The Matthews Team

William Raveis Lifestyles Realty

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

Contact the William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

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Search by Property Type: Luxury Homes | Homes with LandSingle Family HomesCondos | Land

229 Bacon Pond Road Woodbury CT 06798

MLS Number 170537720

  • Condo
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 913

Sought after, upper level Town in Country condo! The only one on the market! Vaulted ceilings, fresh paint and laminate flooring throughout, beautiful floor to ceiling brick fireplace, and spacious deck overlooking the wooded backyard! Kitchen with dining area and combination living/dining room both beaming with natural light! Two bedrooms with generous closet space and laminate flooring, and updated full bath with walk-in shower complete this single-level condo. All new windows and slider! In-ground swimming pool with picnic area, coin-operated laundry facilities with storage space, two designated parking spots plus visitor parking! A quiet complex situated in a private country setting, close to all that Woodbury has to offer!

Listed by Taylor M O'keefe of Drakeley Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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Church Hill Road Woodbury CT 06798

Woodbury, CTChurch Hill Road

Price$139,900

Est. Mortgage: $/month

MLS Number 170537745

  • Land
  • Acreage 2.92
  • Zoning OS100

A private residential lot just past Flanders Nature center. An approved 2.9-acre lot that sits in the Woodbury/Bethlehem/Watertown corner of Woodbury. Easy access to all three town centers and walking distance to acres and acres of Flanders nature preserve. The gradual slope of the parcel lends itself to a level house site or walkout lower level.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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 Hoop Pole Hill Road Woodbury CT 06798
Active With Contract

MLS Number 170537298

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,421
  • Acreage 8.84

Small cape in need of total RENOVATION. In an Estate and in the process of being emptied. 8.84 acre lot with a small stream running though it. There is a barn on the lot that needs total renovation. You enter the main level through a rear porch into a living room with a wood stove. In the back there is a kitchen that goes out to a 3 season porch. Also on this level is a bedroom, laundry and a full bath. Upstairs there is a bedroom and a sewing room/den. Will Not Qualify For FHA mortgage. Need Conventional or Cash! Sold AS IS!

Listed by Sharon McGuire of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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23 Upper Commons Woodbury CT 00432

MLS Number 170535249

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,182

Woodlake living in an updated unit with granite counters and stainless steel appliances. New hardwood flooring throughout main floor. Updated bathrooms. Hybrid AO Smith hot water heater. Nest thermostat helps keep costs down and can be accessed remotely to cool/heat your unit before you get home. Two bedrooms and two full baths on the upper level. Plenty of storage with full basement and pull down attic. Detached one-car garage plus assigned parking space. Tennis courts on property. Plenty of space for walking/running. Kayaking/canoeing on the lake. Tax District is $1.310.33 quarterly and is tax deductible. Trash, water, sewer, plowing, mowing all included. Forget the rakes and shovels. Fireplace does not currently operate. Damper and flue need to be serviced/repaired.

Listed by Chris LaCava of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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59 Hillside Road Woodbury CT 06798

Woodbury, CT59 Hillside Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 170534856

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 9,296
  • Acreage 3.49

This custom built European style home was exquisitely designed by Rick Moisan. It offers a lifestyle rarely found in a home. You enter this architectural masterpiece via the center hall that spans front to back, leading to an exceptional outdoor living area. This area features a heated gunite infinity pool with hot tub, expansive patio, covered sitting area, and exceptional panoramic views of Woodbury and beyond! Inside is a professionally designed chef's kitchen with top of the line appliances and a full walk-in butler's pantry. The office, formal dining room, living room and family room all have their own unique fireplaces. Soaring ceilings and massive windows offer natural light throughout. The upper level primary bedroom has a fireplace, a balcony, sitting room, dressing room and full spa bath. The secondary bedrooms are large and have walk-in closets, en-suite baths and each appointed with its own Juliet balcony. The two story in-law suite has a full kitchen, granite countertops, bedroom, living room and office/den. It has direct access to the pool/patio area. There is also an au pair/guest suite located above the garage. Keep in mind, the 9,200+ sq.ft. is all above grade. The heated walkout basement is over 4,500 sq.ft. and can easily be finished. Please visit the virtual tour so you can experience this breathtaking home “in person”. Do not enter property without a confirmed appointment.

Listed by Heather Weber of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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42 Woodbury Hill Woodbury CT 06798

Woodbury, CT42 Woodbury Hill

Price$399,900

Est. Mortgage: $/month

MLS Number 170533705

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,404

Hard to find Putnam Loft style unit in well-maintained Woodbury Hill Condominium Association. Located just minutes from town, this spacious unit provides a first-floor master suite, a cozy living room with a cathedral ceiling and brick fireplace, a formal dining room, and an efficient eat-in kitchen. The upper floor includes a loft area overlooking the living room, a second full bath, and a good-sized guest bedroom. A full walkout lower level features a finished family room, an office/bedroom, and a half-bath laundry area. Centrally located in the Woodbury Hill Complex and right across from the community in-ground pool and tennis court, this unit has beautiful distant views off the back deck. Other amenities include a two-car attached garage, a slider off the kitchen to an expansive deck, a walkout lower level, and plenty of storage. Don't miss this opportunity to own in Woodbury Hill.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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Upper Grassy Hill Road Woodbury CT 06798

MLS Number 170533333

  • Land
  • Acreage 11.53
  • Zoning OS80

Hard to find 11 plus acre lot surrounded by beautiful homes on Upper Grassy Hill Road. This subdividable parcel is ideal for two or maybe three lots or keep the entire property for seclusion and privacy. No restrictions allows the next owner to hunt, ride quads and motorcycles, build a barn, have animals, or enjoy all that nature has to offer.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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Minortown Road Woodbury CT 06798

MLS Number 170532609

  • Land
  • Acreage 31.8
  • Zoning OS60

Gorgeous hilltop location for the next buyer to build their dream house and get away from the hustle and bustle of everyday life. This 31 acre lot has the potential for beautiful 240-degree views with some clearing. A pristine parcel with mature trees that offers privacy, a level home site, limited wetlands, and no restrictions allowing one the freedom to do as one wishes. The driveway is roughed in allowing for easy viewing either by foot or with a four-wheel drive vehicle. This convenient location is just 10 minutes from four different town centers and close proximity to several public and private schools.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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55 Heritage Drive Woodbury CT 06798

Woodbury, CT55 Heritage Drive

Price$410,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170533130

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,911
  • Acreage 1.36

Serene, Litchfield County, 1900 SF+, 3 Bedroom, 2.5 Bathroom, Sprawling, Open Concept Ranch in the heart of Woodbury. This Impressive Estate boasts a breathtaking, cavernous eat-in kitchen outfitted with Custom Cabinetry, Gorgeous Quartz countertops w/ undermount sink & split handle fixtures, a tile backsplash, and a distinct Island w/ butcher block top. Timeless Brass Hardware perfectly accents the spaces warm energy, making it a universal focal point for all to enjoy. The kitchen gently flows into a grand, naturally illuminated, recessed living room highlighted by original Hardwood Flooring, a masonry/wood burning fireplace and additional space currently being utilized as a home office. The Master Bedroom Suite provides owners a Relaxing Private Oasis with ample closet space, wood floors, and a recently updated private bath w/ an impressive fully tiled shower, a Chic vanity complete with custom stone top. Two additional, sufficient bedrooms with hardwood floors and well-proportioned closet space round out the homes limitless appeal. Potential value unlocked by the opportunity to convert the large 1000 SF+ basement into living space. Professionally landscaped grounds are in peak form with lush, emerald, green grass, new front and rear masonry walkways and tranquil, bucolic acreage. Strong mechanicals, a desirable location, an optimal layout and a desirable neighborhood make this property an opportune choice to make your Home!

Listed by Jason D Malagutti of Regency Real Estate,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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39 Grassy Hill Road Woodbury CT 06798

Woodbury, CT39 Grassy Hill Road

Price$199,000

Est. Mortgage: $/month

MLS Number 170532067

  • Land
  • Acreage 5.63
  • Zoning OS80

Build your dream home on gorgeous 5.6 acres property in tranquil setting, level land, and much more.

Listed by Michael Dimyan of Tower Realty Corp

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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167 Transylvania Road Woodbury CT 06798
Pending Continue to Show

MLS Number 170532062

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,162
  • Acreage 2.45

Wonderful center hall colonial ideally located in Southern Woodbury for quick access to major routes and a short drive to Woodbury historic downtown! The main level provides a generous sized eat in kitchen opening up to fabulous family room with cathedral ceiling, hardwood floors, and masonry brick fireplace. A formal dining room, living room and office, all with hardwood floors, round out the first floor. The upper level includes three good sized bedrooms, and a primary suite with hardwood floors, a vaulted ceiling, walk in closet, and full bath. Located on a 2.45 private acres, this home is barely visible from the road. Priced to sell, this home offers a two car attached garage with a second stairway to the basement, plenty of yard space to picnic, and a stone patio located just off the kitchen/great room.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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 Hillview Lane Woodbury CT 06798

Woodbury, CT17 Hillview Lane

Price$589,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170531204

  • Single Family
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,776
  • Acreage 0.74

Situated at the end of the cul-de-sac, this freestanding spacious reproduction Colonial has everything you need for a comfortable life with the ease of condo living. Located in a very well maintained 21 house complex, the 2/3 bedroom house has many updates and upgrades. The front foyer has the "wow" factor with new tile floor and a gorgeous stairway with iron banisters. The wood floors throughout have been beautifully redone, and propane has been piped to fireplace, dryer (can be gas or electric) and two exterior connections in the rear for a gas grill and gas firepit. There is also an upgraded in depth security system. The highlight on the main level is the two story great room which consists of the family room with gas fireplace and kitchen with custom cabinetry, granite counters and stainless steel appliances by Jenn-Air, KitchenAid and Bosch. A French door leads to the private bluestone patio. The good-sized formal dining and living rooms sit at the front of the house. The spacious first floor primary bedroom has a renovated full bath and walk-in closet. Upstairs there is a loft study or den, hall bath and two additional bedrooms. There is a full basement and two car garage. South Brook is a beautiful complex conveniently located just minutes to town.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 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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The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2022 SmartMLS, Inc.