The Matthews GroupWilliam Raveis

The Matthews Group

Woodbury CT Homes with Acreage

Below, find homes for sale with acreage (5+ acres) in Woodbury, Connecticut below. You may also like to view Litchfield County homes with acreage.

Houses for Sale with Land in Woodbury

For more information or to see any of these properties in person, contact The Matthews Group online or call 860-868-0511

Save time! Create an account to save your favorite listings and get email notifications when similar properties come on the market.

401 Hoop Pole Hill Road Woodbury CT 06798

Woodbury, CT401 Hoop Pole Hill Road

Price$2,200,000

Est. Mortgage: $/month

MLS Number 170405026

  • Single Family
  • Square Feet 6,216
  • Bedrooms 6
  • Bathroom 6
  • Year Built 2003

Stately Colonial with magnificent eastern views of the Litchfield Hills located on 27 peaceful secluded acres. A sweeping driveway through a 10 acre meadow leads you to the hilltop perch of this distinctive residence, a 20'x60' gunite heated pool, a full basketball court and a 1.5 story barn. Upon entry the foyer is flanked by the formal living room with a fireplace and the formal dining room with raised panels and chair rail. Cross the center hall to the informal great room with a coffered ceiling, a wall of windows, floor to ceiling fieldstone fireplace, built-in bookcases and French doors to the flagstone patio. The grand chef's kitchen features marble counters, abundant cabinets to the ceiling, 2 dishwashers, Wolf range and wall ovens and Subzero refrigerator, an island, a raised river-stone fireplace and slider to the patio. First floor has an ensuite bedroom and a screen porch overlooking the pool and the spectacular views. On the second floor all 4 bedrooms are ensuite. The master suite focal point is the stone wall with a raised propane fireplace. There is a dressing room and walk in closet. Laundry is on the second floor. The basement has 3 finished rooms suitable for a variety of uses and a home gym outfitted with Technogym equipment. The large ensuite room over the garage is perfect for guests or home office. Whole house generator. New windows. New in-ground internet cable with 1GB speed. Property abuts Roxbury Land Trust.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

15 Pomperaug Road Woodbury CT 06798

MLS Number 170404818

  • Single Family
  • Square Feet 3,796
  • Year Built 1991
  • Bedrooms 3
  • Bathroom 3

Character, quality, and authenticity define this stunning residence, 80 miles from Manhattan and minutes from the historic towns of Washington and Roxbury. Built in 1991 of the finest materials and recently fitted with numerous upgrades, the antique-style saltbox has a gracious layout with a large, open concept family room interspersed with more formal, intimate spaces. Highlights of the home include wide-board oak flooring, exposed antique wood beams, 4 wood-burning fireplaces, Pella architectural series windows, hand-forged hardware, a covered porch, and 3 landscaped brick patios with meadow views and extensive stone wall perimeters. Other highlights include a whole house generator with in-ground propane tank; second in-ground propane for gas stove in kitchen; alarm system with driveway alarm, central vacuum, central AC. Sale includes 4 parcels, 2 building lots. 7,11,15 Pomperaug rd. Total tax on all parcels is $13,504; 490. Recent updates include: new septic system, new water softener, new cooktop (2020); new hot water heater, new dishwasher (2019), new dryer (2017), new air handlers and condensers (2015). Built with 4 bedroom septic and plumbed for additional bathroom/ bedroom on lower level.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

556 Flanders Road Woodbury CT 06798

MLS Number 170441122

  • Single Family
  • Square Feet 5,403
  • Bathroom 4
  • Bedrooms 5
  • Year Built 2007

Location, Location! One of the best addresses in all of Woodbury and nestled up against acres of Flanders nature preserve, this better than new farmhouse is immaculate. Built with top-quality products throughout, this home cannot be replicated under the current economic climate for almost twice of what it is currently listed. Located only 90 minutes from NYC, this house features a maintenance-free exterior, all oak hardwood flooring and tile throughout, extensive wood moldings, several french doors, and Smarthome technology. The gourmet kitchen features antiqued granite counters, marble backsplash, and Sub Zero and Wolf appliances as well as eating areas that are open to the family room with a fireplace. The family room provides a wall of glass doors leading to a wrap-around porch overlooking the remainder of the gorgeous, level, 50-acre estate. The upper level includes five bedrooms, a luxurious master bedroom and bath, another family room over the garage, and a walk-up attic. So much care and common sense went into the construction of this home including two staircases to the upper level, two staircases to the basement, a main level office with built-ins, a heated three-car garage with a sink, and let's not forget the incredibly efficient geothermal heating and cooling system. Overlook the rolling meadows that allow room for expansion, an inground pool, a guest house or a lot split or two!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

49 Pond Valley Road Woodbury CT 06798

Woodbury, CT49 Pond Valley Road

Price$1,925,000

Est. Mortgage: $/month

MLS Number 170396419

  • Single Family
  • Square Feet 6,014
  • Year Built 1994
  • Property Style Colonial
  • Bathroom 5

MINT! MINT! MINT! Gorgeous 16 acre gated property with park like grounds and amazing water views. Totally private yet minutes from town. Explore the grounds or relax by the pool with built in hot tub. The house is move in condition and the current owners have upgraded just about everything. Wood floors on both levels with 9' ceilings. The large chef's kitchen is open to the family room, both having access to the blue stone patio and in ground pool. There is a sun room with stone floor off the family room also with access to the pool. The other main floor rooms include an office, formal living and dining rooms, a mud room, butlers pantry and 2 half baths. The upstairs includes an amazing master suite with its own sitting room, large walk in closet with a built in safe and a master bath with dual sinks, a whirlpool tub and a steam shower. 3 additional large bedrooms with walk in closets share 2 full baths, 1 jack & jill. There is an upstairs laundry on this level also. Some of the many upgrades include a state of the art alarm system, which includes opening & closing the gate from your phone. There are 2 driveway sensors, a trigger to turn light posts on at night all the way up the driveway, 24 zone sprinkler system you can operate remotely, Sonos speaker system for kitchen, office and patio area. See addendum for additional features. 2 state of the art Furnaces with Whole house humidifier's built in and Filters that include UV lights to kill any bacteria in the air.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

137 Minortown Road Woodbury CT 06798

MLS Number 170407805

  • Single Family
  • Square Feet 4,214
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2000

Spectacular, Unique and Private! A gated drive brings you to this very unique home that gives you the feel of a ski lodge in the mountains. The land is beautifully landscaped and has about 1000' of frontage on the Nonnewaug River a short hike through the woods. There is a small sandy beach in one area and great fishing. A gunite pool with a water fall is right off the great room. The interior has an open floor plan with kitchen, dining and the great room easily accessed. The great room has a vaulted ceiling and a stunning 2 story river stone fireplace. 2 sets of sliders lead to the deck which leads to the pool area. The kitchen has granite counter tops, double ovens, a gas cook top and stainless steel appliances. The main floor master has a walk in closet, a fireplace, sliders to the deck and a master bath with a whirlpool tub and a separate stall shower. There is a main floor laundry room and another full bath on this level. The upper level has 3 additional bedrooms and a full hall bath. There is a finished den in the lower level with a gas fireplace and sliders to the out doors. For the car enthusiast/hobbyist, there is a 24X40 detached barn with 12' insulated doors and 2x6 construction. Bring all your toys! Under 2 hours to NYC makes this a great weekend getaway as well as a full time home. First time on the market! Taxes reflect 8 acres in 490 status

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

575 Weekeepeemee Road Woodbury CT 06798

MLS Number 170433479

  • Single Family
  • Square Feet 2,000
  • Bedrooms 3
  • Year Built 1795
  • Bathroom 1

Unique opportunity to own approximately 87 acres with Antique home in need of T L C and Barnes. There are four lots that make up the 87 acres . One lot in Bethlehem and Three in Woodbury. Lot 1- 7.00 acres Located in Bethlehem, Ct. Lot 2 - 7.22 acres. Lot 3 with house and barns is -11.59 Acres and Lot 4 with 61.76 acres. Sold all together will not divide. Property is currently a operating horse boarding facility. Main Barn with a 60 x 120 indoor riding ring plus 20 stalls. Feed room and tack room. Offices on second floor. Two additional post and beam barns with stalls and loads of storage space and potential. Out door riding ring. The 1795 Colonial needs to be completely redone. It's down to the studs and awaiting to be remodel. Over all this property offers a loads of possibilities.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

109 Sage Road Woodbury CT 06798

MLS Number 170434469

  • Single Family
  • Square Feet 2,057
  • Year Built 1966
  • Bedrooms 3
  • Property Style Contemporary

A Rare Mid-Century Modern in Woodbury, CT. Resting on nearly 7 private acres, the newly reimagined home features elegant stone-walled gardens as well as a mature woodland setting - specimen trees of weeping spruce, Japanese pine, and plum have been freshly planted. At just under 2,000 sq ft, the house is graciously scaled. The first floor offers an open living plan with liv/din room and kitchen area, sunken den with fieldstone floor and wood-burning fireplace, and a large four-season solarium. Glass doors throughout create a seamless transition to the exterior where you'll find a bluestone patio just off the dining area. The kitchen appointed with new Bosch appliances is anchored by a luxurious waterfall island of Statuario Venato quartz. A mudroom with laundry and half bath links the main house to the garage. The 2nd floor boasts a generously sized primary bedroom with gas fireplace and generous closets. The ensuite bath has a large walk-in shower, floating walnut shelf vanity with vessel sink, and imported porcelain tile. The 2nd and 3rd bedrooms are of equal size and share a new full bath with a tub/shower combo. A thorough remodel with uncompromising attention to detail by an award winning NYC interior designer to bring this 1966 home into the 21st Century, including new kitchen, baths, interior and exterior lighting, HVAC, generator and septic. 90± from NYC and minutes from the shops and restaurants of historical Woodbury, this is an opportunity not to be missed.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

60 Peter Road Woodbury CT 06798

MLS Number 170424431

  • Single Family
  • Square Feet 2,016
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1987

Views, Views, Views! Gorgeous views of the countryside from this rolling 20.33-acre plot with acres of open meadow, some woods, and plenty of room for a pool, guest house, or tennis court. Tucked away at the end of a long shared access way, this 2-bedroom Contemporary home has high ceilings and big windows to take in the view from every room. The open floor plan provides large open living space for entertaining many guests. Amenities include a fieldstone fireplace, hardwood floors, expansive deck, and a 3-season porch allowing one to enjoy the outdoors year-round. Bring all the cars and ATVs as there is room to ride and plenty of room for storage in the attached two-car garage or the large barn and two sheds. The barn provides a full second floor that can easily be converted into a 1 or 2 bedroom guest apartment or workshop. This rare find is located in Southern Litchfield County and is only an hour and forty minutes to NYC. There is some work to be done but this is a million-dollar property that won't have any trouble yielding a positive return on investment!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

1917 Main Street North Woodbury CT 06798

MLS Number 170422373

  • Single Family
  • Square Feet 3,523
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1854

Live, work, and play on Main Street North, Woodbury. Over 3500 sq feet in this Italianate Antique home with high ceilings, a gorgeous newer kitchen with an eat-in area, pantry, granite counters, and stainless appliances. The main level office and artist room provide an ideal spot for an in-home business or an antique shop as it once was. All the amenities one would expect in a charming older home including substantial moldings and built-ins, two staircases, specialty stainless skylights, a cupola, and three fireplaces. This Main Street home is situated on a private yet open 6-acre lot with a beautiful 28x53 post and beam barn overlooking a pond, and a 21 x 45 workshop with heat. The barn would make an ideal guest house or just plenty of storage with driveway access and a full walkout lower level. The workshop is heated and perfect for those staying at home to work. Bring the dirtbikes & quads and really enjoy the six-acre parcel or bring the animals and run your own farm. This convenient location is only within 5 minutes to Woodbury, Watertown, and Bethlehem town centers as well as many golf courses and private schools.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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

1785 Main Street North Woodbury CT 06798

Woodbury, CT1785 Main Street North

Price$430,000

Est. Mortgage: $/month

MLS Number 170443506

  • Single Family
  • Square Feet 1,740
  • Year Built 1940
  • Bathroom 2
  • Bedrooms 3

Secluded 8.39 acres horse property on Main Street Woodbury is home to a three-bedroom Cape. This home has wood floors throughout, freshly painted exterior and oversized deck August 2021. The kitchen has plenty of storage space and an island which you can see from the dining room. The living room has a large wood burning fireplace, bay window and new sliders to a private back deck. The Master bedroom is on the main floor, has 3 closets and a full bath. The upper level offers 2 large bedrooms with ceiling fans and a large full bathroom. The lower level is home to the laundry, storage, wood stove, and room to expand with sliders to the outdoors.

Listing Courtesy of Manzi Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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 2021 SmartMLS, Inc.