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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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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.

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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
  • Year Built 1991
  • Bedrooms 3
  • Bathroom 3

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. Sale includes 4 parcels, 2 building lots. 7,11,15 Pomperaug rd. Total tax on all parcels is $13,504; 490. 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). Built with 4 bedroom septic and plumbed for additional bathroom/ bedroom on lower level.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 170441122

  • Single Family
  • Square Feet 5,403
  • Bathroom 4
  • Bedrooms 5
  • 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 a fireplace. The family room provides a wall of glass doors leading to a wrap-around porch overlooking the remainder of the gorgeous, level, 50-acre estate. 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 a sink, and let's not forget the incredibly efficient geothermal heating and cooling system. Overlook the rolling meadows that allow room for expansion, an inground pool, a guest house or a lot split or two!

Listing Courtesy of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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49 Pond Valley Road Woodbury CT 06798

Woodbury, CT49 Pond Valley Road

Price$1,925,000

Est. Mortgage: $/month

MLS Number 170396419

  • Single Family
  • Square Feet 6,014
  • Year Built 1994
  • Property Style Colonial
  • Bathroom 5

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: 3.05% last updated on Oct 14, 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: 3.05% last updated on Oct 14, 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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575 Weekeepeemee Road Woodbury CT 06798

MLS Number 170433479

  • Single Family
  • Square Feet 2,000
  • Bedrooms 3
  • Year Built 1795
  • Bathroom 1

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.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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$1,225,000

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. The spectacular in ground pool has granite deck and is set amongst trees, gardens, waterfall and spa. Cabana has full bath, cabinets, refrigerator and sink for food prep. 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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
  • Year Built 2001
  • Bathroom 5
  • Property Style Colonial

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: 3.05% last updated on Oct 14, 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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41 Steeple View Lane Woodbury CT 06798

MLS Number 170426776

  • Single Family
  • Square Feet 5,983
  • Bedrooms 5
  • Bathroom 5
  • Year Built 1989

Fabulous design and style are evident throughout this 5200 square foot colonial in one of Woodbury's most desirable subdivisions! Located just two-minutes from the town center, this meticulously maintained and updated home provides generous room sizes, several different gathering areas, two fireplaces, extensive moldings, high ceilings, a two-story foyer, an expansive deck & patio, and a gunite pool. The main level includes a front to back formal living room with built-ins, fireplace & game area, a cozy office, a formal dining room just off the kitchen, a family room with a stone fireplace and back staircase, and finally a beautiful kitchen with a large center island and eat-in area overlooking the pool and yard. The upper level offers four guest bedrooms, one of two laundry areas, three full baths, and a luxurious master suite and master bath. A walkout lower level could make an ideal in-law apartment as it provides another gathering room, a second laundry area, a full bath, and your very own movie theater with eight comfy seats. This finished ground-level area conveniently walks out onto the patio surrounding the pool and provides easy access to changing areas and the full bath during picnics and gatherings. Other outdoor space includes gorgeous walkways, stone walls, level yard areas, a circular driveway, mature landscaping, and a three-car garage. Beautifully maintained, designed, and furnished!

Listing Courtesy of Drakeley Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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39 Terrell Road Woodbury CT 06798
Open House

MLS Number 170437920

  • Single Family
  • Next Open House: Sat 10/16 12:00 pm. to 2:00 pm.
  • Square Feet 3,385
  • Bedrooms 4
  • Bathroom 4

Welcome to 39 Terrell Road; breathtaking views highlight this Woodbury homestead. This sprawling Ranch has been meticulously maintained boasting unobstructed westerly views. Nestled on 3.5 picturesque acres that abuts Whittemore Sanctuary, this property features stunning stone work and terraces as well as four total bedrooms, three and a half total baths, in-law apartment, finished lower level with stone fireplace and a three car detached garage with small workshop. A detached HEATED barn has endless possibilities or parking for up to an additional seven cars. The barn is complete with unfinished loft spaces for more storage, workshops or potential living space. The primary bedroom, living room, kitchen and enclosed front porch all capture the incredible view that can only be seen from 39 Terrell Road. New roofing on all three structures, gutters and a new furnace/hot water heater in the main house are all bonuses to this bucolic property. An additional 6 acres is also available for purchase. Just 90 minutes +/- from NYC, steps from Lake Quassapaug and minutes to Historic Downtown Woodbury, your country oasis awaits!

Listing Courtesy of Regency Real Estate,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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88 Curtiss Meadows Woodbury CT 06798

Woodbury, CT88 Curtiss Meadows

Price$889,900

Est. Mortgage: $/month

MLS Number 170433422

  • Single Family
  • Square Feet 5,744
  • Bathroom 5
  • Bedrooms 4
  • Property Style Colonial

Space for everyone! Impeccably maintained and cared for home with close to 6000 square feet of living space and room to comfortably fit all generations under one roof! Nestled on a four-acre parcel in a quiet cul de sac at the southernmost end of Woodbury, this four-bedroom home provides generous room sizes, tons of closet space, two porches, and wood flooring throughout the first and second floor. Over 1500 square feet in the finished walk-out lower level with three rooms, a half bath, and a beautiful four-season sun porch that overlooks the grounds, mature landscaping, and abutting open space owned by Flanders Nature Center. The upper floor provides all good-sized bedrooms with newer wide pine floors, several walk-in closets with built-ins, and three full baths. The main level offers a two-story foyer, formal dining and living rooms with plenty of natural light, an eat-in kitchen overlooking a family room with a fireplace. Don't miss this home with its privacy, access to walking trails & acres of nature preserve, level lot, room for a pool, and plenty of area for outdoor activities. Just 2 minutes from downtown Woodbury, 5 minutes to 84 and 90 minutes to NYC!

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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19 Blueberry Lane Woodbury CT 06798

Woodbury, CT19 Blueberry Lane

Price$859,900

Est. Mortgage: $/month

MLS Number 170422361

  • Single Family
  • Square Feet 5,184
  • Bedrooms 5
  • Bathroom 4
  • Year Built 2009

No detail has been spared in this owner/builder designed, open concept home with five bedrooms and 3.5 baths just minutes from Woodbury's quaint Main Street. A few standout features include high-end appliances, luxury finishes, and detailed moldings. The main floor features 9ft ceilings, a living room with a masonry wood-burning fireplace, a formal dining room, laundry, and powder rooms. Centrally located is the Chef's Kitchen, with white Oak flooring, Pietra Cardosa countertops, pantry, and custom Maple butcher block island. The second floor includes a master suite with walk-in closets and a double base his and hers vanity. 4 additional bedrooms and 2 bathrooms complete the second floor. Located above the garage and accessed via a private staircase, you will find a newly built 880 sqft modern farmhouse space that includes a full bathroom, wet bar, kitchenette, and media area with full theatre surround sound. This space can be used as a guest room, remote learning area or home office. The home also features a spacious mudroom with plenty of seasonal storage. Outside you will find a custom Mahogany deck and bluestone patio with sweeping views of picturesque conservation land. Professionally maintained gardens with cutting flower beds and seasonal beds that change with the seasons. A 3-bay heated garage with 10' ceilings and front-wall garage door operators for maximum ceiling height complete this wonderful home for the car enthusiast.

Listing Courtesy of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.