidewalks throughout town. **Greens, parks, Sr. center, library, schools all close; hiking, fly-fishing, skiing, golf nearby. 90 miles from NYC, 11 miles from Metro North.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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33 Tuttle Woodbury CT 06798

Woodbury, CT33 Tuttle Road

Price$699,900

Est. Mortgage: $/month

MLS Number 170345609

  • Single Family
  • Property Style Cape Cod, Ranch
  • Bedrooms 2
  • Bathroom 2
  • Acreage 22.85

Some of the Best Views in all of Litchfield County! Set back off of sought after Tuttle Road, this hidden gem is completely private and abuts 600 acres of the Flanders Whittemore Sanctuary. Enjoy the simplicity of this charming 1949 two-bedroom cape with three fireplaces or create your own home/compound on this 22.85-acre slice of heaven. All of the main rooms in this cozy single level home enjoy breathtaking sunset views. There is a sunny, spacious living/dining room, an efficient kitchen that opens to a secluded terrace, and a covered porch for dining al fresco during summer showers. Included in the sale are two, two-plus acre building lots ready for friends and family or to sell and ease the pain of purchasing. Ideally located with easy access to exit 15, 16, and 17 off of I84 and a 5-minute ride to historic Main Street Woodbury with all it's fabulous shops and restaurants.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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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480 Main Woodbury CT 06798

Woodbury, CT480 Main Street South

Price$699,000

Est. Mortgage: $/month

MLS Number 170315183

  • Single Family
  • Property Style Antique, Victorian
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.98

This grand Queen Anne Victorian, perched proudly on a hill and locally known as the 'Sage House', has worlds to offer those seeking the charm of in-town living. Enjoy the grandeur of the home's high ceilings, impeccable woodwork, curved bay windows and soaring attached barn - perfect for work or play. The three bedroom home and connected c.2001 1,000SQFT+ barn with radiant heat and stunning tin ceilings are set back on nearly an acre of beautifully-landscaped grounds. Featuring a porte-coche`re, covered porch, brand new top-of-the-line mechanicals and three fireplaces, this move-in-ready antique is walkable to the area's lively town center, with renowned restaurants and shops. Located in the Main Street Design District the home can be used both for commercial and residential purposes - it is as versatile as it is gorgeous. Also part of the Woodbury Historical District, Dr. William Henry Sage resided in the home during the early 20th century and was particularly drawn to the area's beauty, acquiring the land along the river which eventually became part of the town's bucolic Hollow Park. The park and river can be accessed via a private trail out your backdoor. A truly exciting opportunity to own a piece of Woodbury history, less than 90 minutes from NYC!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Oct 22, 2020
* 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.