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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250 Upper Whittemore Middlebury CT 06762

MLS Number 170118237

  • Single Family
  • Bedrooms 6
  • Bathroom 7
  • Acreage 20
  • Square Feet 8,408

The 7,700-sqft home w/ in-law apartment on 20 acres along one of CT's finest roads. Accessed by graveled drive w/ motorized entry gate, the 6-bed home is enveloped in light and provides a generosity of space for entertaining, indoor & out. Crisp white walls, walnut flooring & custom millwork throughout create an ambiance of luxury & easy living w/ every high-end comfort. Interior highlights: great/rm w/ double-height ceilings, wood-burning fireplace, grand-scale windows w/ motorized shades, wet bar w/ 2 Sub Zero beverage refrigerators. Spacious chef's kitchen features white marble countertops, dining area, & French doors to deck w/ full outdoor kitchen. All designer appliances, too many to list. Add'l ground level rms comprise a family rm, sitting rm, office, laundry rm w/ double Bosch washer/dryers, wash basin, & dog bath, mud rm, & two powder rms. Second level features a master suite, w/ 2 dressing rms & bath incl a 2-person walk-in shower, Waterworks standalone tub, marble tiles, heated floors & access to balcony. Two guest bedroom suites each w/ walk-in shower, marble tiles, stone countertop, linen closet. Two children's bedrooms share bath w/ tub shower. An attached in-law apt has loft-style layout w/ full bath & bed. Partially finished basement w/ wine cellar, storage rm. Exterior amenities: in-ground heated pool, deck, built-in irrigation & lighting, covered porch w/ kitchen, gas FP, ceiling fans+heaters, grill/smoker, sink, refrigerator, gas stovetop & lots more!

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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120 Tranquility Middlebury CT 06762

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: 3.75% last updated on Jul 11, 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

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: 3.75% last updated on Jul 11, 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

Price$1,999,900

Est. Mortgage: $/month

MLS Number 170166436

  • 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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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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370 Tucker Hill Middlebury CT 06762

Price$1,495,000

Est. Mortgage: $/month

MLS Number 170141985

  • Single Family
  • Property Style Antique, Tudor
  • Bedrooms 7
  • Bathroom 8
  • Acreage 48

Authentic in every way! Circa 1930's Topsfield is one of Middlebury's grand estates situated on 48+/- acres in the heart of town. Sited at the end of a long private driveway with majestic trees, mature landscaping, an expansive lawn, pastures, and views to the south. Being offered by the original family at a fraction of its replacement value and waiting for the next generation of ownership. Incredible potential to live in the home of ones dreams. Potential conservation easements or subdivision possible as well.

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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

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: 3.75% last updated on Jul 11, 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

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: 3.75% last updated on Jul 11, 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

Price$1,150,000

Est. Mortgage: $/month

MLS Number 170104202

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

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.

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$
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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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

Price$1,149,000

Est. Mortgage: $/month

MLS Number 170175047

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

Owner has put over 400k of updates and improvements to the property of the years! Rare opportunity to own a piece of history. Willowstone Farm sits on over 20 acres of park like grounds and offers an unrivaled New England setting. The property features a large barn with a 5 car garage, an additional 2-stall barn, an outside riding arena that is 100 X 200 in size with rubber footing, and beautiful rolling pastures. The main house is an 1800s Antique that is filled with character and charm. With custom millwork, oversized fireplaces, and wonderful hardwood floors the home has been restored properly with respect to the age it was built. The guest cottage was recently updated and offers great flexibility with an additional 1100 square feet of living space, 2 bedrooms, 2 baths and cozy front porch. Schedule your showing to experience all this property has to offer.

Listing Courtesy of Century 21 AllPoints Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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

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: 3.75% last updated on Jul 11, 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

Price$995,000

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: 3.75% last updated on Jul 11, 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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56 Judd Hill Middlebury CT 06762

Price$955,000

Est. Mortgage: $/month

MLS Number 170179363

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.71

Brand New 4900sqft Custom Colonial with Stone and Shake Siding, Gourmet Kitchen, Great Room and Majestic Views! Hardwood floors throughout. Entire 1st Floor has 9 foot ceilings. Eat-in-Kitchen with Stainless Steel Viking Appliances, Marble Countertops and backsplash, oversized island with breakfast bar, and farmer's sink. Cooks kitchen with double ovens, double sinks, and sun-drenched breakfast nook. Two-Story Great Room with Fireplace. Grand Foyer. Office with beautiful trim and moldings. Dining Room with gorgeous paneling and crown. Mudroom with built-ins. Full bath with marble tile and surround. 2nd Floor Master Suite with 2 walk-in closets and attached full bath with 2 sinks, soaking tub, and marble tiled shower. 2nd Bedroom with attached full bath with 2 sinks and marble tile and surround. Amply Sized 3rd and 4th bedrooms and 4th full bath. Laundry Room. Walk-up attic to 3rd floor currently setup for storage. Full basement with walkout to patio, Fireplace, and potential for additional finished space. 3 car attached garage. Back patio with built-in Firepit. Stone walls. Majestic views!! This home is fully loaded. Be this home's first owner and save yourself the trouble and expense of building your own home! Site plan includes an area for a proposed pool.

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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.