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Middlebury, CT Homes for Sale

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  • /38

    $717,000

    • 3 Beds
    • 2.5 Baths
    • 3,212 Sq Ft

    111 Dwyer Rd, Middlebury, CT 06762

    Elegant Saltbox Colonial in Sought-After Middlebury, Nestled on 2.44 secluded acres, this tasteful saltbox colonial boasts park-like grounds with a private, tree-lined driveway leading to professionally landscaped gardens. Enjoy blooming trees and bushes from spring to fall, creating a picturesque setting. Outdoor living is enhanced with a slate patio, built-in barbecue, and bocce court, perfect

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (203) 693-8485

    111 Dwyer Rd, Middlebury, CT 06762
  • /29

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 2,364 Sq Ft

    105 Jericho Rd, Middlebury, CT 06762

    This beautifully maintained home offers the perfect blend of comfort and space with 3 bedrooms and 2.5 bathrooms. A thoughtfully designed living space welcomes you with a bright and open living room centered around a wood-burning fireplace, creating a warm and inviting atmosphere. A spacious eat-in kitchen provides plenty of room for cooking, dining, and gathering with loved ones. The fully

    Jimmy Edwards Redfin Corporation

    105 Jericho Rd, Middlebury, CT 06762
  • /15

    $649,900

    • 4 Beds
    • 3 Baths
    • 2,878 Sq Ft

    72 Carriage Dr, Middlebury, CT 06762

    A grand Cape Cod-style home, nestled in a wonderful and convenient neighborhood. The interior has been freshly painted, and the main level features primarily hardwood flooring. Just off the foyer, you'll find a sunken living room that welcomes you. The spacious eat-in kitchen has been remodeled and opens to the formal dining room, making it perfect for entertaining. Adjacent to the kitchen is a

    Justin Bette Joseph Bette REALTORS Inc

    72 Carriage Dr, Middlebury, CT 06762
  • /40

    $750,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,806 Sq Ft

    80 Pine Hollow Dr, Middlebury, CT 06762

    Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

    Gina Farra Keller Williams Realty

    80 Pine Hollow Dr, Middlebury, CT 06762
  • /40

    $799,000

    • 4 Beds
    • 4 Baths
    • 3,360 Sq Ft

    200 N Farm Rd, Middlebury, CT 06762

    Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth

    Jackie Desmarais Showcase Realty, Inc.

    200 N Farm Rd, Middlebury, CT 06762
  • /36

    $599,000

    • 3 Beds
    • 1.5 Baths
    • 2,531 Sq Ft

    126 Colonial Ave, Middlebury, CT 06762

    Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully

    Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • /39

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    66 Artillery Rd, Middlebury, CT 06762

    Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls,

    Mary Helen Levine Mary Helen Levine Real Estate LLC

    66 Artillery Rd, Middlebury, CT 06762
  • /7

    $925,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,878 Sq Ft

    22 Somerset Dr, Middlebury, CT 06762

    TO BE BUILT. One of the most desirable neighborhoods in Middlebury! The Avalon Farms community is comprised of lovely homes, manicured lawns, and beautiful gardens resulting in a unique aesthetic. The Cambridge model showcases a classic design combined with today's "must haves" that will meet all your expectations of an open floor plan. The great room with a cathedral ceiling, fireplace, and

    Ellie Gollenberg BHGRE Gaetano Marra Homes

    22 Somerset Dr, Middlebury, CT 06762
  • /8

    $899,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,878 Sq Ft

    294 Christian Rd, Middlebury, CT 06762

    New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style

    Ellie Gollenberg BHGRE Gaetano Marra Homes

    294 Christian Rd, Middlebury, CT 06762
  • /2

    $810,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    6 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    6 Deer Run Rd, Middlebury, CT 06762
  • /22

    $379,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,286 Sq Ft

    346 Middlebury Rd, Middlebury, CT 06762

    Welcome home to this completely renovated and expanded cape located on almost 3/4 acre of private park-like grounds! Conveniently located in the heart of Middlebury just steps from Bristol Park and the Middlebury Greenway, you'll love the open concept modern feel with new kitchen cabinets, granite counters and stainless-steel appliances. The open concept main level provides great space to

    Tanya Uhelsky RE/MAX RISE

    346 Middlebury Rd, Middlebury, CT 06762
  • /40

    $530,000

    • 2 Beds
    • 2 Baths
    • 2,011 Sq Ft

    13 Caveson Ct, Middlebury, CT 06762

    Welcome to this beautifully updated Osborn 2 model located in the highly desirable Steeplechase community, offering the convenience of natural gas, public water, and public sewer. This versatile home features two spacious primary suites-one on the main level and one upstairs-each with its own en-suite bath, providing flexible living arrangements. The main level boasts an open-concept layout with

    Kate Willoughby Gina Jacobs Real Estate

    13 Caveson Ct, Middlebury, CT 06762
  • /16

    $344,900

    • 2 Beds
    • 2 Baths
    • 1,099 Sq Ft

    73 Yale Ave, Middlebury, CT 06762

    This cozy comfortable 2 bed, 2 bath ranch offers the convience of one level living, with a private back yard and plenty of parking. Located close to the business center and RT 84.

    Jacqueline Voegeli Manzi Real Estate

    73 Yale Ave, Middlebury, CT 06762
  • /36

    $459,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    11 Upper Whittemore Rd, Middlebury, CT 06762

    Discover your dream home at 11 Upper Whittemore Rd, a stunningly renovated Brick Ranch nestled on a private, dead-end street with over 1.37 acres of beautiful land. This oasis boasts an unbeatable location because it provides both seclusion and connectivity: you're just moments from the recreational fun of Lake Quassapaug and Quassy Amusement Park, and the property offers easy access to major

    Islam Ahmad Real Broker CT, LLC

    11 Upper Whittemore Rd, Middlebury, CT 06762
  • /40

    $1,085,000

    • 3 Beds
    • 4 Baths
    • 4,138 Sq Ft

    225 Crest Rd, Middlebury, CT 06762

    Exquisite French Provincial MANOR HOUSE In the heart of Middlebury Ct. On a 3.21 acre private corner lot with mature plantings, English Boxwoods, fenced and tree lined. Pool and stone seating area. Double car oversized garage. Circular drive and designated parking for family and guests lined with stone pavers. This stately house 4,138 sq. ft. (not including basement with access to the garden),

    Wilson Lamas Realty Group of New England, LLC

    225 Crest Rd, Middlebury, CT 06762
  • /28

    $499,900

    • 5 Beds
    • 2 Baths
    • 2,428 Sq Ft

    281 Watertown Rd, Middlebury, CT 06762

    Welcome to this stunning Colonial, offering over 2,400 sq. ft. of living space on a rare, level 1-acre lot in one of Middlebury's most desirable locations. The first floor features an inviting eat-in kitchen with updated cabinets, new appliances, a center island, and a cozy fireplace-perfect for gathering. You'll also find a formal dining room and spacious living room, ideal for entertaining. The

    Xin Guo Coldwell Banker Realty 2000

    281 Watertown Rd, Middlebury, CT 06762
  • /24

    $579,900

    • 2 Beds
    • 2 Baths
    • 1,660 Sq Ft

    541 Benson Rd, Middlebury, CT 06762

    MAIN HOUSE (2BR/2BA): Features an open-concept layout w/ gleaming hardwood floors. The updated kitchen is a chef's delight, boasting granite countertops, stainless steel appliances, a gas stove & pantry. The main level includes a bedroom & a NEW spa-like full bath w/ a custom tiled walk-in shower & separate soaking tub. Upstairs is a private primary suite retreat, wrapped in warm pine woodwork,

    Joseph Martino Joseph Martino Real Estate

    541 Benson Rd, Middlebury, CT 06762
  • /34

    $389,000

    • 2 Beds
    • 1 Bath
    • 1,157 Sq Ft

    587 Shadduck Rd, Middlebury, CT 06762

    Welcome to 587 Shadduck Road, Middlebury, CT! This inviting two-bedroom, one-bathroom Cape-style home offers comfort, character, and a highly desirable location. Directly across the street, enjoy access to the Larkin State Park Trail, perfect for walking, running, or biking. Inside, the kitchen is bright and functional, featuring two windows that bring in natural light, warm wood cabinetry, and

    Dave Jones Dave Jones Realty, LLC

    587 Shadduck Rd, Middlebury, CT 06762
  • /39

    $599,900

    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft

    24 Ridgewood Dr, Middlebury, CT 06762

    Truly spectacular remodeled "Cummings" style townhouse in the sought-after Ridgewood at Middlebury community. The reimagined main level showcases a seamless open layout with a refined living and dining area flowing into a designer kitchen featuring a quartz center island, double ovens, granite counters, custom backsplash, and new flooring. Glass sliders invite natural light and open to a private

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • /40

    $530,000

    • 3 Beds
    • 3.5 Baths
    • 3,103 Sq Ft

    2 Dogwood Ct, Middlebury, CT 06762

    Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the best best private streets in the highly sought-after Ridgewood community. The resort style complex people are raving about! This spacious home offers a flexible layout perfect for modern living. The main level features hardwood floors, a half bath, a bright living room, a dining area, and an eat-in kitchen

    Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
  • /2

    $274,900

    • Land
    • 3.33 Acres
    • $82,553 per Acre

    19 Deer Run Rd, Middlebury, CT 06762

    Welcome to Hunting Ridge Estates, a premier 23-lot subdivision offering the perfect blend of privacy and natural beauty. This spacious 3.33-acre rear lot provides ample space to build your dream home in a peaceful, upscale setting. With multiple lot options available, you can choose the one that best suits your vision. Whether you prefer to bring your own builder or take advantage of our

    Jodi Dawley Real Estate Two

    19 Deer Run Rd, Middlebury, CT 06762
  • /4

    $449,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,924 Sq Ft

    1 Richardson Dr, Middlebury, CT 06762

    * TO BE BUILT * WATERBURY ADDRESS, BUT WITH THE AMBIANCE OF MIDDLEBURY! THIS VERY PRIVATE 1 ACRE REAR LOT YIELDS A SUBURBAN FEEL, BUT W/ THE CONVENIENCES OF PROXIMITY TO HIGHWAYS AND SERVICE OF PUBLIC UTILITIES! TRULY A REAR OFFERING! 3/4 BED, 2.5 BATH RSD RANCH W/ VAULTED CEILING & ALL OF TODAY'S DESIGN FLAIR! LOOKING FOR A FAMILY COMPUND? THERE IS A 3/4 ACRE SISTER LOT ADJACENT TO THIS ONE

    Scott Tedesco Tedesco Real Estate

    1 Richardson Dr, Middlebury, CT 06762
  • /2

    $729,900 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    2 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    2 Deer Run Rd, Middlebury, CT 06762
  • /2

    $794,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    15 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    15 Hunting Ridge Rd, Middlebury, CT 06762
  • /2

    $759,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,466 Sq Ft

    28 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    28 Hunting Ridge Rd, Middlebury, CT 06762
  • /40

    $495,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,088 Sq Ft

    604 Lakeside Blvd W, Waterbury, CT 06708

    Perfect blend of comfort and style in this STUNNING 3 bedroom Ranch home, perfectly set on a large, flat lot with SWEEPING WATER VIEWS. A newly paved driveway welcomes you home, adding to the property's impeccable curb appeal. Step inside to discover a bright, open kitchen featuring tile floors, a stylish tile backsplash, quartz countertops, and all-new stainless steel appliances. Sliders open to

    David Aurigemma Regency Real Estate, LLC

    604 Lakeside Blvd W, Waterbury, CT 06708

Why Live in Middlebury

Middlebury, Connecticut, is a picturesque New England town located in New Haven County, known for its scenic beauty and tight-knit community. With a population of 7,500, Middlebury offers a blend of rural charm and urban accessibility, being a short drive from New Haven. The town is surrounded by lush forests, state parks, rolling hills, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor activities. Residents enjoy local attractions such as Meadowview Park, Quassapaug Lake, and the Middlebury Greenway, as well as nearby state forests like Naugatuck, Mattatuck, and Paugussett, which offer extensive trails and recreational opportunities. Middlebury's educational system is highly regarded, with Pomperaug Regional School District No. 15 and Westover School providing top-notch education. The town's largest employers include Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. Middlebury maintains a low crime rate compared to the national average, contributing to its appeal for families and retirees. The housing market features classic New England homes, historic colonials, Cape Cods, and lakeside retreats, with properties often including antique barns and garden areas. Local businesses thrive in Middlebury, with popular spots like Willie’s Wood Smoked BBQ, The Local Gourmet, Vyne Restaurant, and Pies & Pub. The town's biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks. Middlebury is well-connected via Interstates 8 and 84, State Routes 63 and 64, and is close to Tweed New Haven Airport and Windsor Locks International Airport. Despite recent development proposals, the community remains committed to preserving its small-town charm.

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $612,752.
Are home prices dropping in Middlebury?
Yes, home prices in Middlebury are down 6% in the last 12 months.
How many homes have sold over the last 12 months in Middlebury, CT?
120 homes have sold in Middlebury, CT over the last 12 months.
What are the most popular zip codes in Middlebury, CT?
The most popular zip codes in Middlebury, CT include 06762, 06770, 06708, 06798 and 06488.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $579,900. If you put a 20% down payment of $116,000 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $2,850 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $122K a year to afford the median home price in Middlebury.
How are the schools in Middlebury, CT?
Middlebury, CT has highly rated public and private schools. Some of the best schools in Middlebury based on Niche Grades are Westover School, Bethlehem Elementary School and Pomperaug Regional High School. Browse all the schools in Middlebury, CT to learn more.

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$543,283
Median Single Family Sale Price
$520,000
Median Townhouse Sale Price
$540,000
Median 2 Bedroom Sale Price
$676,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
25
Last 12 months Home Sales
120
Months of Supply
2.50
Median List Price
$579,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-3%
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