Middlebury CT Real Estate

Located 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.

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

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120 Tranquility Middlebury CT 06762

Middlebury, CT120 Tranquility Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 170191502

  • Single Family
  • Property Style Mediterranean
  • Bedrooms 3
  • Bathroom 4
  • Acreage 23.69

Tranquility Road is one of the most beautiful roads in America. Starting at the stage coach stop over the one lane stone arched bridge to the watering trough, one steps back in time. The king and queen stone walls that line this Connecticut Historic Route lead to the gates of this estate. The only thing that has changed on this road in hundred years is the construction of 120 Tranquility Road. This magnificent home is perched on the most beautiful promontory of this 23 acre property. The views, open sky, rolling hills, beautiful trees, and historic stone walls surround this private home. The estate is built in a Mediterranean architecture style with all the comforts of a modern house. Being a newer home it has all the bells and whistles of "new", but it also has a formal dinning room with a fireplace. The living room is stately. Its coffered ceiling and stone fireplace give the impression of being in a castle, yet retains the comforts of a home. The first floor master suite has generous closet space, a boudoir, and an amazing bathroom. The first floor also has an office/den/library, indoor lap pool, laundry room and butler's pantry. There are an additional two bedrooms and two bathrooms on the second floor. Additional features are an intercom system, extensive security system, central vacuum, Litron lighting Audio system, house humidifier/dehumidifier, grounds water system, and generator. There is an expandable attic for and additional bedroom or billiards room.

Listing Courtesy of Westbury Realty CT

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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Middlebury CT 06762

Middlebury, CT

Price$2,200,000

MLS Number 170095062

  • Commercial
  • Acreage 10.51
  • Square Feet 5,312

Terrific business opportunity to own and run a very successful recreation club. Currently Edgewood Bath and Tennis Club with fitness center, newly installed paddle courts, playground, basketball courts, tennis courts and beach volleyball. Located in Middlebury, just a few minutes from exit 16 off of I84, this pristine club is on over 10 acres of property and commercially zoned with room for building expansion and the ability to open year round. A rare opportunity to own a Swim & Tennis club with over 4 million in capital improvements and impeccably maintained over the years.

Listing Courtesy of Drakeley Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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289 Burr Hall Middlebury CT 06762

Middlebury, CT289 Burr Hall Road

Price$1,899,900

Est. Mortgage: $/month

MLS Number 170246316

  • Single Family
  • Bedrooms 4
  • Bathroom 8
  • Acreage 10.47
  • Square Feet 8,420

Stunning Mediterranean Colonial Estate situated on a private 10 acre lot nestled in a pristine, quaint Connecticut town. Single Owner, Quality built, custom home. 92,000 ivory bricks and limestone adorn the timeless fa├žade. Cobblestone Driveway. Stunning 1st floor master suite w/ bath, walk-in closet and sitting area. Hand painted murals and detail work throughout done by a local artist. Wine Tasting room with Oak cabinetry, built-in wine fridge and humidor. Professionally designed and installed cinema room with fiber optic ceiling and adjacent full-service pub/bar. Exercise Room. Custom designed stairway and railing stand alone as a piece of artwork. Entire 1st floor has 15' ceilings. Entire 2nd floor has 12' ceilings. This home is loaded with one of a kind features built for this specific home. 3 lighted domes. Multiple terraces. 4 separate Bedroom Suites. Unfinished Space above garage with easy access for potential in-law, aupair, or additional finished space. Applianced La'nai flows into the pool area. Self-Cleaning Gunite pool with in-ground spa tub. Large entertaining area complete with outdoor dining space w/ Fireplace, built-in grill, fountain and stonework. Photos alone cannot do the grandness of this home justice. Every detail of this home was thought out and planned, not a single corner was cut in design, material, or craftsmanship. Perfect home for entertaining. This home was designed with timeless aesthetics and exceptional attention to detail and functionality.

Listing Courtesy of Showcase Realty, Inc.

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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27 Abbott Farms Middlebury CT 06762

Middlebury, CT27 Abbott Farms Road

Price$1,475,000

Est. Mortgage: $/month

MLS Number 170153991

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 7
  • Acreage 7.51

Exquisitely appointed and amazingly constructed! This impressive 6400 sf Colonial, originally slated to be the builder's own home is crafted like none other. Exceptional workmanship & quality design are offered throughout this energy efficient home. At first sight you will be intrigued by the melody of stone, brick, cedar and azek on the exterior along with the balcony covered front entrance and lovely landscaped island and grounds. Inside, a 2 story double sided stone fireplace accents the open formal dining & living areas with finishes such as coffered ceilings, raised panels, detailed moldings and wide board hardwood floors with a striking walnut inlay. The sun-filled sitting room has a beautiful herringbone floor and fireplace. A Gourmet kitchen with top-of-the-line finishes, granite island and walk-in pantry flows into the breakfast area & cathedral family room accented by a detailed 2 story brick fireplace, each having french doors leading to an expansive open and covered balcony with its own fireplace. The 1st Fl. Master Suite features a spa like bath, gas fireplace, balcony and private study. On the 2nd floor are 5 spacious bedrooms each with their own beautifully tiled full baths. The private guest/au pair suite has its own laundry facilities. A walk-out lower level offers 12 ft ceilings with options for a movie room, gym & more play space, roughed plumbing for a full bath & fireplace opening. This home represents the finest new construction available.

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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135 Crest Middlebury CT 06762

Middlebury, CT135 Crest Road

Price$1,324,000

Est. Mortgage: $/month

MLS Number 170113819

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 6
  • Acreage 3.05

https://youtu.be/gHF8TnEVr7s   Mid Century Modern set in Historic Middlebury on 4 acres with mature plantings pool and pool house. Wander through the uber chic front courtyard to this home's one level expanse offers separate living and entertaining space and providing all the modern amenities. In true Bauhaus fashion, materials flow continuously from inside to out with clean lines and illumination from walls of glass. New commercial grade kitchen features stainless cabinets and appliances for a thoroughly modern look. 2 full size Sub Zeros, 6 burner Wolf Range, breakfast nook with atrium windows. Stunning Great room with fireplace integrated into a wall of granite w/ wet bar. Partial floating walls with custom built-ins delineate the dining area and provide storage. Master bedroom offers den w/ fireplace & recently renovated glass tile bath w/ heated floor, separate dressing area, designer fixtures & floor-to-ceiling window. Most rooms walk out to over 900 sq ft of Ipe decking w/ metal railings and built in grill station. Media Room with built ins off kitchen for casual gathering. View overlooks mature woodlands and heated gunite pool in a tree house setting fantastic for relaxing with complete privacy and for taking in Fall foliage. Lower level features game room, gym, full bath, cedar closet. Semi-circular driveway with separate lead to the garage, oil and stone driveway lined with Belgian blocks & bordered w/ a stone wall. Multi-zone heat and air w/ whole house generator.

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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54 Falcon Crest Middlebury CT 06762

Middlebury, CT54 Falcon Crest Road

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170238298

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 5.19

Looking for privacy and a home that has it all? You've found it here- quality custom built one owner home on a 5+ acre fully landscaped lot- open floor plan features a eik with large dining area- big fdr- huge family rm on main level with full length windows- flr or library with fireplace- breath taking main level master bedroom suite with tray ceiling, bay window, chandelier, built ins, 2 walk in closets and a master bath that will blow you away- 3 oversized bdrms on the upper level all have full baths & walk in closets- walk out ll has a kit, dr/lr combo, bdrm & full bath with a seperate entrance leading to an oversized patio- 3 car gar- 4 zone heating system- 3 central ac units- central vac- intercom- main level laundry rm- all anderson windows- this home must be seen to appreciate!!!

Listing Courtesy of Vitale Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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470 South Middlebury CT 06762

Middlebury, CT470 South Street

Price$1,075,000

Est. Mortgage: $/month

MLS Number 170239951

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 6
  • Bathroom 6
  • Acreage 20.9

Unique opportunity to acquire the beautiful Willowstone Farm with rolling pastures and an amazing park-like setting. Possibilities for Investors seeking large acreage, Bed & Breakfast, family compound, equestrian use and more! Featuring a large barn with attached five-car garage, recently updated guest cottage, 100 x 200 riding arena, additional two stall barn and main house filled with 1800's charm. Enjoy the custom millwork, wide hardwood floors restored to their original look. Minutes from the Oxford Airport, 90-minute commute to NYC and conveniently located close to private schools. Come home to this country farm estate and enjoy the natural surroundings in this classic New England farmhouse.

Listing Courtesy of Global Real Estate Network

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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68 Abbott Farms Middlebury CT 06762

Middlebury, CT68 Abbott Farms Road

Price$999,900

Est. Mortgage: $/month

MLS Number 170101000

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 5
  • Bathroom 6
  • Acreage 2.8

Luxurious 5 Bedroom, 4.2 Bath Brick Colonial with Elevator, set on private 2.8 acre cul-de-sac lot. Magnificent construction. Stunning Entry Foyer. Eat-in-Kitchen with generous counterspace and island, Viking Appliances, Butler's Pantry, and sun-drenched breakfast nook. Open concept to Grand 2-Story Great Room with Fireplace. Gorgeous Sunroom Sitting Area. Formal Living Room with detailed ceiling painting and Fireplace. Formal Dining Room with classic trimwork. Study with warm built-in bookshelves and cabinets. Two first floor Bedrooms with full bath. Master Suite with large closets and attached full bath with Marble, Steam Shower, and Jetted Tub. Additional Bedrooms and Bonus Room upstairs. Second Kitchen. Laundry Room. Large Trex Deck and Paver Patio. Professional Landscaping. 3 car heated garage. Strong Mechanicals including Hydro Air, Central Air, Central Vac, Generator, Security System. Loaded with details and high-end extras including Hunter Douglas blinds, 3 Ovens, Warmer, 2 Dishwashers, Ice Maker, Wine Cooler, Elevator that services all floors… Too Much to List! Quiet neighborhood only minutes from I-84. 90min from Manhattan. Less than 10min from Oxford Airport. 60min from Bradley International Airport. 90 min from Laguardia Int'l Airport.

Listing Courtesy of Showcase Realty, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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75B Gleneagle Middlebury CT 06762

Middlebury, CT75B Gleneagle Road

Price$899,900

Est. Mortgage: $/month

MLS Number 170154125

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 4
  • Bathroom 3
  • Acreage 4.7

Fabulous, quality new construction in established neighborhood of high end properties. Public water and sewer in this conveniently located, desirable neighborhood of custom homes. Four different models to choose from including our contemporary ranch with a first floor master suite OR completely customize your own home. Our premier home development company has over 39 years experience in the Connecticut home building industry. Amazing opportunity for a brand new high quality home of your choice in an ultra convenient cul de sac location surrounded by nature. Three Mile Hill Estates is a beautiful private cul de sac with underground utilities, lovely granite curbing, elegant and decorative street lighting and gazebo in cul de sac. Serene setting yet convenient to I84 Please inquire for options available.

Listing Courtesy of Douglas Elliman of Connecticut

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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72 East Farm Middlebury CT 06762

Middlebury, CT72 East Farm Road

Price$895,000

Est. Mortgage: $/month

MLS Number 170213982

  • Single Family
  • Bedrooms 6
  • Bathroom 7
  • Acreage 2.41
  • Square Feet 9,080

UNPARALLELED CONSTRUCTION. ARCHITECTURALLY DESIGNED. UNPRECEDENTED VALUE. This GRAND ESTATE offers all you will need! Enter a dramatic light filled 2 story foyer with gorgeous double curved staircase. With exquisite details throughout you will find a wonderfully spacious, light filled, well thought out floor plan for grand entertaining or large gatherings. SUN DRENCHED 2 story living room with Herring Bone flooring and wet bar over looks a resort like OUTDOOR OASIS with in ground AQUA Pool, pool house, outdoor kitchen and more. LUXURIOUS MASTER SUITE with 13' ceilings, fireplace, sitting area and french doors to pool and gardens. Gourmet eat in kitchen with family room and fireplace. Stunning Walnut Paneled first floor library and screening room. Front entrance circular driveway in addition to a separate side driveway entrance for 3 car garage. Gorgeous level property in very desirable Middlebury cul de sac location where nature abounds. 20 minutes to Bantam Lake, 90 miles to NYC, 15 minutes to Oxford Airport. Stunning property that CANNOT BE REPLACED AT THIS PRICE. SPLENDID HOME TO MAKE YOUR OWN! MUST SEE!

Listing Courtesy of Douglas Elliman of Connecticut

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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40A Gleneagle Middlebury CT 06762

Middlebury, CT40A Gleneagle Road

Price$889,000

Est. Mortgage: $/month

MLS Number 170154117

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.68

Fabulous, quality new construction in established neighborhood of high end properties. Public water and sewer in this conveniently located, desirable neighborhood of custom homes. Four different models to choose from including our contemporary ranch with a first floor master suite OR completely customize your own home. Our premier home development company has over 39 years experience in the Connecticut home building industry. Amazing opportunity for a brand new high quality home of your choice in an ultra convenient cul de sac location surrounded by nature. Three Mile Hill Estates is a beautiful private cul de sac with underground utilities, lovely granite curbing, elegant and decorative street lighting and gazebo in cul de sac. Serene setting yet convenient to I84 Please inquire for options available.

Listing Courtesy of Douglas Elliman of Connecticut

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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192 Watertown Middlebury CT 06762

Middlebury, CT192 Watertown Road

Price$850,000

Est. Mortgage: $/month

MLS Number 170199777

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 5
  • Acreage 4.59

It is our pleasure to present this totally remodeled 10 room center hall colonial overlooking 4.57 beautifully landscaped acres on a lovely country road in historic Middlebury, CT convenient to I 84. The exterior is cedar clapboard & stone, all windows are now Marvin True Divided light & all new exterior doors. There are 2 car attached as well as 2 car under garages.A separate front entrance leads to a mezzanine level office/au pair/guest suite w/newly added full bath.Wide trim, molding & 2 sets of interior leaded glass French doors add an air of graciousness throughout.Generously sized dining room, family room & library w/built-ins all have fireplaces.The newly designed eat-in-kitchen is fully equipped w/chef grade appliances including professional 60" gas burner. Kitchen eating area includes a cozy fireplace.To complete the main level & off the kitchen is the 4 season all glass sun room overlooking an expansive stone patio w/gas grill, fire pit & separate structure w/built-in bar.Upstairs the 24 X 24 master suite has a sitting area, fireplace & 2 decks. Newly added is a huge walk-in cedar closet w/California built-ins & another closet w/chandelier & built-ins.The sumptuous marble full bath has a make-up alcove.There are additional large bedrooms & baths on this floor.Even more, 2 finished rooms & 1/2 bath on lower level.See Special FeaturesThis warm & inviting home boasts classic elegance while incorporating today's latest amenities.Come & take a look, you'll stay forever!

Listing Courtesy of Weichert Madison and Post

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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.

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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.