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The Matthews Group

Woodbury CT Luxury Homes for Sale

Find the latest luxury homes for sale in Woodbury. 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. You may also be interested in viewing luxury real estate listings in Litchfield County.

Luxury Homes in Woodbury Connecticut

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49 Pond Valley Road Woodbury CT 06798

Woodbury, CT49 Pond Valley Road

Price$2,350,000

Est. Mortgage: $/month

MLS Number 170396419

  • Single Family
  • Square Feet 6,014
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1994

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

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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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: 2.78% last updated on Jul 22, 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.

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15 Pomperaug Road Woodbury CT 06798

MLS Number 170404818

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

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. 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).

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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117 Painter Hill Road Woodbury CT 06798

Woodbury, CT117 Painter Hill Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 170417157

  • Single Family
  • Square Feet 3,166
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2002

Magical, 24 acre retreat with light-filled contemporary home on scenic Painter Hill. Designed and built to take in the outdoors, this 3BR home will steal your heart with vaulted ceilings, skylights, and numerous access points to the decks and terraces on two levels. The main floor features a beautiful custom kitchen with center island, open to the living, dining and family entertaining areas. Expansive main floor master suite is privately tucked at one end of the home and includes walk-in dressing room, full bath and access to a private deck. A guest suite with FP is also on the main floor. Upstairs, a bright and modern loft space makes working from home a true delight. The walk-out lower level features a large living/recreation room with FP, as well as an additional guest suite with full bath. A gym is also located on the lower level. The outdoor spaces are as important as the interior, and include a large stone terrace overlooking the stream-fed pond. The stream is the heartbeat of the property, providing the music of two waterfalls as it wraps around the pond - providing a calm and soothing backdrop both day and night. The mature gardens and lawn include many specimen trees, native plantings and towering pines. An original mid-century modern detached garage includes additional space that would be a fantastic cabana for a future pool. Located on the Roxbury/Woodbury line amidst the treasured homes of artists and bon vivants, this is a very special place to call home.

Listing Courtesy of Compass Connecticut, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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64 Hillside Road Woodbury CT 06798

Woodbury, CT64 Hillside Road

Price$1,399,000

Est. Mortgage: $/month

MLS Number 170418685

  • Single Family
  • Square Feet 6,965
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1987

Luxurious, secluded country estate w/pool. You will fall in love with this custom built colonial that leaves nothing to be desired. Set back on a quiet country road in historic Woodbury, CT this home is on 4.42 verdant acres and offers privacy and a beautiful New England landscape. The first floor offers plenty of space for entertaining with an oversized family room with stone fireplace, sun room, den with fireplace, game parlor, LR and formal DR with fireplace. This home features large open kitchen with island, granite counters, Viking cooktop, double ovens and custom cabinetry. On the second floor are 4BRs and 3 full baths. The huge master suite has a formal fireplace, window seats, walk-in closets, and balcony. Suite also includes a sophisticated 14x15 wood paneled room with bookshelves and center island that could double as a study and closet. Enjoy sunset views in rear of house from multi level decks, outdoor fireplace, and spectacular in ground pool. Pool has granite deck and is set amongst trees, gardens, waterfall, jacuzzi and cabana. Fully finished basement, 7 car garage w/in-law/staff quarters, kitchen & wood stove, approx 1200 sq ft not included in total sq ft. This home has been host to many gatherings with plenty of room for family and friends. If you are looking for a private retreat to call home, you've just found it. You will never want to leave!

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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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: 2.78% last updated on Jul 22, 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.

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556 Flanders Road Woodbury CT 06798

MLS Number 170405760

  • Single Family
  • Square Feet 5,403
  • Bedrooms 5
  • Bathroom 4
  • 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 fireplace. The family room provides a wall of glass doors leading to a wrap-around porch overlooking the gorgeous level and private 3 acre plot. 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 sink, and lets not forget the incredibly efficient geothermal heating and cooling system, which is secured with 4 inches of foam plus fiberglass insulation throughout the home for maximum performance. The three acre plot provides plenty of lawn and room for a barn, guest suite or a pool. --

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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198 Plumb Brook Road Woodbury CT 06798

Woodbury, CT198 Plumb Brook Road

Price$990,800

Est. Mortgage: $/month

MLS Number 170406410

  • Single Family
  • Square Feet 5,411
  • Bedrooms 4
  • Bathroom 5
  • Year Built 2001

This magnificent 5,411 sq ft home which offers a perfect balance of elegance, livable refinement & classic appeal is situation on 3.84 private, park like acres adjacent to Flander's Nature Center. The property is beautifully landscaped & has an exquisite gunite heated pool & spa, custom stone work & gardens, a perfect outdoor retreat. This 11-room colonial welcomes you with a grand entrance and striking chandelier. The first floor has an expansive open floor plan which includes a formal living room & dining room, office, a large eat in kitchen that overlooks the pool & gardens, a family room with hard wood floors, 9-foot ceilings & a gas fireplace and one full and one-half bath. The second floor includes a lovely master bedroom suit with walk-in closet and a spa tub, three additional bedrooms & another full bath. The walk out lower level is another glorious living area with floor to ceiling windows, custom mahogany wine cellar, full bath & large entertainment area. French doors lead out to the stunning pool area with outdoor granite bar equipped with refrigerator & storage. This property also has two waterproof AZEK decks with lighting & a 2-story barn with cupola equipped with heat, air conditioning & electrical. There is a security system, sound system, underground propane tank & generator that services the entire house including the heated pool. This country estate has been meticulously maintained and is truly one of a kind. Floor Plan https://www.planomatic.com/mls64918

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

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25 Gate Post Lane Woodbury CT 06798

Woodbury, CT25 Gate Post Lane

Price$849,900

Est. Mortgage: $/month

MLS Number 170409430

  • Single Family
  • Square Feet 6,698
  • Bedrooms 5
  • Bathroom 5
  • Year Built 1998

THE PERFECT STAYCATION…just unpack, relax and enjoy your new home and all it has to offer! The circular driveway sets the stage for this palatial home. Step into the Entry Foyer with its towering ceilings and sweeping staircase. The main level includes an open formal Living/Dining Room, an updated eat-in kitchen with white cabinetry, granite countertops and newer appliances and overlooks the patio and pool area. The Family Room also accesses the pool through sliding glass doors and has cathedral ceilings, a beautiful stone fireplace and plenty of room for your biggest furniture! Surround sound is wired throughout the inside and outside. Also on the first level is a home office and a Master Bedroom Suite with French Doors to the pool area, a Master Bath with standup shower, soaker tub, double sinks and a huge walk-in closet. Upstairs you will find a second Master Bedroom Suite with its own Bathroom and walk-in closet. 3 more bedrooms and another Full Bath complete the upper level along with plenty of closet and storage space. Now to the fun part! In the lower level you will find an amazing Rec Room with pool table, bar, movie room and home gym. There are sofas to relax in and games galore. All of this is available for purchase as well. Outdoors, starting from the front, is a synthetic golf green with 2 sand bunkers, and a hammock. The backyard is an outdoor oasis with the inground pool, poolhouse, picnic areas, 3 firepits and a playscape for the youngsters. Perfect Staycation

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

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