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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120 Tranquility Middlebury CT 06762

Middlebury, CT120 Tranquility Road

Price$1,900,000

Est. Mortgage: $/month

MLS Number 170307948

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 23.69
  • Square Feet 6,161

Set on an expansive, lush green 23 acres surrounded by king and queen stone walls, you will find this premiere estate at 120 Tranquility Road. The rolling hills, the greenery, the unbelievable landscaping, will transport you to your very own personal paradise. The majestic ambience you feel approaching this home is an unparalleled experience that words cannot do justice. It is quite literally awe-inspiring as you drive through the gates that lead to this home. As you approach you will be struck by the beauty of the watering trough, stone arched bridge, and impeccably manicured gardens and lawn which elicit thoughts of an elegant palace. This estate was built using Mediterranean influences and boasts all of the amenities of a modern home. You just simply cannot find another home with such beauty, elegance, and remarkable surrounding nature. From the stately living room, to the indoor lap pool, right down to every intricately designed bedroom and bathroom, this home is like owning your own private castle in the countryside. The living room is adorned with a coffered ceiling and stone fireplace. The first floor master suite has abundant closet space, a boudoir, and a gorgeous bathroom. The first floor welcomes you with 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.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 170333156

  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 Farms Middlebury CT 06762

Middlebury, CT7 East Farms Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170251554

  • Single Family
  • Property Style European
  • Bedrooms 4
  • Bathroom 7
  • Acreage 1.97

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: 2.87% last updated on Sep 17, 2020
* 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 170327759

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

Have you decided the perfect home for your family may be just a dream…that you may never find the sumptuous, impeccable, grand escape that you have been imagining? Well, let us show you this one-in-a-million, luxurious home situated in the gorgeous hills of Middlebury, CT. It just may be what you're looking for! Close to everything with easy access to highways and Oxford Airport, just a 2 hour drive from NYC and 3 hours to Boston. This home boasts 6 large unique bedroom suites - all with en-suite baths. The first floor master suite is your own secluded oasis featuring a private den, balcony, fireplace, incredible walk-in closet/dressing room, plus a soaking tub in the luxurious en-suite bath. The sleek and modern interior will adapt easily to your décor and furnishings. Soaring ceilings provide a light and airy feeling in the home, while the parquet, marble and wood floorings throughout the home, are simply exquisite. This open-concept, custom kitchen is a chef's paradise with top-of-the-line Viking appliances, quartz counters and plenty of room for family and friends to gather and enjoy special moments together. You will delight in the 6 fireplaces spread throughout the home, with one ideally situated outside, on the expansive deck, allowing for extended outdoor entertainment into the colder months. There are so many features in this home - you must come see this home yourself! Call today! See how dreams do come true!

Listing Courtesy of Coldwell Banker Realty 2000

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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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Leonard Middlebury CT 06762

Middlebury, CTLeonard Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170295141

  • Single Family
  • Property Style Colonial, Ranch
  • Bedrooms 5
  • Bathroom 4
  • Acreage 3.1

Come and dream your loveliest dream. Welcome to wonderful Middlebury. Sweet views, meadow with farmers walls and dramatic outcropping.

Listing Courtesy of Divine Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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$999,000

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 Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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 Farms Middlebury CT 06762

Middlebury, CT72 East Farms Road

Price$899,900

Est. Mortgage: $/month

MLS Number 170277468

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 7
  • Acreage 2.41

New Taxes and Assessment. Romanesque Mansion Estate with In-ground pool, pool-house cabana, and outdoor kitchen set on cul-de-sac of like homes in Middlebury's premiere neighborhood. 6 Bedrooms, 7 total bathrooms, and plenty of space for entertaining and impressing! Grand waterfall staircase entry. 2-Story sun-drenched Living Room with Fireplace, wetbar, and herring bone flooring. Library/Study/Office/Den with Black Walnut wood paneling. Dining Room with Brazilian Cherry flooring. Chef's Kitchen with high-end Stainless Steel appliances, granite, and open floorplan to Family Room with Fireplace. 1st Floor Master Suite with Fireplace, 2 walk-in closets, sitting area, walk-out to patio/pool, and remodeled attached full bath. Second Floor with 5 additional bedrooms, remodeled bathrooms, bonus room, and hardwood floors throughout. Basement with Bar and Exercise Rooms. In-ground pool and patio area with full pool cabana with running water and electricity and outdoor kitchen. Park-like grounds with professional landscaping. 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. Assessment and Taxes go into effect in April 2020.

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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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120 Skyline Middlebury CT 06762

Middlebury, CT120 Skyline Drive

Price$799,900

Est. Mortgage: $/month

MLS Number 170325487

  • Single Family
  • Property Style Cape Cod, Ranch
  • Bedrooms 4
  • Bathroom 6
  • Acreage 3.59

This custom-designed shingle and stone home was crafted by one of New England's preeminent builders. The main level is a sprawling ranch offering an open floor plan including a gorgeous custom kitchen with 48 inch Subzero fridge, Wolfe 6 burner double oven gas range, breakfast bar and informal dining area. A walk in pantry and butler's pantry are just a few of the touches that will excite the home chef. The handsome great room features coffered ceiling, stone fireplace, wet bar with built in ice maker and refrigerator drawers. Formal dining room features trey ceiling and raised panels. The fabulous master en suite with double walk in closets and a spa-like bath with double vanities, soaking tub and walk in shower is located in a private wing of the home. Two2 generously size bedrooms with Jack and Jill bath, tile shower and granite counters is located in another wing of the house. In addition, 2 garages are attached at the main level. The expandable second floor features a private office, bath, and loft. A 1000 sq ft walkout level in-law apartment offers a beamed ceiling and a fabulous kitchen, bedroom, bath and laundry. 4 more heated garages with high ceilings to accommodate a lift. Energy star 4 zone propane heat, city water, and sewer. Nestled on almost 4 acres yet close to restaurants and shopping. Truly a rare find! Be sure to view virtual tour!

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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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109 Stony Brook Middlebury CT 06762

Middlebury, CT109 Stony Brook Road

Price$720,000

Est. Mortgage: $/month

MLS Number 170312487

  • Single Family
  • Property Style Contemporary, Modern
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.74

Welcome to Middlebury, where noted architect Joseph Stein introduced the Modernist Movement to this bucolic corner of northwest CT. Trained under Walter Gropius, founder of the Bauhaus School of Design, and educated at the same school of design as the Harvard Five, Stein's belief that his client's lives could be enhanced by the space he designed is evident throughout this mid-century modern. With an eye on the natural contours of the land and an appreciation for the beauty of old-growth trees, Stein sited the home to create a modern form that gently cascades into the woodlands that surround it. The discovery of a unique elbow tree, scenic pond, and seasonal creek inspired floor-to-ceiling window scapes in every room. With repeating window patterns, exceptional materials, and a clear understanding of the needs of a five-person household, Stein delivered a four-bedroom home with two master suites, two stories of living space, and a two-car garage while using interior walls to house extensive closets for storage. With appreciation for the enduring beauty and texture of naturalized perennial gardens outdoor spaces have been framed with dry stacked stone walls, bluestone pathways, and pea gravel gathering spots. The effect is a simply modern and timeless - an enviable escape less than two hours from Manhattan and close to the highly-rated restaurants and shops of the NW corner. First time on the market.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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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70 Atwood Middlebury CT 06762

Middlebury, CT70 Atwood Street

Price$699,900

Est. Mortgage: $/month

Pending

MLS Number 170330181

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 5
  • Acreage 1.03

Amazing home located on a quiet dead end street. Quality construction with stucco and stone exterior. High ceilings, gorgeous hardwood floors, granite throughout kitchens and bathrooms, spacious bedrooms with walk in closets, high efficiency gas boiler with 5 zones, composite decking and a beautiful stone patio in backyard. Potential inlaw with full kitchen and walk out. This property is great for entertaining with a built in grill and pizza oven. Great location near major highways, parks and police station. Property has a three in a half car garage, underground utilities and city water and sewer. This is a must see home!!!!

Listing Courtesy of Better Living Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

20 Highridge Middlebury CT 06762

Middlebury, CT20 Highridge Road

Price$654,000

Est. Mortgage: $/month

MLS Number 170316668

  • Condo
  • Property Style Townhouse
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,625

Wow! One of a kind custom Bristol unit will impress you at every turn! High end, quality upgrades and careful attention to detail combine to offer gracious style for the discriminating buyer. Dramatic cathedral ceiling and abundance of windows allow natural light to accentuate many fine features of this home including the stunning hardwood floors, custom kitchen cabinetry and tiled backsplash, wainscoting, crown moulding and built-ins throughout the home. Spacious first floor master suite features fabulous double shower and walk in closets. Living room french doors open to the deck for relaxing and entertaining, while the massive lower level family room offers an impressive wet bar, half bath and plenty of additional space for family and friends. Upstairs, an inviting loft is the perfect spot to curl up with a favorite book, while three bedrooms and two full baths round out this upper level. Impeccably maintained, you must see for yourself all that this special home has to offer. This is one of only two Bristol models in the Ridgewood complex. Enjoy the pool, club house, gym and many other amenities that make Ridgewood a wonderful place to live. Convenient access to I -84 and 90 minutes to NYC.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

109 Stony Brook Middlebury CT 06762

Middlebury, CT109 Stony Brook Road

Price$640,000

Est. Mortgage: $/month

MLS Number 170312102

  • Single Family
  • Property Style Contemporary, Modern
  • Bedrooms 4
  • Bathroom 4
  • Acreage 4.14

Welcome to Middlebury, where noted architect Joseph Stein introduced the Modernist Movement to this bucolic corner of northwest CT. Trained under Walter Gropius, founder of the Bauhaus School of Design, and educated at the same school of design as the Harvard Five, Stein's belief that his client's lives could be enhanced by the space he designed is evident throughout this mid-century modern. With an eye on the natural contours of the land and an appreciation for the beauty of old-growth trees, Stein sited the home to create a modern form that gently cascades into the woodlands that surround it. The discovery of a unique elbow tree, scenic pond, and seasonal creek inspired floor-to-ceiling window scapes in every room. With repeating window patterns, exceptional materials, and a clear understanding of the needs of a five-person household, Stein delivered a four-bedroom home with two master suites, two stories of living space, and a two-car garage while using interior walls to house extensive closets for storage. With appreciation for the enduring beauty and texture of naturalized perennial gardens outdoor spaces have been framed with dry stacked stone walls, bluestone pathways, and pea gravel gathering spots. The effect is a simply modern and timeless - an enviable escape less than two hours from Manhattan and close to the highly-rated restaurants and shops of the NW corner. First time on the market. Offered with additional acreage under MLS No. 170312487.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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

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.