Woodbury CT Homes for Sale

Find the latest homes for sale in Woodbury, CT. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. Contact us for more information and to schedule a showing.

Learn more about Woodbury CT >>

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: 4.28% last updated on Mar 21, 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

97 Owl Ridge Woodbury CT 06798

Price$1,490,000

Est. Mortgage: $/month

MLS Number 170111461

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 3.66
  • Square Feet 4,000

Spectacular property in Woodbury, Ct. Quite possibly the most charming corner of Litchfield county. Exquisite and unique custom built estate surrounded by acres of natural paradise. This fabulous home is built with state of the art quality components, superior materials & craftsmanship! Come and fall in love with this breath-taking property in the Estates of Owl Ridge.Home Built By Corbo.Only 1h and 15 min. from Manhattan.This is the last building lot with magnificent views.You must come and see this most charming corner of Woodbury CT!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

40 Peter Woodbury CT 06798

Price$925,000

Est. Mortgage: $/month

MLS Number 170088765

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 4
  • Acreage 3.13

Set back from the road with a circular driveway, the 3,400 sq/ft single-level home is appointed with a formal dining room, spacious formal living room with one of five fireplaces and a wall of windows that allows a bright entertaining space. The large-scale kitchen with sunny views boasts a walk-in pantry, Sub Zero and Wolf appliances, eat-in dining area, warm family room with brick fireplace, walk-out to stone terrace and built-in grill area. Three generous sized bedrooms include a peaceful master bedroom with third fireplace and walk-out to garden, en suite bathroom with glass shower, and dressing room..a clothes lover's dream! Other interior highlights include a walnut-paneled library with fourth fireplace, laundry room, and full basement with fireplace and plenty of storage space. Outdoors you'll enjoy Woodbury summers in your beautiful bluestone-wrapped Gunite pool-on of the focal points of the 3+/-acre lot with lighted tennis court, stone terrace, an abundance of perennial gardens and specimen plantings, and room for many outdoor activities of your choice. Completing the main property is a pool house with loft bedroom and 1 full bath as well as a sitting area and two additional garage spaces.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

97 Owl Ridge Woodbury CT 06798

Price$899,900

Est. Mortgage: $/month

MLS Number 170141819

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

Once in a lifetime opportunity to build your dream house on this beautiful private lot, this home is part of the Owl Ridge Estates surrounded by 100 acres of protected nature preserve if you have been searching for luxurious residence nestled in quaint New England setting this is it.Fall in love with this unique community.Great school system,low taxes,80 minutes from NYC 40 minutes from New Haven This is just incredible price for a high end new construction in this premium location, call for survey map and brochures,only 1 lot left!!!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

100 Cat Swamp Woodbury CT 06798

Price$799,000

Est. Mortgage: $/month

MLS Number 170140365

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 3
  • Acreage 4.62

Moison Designed Estate, combining the elegance of the past with all the conveniences of new! Located on over 4.5 stunning acres, this New "Old" home is sited to maximize views of the property, including the graceful pond and charming two story horse barn. Set privately on one of the most treasured streets in Woodbury, this Cape offers an open floor plan with four fireplaces, wide board pine floors and generous public spaces. A true escape, this gracious home is surrounded by gorgeous grounds including stone walls, patios, boxwood gardens and features a screened porch. Just minutes from Main Street in Woodbury, this home truly has it all!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

43 River Bend Woodbury CT 06798

Price$779,000

Est. Mortgage: $/month

MLS Number 170170593

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.04

Sophisticated Colonial on 2 park like acres with mature landscaping of fruit trees, Japanese maples, hydrangeas, stone walls, privacy and exterior lighting that surround the home. The yard is fully fenced with views of over 10 acres of land preserve that includes the Pomperaug river. This home offers high end finishes and fabulous details throughout, hardwood floors, 4 bedrooms, (potential 5th) 3.5 baths and 4 fireplaces Enjoy the open floor plan, living room with vaulted ceilings, reclaimed wood wall feature, fireplace and wood beams. Updated bright kitchen with gorgeous light, 4'x10' center island with quartz counter, 2 sinks, professional stove, Caesar stone counters and custom cabinetry. The Kitchen opens to charming family room with Blue Stone Fireplace. The fabulous oversize sun filled dining room boasts a large fireplace and is lined with French doors that lead to a Blue Stone patio for outstanding outdoor entertaining. The main level also has one of two master bedrooms with vaulted ceilings, hardwood floors, fireplace and master bath with stone shower and and large soaking tub. The upper level consists of the second master bedroom with built in shelving and a full bath and 2 additional bedrooms. The lower level of the home is finished with a large media/play room, a second area for a gym and ample storage. The three-car garage has a finished upper level which could be a great game room. This home is fully renovated and ready for you just to unpack and enjoy!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

466 Main Woodbury CT 06798

MLS Number 170047103

  • Commercial
  • Acreage 3.28
  • Square Feet 8,000

To be built - 8000 to 10000 metal building. Five 12' doors, level lot with many possibilities. Rent to multiple tenants or run your own business out of one of Woodbury's last industrial sites. Great exposure and minutes to all major routes.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

270 Main Woodbury CT 06798

MLS Number 170158464

  • Commercial
  • Acreage 1.09
  • Square Feet 4,302

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. The incredibly well maintained property and multiple buildings have tremendous potential for a variety of commercial and mixed use occupancy (Professional office, retail, home business, residential rental etc. ) Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. The property is high visibility with ample public parking adjacent to the property boundaries. Interior features include wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage. Perfect for in-home business and professional uses.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

270 Main Woodbury CT 06798

Price$699,000

Est. Mortgage: $/month

MLS Number 170156120

  • Single Family
  • Property Style Antique
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1.09

The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details. Wide plank hardwood flooring, 5 fireplaces, and extensive period moldings are intact and well preserved. This well configured property features a 3,310/sf. primary residence with large public rooms which can either serve as spacious residential quarters or as commercial spaces within the Main Street Design District. A large detached, remodeled and fully equipped guest house and additional garage and barn storage complete this amazing property. Endless opportunities for a combination of residential and commercial applications with additional rental income streams. This is a very special property steeped in local history and heritage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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

138 Quanopaug Woodbury CT 06798

Price$679,900

Est. Mortgage: $/month

MLS Number 170119895

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.63
  • Square Feet 3,634

Cool brand new contemporary home on quiet cul de sac drive abutting acres of open space. Gorgeous open floor plan with 2 story cathedral ceiling, large spans and fabulous kitchen opening to great room. Plenty of private outdoor entertaining space including a back patio out of the walkout lower level, upper deck off the great room and open wraparound front porch. The home is about 80% complete and there is still time to pick out some finishes. The upper level offers a master suite with luxurious master bath and large closet/dressing area, 3 bedrooms with two full baths, a balcony overlooking great room and a laundry room. The lower level has plenty of headroom to make a play or game room and a french door opening to a large patio. Many extras including first-floor study, cobblestone lined driveway and walkway, stone veneer and massive mahogany front door. Quiet location on cozy cul de sac.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.