The Matthews TeamWilliam Raveis

The Matthews Team

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 Team at 860-868-0511 with any questions or to schedule a private tour.

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7 E. Farm Road Middlebury CT 06762

Middlebury, CT7 E. Farm Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 170453155

  • Single Family
  • Square Feet 9,478
  • Bathroom 7
  • Bedrooms 4
  • Property Style Colonial, European

Old-world elegance with dynamic views of Atwater Pond. This estate includes 3 building lots acquired to buffer and provide seclusion, along with a bordering land trust. This European Inspired Country Manor is designed with 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 art that surrounds you. The splendid living room boasts a circa 1776 antique French chestnut mantel accenting a hand-built 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 bluestone 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 bluestone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The three lots can be used to add more gardens, add a pool and pool guest house, all while providing exquisite views of Atwood Pond ... continued in the addendum

Listing Courtesy of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 170460790

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

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: 3.56% last updated on Jan 20, 2022
* 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 Road Middlebury CT 06762

Middlebury, CT7 East Farm Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170251554

  • Single Family
  • Square Feet 9,478
  • Property Style European
  • Bedrooms 4
  • Bathroom 7

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 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: 3.56% last updated on Jan 20, 2022
* 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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194 Artillery Road Middlebury CT 06762

Middlebury, CT194 Artillery Road

Price$1,225,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170437369

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

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: 3.56% last updated on Jan 20, 2022
* 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

Pending Continue to Show

MLS Number 170437366

  • Single Family
  • Square Feet 8,201
  • Bedrooms 7
  • 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: 3.56% last updated on Jan 20, 2022
* 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: 3.56% last updated on Jan 20, 2022
* 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$899,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170407681

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

7410sqft Stately Colonial Williamsburg brick home w/ 1st floor master, in-law style unit with separate entry, and garages capable of holding 14 cars. 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 listed with 1 additional building lot as MLS#170437366 and with 2 additional building lots as MLS#170437369.

Listing Courtesy of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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

21 Cambridge Court Middlebury CT 06762

Middlebury, CT21 Cambridge Court

Price$825,000

Est. Mortgage: $/month

MLS Number 170459456

  • Single Family
  • Square Feet 3,502
  • Year Built 2004
  • Bedrooms 3
  • Bathroom 4

Spectacular home in Middlebury's Renowned Avalon Farms! One owner home has been meticulosly maintained, upgraded and decorater styled. The 2 story foyer is illuminated by the beautiful paladium stlye window and gorgeous chandelier. The flowing staircase leads to the open loft area. The designer, chef's kitchen is gorgeous with White cabinetry, quartz countertops and stunning features. Custom plantation shutters, large island with black walnut wood countertop is the highlight! Watch the kitchen activity from the breakfast countertop with room for 4+ stools. Farm sink, soft close cabinets, gas cooktop with pot filler, wine cooler, dishwasher, designer refrigerator and brand new convection double wall ovens. Glass front cabinets enhance the coziness of this beautiful gathering place. Designer light fixtures along with recessed lighting all on dimmer switches! Kitchen is open to dining area with french doors to patio. Family/great room with cathedral ceiling is accented by expansive windows. Large stone fireplace can be wood or gas. Formal dining room is also open to great room with exquiste crown mouldings, chair rail and raised panel wood work. Great room French doors open into the formal living room with gas fireplace and oversize window over looking expansive rear yard. Barn doors to foyer from formal living room makes this the perfect spot to settle in for a cozy night!

Listing Courtesy of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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

103 Periwinkle Drive Middlebury CT 06762

Middlebury, CT103 Periwinkle Drive

Price$650,000

Est. Mortgage: $/month

MLS Number 170441699

  • Condo
  • Square Feet 2,476
  • Bedrooms 2
  • Bathroom 3
  • Year Built 2004

Welcome to Benson Woods! All the "bells and whistles" in this immaculate model room. No expense has been spared! In the kitchen, you'll find the Wolf appliance suite w/BEST custom hood, Sub-Zero refrigerator, ASKO dishwasher, Travertine tile, and a walk-out private deck. This Winthrop unit offers 2982 square feet with covered farmhouse front porch, 2-3 bedrooms, 2 full and 1 half baths, 2 car garage, gas heat and central air conditioning! Main level offers: great room with soaring ceiling heights, triple crown molding and gas fireplace, dine-in kitchen that opens to dining area, a powder room, master bedroom suite with vaulted ceiling, gas fireplace, full bath, Jacuzzi tub, multi-jet shower, radiant heat, and two walk in closets, and a 2nd bedroom. Upper level offers full bath and a large loft with balcony overlooking the great room , a walk-in cedar closet which can be turned into an office or 3rd bedroom. California Closets throughout, sound system installed, central vacuum. Finished basement features wet bar, wine closet, and pool table. Additional amenities include Multi zone heat and a one year membership to Edgewood Bath and Tennis club which is just steps away, offering pool, tennis courts, gym and an array of summer programs for the entire family! Furniture available for sale.

Listing Courtesy of RE/MAX RISE

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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193 Ridgewood Drive Middlebury CT 06762

Middlebury, CT193 Ridgewood Drive

Price$619,995

Est. Mortgage: $/month

Open House

MLS Number 170365141

  • Condo
  • Next Open House: Sat 01/29 10:00 am. to 5:00 pm.
  • Square Feet 2,485
  • Bedrooms 3
  • Bathroom 3

The open-concept kitchen and great room provide the ideal space for entertaining. The casual dining area is adjacent to the kitchen and provides a convenient and intimate setting. The primary bedroom suite and two secondary bedrooms are located on the second floor. The second-floor loft offers endless opportunities for a flexible space, home office or yoga space. Secluded flex room with double doors makes for the perfect home office and the rear deck provides ample space for outdoor entertainment. this home includes Deck and Gas Direct Fireplace on Main Level and luxurious primary bath. Upgraded designer finishes already included in this home.

Listing Courtesy of Thomas Jacovino

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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11 Ridgewood Drive Middlebury CT 06762

Middlebury, CT11 Ridgewood Drive

Price$615,995

Est. Mortgage: $/month

MLS Number 170418307

  • Condo
  • Square Feet 2,485
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2022

The unique entry to the Denton maximizes the space and flow from the foyer into the open plan dining room, great room, kitchen, and casual dining area. A private office is also located off of the entry foyer. The second floor features a primary bedroom suite with cathedral ceiling as well as two additional bedrooms, a spacious loft, and a convenient laundry. Still time to personalize your designer finishes. Don't miss this opportunity-call today!

Listing Courtesy of Thomas Jacovino

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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

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 2022 SmartMLS, Inc.