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The Matthews Team

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 Team online or call 860-868-0511

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168 Upper Grassy Hill Road Woodbury CT 06798

MLS Number 170480181

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,354
  • Acreage 7.08

Fly in for the weekend! Gorgeous cape home abutting a local AIRSTRIP offering the possibility of flying home with the appropriate permission. Recently built with security in mind, you will love this pristine cape with all the measures taken for security and living off the grid. Nestled up against the Roxbury/Woodbury line this home abuts the old Roxbury airport, a 38x60 clear-span heated barn for all your toys, and is an incredibly efficient home with state-of-the-art heating, electrical, and engineering. Some of these mechanical upgrades include a 45 KW diesel generator plumbed to the oil tank, a solar array that makes more power than the property can use including heating and AC, electric gates with automatic watering systems on the walls and plantings, a casino grade security camera system, a 400 amp split service to operate the generator and solar in synchrony, and extensive underground and outdoor lighting to light up every inch of the 7 plus acres. Let's not forget the house, which has a welcoming open floor plan with lots of light, a gorgeous kitchen/great room with a cathedral ceiling, the main level master bedroom, and plenty of room for expansion. Built to last this contemporary cape provides all foam insulation, a 60-year roof, copper gutters, cedar shake siding with azek trim, and garage space for 16 or more vehicles. There is plenty of outdoor space including a ground-level deck with retractable awning, and a glass solarium with electricity and cable.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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452 Middle Road Turnpike Woodbury CT 06798

Woodbury, CT452 Middle Road Turnpike

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170497866

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,325
  • Acreage 11.27

Private story book stone and shingle home on over 11 acres. Eleven Rooms include two primary bedrooms on the main level. Spacious living room and family room overlook the park-like grounds. Cozy sitting room with fireplace has French door that leads to stone patio. Kitchen has been remodeled and includes stainless steel appliances. There are five fireplaces, oak pegged floors and oodles of charm. In ground heated pool, rolling lawn, specimen trees and early stone walls. Detached two bay garage/barn with finish space above and multiple sheds. Many updates and improvements include cedar shake roof, irrigation system, bathrooms, landscaping, pergola, pool heater, heated studio above garage - to many improvements to list, call for complete list. 2 hours from NYC.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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137 Minortown Road Woodbury CT 06798
Pending Continue to Show

MLS Number 170494374

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,674
  • Acreage 10.18

As you pass the gated entrance and tall trees that line the drive approaching this private country getaway, you'll think you're on vacation. Whether entertaining guests or just relaxing, the 1000 sq ft Great Room with 16' Cathedral Ceiling and soaring riverstone fireplace make every day special. Sunlight streams through the arched windows facing the back of the home with a 50' deck that leads to the outstanding heated gunite pool. The first floor primary bedroom suite with fireplace and sliders to the deck adjoins a full bath with heated floor, jetted tub & walk-in shower. Adjoining the Great Room is the spacious kitchen with granite counter, double-oven, heated tile floor and stainless steel appliances. A full bath & separate laundry room are close by and lead to the attached two-car garage. There's plenty of room for guests in the three bedrooms with full bath on the upper level. A finished walk-out lower level with fireplace adds 540 sq ft to the home & is adjacent to an unfinished space with wine closet & mechanicals including a hydro-air heating system. Car enthusiasts & hobbyists will appreciate the detached 24 x 40 garage/barn with 12' insulated doors & 2x6 construction. The private 10+ acre parcel includes a large, level lawn with playscape and a path leading through the forest to 1000' of river frontage for fishing or just getting close to nature. Private and pristine, this stay-cation paradise is just a few minutes from shopping & Woodbury's acclaimed restaurants.

Listed by Tom Greto of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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575 Weekeepeemee Road Woodbury CT 06798

MLS Number 170433479

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 2,000
  • Acreage 87.5

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.

Listed by John Sniffen of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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511 Weekeepeemee Road Woodbury CT 06798

MLS Number 170497768

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,861
  • Acreage 12.55

Privacy abounds in this charming Gentleman's Farm. Welcome home to 511 Weekeepeemee Rd in the lovely town of Woodbury, CT. This sprawling farmhouse colonial is nestled on 12+ private acres. If space is what you desire this home will not disappoint. Walking into the front entry you are greeted by solid hardwood floors which flow throughout the main level where you will find every room to be oversized. The kitchen is complete with wood cabinets, granite countertops, and stainless steel appliances, and is open to a family room with the most impressive stone fireplace. The formal dining room is adjacent to the formal living room giving you great space to gather with family and friends. Those that love to entertain will be thrilled to find a massive great room with a wood-burning stove over the garage which will make the perfect place for your next party! Upstairs you will find a large primary suite complete with changing area and full bath. This level also has 3 additional oversized bedrooms and a full bath! Outside you can relax on a freshly painted deck overlooking your backyard with plenty of perennials, a butterfly garden, and a gazebo area abutting a large hayfield perfect for watching the evening sunset. Just a short walk from the house every horse lover will be delighted to find an 8-stall barn with electricity and water, 2 paddocks, a riding ring, and even a round pen! This is a truly special home and a must-see! ** AGENT OWNER **

Listed by Heather Crabtree of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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258 Flanders Road Woodbury CT 06798
Open House

MLS Number 170499443

  • Single Family
  • Next Open House: Sun 06/26 11:00 am. to 1:00 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,210

Meander up your drive, past the neighboring picturesque horse paddocks to this private oasis tucked amongst just under six acres of nature with gunite pool and spa, oversized wrap decking and a large screened porch. No need to leave unless you take the few minute trip into historic Woodbury town center to enjoy all this little town has to offer. Expansive, remodeled kitchen opens to family room with fireplace number one, steps right into the screened porch. Formal front living room with fireplace number two, and a large dining room with wet bar/ butlers pantry and large - very large, built in china closet. Convenient mud room / laundry room between garage and kitchen. Upstairs.....step down into master bedroom wing with two skylights and two dormers to let the sunshine dance thru. Master bath with sunken jetted tub, new double sink granite topped vanity and walk in closet. Three additional bedrooms all have walk in closets. Hardwood flooring on both levels. Central Vacuum, security system. Brand new gas pool heater, generac generator, top of the line furnace. Just in case you need more space, the full walk out lower level could be finished for a great recreation room/ movie theatre.

Listed by Mary Ann Bennett of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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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428 Washington Road Woodbury CT 06798

Woodbury, CT428 Washington Road

Price$645,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170498028

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,910
  • Acreage 7.06

Tucked away on 7 acres plus 1/3 ownership interest in 4.76 acres of open space. On the cusp of Woodbury and Washington Town line. Over the top maintenance makes this a wonderful seller to buy from! The interior has been updated with a new gourmet kitchen in the great room with 18' vaulted ceiling show casing the tall stone fireplace. Dining room table can accommodate large holiday gatherings especially inviting with a roaring fire! Primary and two secondary bedrooms are on the main floor for convenient one level living. Second floor family/ movie room makes for a quiet escape. If the new granite, stainless and custom cabinetry kitchen are not enough, the expansive outdoor living space will leave you wanting nothing but to be out there entertaining for three seasons. Another gourmet kitchen, granite, refrigerator, sink, grill, electric burners and separate pizza oven! Chilly nights? Relax by the stone fire pit. Extensive decking, stone work and 3 covered porches. Recently hosted an amazing wedding! Lower level has a full laundry room, a work shop nice enough to be used as an office and an additional garage to hold the toys or classic car.

Listed by Mary Ann Bennett of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1917 Main Street North Woodbury CT 06798
Pending Continue to Show

MLS Number 170422373

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 3,523
  • Acreage 6

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.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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