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Middlebury, CT Homes for Sale with Acreage

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  • /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

    $630,000

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

    700 Watertown Rd, Middlebury, CT 06762

    Looking for timeless character? It's here in this beautifully maintained 1700s Vintage Colonial, where historic charm meets 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

    Agent Photo

    Erin Giguiere

    Regall Realty, LLC

    (475) 244-1504

    700 Watertown Rd, Middlebury, CT 06762
  • /38

    $975,000

    Open Sun 12PM - 2PM Coming Soon
    • 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
  • /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
  • /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

    $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

    $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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /35

    $385,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 1 Bath
    • 1,489 Sq Ft

    818 Middlebury Rd, Middlebury, CT 06762

    Tucked away on a beautifully secluded setting, this storybook Cape blends timeless charm with thoughtful updates throughout. The distinctive wood and stone exterior creates unforgettable curb appeal, while the inviting interior offers warmth, character, and functionality. The sun filled living room features hardwood floors, exposed beamed ceilings, and a stunning fireplace with insert, creating

    Brandy Hall Higgins Group Real Estate

    818 Middlebury Rd, Middlebury, CT 06762

Home Trends in Middlebury, CT

Housing Trends

Median Sale Price
$546,230
Median Single Family Sale Price
$574,900
Median Townhouse Sale Price
$547,460
Median 2 Bedroom Sale Price
$649,500
Median 1 Bedroom Sale Price
$222,500
Average Price Per Sq Ft
$286
Number of Homes for Sale
18
Last 12 months Home Sales
110
Months of Supply
2.00
Median List Price
$589,750
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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