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

32 Hoop Pole Hill Woodbury CT 06798

Woodbury, CT32 Hoop Pole Hill Road

Price$799,900

Est. Mortgage: $/month

MLS Number 170381173

  • Single Family
  • Property Style Ranch, European
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.04

Something a little different! Gorgeous French Country inspired design and charm set above the Sprain Brook River on a private four plus acre lot offers one level living at its best This sought after desirable open floor plan with 12+ foot ceilings allows for a spacious feeling and flow throughout the entire main level. The gourmet country kitchen has gleaming concrete counter tops and opens up to the great room featuring massive decorative columns, windows and doors overlooking the back, fireplace and impressive moldings throughout. Most of the sq ft is throughout the first floor including three bedrooms each with en-suite baths, a sitting room off the foyer and a formal dining room with interior French doors and room for 20. The upper level provides a private office with built ins and a fourth bedroom with en-suite bath. Potential expansion in the walk out lower level with high ceilings and comfort due to insulated concrete forms used in construction. The exterior includes private lounging space, two sheds, fencing for a horse and views of the River. Tough to replicate this home for the money!

Listing Courtesy of Drakeley Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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23 Silver Brook Woodbury CT 06798

Woodbury, CT23 Silver Brook Lane

Price$749,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170386710

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

Every now and then a perfect home comes along with all the extras like a circular driveway, attached two car garage plus a separate barn for 2 extra cars, large front porch, high end trim and many many windows throughout the home. The large kitchen with gas fireplace and sitting area makes everyday the place to be with sliders out to the private patio overlooking the acres and acres of land belonging to Flanders Nature Center!! One of the best things is the often requested first floor master bedroom and bath with plenty of closet space. As you enter the home you see straight into the living room with large fireplace and again windows everywhere. The unfinished large basement has a walkout slider and roughed in bathroom plumbing. Flanders Woods subdivision is well established with beautiful homes and only minutes to the center of Woodbury - recently voted Best Small Town in Connecticut! Nearby are the schools, library, community center, community theater, Hollow Park with summer concerts and sporting events, post office, grocery and drug stores, medical offices, hiking trails throughout plus the great tower overlooking the whole town and yet only `1/2 hr. to train station and 1 1/2 hr by car to NYC. This home is easy to show!

Listing Courtesy of Drakeley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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$724,900

Est. Mortgage: $/month

MLS Number 170294859

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

Golden investment opportunity to own very desirable rental units AND a separate retail space; choice location in vibrant, walkable, in-town setting. Ideal for Investors, 1031 Exchange or End Users. 3 residential units (2 separate units in the historic main house, plus 1 in additional cottage) and 1 modern retail space offer the best of both the residential and retail markets in Woodbury. Strong financials and rental history - currently generating $6,650 in monthly rents alone. Generous off-street parking, backyard, a post & beam barn, and landscaping complete this high-visibility, turnkey opportunity. Not to be missed! The Bull House property is a truly unique, once-in-a-lifetime investment opportunity to own a slice of Woodbury & Litchfield County history!

Listing Courtesy of Drakeley Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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102 Stagecoach Woodbury CT 06798

Woodbury, CT102 Stagecoach Road

Price$680,000

Est. Mortgage: $/month

MLS Number 170385903

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Acreage 1.81
  • Square Feet 4,054

Sprawling custom colonial w/ front porch situated at the end of cul de sac is destined to impress. No detailed was missed when envisioning this masterpiece. Gleaming hardwoods greet you at the front door and carry you throughout this entire home. Custom woodwork, moldings, raised panels, wainscoting and built in's at every turn create a stately presence. Oversized family room w/ stone fireplace takes center stage flanked by custom built in's. Hardwood open rail staircase ushers you from floor to floor, a statement piece in its own right. The heart of every home can be found in this custom kitchen w/ granite countertops, custom backsplash, center island and vaulted ceiling. Perks of this home are in abundance…butler's pantry, mudroom directly off of garage, recessed lighting and surround sound. 1st floor office makes for a must have on most buyers wish list. Master bedroom w/walk in closet & master bathroom with full tile shower, radiant heat travertine floors and his/her vanities. French doors open up to an expansive multi-tier deck overlooking an unobstructed peaceful and private backyard, the perfect destination to entertain or just relax! Fully finished walkout basement w/recessed panels and fireplace is the perfect setup for whatever your heart desires including the possibility for an in law suite. This home has been newly painted with new garage doors, driveway and most mechanicals. There is a place for everyone's wants or needs…this home will not last!

Listing Courtesy of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Tuttle Woodbury CT 06798

Woodbury, CT40 Tuttle Road

Price$675,000

Est. Mortgage: $/month

MLS Number 170384709

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 3
  • Acreage 3.15

Gorgeous colonial featuring bright open floor plan. A true entertaining home with fantastic kitchen offering breakfast bar island, built in Miele steamer, beverage cooler, hutch and eat in nook open to living room with beautiful fireplace, recessed lighting, 9' ceilings with sliders leading to over sized deck for gatherings overlooking private yard and your own tennis courts! Expansive 1st floor includes large dining room with built ins and Den/Office with more built ins. Theater lights lead you upstairs to Master suite featuring soaring cath ceilings, walk in closets and spacious master bath. Down the hall find 3 more large bedrooms with lots of closet space, and 5th bedroom/bonus room. Lower level offers indoor batting cage and game room with sliders leading to patio and fenced in yard for fur babies. Organic insulation is one of the many features this home offers. Check back shortly for professional photos delayed due to rain.

Listing Courtesy of Stacy Blake Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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24 Fawn Meadow Woodbury CT 06798

MLS Number 170372765

  • Single Family
  • Property Style Cape Cod, Farm House
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.88

TO BE BUILT! Welcome to Fawn Meadow Estates, Lot #17. 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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1204 Main Woodbury CT 06798

MLS Number 170362476

  • Single Family
  • Property Style Colonial
  • Bedrooms 8
  • Bathroom 9
  • Acreage 4.34

The Main House was built in 1827, an addition was added in the 1990's. The property is within "Woodbury Historic District No.2" Part of the history of Woodbury can be found out front on the stone wall facing the street - A Benjamin Franklin Mile Stone Marker. Previously was The Longwood Country Inn. Just recently it was The Olive Tree Restaurant - the dining room seats 50, in the Summer the patio can serve 40. The property is 4.34 acres which extends back to 240' of frontage on the Pomperaug River. This large Colonial has 8 Bedrooms - 6 have full bathrooms, 2 share a full bathroom, 6 Fireplaces and Hardwood Floors. A blue stone patio lies out back. Beautiful flowering shrubs and perennial flowers can be found around the property. Gorgeous sunsets year round! This property can be used for an Inn, a restaurant or a private home, or a gathering place for families and friends to spend Holidays or to just get together yet still have their own space!

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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 Woodside Woodbury CT 06798

Woodbury, CT5 Woodside Circle

Price$630,000

Est. Mortgage: $/month

MLS Number 170388992

  • Single Family
  • Property Style Farm House
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.39

Modern farmhouse completed in 2019 set on almost 3 acres of land, the house has four bedrooms, 2 1/2 baths, in a large two car garage. Luxurious high-end finishes adore the first floor. The first floor is as perfect for every family as it is for entertaining with an open floor concept including dining living room area in large kitchen with a built-in breakfast nook. The second floor contains a master suite with a private bathroom, Additional three bedrooms, and the laundry room. This house was designed to be energy-efficient including without compromise.

Listing Courtesy of Blue Lighthouse Realty, Inc

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$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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67 Hurds Hill Woodbury CT 06798

Woodbury, CT67 Hurds Hill Road

Price$599,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170373279

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 2.04

Over $900,000 in value in this meticulously maintained and cared for home, barn and property. Sought after low maintenance single level home located in the most desirable Woodbury location, in Tribury corner of town. Set back on a level and open two plus acre lot, this completely renovated home is only 5 minutes from Exit 16 off of route 84 and just a few minutes from Woodbury and Middlebury town centers. Designed to accommodate 14 vehicles in the heated attached garage, heated garage under and in the detached post and beam barn. All space was designed and laid out to optimize work space,, the room for a car lift, and plenty of elbow room to work. It's impossible to replicate what this home offers for the current list price with today's soaring construction prices. There are many professionally landscaped gardens, plenty of yard for ball and room for an addition or a pool down by the greenhouse or the post and beam barn. A perfect home for car enthusiasts, those looking to scale down to a single level home or those looking for a great yard and party barn! This home has it all!

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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74 Middle Quarter Woodbury CT 06798

MLS Number 170380094

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 3
  • Acreage 4.7

Beautiful 1835 Mini Farm, updated Farmhouse with four bedrooms, a Barn/Garage on 4.7 acres of pasture and light woods and stream. Just a short walk to Main St for great restaurants, Breakfast at West Egg, Ovens of France, Dinner at Good News Cafe, John's Cafe and The Marketplace, among many other great restaurants and shops. Open Floor Plan with Hardwood floors throughout and wrap around porch. There is a deck with entry from Kitchen and Living Room for easy entertaining. Mature Gardens and stone walls. Level land for play or farming. Hiking Trails is accessed right from the property. Solar panels for great energy efficiency and are owned outright. One of a kind property!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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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Town Line Woodbury CT 06798

MLS Number 170314046

  • Land
  • Acreage 33.71

Beautiful open farmland at the end of Town Line Road off of Main Street North. Nestled in the Woodbury, Watertown, and Bethlehem corner this secluded parcel offers easy access to everything. Three town centers, many restaurants, private schools, golf courses, and minutes to route 8. Most of the property abuts 50 acres of open space owned by the Town of Woodbury ensuring complete privacy and easy access to the Nonnewaug falls. A terrific opportunity to live off the grid!

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.04% last updated on Apr 15, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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 2021 Smart MLS, Inc. All rights reserved.