23

Middlebury, CT Homes for Sale

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  • /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
  • /40

    $785,000

    • 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
  • /2

    $739,900 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
  • /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

    Jonna Dibble BHGRE Gaetano Marra Homes

    22 Somerset Dr, 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 Century 21 Bette Real Estate

    72 Carriage Dr, 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
  • /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
  • /38

    $659,900

    • 4 Beds
    • 4 Baths
    • 4,200 Sq Ft

    3 Brookside Dr, Middlebury, CT 06762

    Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the

    Shagufta Zahid S Factor Realty Group LLC

    3 Brookside Dr, Middlebury, CT 06762
  • /40

    $689,000

    • 4 Beds
    • 5 Baths
    • 3,254 Sq Ft

    84 Munson Rd, Middlebury, CT 06762

    Experience comfort, space, and scenic surroundings at 84 Munson Road, Middlebury, CT 06762, a well-situated home set in a peaceful and desirable community. This inviting property offers a thoughtfully designed layout with generous living areas filled with natural light, creating a bright and welcoming atmosphere. The main level provides ideal flow for everyday living and entertaining, while the

    Thomas Mele Dorrance Realty

    84 Munson Rd, Middlebury, CT 06762
  • /19

    $284,900

    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft

    152 Glenwood Ave, Middlebury, CT 06762

    2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

    Don Orsini West View Properties, LLC

    152 Glenwood Ave, Middlebury, CT 06762
  • /24

    $229,900

    • Land
    • 4.67 Acres
    • $49,229 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

    Scott Tedesco Tedesco Real Estate

    75 Gleneagle Rd, Middlebury, CT 06762
  • /5

    $1,600,000

    • Land
    • 29 Acres
    • $55,172 per Acre

    0 White Birch Unit 24141986, Middlebury, CT 06762

    Attention Builders, Developers, and Investors: fully approved 10 LOT Subdivision for sale in the charming town of Middlebury, CT (29 Acres total) With comprehensive approvals in place including Planning & Zoning, Wetlands, and Health Department clearances, you can get straight to work developing your vision. Each lot is designed to feature a private well and connection to public sewer. Middlebury

    Donna Kennedy Compass Connecticut, LLC

    0 White Birch Unit 24141986, Middlebury, CT 06762
  • /39

    $574,000

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

    24 Ridgewood Dr, Middlebury, CT 06762

    Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • /2

    $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
  • /40

    $599,900

    • 5 Beds
    • 2 Baths
    • 1,924 Sq Ft

    292 Park Road Extension, Middlebury, CT 06762

    Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living.

    Tammy Ferrauola Eagle Eye Realty PLLC

    292 Park Road Extension, Middlebury, CT 06762
  • /40

    $499,900

    • 3 Beds
    • 3.5 Baths
    • 1,918 Sq Ft

    637 Watertown Rd, Middlebury, CT 06762

    Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home.

    Jonna Dibble BHGRE Gaetano Marra Homes

    637 Watertown Rd, Middlebury, CT 06762
  • /37

    $759,000

    • 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
  • /12

    $699,900

    • 5 Beds
    • 4 Baths
    • 2,345 Sq Ft

    10 Old Waterbury Rd, Middlebury, CT 06762

    RARE OPPORTUNITY to find 4 units in MIDDLEBURY, CT! LOCATION! LOCATION! One parcel with (.41 acre) consists of a detached, 1 bedroom single family, approximately (620 s.f.), 3 units w/1 car garage under and in-ground pool. 2 car detached garage, in addition to plenty of off street parking. Public water and sewer. Separate utilities paid by tenants. Single family has oil heat and 3 family is

    Judith Caputo Advantage Realty Group, Inc.

    10 Old Waterbury Rd, Middlebury, CT 06762
  • /19

    $229,000

    • 1 Bed
    • 1 Bath
    • 889 Sq Ft

    35 Nutmeg Rd Unit D1, Middlebury, CT 06762

    Middlebury Commons, Highly desirable 55+ community conveniently located to town center and all of its amenities. Bright second floor unit has primary BR with walk-in closet plus den/office that can serve as 2nd BR. Eat-in kitchen, laundry area, LR/DR combo with french door to deck overlooking private rear yard. Move right into this beautiful unit.

    Karen Stanco Showcase Realty, Inc.

    35 Nutmeg Rd Unit D1, 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
  • /24

    $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

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 $618,485.
Are home prices dropping in Middlebury?
Yes, home prices in Middlebury are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Middlebury, CT?
125 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, 06708, 06770, 06488 and 06795.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $569,900. If you put a 20% down payment of $114,000 and had a 30-year fixed mortgage with an interest rate of 6.1%, your estimated principal and interest payment would be $2,760 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $118K a year to afford the median home price in Middlebury. Learn how much home you can afford with our Home Affordability Calculator.
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 Trends in Middlebury, CT

Housing Trends

Median Sale Price
$547,460
Median Single Family Sale Price
$515,000
Median Townhouse Sale Price
$544,513
Median 2 Bedroom Sale Price
$704,850
Median 1 Bedroom Sale Price
$229,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
19
Last 12 months Home Sales
125
Months of Supply
1.80
Median List Price
$569,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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