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Middlebury, CT Homes for Sale

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  • /38

    $975,000

    • 4 Beds
    • 3 Baths
    • 4,451 Sq Ft

    286 Mirey Dam Rd, Middlebury, CT 06762

    Set in one of Middlebury's most desirable neighborhoods, this lovingly maintained 4,450 sq. ft. Colonial welcomes you with a beautiful paver driveway, manicured lawn, and timeless curb appeal. Step inside the sunny two-story foyer and feel right at home. The spacious eat-in kitchen is designed for gathering, featuring granite counters, a center island, breakfast bar, and generous dining area. For

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    (475) 281-3510

    286 Mirey Dam Rd, Middlebury, CT 06762
  • /39

    $630,000

    $19K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    700 Watertown Rd, Middlebury, CT 06762

    Looking for timeless character? This beautifully maintained Vintage Colonial has historic charm with thoughtful modern updates. Set on 1.25 meticulously landscaped acres, this 5-bedroom, 3-bath home offers warmth, space, and exceptional versatility. Gorgeous grounds with mature plantings, classic New England stone walls, and inviting patio spaces create a private outdoor setting perfect for

    Agent Photo

    Erin Giguiere

    Regall Realty, LLC

    (475) 244-1504

    700 Watertown Rd, Middlebury, CT 06762
  • /35

    $679,900

    $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,162 Sq Ft

    90 Fenn Rd, Middlebury, CT 06762

    The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (203) 592-0186

    90 Fenn Rd, Middlebury, CT 06762
  • /2

    $699,900

    • Land
    • 2.31 Acres
    • $302,987 per Acre

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

    This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (475) 255-6254

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
  • /29

    $774,900

    New Construction $39K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,877 Sq Ft

    20 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting Ridge Road (aka Lot 11) is to be built. It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms and a 2 car attached garage. The primary bedroom boasts walk-in

    Jodi Dawley Real Estate Two

    20 Hunting Ridge Rd, Middlebury, CT 06762
  • /36

    $249,900

    $20K PRICE INCREASE
    • Land
    • 4.67 Acres
    • $53,512 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    SHOVEL READY! LAST AVAILABLE HOMESITE IN THIS UPSCALE SUBDIVISION OF FINER HOMES. PUBLIC WATER & SEWER LATERALS ALREADY EXTENDED TO PROPERTY. CLOSE TO EVERYTHING, BUT EXTREMELY PRIVATE. MINIMUM SQ FOOTAGE 2800SF.

    Scott Tedesco Tedesco Real Estate

    75 Gleneagle Rd, Middlebury, CT 06762
  • /38

    $759,900

    New Construction 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
  • /2

    $299,900

    • 4 Beds
    • 1 Bath
    • 1,848 Sq Ft

    1252 Straits Turnpike, Middlebury, CT 06762

    SUBJECT TO PROBATE APPROVAL, AS-IS, WHERE-IS CONDITION NO FHA, CHFA OR VA LENDING AVAILABLE. NEEDS WORK. LOTS OF HARDWOOD FLOORS, DETACHED 2 CAR GARAGE WORKSHOP AND STORAGE LOFT. LARGE ROOMS, SHARED DRIVEWAY

    Gianna Alberti ALBERTI REALTY ASSOCIATES, LLC

    1252 Straits Turnpike, Middlebury, CT 06762
  • /40

    $765,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 3.5 Baths
    • 3,302 Sq Ft

    168 N Farm Rd, Middlebury, CT 06762

    Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete

    Karen Stanco Showcase Realty, Inc.

    168 N Farm Rd, Middlebury, CT 06762
  • /2

    $849,900

    New Construction $40K PRICE INCREASE
    • 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
  • /38

    $834,900

    New Construction $75K PRICE INCREASE
    • 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
  • /14

    $529,900

    • 3 Beds
    • 1.5 Baths
    • 1,811 Sq Ft

    61 Sandy Hill Rd, Middlebury, CT 06762

    Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • /13

    $399,000

    • Land
    • 1.5 Acres
    • $266,000 per Acre

    1140 Southford Rd, Middlebury, CT 06762

    Exceptional opportunity to acquire a 1.5-acre industrial development parcel located along the highly visible Southford Road corridor in Middlebury. Situated within the IG-40 (Gateway Industrial Design District), this property is ideally suited for flex industrial, contractor headquarters, light manufacturing, or office-warehouse development. The site benefits from access to public water and

    Robert Ghent Ghent Realty Advisors

    1140 Southford Rd, Middlebury, CT 06762
  • /20

    $779,000

    • 3 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    38 Avalon Dr, Middlebury, CT 06762

    Welcome to Avalon Farms community, located in one of Middlebury's distinctive residential communities, known for its beautifully built, upscale homes. The home is known for its European inspired architecture, beautifully preserved, natural surroundings, at the end of a cul-de-sac, which suits any stage of life you're in. Step inside to a grand two-story foyer that sets the tone for the homes

    Tracy Wilson Lamacchia Realty

    38 Avalon Dr, Middlebury, CT 06762
  • /14

    $699,990

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    321 Artillery Rd, Middlebury, CT 06762

    Large Colonial with charm and character ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please. The formal living room complete with a large picture window and marble fireplace will serve as a great place to relax at the end of a long day. The dining room is ready to host

    Frank Durante William Raveis Real Estate

    321 Artillery Rd, Middlebury, CT 06762
  • /29

    $690,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,734 Sq Ft

    70 Pine Hollow Dr, Middlebury, CT 06762

    A private hilltop retreat at the end of a quiet cul-de-sac, this stunning 8-room contemporary is set well back from the road on a picturesque knoll, offering exceptional privacy and a peaceful natural setting. Custom built and proudly maintained by its original owner, the home features soaring ceilings, expansive rooms, and walls of windows that flood the interior with natural light. The open,

    Lynn LaForme Regency Real Estate, LLC

    70 Pine Hollow Dr, Middlebury, CT 06762
  • /38

    $750,000

    $9K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,753 Sq Ft

    117 Crest Rd, Middlebury, CT 06762

    Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

    Lori Geraci BHGRE Gaetano Marra Homes

    117 Crest Rd, Middlebury, CT 06762
  • /2

    $839,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    8 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run Road (aka Lot 16) is just beginning construction. There are several other lots and plans to choose from or will build to suit! City water and sewer.

    Jodi Dawley Real Estate Two

    8 Deer Run Rd, Middlebury, CT 06762
  • /26

    $479,900

    Open Sun 1PM - 3PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    42 White Ave, Middlebury, CT 06762

    Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan,

    Justin Cabral West View Properties, LLC

    42 White Ave, Middlebury, CT 06762
  • /39

    $569,900

    • 3 Beds
    • 2.5 Baths
    • 2,428 Sq Ft

    72 Ridgewood Dr Unit 72, Middlebury, CT 06762

    Immaculate 3 bedroom 2.5 bathroom Portman unit in the Sought-After Ridgewood Community! Built by luxury Toll Brothers, with apprx. 2400 SqFt & a remodeled FINISHED BASEMENT. The main level features an open floor plan with gleaming hardwood floors, tons of natural light & hunter Douglas shades. The eat in kitchen offers stainless steel appliances, granite countertops, a gas cooktop that brings a

    Jay Irvine Serhant Connecticut, LLC

    72 Ridgewood Dr Unit 72, Middlebury, CT 06762
  • /34

    $2,195,000

    • 3 Beds
    • 2.5 Baths
    • 3,863 Sq Ft

    397 White Deer Rock Rd, Middlebury, CT 06762

    Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bungalow is privately set on 14.85 serene acres with a path to your own cove frontage. Thoughtfully designed with the current owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point

    Peter Klemm Klemm Real Estate Inc

    397 White Deer Rock Rd, Middlebury, CT 06762
  • /37

    $2,850,000

    • 8 Beds
    • 8 Baths
    • 9,619 Sq Ft

    775 South St Unit 777, Middlebury, CT 06762

    Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the

    Kary Apanovitch Coldwell Banker Realty

    775 South St Unit 777, Middlebury, CT 06762
  • /35

    $559,900

    • 3 Beds
    • 2.5 Baths
    • 3,179 Sq Ft

    3 Winding Trail, Middlebury, CT 06762

    Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors,

    Mayra Perez Showcase Realty, Inc.

    3 Winding Trail, Middlebury, CT 06762
  • /40

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 3,877 Sq Ft

    57 Mistywood Ln, Naugatuck, CT 06770

    Welcome to 57 Mistywood Lane. This home is located on a cul de sac which is private and quiet. It's like your own private oasis. The back yard is a wild life haven. The wildlife is phenomenal! Half of the property is in Naugatuck and half is in Middlebury. This spacious contemporary boasts four bedrooms and two and a half baths. There are nearby hiking and horseback trails. Hop Brook State Park

    Carolyn Butkevich Regency Real Estate, LLC

    57 Mistywood Ln, Naugatuck, CT 06770

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 $660,054.
How many homes have sold over the last 12 months in Middlebury, CT?
103 homes have sold in Middlebury, CT over the last 12 months.
What is the average household income in Middlebury, CT?
The average household income in Middlebury, CT is $150K.
What are the most popular zip codes in Middlebury, CT?
The most popular zip codes in Middlebury, CT include 06762, 06708, 06770, 06795 and 06798.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $590,625. If you put a 20% down payment of $118,100 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $2,990 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $128K a year to afford the median home price in Middlebury. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Middlebury is $150K.
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, Pomperaug Regional High School and Bethlehem Elementary School. Browse all the schools in Middlebury, CT to learn more.

Home Prices in Middlebury, CT

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$574,900
Median Townhouse Sale Price
$549,936
Median 2 Bedroom Sale Price
$414,950
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$285
Number of Homes for Sale
23
Last 12 months Home Sales
103
Months of Supply
2.70
Median List Price
$590,625
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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