Middlebury CT Real Estate

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
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: 4.17% last updated on Apr 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

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: 4.17% last updated on Apr 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: 4.17% last updated on Apr 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

429 Mirey Dam Middlebury CT 06762

Price$739,900

Est. Mortgage: $/month

MLS Number 170182152

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.1
  • Square Feet 3,866

Welcome to a home where high end and tranquility come together. Stunning curb appeal with classic brick exterior, professional landscape and a dramatic front entrance. Step into the two story foyer and take in the details of the formal dining and living room with archways, custom curtains, coved ceilings and walls. The openness of the stairway leads you to the top floor with a balcony overlooking the main living space. As you make your way into the sunken family room you will be greeted by large windows, cathedral ceilings and a stone, gas, fireplace. This room opens up to the custom kitchen with tons of cabinet space, two Wolfe Ovens, custom built hood vent, Subzero refrigerator and a wine cooler. The sunroom overlooks the heated pool, flat green yard, plus the surrounding Land Trust, making this the perfect private oasis. At the end of the day step into your master suite where high end continues. A gas log fireplace, his and hers walk ins and a luxurious bathroom for pampering. Upstairs hosts two bedrooms with walk in closets and a Jack and Jill bathroom, plus a third bedroom and full bath. An ADDITIONAL 1650 in square feet located in the lower level for an extra living area and an office which could easily be converted into an in law apartment. New whole house generator, Buderus Furnace, on demand tankless hot water heater, plus a new water softener system. Award winning Region 15 Schools, 90 minutes from NYC and 120 minutes from Boston.

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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: 4.17% last updated on Apr 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: 4.17% last updated on Apr 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

35 Gleneagle Middlebury CT 06762

Price$675,000

Est. Mortgage: $/month

MLS Number 170183306

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.05

Magnificently Built and Updated Brick Colonial on Cul-de-Sac road with 5 car garage, addition, and gorgeous grounds and paver patio with firepit! Gorgeous front entry Foyer drenched in natural light with beautiful flooring. Updated kitchen with abundant counter space atop Marble countertops. Double Viking Ovens, cooktop, Sub-Zero refrigerator, large breakfast bar island, and eat-in nook with slider to patio. Family Room with trey ceilings, Fireplace, and slider to patio. Formal and Elegant Dining Room with simulated wood paneling. Living Room with fireplace currently being used as office. Laundry room with cabinets and granite countertops. Office/Den for additional 1st floor space. Upstairs large Recreation Room. 4 Bedrooms, including Master Suite with trey ceilings, walk-in closet, and attached full bath with double granite top sinks, skylight, jetted tub, and stand-up shower. Finished Basement with additional full bath. 3 car attached garage and 2 car garage addition with heated garage space! Paver patio with firepit and stonewall. Private yard. Great location has easy highway access, but is on a quiet, neighborhood street. Only second owner of this home, was a builder's own home.

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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

27 East Farms Middlebury CT 06762

Price$674,900

Est. Mortgage: $/month

MLS Number 170174524

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

Sophisticated elegance describes this well appointed 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: 4.17% last updated on Apr 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

705 Breakneck Hill Middlebury CT 06762

MLS Number 170169395

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 4
  • Acreage 4.85

JUST REDUCED to $619,000! Pristine & Ready to be seen! This captivating home welcomes you from the moment you step through the front door--from the gleaming HW floors to the 2 warming-gas fireplaces in living/dining, recessed lighting & open floor plan. A spectacular home for all ages! Large private screened in porch w/generator hookup overlooking its 4.85 acres makes for a fabulous place to enjoy coffee or a quiet evening w/friends & family. The totally remodeled kitchen is a sheer delight with over-sized island, granite counters & high-end Thermador appliances. As if that isn't enough the Butler's Pantry is equipped with Miele cafe system, separate sink & an abundance of storage. Finishing off the main level is a conveniently located laundry room & two main floor bedrooms & full bath. But let's not limit ourselves because behind one of the bedroom walls is plumbied to easily convert this space into in-law/au-pair living with its own entrance. Now head on upstairs & through the double doors to the magnificent master bedroom suite with separate sitting area, luxurious double sinks, over-sized shower, walk in closet & unbelievable dressing area not to mention additional storage. The upper floor is polished off with two more impressive bedrooms & main bath with granite & double sinks. As if all of this is not enough the impeccably finished lower level offers a quiet place to tuck away for extended living & more storage. Don't regret not getting in to see this stunner!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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

215 Upper Whittemore Middlebury CT 06762
Pending

MLS Number 170112584

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 4.18

Set on 4+ acres of beautifully landscaped property on a most desirable Middlebury street, this home sparkles. It was built with care and offers spacious rooms and lots of architectural interest. There is a 40' front porch so that you can enjoy the natural surroundings as you entertain family and friends. The living room offers a masonry fireplace French doors to the 22' X 15' dining room. A fabulous kitchen provides lots of opportunities for gathering friends and family as you prep food and entertain. First level also offers the master suite, powder room, laundry room and a gorgeous year round sun room that provides access to the expansive deck. Upstairs, 3 additional bedrooms, a full bath as well as a bonus room over the 3 car garage. Don't miss the walk out full basement with an overhead door and easy access to the property. All in pristine condition!

Listing Courtesy of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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

156 Judd Hill Middlebury CT 06762

Price$574,900

Est. Mortgage: $/month

MLS Number 170011573

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.75

A beautiful five bedroom Center Hall Colonial sits conveniently close to the center of town, the Middlebury Greenway (trolley trail) and the Middlebury Green. Built in the 1940's - the absolute best era of home building, this classic home provides all the charm and quality of the 30's and 40's including arched openings, built-ins throughout, extensive trim, hardwood floors and generous room sizes. On 2 park-like acres with easy access to I-84 and the highly rated Region 15 school system, this meticulously maintained and renovated home couldn't be more ideally located. The exterior offers a large in-ground heated salt-water pool designed and built by Scott Pools with numerous large granite accent pieces as well as a stone pool sweep. There are several outdoor living spaces including a bluestone patio, a 70' deck with pergola, private deck off the master suite and an enclosed three-season porch overlooking the front of the property. The home also has new mechanicals, including a new well pump, well tank, boiler, indirect water heater and a lifetime roof. It is a solar home with separate access to an in-law suite.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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

103 Periwinkle Middlebury CT 06762

Price$549,000

Est. Mortgage: $/month

MLS Number 170117998

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,476

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 Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 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

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.