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.

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

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105 Old Grassy Hill Woodbury CT 06798

Price$2,800,000

Est. Mortgage: $/month

MLS Number 170010438

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 57.87

This outstanding private retreat is set on 57+ acres at the end of a cul-de-sac and is bordered by a large pond and the Flanders Nature Center, The property offers beautiful views, hiking trails through the woods and a secluded setting. Custom designed by the architect Moisan, the home features quality details, a gourmet kitchen, and grand entertainment spaces. Something special!

Listing Courtesy of Coldwell Banker Res Brokerage

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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505 Upper Grassy Hill Woodbury CT 06798

Price$1,485,000

Est. Mortgage: $/month

MLS Number 170056391

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • Acreage 6.62

Award-winning sunsets and serene living await you on this spacious estate known as Cardinal Hill. Graced with a beautiful heated in ground swimming pool, tennis court, and barn, this 1940's Colonial was solidly built in this lovely section of Litchfield County. Discover all the wonderful shops in this antique district and come home to relax on a warm sunny day as you take in the extraordinary views for miles, available because the property is located in one of the highest elevations in Woodbury. Enjoy outstanding entertainment opportunities on picturesque grounds lined with stonewalls and stone terraces. Extra building on property houses a two-bay garage with attic and large gym with half bath. Additionally, the one-bedroom 1066 square ft. guesthouse with kitchen and living room is the perfect in-law apartment. Abutting guest house is a 480 square foot home-office with cathedral ceiling and separate heating and cooling. Total square footage (including unfinished basement) equals 7267 sqft. Located just minutes from I-84, this dream house is calling you home!

Listing Courtesy of Global Real Estate Network

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Price$1,200,000

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: 4.17% last updated on Apr 18, 2019
* 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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132 Stone Pit Woodbury CT 06798

Price$649,000

Est. Mortgage: $/month

MLS Number 170115681

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 4
  • Bathroom 3
  • Acreage 5

Custom designed Ranch on private lot has elegant open floor plan with oversized rooms and vaulted ceilings! Spacious master suite has luxurious bath, bamboo floors, sitting room, and exercise room. Convenient central vacuum system, even in the garage. Music/intercom system throughout with hookups for all your modern devices. Soaring vaulted ceilings in kitchen and family room. Four-zone hydro-air system with electrostatic filters and all systems of the highest quality. Potential fourth bedroom in main floor office space. This home is secluded yet convenient to town, shops and restaurants. Just 15 minutes to I-84. A must see!

Listing Courtesy of Global Real Estate Network

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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158 Scuppo Woodbury CT 06798

Price$640,000

Est. Mortgage: $/month

MLS Number 170155788

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 3
  • Acreage 9.13

Privacy, views, views, location, location!! Convenience to highway and completely private on 9.13 acres with magnificent views,property abuts 14 acres of natural preserves.Custom built colonial features gourmet kitchen with large pantry,opens to light and bright fam.Rm with custom woodwork and spectacular fireplace. 1st floor office,master bedrm suite w/dressing room, 2nd office and covered balcony. Additional 650 sq ft finished in basement

Listing Courtesy of Coldwell Banker Residential Brokerage

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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339 Hoop Pole Hill Woodbury CT 06798

Price$589,900

Est. Mortgage: $/month

MLS Number 170081519

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5

Views, Views, Views!! The best views in all of Woodbury. Long distant views from the hilltop off of Hoop Pole Hill Road. Enjoy the breezy summer nights on your stone terrace next to your vanishing edge gunite pool with jacuzzi. 5-acre plot with a level house site and privacy from your neighbors. Light and bright contemporary home with a wall of glass to take in those sweeping views of Litchfield County. Amenities provide 4 to 5 bedrooms and three full baths, generous sized dining room overlooking living room with 24' soaring cathedral ceiling and a wall of glass. Recently refinished oak flooring, paint inside and out and finished lower level, an ideal spot for an in-law suite. Beautiful outdoor space with spacious yard, privacy from neighbors and room for outbuildings or expansion. Million dollar VIEWS for less!

Listing Courtesy of Drakeley Real Estate, Inc.

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%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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18 Crane Woodbury CT 06798

Price$549,900

Est. Mortgage: $/month

MLS Number 170162564

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 11.12

This home has a little bit of everything! Located on a quiet, tucked away small cul de sac, this sprawling 3300 square foot colonial offers 11 plus acres of privacy, great outdoor space with an in-ground pool & patio and an additional 780 square feet in the walkout lower level. A comfortable center hall home with kitchen/great room overlooking gas fireplace, formal dining & living rooms and an 18 x 24 main level family room with propane stove. The upper level provides four generous sized bedrooms including a fantastic master bedroom suite. Awesome outdoor space including multi-level deck and patio all overlooking the pool that is nestled up against the backyard and acres of woods. Many extras including a full walkout lower level with finished rooms, plenty of lower level storage, a paved driveway, 4 car garage, and a generator hook up. Tough to find this much house on 11 plus acres of land just minutes away from everything!!

Listing Courtesy of Drakeley Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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110 Whittlesey Woodbury CT 06798

Price$529,900

Est. Mortgage: $/month

Open House

MLS Number 170130247

  • Single Family
  • Next Open House: Sun 28th 1:00 pm - 3:00 pm
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3

WELCOME TO 11O WHITTLESEY! DON'T MISS OUT ON THE OPPORTUNITY TO MAKE THIS CHARMING COLONIAL YOUR NEW HOME!!! AS YOU DRIVE UP YOU'LL SEE THAT THIS HOME BOAST OF 5+ACRES OF GORGEOUS GREENERY!!! IT'S BEAUTIFULLY DESIGNED FOR GRACIOUS LIVING AND IT BOASTS OF PLENTY OF SPACE AND TONS OF SUNLIGHT! 9rms, 4 bedrooms and 2.5 baths. 3 car garage with NEW never rot wood siding, the stunning and open kitchen boasts of an angled center island, granite counter tops, custom cabinets, NEW pendant lights, NEW stainless steel refrigerator, NEW electronic faucet and a NEW garbage disposal. NEW ceiling fans and gleaming hardwood floors throughout. The spacious living room is where you can cozy up to the brick wood burning fireplace while enjoying your favorite beverage! Formal dining room, family room and an additional room for an option of an office or a den. The master bedroom has a cathedral ceiling, master bath with his and her sinks, spacious shower and an Xtra large walk in closet! ALL bedrooms have new carpets, new chandeliers, and new fixtures! The laundry room is on the main level, central air, Culligan water softener system and more for you to see!!!

Listing Courtesy of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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130 Tuttle Woodbury CT 06798

Price$499,900

Est. Mortgage: $/month

MLS Number 170150955

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Acreage 5.09
  • Square Feet 3,014

Too many features to describe in one reading. Must see interior. Crown moldings, medium wide hardwood 1st & Lower Levels. Plenty of storage. Large wood deck with spiral stairs to lower level patio and terraced rear lot. Walkout basement to patio. Master Suite, LR and Kitchen access to wood deck. Main levels with approximately 3,000 SF with added 1,000 SF in finished basement. Solid wood raised panel door, crown moldings and chair rails, vaulted ceiling in LR w/FPL. Fenced in court yard at front entry. Kitchen with granite and marble tops, island with cook top, double wall oven, refrigerator and dishwasher, window box at sink, breakfast nook with access to wood deck. Plenty of cabinets. Walk through to vaulted ceiling LR or DR. Front entry open with wide stairs to upper level, den/office with built ins with lavatory. Main level Master Suite with access to wood deck, 2 WIC to master bathroom. Master bathroom with spa tub, double sinks and glass enclosed shower. This is truly a must see to appreciate. Upper level with 2 BRs, bathroom, overlook to LR below, storage space. Finish Lower level with open FR, den/office with wine cellar, mirrored exercise rm, wet bar in side room. The FR has FPL and built ins and access to patio and terrace rear yard. Town states 1,000 SF. Hardwood floor and open stairway to upper levels. Feels like part of the main living area.

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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147 Hoop Pole Hill Woodbury CT 06798

Price$475,000

Est. Mortgage: $/month

MLS Number 170137810

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 7.6

Country Living at its best! This turn key home offers the best in Farmhouse style. Nothing to do but sit back and relax on your own private 7.6 acre lot. The main floor of the house is perfect for entertaining and everyday living. As you enter into the large foyer you will find a home office through the Barn Door, to the right is a room fit for a playroom or a formal dining room. As you continue straight through the foyer you find the extremely large eat in kitchen with a double oven, granite countertops and stainless steel appliances, access to the extraordinary deck with covered seating area and covered hot tub, to your left the family room with a wood burning fireplace to cozy up to and storage cabinets to store everyone's belongings which is perfectly located as you enter from the garage. The back of the home is where you will find the second staircase that leads to the Master bedroom, with sitting area,walk-in closet and master bath. On the second floor you will also find a laundry room, entertainment room and 3 spacious bedrooms. The third level creates endless possibilities. The yard is fenced for small animals, with chicken coop and small barn. Just 90 minutes from NYC in a quaint New England town.

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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135 Old Sherman Hill Woodbury CT 06798

MLS Number 170166269

  • Single Family
  • Property Style Contemporary
  • Bedrooms 5
  • Bathroom 5
  • Acreage 5.5

One of a kind property on over 5 Acres of land with beautiful meadows, a riding rink, and 5 stall horse barn! The horse barn features running water, electricity, and a garage bay. Pull right in to your circular driveway that leads up to a stunning California style Contemporary. The home was custom designed and features a family room with vaulted ceilings and fireplace, a formal dining room with built ins, a cozy study/formal living room with a stone fireplace and bookshelves, an eat in kitchen that leads to a sunroom with sliders to a private deck that overlooks park like grounds, and 3 bedrooms on the main level. The master suite is on the second floor and offers another fireplace, full bath, wet bar, private balcony, and plenty of closet space. The walk out lower level adds additional living space with another bedroom, and 2 other finished rooms for possible exercise room, home theater, and/or family room. Truly a serene setting. Schedule your showing today. Seller to install new septic prior to closing.

Listing Courtesy of Century 21 AllPoints Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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Lot 57A Transylvania Woodbury CT 06798

MLS Number 170105113

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 5.76
  • Square Feet 2,000

ANOTHER ENERGY STAR NEW CONSTRUCTION home to be built by local area custom home developer Connecticut Residential. MODERN FARMHOUSE CAPE proposed for this oversized woodsy lot located in Southern Woodbury. Brand New open floor plan design offers RIGHT SIZED HOME and rooms. 3 BEDROOMS including 1 FLEXIBLE MAIN LEVEL BEDROOM/STUDY give this home maximum usability for many buyer types. 2 car attached garage leads to LARGE USABLE MUD ROOM and an upper level laundry room area is large enough to double as a SECOND FLOOR UTILITY OR CRAFT SPACE. Full front porch and LARGE LOT ACREAGE round out this innovative offering. Great Southern Woodbury location with EASY ACCESS TO I-84 East or West at exit 14 or 15. Approximate build time of 6-9 months depending on time of the year. Lot has some exposed ledge rock so any necessary blasting has been included in the offered price. Other home plan designs are available including Colonial, Ranch, master bed down, etc...

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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.