29

Middlebury, CT Homes for Sale

Section Image Section Image Section Image
  • /35

    $699,900

    • 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
  • /40

    $649,000 Open Sat 11:30AM - 2PM

    • 5 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    700 Watertown Rd, Middlebury, CT 06762

    Step into timeless character with this beautifully maintained 1700's Vintage Colonial, where historic charm meets thoughtful modern updates. Set on 1.25 acres with significant landscaping and professional tree work, this 5-bedroom, 3-bath home offers space, warmth, and versatility both inside and out. Designed for comfortable living and effortless entertaining, the home features a spacious layout

    Agent Photo

    Erin Giguiere

    Regall Realty, LLC

    (475) 244-1504

    700 Watertown 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
  • /32

    $599,900

    • 3 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762

    Welcome to this beautifully maintained **Portman Elite** model in the highly desirable Ridgewood of Middlebury community. This bright and inviting home offers 3 bedrooms and 2.5 baths, thoughtfully designed for modern living and low maintenance comfort. The main level features an open layout with a spacious living area, dining space, and a well-appointed kitchen ideal for everyday living and

    Agent Photo

    Mary Ann Hebert

    BHGRE Gaetano Marra Homes

    (475) 267-4261

    2 Arrowwood Ct Unit 2, Middlebury, CT 06762
  • /29

    $774,900 New Construction

    • 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
  • /40

    $950,000

    • 5 Beds
    • 2.5 Baths
    • 3,301 Sq Ft

    851 South St, Middlebury, CT 06762

    Welcome to this beautifully updated home which offers modern comfort, high-end finishes & peace of mind with several upgrades already completed! Located in Middlebury's South Street neighborhood this Colonial is 3300 sq ft on a 1.85 acre lot. Step in to a bright & inviting foyer feat. a high ceiling, a custom wood & glass front door & a stunning custom handrail leading the expansive 4 bedrooms.

    Jackie Desmarais Showcase Realty, Inc.

    851 South St, 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
  • /2

    $849,900 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
  • /38

    $834,900 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
  • /9

    $939,000 New Construction

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

    41 Somerset Dr, Middlebury, CT 06762

    Under Construction in One of Middlebury's Most Desirable Neighborhoods! Welcome to the Avalon Farms community-known for its beautiful homes, manicured lawns, and thoughtfully designed landscaping that create a truly picturesque setting. The Cambridge model blends classic design with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious

    Jonna Dibble BHGRE Gaetano Marra Homes

    41 Somerset Dr, Middlebury, CT 06762
  • /14

    $729,990

    • 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

    • 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
  • /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
  • /19

    $224,900

    • 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
  • /30

    $399,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    863 Whittemore Rd, Middlebury, CT 06762

    Nestled in the desirable town of Middlebury and within walking distance to Westover School, this home suits a variety of lifestyles. Perfect blend of space and manageable living! Ideal for buyers seeking privacy and land without overwhelming upkeep, this well-maintained split-level home offers 1.3 acres of usable land with a comfortable, efficient layout. The main level features a welcoming

    Marisela Agelvis West View Properties, LLC

    863 Whittemore 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
  • /36

    $599,900

    • 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
  • /36

    $429,900

    • 3 Beds
    • 1.5 Baths
    • 1,572 Sq Ft

    301 Steinmann Ave, Middlebury, CT 06762

    Pleased to present this charming, turn-key colonial home which offers a warm and inviting atmosphere. This three-bedroom residence features a spacious kitchen that connects seamlessly to the dining room, which is alongside a large family room highlighted by a high efficiency fieldstone fireplace. Additional features include: A four-season sunroom leading to an outdoor grilling and relaxation

    Dawn Ciappetta Coldwell Banker Realty

    301 Steinmann Ave, 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
  • /12

    $599,900

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

    10 Old Waterbury Rd, Middlebury, CT 06762

    4 UNITS IN MIDDLEBURY-NOT ONLY "NEXT TO IMPOSSIBLE" TO FIND, BUT UNBELIEVABLY PRICED AT $599900! THIS "ONCE IN A LIFETIME" OPPORTUNITY CAN BE YOURS! LIVE IN ONE, AND COLLECT RENT FROM THE OTHER THREE UNITS, OR, ADD THIS ONE TO YOUR INVESTMENT PORTFOLIO AND "WATCH IT GROW"! One parcel (.41 ACRE), ON "PARKLIKE" GROUNDS WITH THE ATMOSPHERE OF NATURE ON A SHORT, NO-THRU STREET, consists of a

    Judith Caputo Advantage Realty Group, Inc.

    10 Old Waterbury Rd, Middlebury, CT 06762
  • /40

    $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
  • /24

    $529,000

    • 3 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    283 Whittemore Rd, Middlebury, CT 06762

    Thoughtful updates, versatile living space, and an unbeatable location come together at this gorgeous, meticulously maintained Middlebury home which offers the perfect blend of comfort and functionality and a layout designed for both everyday living and gracious entertaining. Freshly painted throughout, the home feels bright, clean, and move-in ready from the moment you step inside. The heart of

    Jennifer Sisco RE/MAX Heritage

    283 Whittemore Rd, Middlebury, CT 06762
  • /40

    $550,000

    • 4 Beds
    • 3 Baths
    • 3,168 Sq Ft

    45 Michael Ln, Naugatuck, CT 06770

    Welcome to 45 Michael Lane - a beautifully maintained 4-bedroom, 3-bath Colonial set on nearly 3/4 of an acre along a private, association-maintained road in the sought-after Whittemore Glen neighborhood. This home delivers the space and warmth today's buyers are looking for, inside and out. The formal living room impresses with hardwood floors, crown molding, and a wood-burning fireplace. The

    Andrew Walker Compass Connecticut, LLC

    45 Michael 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
  • /40

    $599,900 Coming Soon

    • 4 Beds
    • 4 Baths
    • 2,763 Sq Ft

    81 Amanda Ln, Naugatuck, CT 06770

    Welcome to this beautiful center hall colonial situated at the end of a cul-de-sac private road on the Middlebury, Oxford line, first floor offers an amazing layout for everyday living or entertaining, featuring an exceptional updated kitchen with stainless steel appliances, peninsula with seating, and separate eat-in area with view of private back yard, leads into a family room complete with

    Donald Fitzgerald, Jr. Showcase Realty, Inc.

    81 Amanda 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 $657,941.
How many homes have sold over the last 12 months in Middlebury, CT?
109 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, 06795 and 06779.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $595,125. If you put a 20% down payment of $119,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,950 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $126K 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
$564,950
Median Townhouse Sale Price
$547,460
Median 2 Bedroom Sale Price
$676,000
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$284
Number of Homes for Sale
24
Last 12 months Home Sales
109
Months of Supply
2.60
Median List Price
$595,125
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-4%
How to Buy a Home How to Finance a Home How to Sell a Home