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 6
  • 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 exclusive 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: 2.99% last updated on Jul 30, 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

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: 2.99% last updated on Jul 30, 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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68 Whittlesey Woodbury CT 06798

MLS Number 170307965

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

Litchfield County Retreat. Gently wind up this driveway to a nature oasis-totally private, yet still connected to a lovely neighborhood. Perfectly sited and surrounded by 42 acres of lush, preserved open space you'll find this detailed, custom home in immaculate condition. Designed by the owners to be low maintenance and eco friendly, the home flows with clean lines and an open floor plan. Upgrades in quality are evident throughout,from your first steps onto the curved, wrap-around mahogany front porch to the interior areas that showcase an abundance of natural light, 9' ceilings, arched openings, red oak flooring and rounded wall corners. Are you searching for a fantastic work-from-home opportunity? The large, bright bonus space over the three car garage includes a kitchenette, ample storage and even a separate entrance. The patio, embraced by stone walls and perennial gardens, integrates beautifully with ipe hardwood decking. Ideally located, 5 minutes from historic Woodbury Center and close to the Roxbury line. Please view the detail sheet to this home attached!

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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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Chohees Woodbury CT 06798

Woodbury, CTChohees Trail

Price$800,000

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. There is an Eversource easement in place. Eversource has made the land easily accessible with processed roadways. Motivated seller! Land previously appraised at $950,000 in 2015.

Listing Courtesy of Gina Jacobs Real Estate & Property Management

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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556 Flanders Woodbury CT 06798

Woodbury, CT556 Flanders Road

Price$799,900

Est. Mortgage: $/month

MLS Number 170289476

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3

Fall in love with this breath taking property in one of the most charming corners of Connecticut. This is your perfect hideaway from city life. Open your eyes to a new world of open spaces, fresh, pristine air, and endless green acres surrounding your private tranquil paradise. Exquisite custom built estate surrounded by 200 acres of the natural unparalleled beauty of Flander's Nature Center. This fabulous estate is built with state of the art quality components, superior materials and craftsmanship. You simply can not find another property like this so close to Manhattan, yet far enough to feel like you are on vacation every day. This is your ultimate dream home. Built in 2008 with absolutely nothing spared. Exceptional features including extremely efficient geothermal heating and cooling, as well as smart home technology. The gourmet kitchen features antique granite counters, marble backsplash, SubZero & Wolf appliances. Kitchen and eating area are open to the family room with cozy fireplace and a wall of glass doors leading to a wrap-around porch making it ideal for entertaining. Master bedroom is enhanced by a gas fireplace, master bath features Crema Marfil marble. The highly efficient geothermal heating and cooling system is secured with 4 inches of foam plus fiberglass insulation throughout for maximum performance. This exceptional home is everything you've been waiting for. Don't miss this special opportunity to escape the city life and wake up in your own lush eden.

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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701 Middle Road Woodbury CT 06798

MLS Number 170316428

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.07
  • Square Feet 5,771

Vacation at home! Amazing property with plenty of room for everyone. Gorgeous level 4 acre lot...perfect for entertaining, reunions or just a quiet getaway. Relax and let the day to day hustle/bustle disappear. Beautiful gunite in-ground pool, hot tub, tiered decks, wrap around porch and gazebo. Exterior lighting for an evening volley ball or badminton game. The house offers a flexible floor plan with functional open spaces, cathedral ceilings and walls of glass. The great room is at the center of the residence with the focus being the stunning floor to ceiling stone fireplace. Nicely equipped kitchen with plenty of storage. Cozy den. Main level guest room with separate entry. Fantastic game room with wet bar, wine chiller, and sliders out to pool. The master bedroom is vaulted, with full bath, walk in closet, built ins, remodeled laundry room and access to private deck. Amazing loft overlooking the great room...currently used as a gym. Two additional (very spacious) guest rooms and full bath complete the upper level. The lower level (1700sqft) is fully finished (possible in-law space) with separate entry. Currently used & permitted for home business. Newer propane heating system! Solar panels. Garage is attached...room for two vehicles plus 3rd bay for storage/recreational vehicle. Circular driveway. Located in the picturesque town of Woodbury. Enjoy parks and land preserves; antique shops; restaurants, shopping and more. Book your permanent stay-cation now!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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17 Gate Post Woodbury CT 06798

Woodbury, CT17 Gate Post Lane

Price$759,000

Est. Mortgage: $/month

MLS Number 170320661

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 10.23

A rare opportunity at this price point. Stately Georgian Colonial with Celebrity appeal. This one owner master piece was custom built on a secluded lot at the end of a long driveway. The dramatic curb appeal is apparent as you drive up to the property with stone walls, lush landscaping and a beautiful stucco exterior. As you enter the home the open floor plan creates a perfect environment for entertaining with 23 foot ceilings, marble floors, 23 foot floor to ceiling palladium windows, and a balcony that sits high above the family room. The attention to detail is one of a kind with fine trim work and moldings through out the home. The home features 2 master bedrooms one on the first floor and one on the second, both complete with large closets and full master baths. The other 2 bedrooms both have ensuite baths and great size and storage. Other noteable features include a 3 car garage, mud room, dining room, and over 10 acres of land. There is no kitchen in this property which is why there is a huge discount in list price on this property. AS-IS.

Listing Courtesy of Century 21 AllPoints Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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$714,900

Est. Mortgage: $/month

MLS Number 170294325

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

3 building compound in heart of vibrant Historic District works as a Family Retreat from city life OR as rentals. 5600 TOTAL s.f. 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, rare opportunity. Great Mechanicals. Condition V.Good / Excellent. Very Motivated Seller. Make an Offer! LOCATION! 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. CURRENT REVENUE! $79,000/yr: $43,200 via The Bull House; $14,400 via 1 BR 700 s.f. apartment, $21,600 via retail 2200 s.f. space, 8-ft ceilings. 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. FLEXIBILITY! Live onsite and collect revenues; OR live offsite, run store & collect revenues (as present owners do). This special property has not reached full potential: A once-in-a-lifetime chance to live, work and thrive in Litchfield Co. MOTIVATED SELLER.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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$714,900

Est. Mortgage: $/month

MLS Number 170294859

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

3 building compound in heart of vibrant Historic District works as Family Retreat from the city, or as rental / business: 5600 TOTAL s.f. includes: The Bull House (2700 s.f., fully restored; two gorgeous 2 BR residences, spacious rooms, period details)! Also, a 2200 s.f. Retail bldg (2-stories + full basement), and a 1 BR apt. (700 s.f., attached to Retail). 2-story, post & beam barn zoned commercial. Lush landscaping. Patios, fenced-in backyard, generous parking complete this highly-visible and rare opportunity. Great Mechanicals. Condition V.Good / Excellent. V. Motivated Seller. Make an Offer! CURRENT REVENUE! $79,000/yr: $43,200 via The Bull House; $14,400 via 1 BR 700 s.f. apartment, $21,600 via retail 2200 s.f. space, 8-ft ceilings. Additional income avail via 800 s.f antique barn: Full electric, separate septic, access to water supply; ready for development into residence, office. LOCATION! 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 urban demand surge in weekend and business opportunities. FLEXIBILITY! Live onsite and collect revenues; OR live offsite, run store & collect revenues (as present owners do). This special property has not reached full potential: A once-in-a-lifetime chance to live, work and thrive in Litchfield Co. MOTIVATED SELLER.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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91 Great Hollow Woodbury CT 06798

Woodbury, CT91 Great Hollow Road

Price$709,000

Est. Mortgage: $/month

MLS Number 170319516

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 4
  • Acreage 1.38

The country home you have been searching for! Historic meets chic in this stunning one of a kind bow house. Tucked on a quiet country road just one mile from Woodbury center, this home's unique features are testaments to quality craftsmanship of bygone days including paneled and wainscoted walls, hand forged hinges and hardware, exposed beams, wideboard floors, pocket doors, true divided light wavy glass windows and built-ins galore. Built in 1986, with a addition in 1993, this home's open and flexible floor plan offers endless options for living, entertaining and home office. A gracious enclosed porch welcomes you home and offers the perfect setting for casual relaxation. The country kitchen features a large bay window, granite island and built in hutch. Access the home's upper level from two staircases to find a large master suite and second en suite bedroom plus a dramatic third bedroom (or artist loft!) overlooking the backyard gardens. A large addition on the back of the home offers additional space for entertaining or relaxing, with french doors opening to the lovely new cedar deck. The spacious lower level offers a full bath and three additional rooms -a perfect space for guests, in-law, or au pair and has private walk out to the back yard. Roof is two years young and the exterior has just been repainted. This elegant home is the real deal and located just 90 minutes from NYC in the town Reader's Digest named the most charming small town in Connecticut.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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29 Steeple View Woodbury CT 06798

Woodbury, CT29 Steeple View Lane

Price$699,000

Est. Mortgage: $/month

Pending

MLS Number 170306833

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.62

Move right in and enjoy summer in this stunning colonial set on over an acre of private fenced yard with a heated pool and extra space for games and relaxing. Everything has been done for you! Newer roof, newer central air, newer windows, and much more - meticulously maintained so you will not have to do a thing except add your own style. The sprawling first floor has a front to back living room with French doors out to a gorgeous stone patio with both covered and uncovered seating areas. On the other side of the first floor is an family room spacious enough for theater seating and a pool table! The long spacious kitchen has granite counters, updated appliances - including a beautiful double wall oven - and a roomy eating area. Off the kitchen is an elegant dining room with a fireplace - think formal entertaining/holidays - and off the foyer is an office perfectly set behind French doors and with a fireplace of its own! The upper level offers three large bedrooms and a unique master suite with a fireplace, very large updated bathroom, and a sitting room that houses another small office, walk in closet, and is currently used as a home gym. The lower level is finished, complete with a full bath! The landscaped yard has a built in irrigation system and the property can be enjoyed from the grand patio off the back of the home offset by a blue slate floor and stylish columns. Too much to list here! Only 1.5 hours from NYC for a getaway but perfect for a year round lifestyle!

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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.