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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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: 3.55% last updated on Aug 22, 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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283 Saw Pit Hill Woodbury CT 06798

Price$899,900

Est. Mortgage: $/month

MLS Number 170196322

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 6
  • Acreage 9.27

Incredible value! An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces & designed with every luxurious amenity imaginable. Gorgeous wrap around mahogany covered porch (with hot tub). Stunning two-story entry. A chef's kitchen offering the most discriminating buyer a large center isle, custom cherry cabinets, granite counters, handmade copper sink, Subzero, Viking stove, two dishwashers, convection oven & large dining area. Open concept seen and 9+ft ceilings throughout. Formal dining rm (w/custom cabinetry & limestone counters) living rm w/wet bar, gas fireplace & superb piano rm. Brazilian cherry flooring. An abundant use of windows & French doors blend the interior & outdoor spaces. Private office, full bath & powder rm complete main lvl. Impressive master suite w/octagonal ceiling, Brazilian cherry floors, gas fireplace, walk-in closet (organizers) & elegant bath (claw foot tub, antique vanity & tiled shower with jets/body sprays). Three additional guest rms (two share a bath, one an en-suite), & media rm w/vaulted ceiling & entertainment center. The finished lower level (possible in-law space) offers a recreation area, full bath, game rm, den & transitions easily to the exterior to enjoy the salt water sports pool w/water fall & deck jets, patio area & outdoor kitchen. Whole house audio system. Energy Star Rated Home. Look no further...this truly is a spectacular home set in an idyllic setting!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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32 & 40 Peter Woodbury CT 06798

Price$895,000

Est. Mortgage: $/month

MLS Number 170212725

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 5
  • Bathroom 7
  • Acreage 5.36

If you are looking for an exceptional home with quality craftsmanship and style, look no further. This brilliantly designed home includes 2 lots #32 and #40 on 5 stately acres in Woodbury, CT. Grace and sophistication is brought to life yet is relaxed enough to call a family retreat. The main home is impeccably well kept offering single level living on 3 acres with a versatile open floor plan, tennis court and a pool house. You enter your property from a lovely tree-lined driveway boasting gorgeous perennial flower gardens that evoke beauty and peacefulness. Thru the entryway foyer, there is a splendid living room complete with oversized fireplace and impressive panoramic view of a gorgeous landscaped courtyard and bluestone patio. The large scale comprehensive kitchen boasts a walk in pantry with auto lighting, two SubZero refrigerators, Wolf dual-fuel range with griddle, KitchenAid dishwasher, eat in dining area and a family room with an oversized brick fireplace and built in two speaker sound system. The library is magnificently crafted with walnut raised paneling, bookcases, a double closet and cabinets. There are three generous sized bedrooms including a welcoming master with a fireplace, walkout and en suite bathroom. Enjoy summer soirees in your beautiful bluestone wrapped Gunite pool and professionally lit hard surface tennis court. Great commuter location just 90 minutes from NYC. Perfect for multi-family, weekenders or rental. To see it is to fall in love with it!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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 Quassuk Woodbury CT 06798

Price$639,900

Est. Mortgage: $/month

Pending

MLS Number 170192126

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 6.64

Private gated entry, 6+ acres, with a must-see Pool Paradise! Just 90 mins to NYC, this beautiful 4 bedroom Colonial on over 6 acres of land provides plenty of space for living and playing. The majestic entryway leads to the kitchen featuring stainless appliances and granite countertops. Enjoy a meal at the enormous island, or move to the eat-in area for additional seating. The kitchen flows into the formal dining and living room, as well, so you can see your guests and family members from each area. The living room has a cozy fireplace and hardwood floors throughout. First floor also features an office. Upstairs, you will find 4 bedrooms and a bonus room with plenty of space to work out, watch a movie, or just relax. The lower level stands out with an amazing game/media room complete with a wet bar, half bath, and so much more! There is additional storage on this level and all utilities are hidden so your entertainment setup is seamless.Step outside and enjoy the gorgeous in-ground pool complete with concert-style lighting and a separate pool house, as well as the stone patio and fire pit off the back of the house. The pool area features an 11-speaker stereo system for amazing sound, as well as cable and WiFi hookups at the pool house. There is an automated gate at the property entrance and additional safety features such as a whole-house alarm system, automated garage doors controlled by an app, setup for 5 outdoor cameras, and a whole house generator. This is a must-see!

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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547 Flanders Woodbury CT 06798

Price$550,000

Est. Mortgage: $/month

MLS Number 170188887

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 4
  • Bathroom 2
  • Acreage 5.64

The perfect antique home! Classic and updated, very well cared for 4 BR antique home on 5.6 park-like acres with two ponds. Original floors and windows (all windows reglazed and insulated with modern storm windows). Generator, new furnace, freshly painted exterior, Artist's Studio with fireplace and loft, had been used as an antique business by prior owner, could easily become an in-law suite or main floor master. Studio wing also has separate kitchen and additional separate bedroom. Eat-in kitchen has soapstone counters, six burner DCS range, farmhouse sink and pantry with plenty of storage. Walk up attic with plenty of headroom just waiting to be converted into additional living space. Property also features a fenced in garden and two outbuildings. Detached 3 car garage/barn with unfinished space above, and separate small outbuilding also usable as a small studio or workshop. With the studio, walk-up attic and the garage/barn there are a multitude of possible ways to enjoy this property.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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$519,900

Est. Mortgage: $/month

MLS Number 170224524

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 5.42

Built in 2004 however this home is so pristine it looks like it was built within the past five years. Absolutely stunning home with excellent floor plan. This home offers four bedrooms, 2.5 baths, beautiful HW flooring, Granite kitchen, and freshly painted throughout. Master suite features trey ceiling and double sink vanity; other bedrooms all of great size. Kitchen features granite counters and SS appliances. Elevated great room with large fireplace, loads of windows and tons of space for family and friend gatherings. Enjoy the patio on the backyard and the serene environment with large natural stone. Meticulously maintained and situated on the end of culdesac street with loads of privacy. Have piece of mind with the Generac whole house generator that is only a couple years old. Home is move in ready, and waiting for it's new owners. Come see; fall in love and make an offer!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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544 Old Sherman Hill Woodbury CT 06798

MLS Number 170224441

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 2
  • Acreage 30.97

Amazing opportunity to own updated home with old world charm and modern updates on over 30 acres!! Picturesque New England setting with stone walls, barns, your own pond and privacy galore. Home remodeled in 2007. Renovated kitchen offers eat in area, breakfast bar, new cabinetry, tumbled marble backsplash and oak hardwood floors. Three season sunroom off of dining room. Living room provides one of the homes three fireplaces. First floor bedroom with fireplace, is currently being used as a family room and is located across from a full updated bathroom. Enter the second level into a large living area which leads to two bedrooms, one with a full bathroom. Other upgrades include newer roof, oil tank, hot water heater, plumbing and furnace. Enjoy the shade from the mature trees and the deer that graze and drink from the pond. So many options available for this property; fishing, horses, livestock, trails and an open field, possibilities are endless!

Listing Courtesy of Coldwell Banker Res Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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 ring, 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. Home is in need of some cosmetic updating.

Listing Courtesy of Century 21 AllPoints Rlty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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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527 Flanders Woodbury CT 06798

Price$374,900

Est. Mortgage: $/month

MLS Number 170208707

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 2
  • Acreage 5

Opportunity is knocking! Bring the horses, animals or cars to this classic New England Cape with six bays of garage space. A solid well built home that is move in ready but needs some minor updating. Lots of trim and built-ins throughout this home including crown molding, bookshelves in several rooms, and a corner hutch in the living room. Other amenities provide hardwood floors throughout the first floor, a dining room that can also be the first-floor master bedroom and the upper bedrooms have both been recently painted and new carpet added. Gorgeous outdoor space including 5 acres of open meadow, an open front porch, private back deck with an awning and an in-ground gunite pool with stone patio. A two car attached garage and a separate four-car garage with propane heat are ideal for a workshop or storage for your many cars.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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.

Save FavoriteSchedule A VisitAsk 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 2017 Smart MLS, Inc. All rights reserved.