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.

Time Saving Tip: Sign up for a free account to save your favorite listings and get notified when new properties match your criteria.

r=1-12
56 Judd Hill Middlebury CT 06762

Price$899,900

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: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

40A Gleneagle Middlebury CT 06762

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: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

71 East Farms Middlebury CT 06762

Price$875,000

Est. Mortgage: $/month

MLS Number 170169648

  • Single Family
  • Bedrooms 5
  • Bathroom 8
  • Acreage 1.9
  • Square Feet 6,691

Fabulous custom brick home on landscaped lot with circular drive. A marble foyer with a curved staircase introduces the main floor. Across the foyer is an elegant dining room. Pass thru the butler's pantry to a chef's dream kitchen with granite counters, gas cooktop and built-ins to display your special wares. The kitchen flows to a roomy breakfast area with access to a cedar deck. A spacious living room has a see-through fireplace to a custom formal library. Relax in the family room or spend time in a light filled sunroom. The second floor features a master bedroom suite with a tray ceiling, generous sitting area and expansive bathroom. There are four additional bedrooms each with their own baths. Additional 1000 sq. ft. finished walkout lower level apartment which can easily become a mother-in-law suite. The back yard has room enough to install a tennis court or a pool! Only 90 minutes from NYC! You will love living and entertaining in this gracious home.

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

192 Watertown Middlebury CT 06762

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: 3.81% last updated on Jul 18, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

75A Gleneagle Middlebury CT 06762

Price$849,900

Est. Mortgage: $/month

MLS Number 170154111

  • Single Family
  • Property Style Colonial
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

52A Gleneagle Middlebury CT 06762

Price$759,900

Est. Mortgage: $/month

MLS Number 170154095

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.6

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: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

835 South Middlebury CT 06762

Price$699,901

Est. Mortgage: $/month

MLS Number 170178036

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 7.16

Welcome to this marvelous custom built home by HOBI award winning Eric Strachan. Nestled into 7 acres of tranquility on South street in Middlebury. This attractive colonial is set on an interior lot. Outdoor hot tub sits comfortably near cupola and adjacent to flagstone patio overlooking endless acres of privacy. Partially cleared land has potential for many uses such as a horse farm or other recreational hobbies. Plotted pad area ideal for an in-ground pool with a waterfall edge. Detached barn with two additional garage bays and a second story loft offer separate storage and bonus room area. Front entry welcomes you to an expansive two story foyer leading to a welcoming family room with beautiful floor to ceiling stone masonry fireplace and skylights overhead. Elegant formal living room with arched transom windows and a gas fireplace. The well designed eat-in kitchen basks in sunlight, granite counter tops, maple glazed cabinets and a large breakfast bar. Spacious first floor master suite with walk-in closet, Jacuzzi tub and a stand-up shower. Upstairs open catwalk overlooks the main living area and foyer. Three additional large bedrooms, two with a jack-and-jill bathrooms, and a walk-in closet. Additional features; hardwood floors throughout, generator, hydro air heat, dual a/c, central vac, custom crown molding and wainscoting, main level laundry room, and much more. Move quick this custom built home and your own private oasis will not last long at this price!

Listing Courtesy of Dave Jones Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

249 South Middlebury CT 06762

Price$675,000

Est. Mortgage: $/month

MLS Number 170022837

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 6
  • Bathroom 4
  • Acreage 5.65

The Mead Manse.This charming, historic family home, dating back to 1799 and lovingly updated, is one of the original prestigious houses situated in the heart of old Middlebury on South Street. For over two centuries it has been a landmark with its gorgeous wrap-around stone porch. A home that exudes of warmth, peace and hospitality it provides a wealth of wonderful living spaces from peaceful privacy sitting by one of the many fireplaces, walks in the parkland gardens, or entertaining in the formal dining room or simply having a casual drinks party on the porch. The property is listed on 5.4 acres including the opportunity to subdivide and build a second property. However, the owners would consider completing the subdivision and selling the house with 1.4 acres. Middlebury is situated between New York and Boston, and is just 4 miles from the antique shops of Woodbury.

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

20 Highridge Middlebury CT 06762

Price$669,000

Est. Mortgage: $/month

MLS Number 170208737

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

Stunning Bristol unit with ALL the upgrades and a completely finished walk-out basement with wet bar! First floor master suite with walk in shower for your comfort. Beautiful wood floors in living room, dining room and loft. Custom built-ins throughout make this home extra special. Three bedrooms on second floor with loft for extra comfort. Lower level family room, with full wet bar, has entertainment area, game area, work space and 1/2 bath. 3650 square feet of pure style defines this unit. Whether sitting on the deck with your morning coffee, enjoying a fall fire and watching the snow, or entertaining friends and family in the warmth of the family room, this home is special. Call to see today.

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

160 Watertown Middlebury CT 06762

Price$650,000

Est. Mortgage: $/month

MLS Number 170205809

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Acreage 3.55
  • Square Feet 5,361

Welcome to 160 Watertown Rd,a custom built, brick Colonial with a tasteful touch of Contemporary flare. This wonderful home is offered by the original owners, who have meticulously and lovingly cared for this home. Upon arrival, brick pillars set the stage for what's inside. Combination of mature landscape and long driveway ensures privacy on this level, park-like home site, featuring irrigation to maintain the look all season long. Enter the 3 car garage, side entrance w/ mud & laundry room, or the beautiful front, open foyer with dramatic chandelier, marble tile, and sweeping helical staircase, straight from a fairy tale. Main level full French doors and many unique details, including a Library/Office, a Parlor with a Grande Piano used for entertaining with ceiling open to the 2nd floor look-over, tandem to the Formal Dining Room w/tray ceiling and accent lighting. Straight ahead is the Family Room with floor to ceiling field-stone fireplace and flooded natural light from the wall of windows, sky lights, and wall of French Doors that lead to the 2 level Mahogany deck. Kitchen features granite, stainless, island and French Doors to full glass Solarium that enjoys year round use with heat and central air. Main level Master Suite features master spa bath, dual walk in closets, & French doors to Mahogany deck. 2nd floor has poss. 2nd master w/ full bath and 2 other bedrooms, & media room with skylights wired for sound. Temperature controlled wine cellar in lower level.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

400 Charcoal Middlebury CT 06762

Price$650,000

Est. Mortgage: $/month

MLS Number 170209565

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 4
  • Acreage 4.9

PRIVACY AT ITS FINEST SET BACK ON ALMOST 5 ACRES! Blue ribbon school district. Feel like every day is a get-a-way! Over-sized Colonial with 6 total bedrooms and 3 1/2 bathrooms with a separate in-law style wing. A GRAND entrance invites you into a 2-story foyer and turned staircase with full second level catwalk. Off the foyer is an elegant formal living room and great room that extends into the billiard room. Living room with wood-burning fireplace. Hardwood floors flow through both levels. Your eat-in kitchen pours natural sunlight in and boasts granite counters with tile back-splash, custom hand-made oak cabinets, stainless appliances, and large dry bar. Off kitchen is an attractive formal dining area. Double french doors within the kitchen lead to 4-season room with vaulted ceilings and views to the backyard. Second level offers a tray ceiling at the top of the foyer and 4 sizable bedrooms. The MASSIVE master on-suite is the true definition of a private oasis! Vaulted ceilings, large open floor plan area, walk-in closet, bathroom with granite floors, double vanity, jetted tub, and stand-up shower. In-law style wing with private laundry area, eat-in kitchen and 2 bedrooms. Your dream backyard with full irrigation system has separate areas to entertain and relax. On the first main level is a trex-style deck off kitchen which leads to the hot tub area and second tier lead up to the upper level where your in-ground gunite pool awaits. WELCOME HOME!

Listing Courtesy of Regency Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

27 East Farms Middlebury CT 06762

Price$649,900

Est. Mortgage: $/month

MLS Number 170174524

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 1.85

ABSOLUTELY STUNNING HOME! **Show Stopper in lovely **EAST FARMS** cul de sac. OVER $200,000 IN NEW UPGRADES! **NEW KITCHEN** HW FLOORS **EXTENSIVE TRIM ** LIGHT FIXTURES**NEW MASTER BATH** Brick pillars, circular driveway & stone wall leads to grand entry foyer w/turning staircase & open spacious living areas including the formal LR w/HW flrs, crown molding & bow window; adjacent DR also has HW flrs & crown molding & includes built-in serving station & gas fireplace. The Chef's kitchen highlights granite counters with tile backsplash, stainless steel appliances (6 burner Thor gas range, hood & Fisher-Paykel refrigerator & dishwasher) & stainless steel farmers sink; massive center isle w/wine refrigerator; and expansive brkfst nook w/sliders to the deck overlooking private, serene yard! The open FR boasts gas fpl! Custom Ethan Allen window treatmts thruout! Main flr MBR suite features NEW luxurious bath w/double sink vanity, glass door shower & free standing claw foot tub! Also on the main level is a 12x10 office, laundry rm, mudroom & access to 3 car garage. 2nd flr hosts 3BRs w/ **NEW HW flrs** all with private baths & French doors to fabulous bonus room w/back staircase. Be surprised by additional 1500sqft walkout lower level with greatroom w/gas fpl, built-ins, sliders to the patio & wet bar opens to 5th BR with full bath, kitchenette & exercise room. Possible in-law. Level yard w/room for pool, 3 car garage. Borders 21 acre Fish & Game Preserve

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.81% last updated on Jul 18, 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.

Save FavoriteSchedule A VisitAsk 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.