The Matthews GroupWilliam Raveis

The Matthews Group

Middlebury CT Real Estate

Lake in Middlebury ConnecticutLocated approximately 90 miles north of New York City, Middlebury is a great escape from the non-stop activity of New York City. With easy access to the surrounding towns of Waterbury, Watertown, Woodbury, Southbury, and Naugatuck, Middlebury is comfortably accessible to restaurants, shops, and activities for the entire family. Middlebury’s Lake Quassapaug is a local favorite, with Quassy Amusement Park being right on the shore prompting a day filled with water activities, fun, & games for the whole family. Browse current Middlebury CT real estate listings below.

Middlebury Real Estate for Sale

Contact The Matthews Group at 860-868-0511 with any questions or to schedule a private tour.

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9 Bristol Road Middlebury CT 06762

Middlebury, CT9 Bristol Road

Price$3,995,000

Est. Mortgage: $/month

MLS Number 170373397

  • Single Family
  • Square Feet 6,554
  • Bedrooms 5
  • Bathroom 5
  • Year Built 1962

https://youtu.be/mrrIdghSV14Lake living at its finest! Custom Greek Revival built from foundation up by current owners. An entertainers dream, this 5 bedroom, 4.5 bath home has 6 acres of direct frontage on Lake Quassapaug with its own drive in boathouse with power lift and private beach. Lake facing pool with separate spa and pool house with kitchen. Lakeside terrace with stone firepit. Stunning public spaces on main level including an enormous eat in kitchen with fireplace and entertainment area with projection video system. Commercial grade appliances include Traulsen refrigerator and freezer and 48" Viking range. Luxurious primary bedroom suite includes fireplace, office and its own gym with stunning lake views! An en-suite guest room, and 3 additional bedrooms with shared bath and laundry complete the second floor. 1200 square feet of heated garage space for 4 cars. Many smart home features, geothermal heat, generator, slate roof, random width hardwood flooring, just a few of the custom finishes. Room for tennis court if desired. Do not miss your chance to make this your own ultimate lake compound. Easy access from I-84, under 2 hours from NYC, 2.5 hours from Boston.

Listed by 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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5 Bristol Road Middlebury CT 06762

Middlebury, CT5 Bristol Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 170415685

  • Single Family
  • Square Feet 1,680
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1928

First time on market in over 100 years. 5+ acres of direct frontage on Lake Quassapaug with 1928 Cottage in need of renovation or build your dream home. Shares a private cove with its own drive in boathouse. Fabulous western sunsets across the lake with gentle sloping lawn and mature plantings and trees. Very special setting. Surrounded by multimillion dollar estates. 2 hours to NYC, 3 hours to Boston, less than 1 hour to Hartford or New Haven. 10 minutes to Oxford Airport.

Listed by 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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59 East Farm Road Middlebury CT 06762

Middlebury, CT59 East Farm Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 170421656

  • Single Family
  • Square Feet 7,126
  • Bedrooms 5
  • Bathroom 6
  • Year Built 2001

This stately home has both classic finishes and simplistic elegance. Situated in a prestigious neighborhood, with two acres of lush grounds, attention has been paid to every detail of this home. From the exterior brickwork, limestone, and bluestone, along with the gardens, which showcase different plantings year round, to the interior moldings and millwork throughout. Tastefully decorated with modern finishes, and an endless amount of upgrades, give this home the feel of a new build. Nine foot ceilings, gleaming hardwood floors, and large windows ensure that light pours into every corner of this home. This spacious home has a spot for everyone, including five bedrooms, five and a half baths, pluds a gorgeous owners retreat complete with dressing room and spa like bath. The formal living and formal dining room, set on either side of the grand foyer, each have their own detailed fireplace, tray ceilings, chic light fixtures and classic woodwork. The kitchen is the heart of the home, which hosts a large kitchen island, a casual eating area, quartz counter tops, glass backsplash, a viking stove and subzero refrigerator, all to inspire your inner chef. The family room offers coffered ceilings, a stone fireplace, and views of the backyard. The tucked away office gives sophistication while you work or study, with built-ins and smokey finishes. Take time to relax in the sunroom with French doors which lead to the best part of this home, the patio. Please see Additional Remarks...

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/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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7 East Farm Middlebury CT 06762

Middlebury, CT7 East Farm

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170251554

  • Single Family
  • Square Feet 9,478
  • Bedrooms 4
  • Bathroom 7
  • Year Built 1999

Old world elegance on Atwater Pond. This European Inspired Country Manor is designed with the artful detail and a grand size similar to distinguished French and English manors. Enter into the grand sweeping foyer with 20' ceilings, marble and porcelain floors and the impressive custom curved stairway. Continue and find outstanding details everywhere. With the authentic French stone floor reproduction, and other French and English influences, this marvelous home is to a level of art. The splendid living room boasts a circa 1776 antique French chestnut mantel accenting a hand build limestone fireplace. The 12' ceilings with hand sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the blue stone floors and brick trim. A focus point of the elegant dining room is the double tier octagonal tray ceiling along with the custom hand painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the wide blue stone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The captivating French country kitchen equipped with custom cabinets, high end appliances, center island breakfast bar continues to provide a great space for entertaining and relaxing. The Library is appointed with walnut panels surrounding a superb fireplace detailed ... continued in addendum

Listing Courtesy of Keller Williams 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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420 Burr Hall Road Middlebury CT 06762

Middlebury, CT420 Burr Hall Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 170409946

  • Single Family
  • Square Feet 6,563
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2018

Stunning custom built home in a desirable Middlebury location! Nestled on almost 3 acres this home features a beautiful grand entrance with a stone & iron gate providing privacy. The beautiful, expansive driveway of stone pavers leaves plenty of parking for guests & family. A drivable front walk way leads to the main entrance of the house. As you enter the home you will be drawn to the beautiful foyer with 14 ft. ceilings! There is a large formal dining that also features a 14 ft. ceiling & large widows to let in the day's sunlight as well as a home office with french doors. With hardwood floors throughout & a very spacious great room with a floor to ceiling stone fireplace & custom builtins you will be drawn to the beautiful backyard view & composite, low maintenance extra large deck. Next you will make your way to the large eat in kitchen which features SS appl., an oversized kitchen island/breakfast bar ideal for the chef of the house! The island features a wine/beverage chiller, a prep sink & plenty of counter space. 4 BRS to include a master suite, a walk in closet with builtins, an oversized walk in shower & double sinks. 3 additional spacious bedrooms leaves plenty of room for family or guests. The lower level has a fireplace & can easily be finished if you need the extra space & is walk out to a gorgeous covered patio. Security system in place with remote access will remain. Custom stone work will amaze you throughout the property! Schedule your private showing today!

Listing Courtesy of Showcase Realty,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 Sandy Beach Aka Tylers Cove Middlebury CT 06762

MLS Number 170430641

  • Single Family
  • Square Feet 1,981
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2000

Luxurious lake lifestyle awaits! Nestled in Tyler's Cove this chic contemporary with direct water frontage is an entertainer's dream! The spacious interior boasts four levels of fully finished living space, custom finishes with large windows bringing the outdoors in with stunning lake views from nearly every room. Kitchen complete with stainless steel appliances, sub zero refrigerator/freezer, granite counters and custom cherry cabinetry along with full updated baths. Enjoy energy efficient geothermal heating with radiant heated hard wood floors throughout, plus fireplace with wood insert for those chilly nights. Relax and enjoy the breathtaking lake views on one of the multiple balconies, oversized mahogany deck or blue stone patio. Gather for a bonfire, soak in the hot tub or rinse off in the peaceful outdoor shower. The lush landscaping, private beach and new 30 plus feet dock is what makes this home one you won't want to miss. A three story heated barn with loft, workshop and plenty of room for storage and multiple vehicles. A fabulous, private retreat just 90 miles from NYC and minutes from Oxford airport. Come and enjoy wonderful local restaurants, many scenic hiking trails and fabulous antique shopping! Relax, refresh and recharge in beautiful Lake Quassapaug!

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/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 Tylers Cove Middlebury CT 06762

Middlebury, CT19 Tylers Cove

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170430567

  • Condo
  • Square Feet 1,981
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2000

**Street number has changed to 49** Luxurious lake lifestyle awaits! Nestled in Tyler's Cove this chic contemporary with direct water frontage is an entertainer's dream! The spacious interior boasts four levels of fully finished living space, custom finishes with large windows bringing the outdoors in with stunning lake views from nearly every room. Kitchen complete with stainless steel appliances, sub zero refrigerator/freezer, granite counters and custom cherry cabinetry along with full updated baths. Enjoy energy efficient geothermal heating with radiant heated hard wood floors throughout, plus fireplace with wood insert for those chilly nights. Relax and enjoy the breathtaking lake views on one of the multiple balconies, oversized mahogany deck or blue stone patio. Gather for a bonfire, soak in the hot tub or rinse off in the peaceful outdoor shower. The lush landscaping, private beach and new 30 plus feet dock is what makes this home one you won't want to miss. A three story heated barn with loft, workshop and plenty of room for storage and multiple vehicles. A fabulous, private retreat just 90 miles from NYC and minutes from Oxford airport. Come and enjoy wonderful local restaurants, many scenic hiking trails and fabulous antique shopping! Relax, refresh and recharge in beautiful Lake Quassapaug!

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

194 Artillery Road Middlebury CT 06762

Middlebury, CT194 Artillery Road

Price$1,225,000

Est. Mortgage: $/month

MLS Number 170437369

  • Single Family
  • Square Feet 8,201
  • Property Style Colonial
  • Bathroom 7
  • Year Built 1962

7410sqft Stately Colonial Williamsburg brick home w/ 1st floor master, in-law style unit with separate entry, garages capable of holding 14 cars, and 2 separate building lots! Single owner home. First time ever offered for sale! Absolutely gorgeous grounds with 3 brownstone patios, professional landscaping, and serene setting all with a view! The curb appeal of this home is unparalleled. Hardwood floors throughout including under much of the carpet. Large eat-in-kitchen. Dining room with fireplace. Sunken living room with fireplace, and built-ins. Sunroom with bay window, gas fireplace and slider to deck. Main level master suite w/ full bath, walk-in closet, and hardwood floors. Several additional bedrooms and baths on the 2nd and 3rd floors totaling 7 bedrooms and 7 baths in the entire home. Above garage living space with separate entry and open floorplan includes 2nd eat-in-kitchen, living room, bedroom, full bath and laundry. Fully finished basement with recreation room and gym space. Attached garage and carriage house are heated. Great for any car enthusiast. Architectural roof replaced in 2019. Strong mechanicals, including automatic generator, sec sys, city sewer, central air. Also 2 additional building lots! Building lots currently taxed at PA490, listing data reflects this. Acreage, assessment, and taxes reflect both parcels. Also listed without lots as MLS#170407681 and with 1 additional lot as MLS#170437366.

Listing Courtesy of Showcase Realty,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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1860 Middlebury Road Middlebury CT 06762

Middlebury, CT1860 Middlebury Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170349104

  • Single Family
  • Square Feet 3,782
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2006

Meticulous attention to details in this outstanding home! including second-floor master suite, walking closets in all the bed rooms, extensive trim work, open floor plan, 10' ceilings, spectacular entertaining both indoors and out, inground heated pool, the finished basement comes complete with a wet bar.

Listing Courtesy of Vila Real Agency

$
$
%
$/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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225 Crest Road Middlebury CT 06762

Middlebury, CT225 Crest Road

Price$1,099,000

Est. Mortgage: $/month

MLS Number 170417662

  • Single Family
  • Square Feet 4,138
  • Year Built 1975
  • Property Style French
  • Bedrooms 3

Nestled in the heart of Middlebury on 3.21 acres, this home will wow you from the moment you arrive. A chef's kitchen, high ceilings, grand gallery, library, sun room, terrace and a master wing as nice as the finest 5 star resort. The garden is accessed by multiple points throughout the home and stone patios are in key locations for ease of entertaining both inside and out. The grand gallery features a gorgeous fireplace mantle imported from France. A full, unfinished basement with a walk-out for a future gym or additional space if needed. The grounds are exquisite with an encompassing hedge, shade gardens, mature trees and evergreens for year round privacy. The Gunite pool was recently resurfaced and the roof is only a few years old. 90 miles from Manhattan to your little slice of heaven. If the Ritz Carlton designed and built custom homes, this would be it!

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

194 Artillery Road Middlebury CT 06762

Middlebury, CT194 Artillery Road

Price$1,025,000

Est. Mortgage: $/month

MLS Number 170437366

  • Single Family
  • Square Feet 8,201
  • Property Style Colonial
  • Bathroom 7
  • Year Built 1962

7410sqft Stately Colonial Williamsburg brick home w/ 1st floor master, in-law style unit with separate entry, garages capable of holding 14 cars, and separate building lot! Single owner home. First time ever offered for sale! Absolutely gorgeous grounds with 3 brownstone patios, professional landscaping, and serene setting all with a view! The curb appeal of this home is unparalleled. Hardwood floors throughout including under much of the carpet. Large eat-in-kitchen. Dining room with fireplace. Sunken living room with fireplace, and built-ins. Sunroom with bay window, gas fireplace and slider to deck. Main level master suite w/ full bath, walk-in closet, and hardwood floors. Several additional bedrooms and baths on the 2nd and 3rd floors totaling 7 bedrooms and 7 baths in the entire home. Above garage living space with separate entry and open floorplan includes 2nd eat-in-kitchen, living room, bedroom, full bath and laundry. Fully finished basement with recreation room and gym space. Attached garage and carriage house are heated. Great for any car enthusiast. Architectural roof replaced in 2019. Strong mechanicals, including automatic generator, sec sys, city sewer, central air. Also additional building lot! Building lot currently taxed at PA490, listing data reflects this. Acreage, assessment, and taxes reflect both parcels. Also listed without lot as MLS#170407681 and with 2 additional lot as MLS#170437369.

Listing Courtesy of Showcase Realty,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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

54 Falcon Crest Road Middlebury CT 06762

Middlebury, CT54 Falcon Crest Road

Price$998,000

Est. Mortgage: $/month

MLS Number 170428035

  • Single Family
  • Square Feet 6,971
  • Bedrooms 5
  • Bathroom 7
  • Year Built 1992

Custom built single-owner home set on private 5.19 acres in premiere Middlebury neighborhood. High Quality construction throughout. Unmatched 1st Floor Master Suite feels like a luxury retreat with built-ins, crown molding, trey ceilings, bay window, oversized attached full bath with travertine marble floors and vanities, jetted tub, walk-in shower, and 2 walk-in closets. 3 additional Bedroom Suites upstairs, all with their own private attached full baths and walk-in closets. 2 of these bedrooms have access to an outdoor balcony. The 3rd bedroom has a sitting area attached. Formal Living Room with Fireplace, built-in shelving and desk, high end trim, and French doors. Large Formal Dining Room perfect for Holidays. Open Floorplan between Eat-in-Kitchen and Oversized Family Room. Full length windows drench these rooms with natural light. Large Finished Walk-out basement with separate access to large patio. 2nd Kitchen perfect for entertaining or guests, large family room, more sleeping quarters, and another full bath. All of the bells and whistles. Quiet neighborhood only minutes from I-84. 1hr 45min from Manhattan. 15 min from Oxford Airport. 1hr from Bradley International Airport. 1hr 35 min from Laguardia Int'l Airport.

Listing Courtesy of Showcase Realty,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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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.