Middlebury, CT Homes for Sale with Acreage

/40
$615,000
- 4 Beds
- 3 Baths
- 2,528 Sq Ft
700 Watertown Rd, Middlebury, CT 06762

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio

Erin Giguiere

Regall Realty, LLC

700 Watertown Rd, Middlebury, CT 06762
Explore Middlebury
/35
$679,900

Open Sun 11AM - 1PM $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

Mary Ann Hebert

BHGRE Gaetano Marra Homes

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. Lot assessments #12 - $128,940 2.31

Mary Ann Hebert

BHGRE Gaetano Marra Homes

Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
/23
$669,000
- 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

Simonne Corriveau

KW Legacy Partners

70 Pine Hollow Dr, 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
$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
/40
$499,000

Open Sat 10:30AM - 12:30PM
- 4 Beds
- 2.5 Baths
- 2,157 Sq Ft
880 Whittemore Rd, Middlebury, CT 06762

Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city water and city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler. Inside, a classic center hall

Christina Zainc BHGRE Gaetano Marra Homes

880 Whittemore 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
/31
$749,900

Open Sat 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 2,806 Sq Ft
80 Pine Hollow Dr, Middlebury, CT 06762

Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

Gina Farra Keller Williams Realty

80 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
/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
/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
/37
$650,000
- 3 Beds
- 2.5 Baths
- 2,360 Sq Ft
200 Northridge Dr, Middlebury, CT 06762

Welcome to this beautifully updated contemorary ranch offering an open floor plan, vaulted ceilings, and an inviting sense of space. Nestled among million dollar homes, this property combines comfort, style, and an exceptional location. The spacious living area features a cozy wood burning fireplace and flows seamlessly into the renovated kitchen with abundant cabinetry, a breakfast bar, a coffee

Christina Zainc BHGRE Gaetano Marra Homes

200 Northridge Dr, Middlebury, CT 06762

Connecticut New Haven County

Home Prices in Middlebury, CT

The median home sale price in Middlebury, CT is $557,000, down 1% year-over-year. Homes in Middlebury sell in 79 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price $557,000	Median Single Family Sale Price $555,450
Median Townhouse Sale Price $560,000	Median 2 Bedroom Sale Price $449,900
Median 1 Bedroom Sale Price $222,500	Average Price Per Sq Ft $282
Number of Homes for Sale 26	Last 12 months Home Sales 116
Months of Supply 2.70	Median List Price $575,000
Median Change From 1st List Price 2%	Median Home Sale Price YoY Change -1%

How to Buy a Home How to Finance a Home How to Sell a Home

In Middlebury, there are currently 14 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Middlebury, CT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Middlebury and discover the potential and freedom that comes with owning your own piece of property.

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