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Middlebury, CT Homes for Sale

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  • 700 Watertown Rd, Middlebury, CT 06762
    700 Watertown Rd, Middlebury, CT 06762
    700 Watertown Rd, Middlebury, CT 06762
    /40

    $615,000

    Open Sun 1PM - 3PM
    • 5 Beds
    • 3 Baths
    • 2,528 Sq Ft

    700 Watertown Rd, Middlebury, CT 06762

    This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates throughout. Set on 1.25 meticulously landscaped acres, this 5-bedroom, 3-bath home offers warmth, space, and versatility. Built-in equity is an added bonus, with a recent appraisal valuing the home at $715,000. The stunning grounds feature mature plantings, classic New England stone walls, and inviting

    Agent Photo

    Erin Giguiere

    Regall Realty, LLC

    700 Watertown Rd, Middlebury, CT 06762
  • 90 Fenn Rd, Middlebury, CT 06762
    90 Fenn Rd, Middlebury, CT 06762
    90 Fenn 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

    90 Fenn Rd, Middlebury, CT 06762
  • Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
    Lots 12,13, 14 Mirey Dam 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

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
  • 70 Pine Hollow Dr, Middlebury, CT 06762
    70 Pine Hollow Dr, Middlebury, CT 06762
    70 Pine Hollow Dr, Middlebury, CT 06762
    /23

    $669,000

    Open Fri 6PM - 7:30PM
    • 3 Beds
    • 2.5 Baths
    • 2,734 Sq Ft

    70 Pine Hollow Dr, Middlebury, CT 06762

    Nestled on 1.22 acres of park-like grounds, this 2,734 sq ft contemporary offers the privacy & serenity you've been searching for, lovingly maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors

    Agent Photo

    Simonne Corriveau

    KW Legacy Partners

    70 Pine Hollow Dr, Middlebury, CT 06762
  • 20 Hunting Ridge Rd, Middlebury, CT 06762
    20 Hunting Ridge Rd, Middlebury, CT 06762
    20 Hunting Ridge 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
  • 75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle 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
  • 28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    /38

    $759,900

    New Construction
    • 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
  • 1252 Straits Turnpike, Middlebury, CT 06762
    1252 Straits Turnpike, 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
  • 36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    36 Independence Cir, Middlebury, CT 06762
    /40

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    36 Independence Cir, Middlebury, CT 06762

    Welcome to this impressive 3,512-square-foot Colonial offering 10 spacious rooms 4 bedrooms 3.5 baths and a 2 car attached garage. Thoughtfully maintained and updated this home features newer mechanicals installed in 2023 including a furnace and water heater. Large deck for convenient outdoor grilling The elegant interior showcases hardwood flooring throughout crown molding and chair rail

    David Hughes Century 21 AllPoints Realty

    36 Independence Cir, Middlebury, CT 06762
  • 168 N Farm Rd, Middlebury, CT 06762
    168 N Farm Rd, Middlebury, CT 06762
    168 N Farm Rd, Middlebury, CT 06762
    /40

    $729,900

    $35K PRICE DROP
    • 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
  • 6 Deer Run Rd, Middlebury, CT 06762
    6 Deer Run 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
  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge 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
  • 25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    25 Avalon Dr, Middlebury, CT 06762
    /39

    $879,900

    Open Sat 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 3,494 Sq Ft

    25 Avalon Dr, Middlebury, CT 06762

    Located in one of Middlebury's most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premium, fully usable flat lot surrounded by mature pines for year round privacy, the home features Hardie Plank siding and

    Connie Widmann William Raveis Real Estate

    25 Avalon Dr, Middlebury, CT 06762
  • 1140 Southford Rd, Middlebury, CT 06762
    1140 Southford Rd, Middlebury, CT 06762
    1140 Southford 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
  • 117 Crest Rd, Middlebury, CT 06762
    117 Crest Rd, Middlebury, CT 06762
    117 Crest Rd, 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
  • 61 Sandy Hill Rd, Middlebury, CT 06762
    61 Sandy Hill Rd, Middlebury, CT 06762
    61 Sandy Hill 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 on Over 5 Acres in Middlebury Discover the perfect blend of character, comfort, and country living in this enchanting Cape-style home set on more than 5 picturesque acres in Middlebury. Rich with original charm, the home features beautiful hardwood floors throughout, 3 bedrooms, and 1.5 baths. Outside, the property truly shines. Equestrian enthusiasts will appreciate the horse

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • 397 White Deer Rock Rd, Middlebury, CT 06762
    397 White Deer Rock Rd, Middlebury, CT 06762
    397 White Deer Rock Rd, 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
  • 775 South St Unit 777, Middlebury, CT 06762
    775 South St Unit 777, Middlebury, CT 06762
    775 South St Unit 777, 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
  • 413 Watertown Rd, Middlebury, CT 06762
    413 Watertown Rd, Middlebury, CT 06762
    413 Watertown Rd, Middlebury, CT 06762
    /40

    $485,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,251 Sq Ft

    413 Watertown Rd, Middlebury, CT 06762

    Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a

    Emily Fitzgerald William Raveis Real Estate

    413 Watertown Rd, Middlebury, CT 06762
  • 57 Mistywood Ln, Naugatuck, CT 06770
    57 Mistywood Ln, Naugatuck, CT 06770
    57 Mistywood Ln, Naugatuck, CT 06770
    /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
Connecticut New Haven County Middlebury

Real Estate & Homes for Sale in Middlebury, CT

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.

Learn more about living in Middlebury

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $658,402.
How many homes have sold over the last 12 months in Middlebury, CT?
105 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, 06798 and 06478.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $571,950. If you put a 20% down payment of $114,400 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $2,880 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $123K 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

The median home sale price in Middlebury, CT is $547,460, down 4% year-over-year. Homes in Middlebury sell in 83 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$547,460
Median Single Family Sale Price
$555,000
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
$282
Number of Homes for Sale
19
Last 12 months Home Sales
105
Months of Supply
2.20
Median List Price
$571,950
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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