Middlebury, CT Homes for Sale with Acreage

/35
$660,000

$40K 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
Explore Middlebury
/38
$950,000
- 5 Beds
- 3.5 Baths
- 4,114 Sq Ft
552 Breakneck Hill Rd, Middlebury, CT 06762

Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home

Rebecca Doh

W. Raveis Lifestyles Realty

552 Breakneck Hill Rd, Middlebury, CT 06762
/37
$590,000

$25K PRICE DROP
- 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
/23
$649,900

$19K PRICE DROP
- 3 Beds
- 2.5 Baths
- 3,174 Sq Ft
70 Pine Hollow Dr, Middlebury, CT 06762

SELLER MOTIVATED! Nestled on 1.22 acres of park-like grounds, this large contemporary offers 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

Simonne Corriveau

KW Legacy Partners

70 Pine Hollow Dr, Middlebury, CT 06762
/40
$1,399,900
- 4 Beds
- 3.5 Baths
- 5,237 Sq Ft
67 Abbott Farms, Middlebury, CT 06762

This custom-built classic brick colonial sits in one of Middlebury's most desirable neighborhoods. A private drive leads to a circular driveway with Belgian block accents, welcoming you into a gracious foyer with a sweeping staircase, on the left a formal living room and on the right a beautiful dining room-both ideal for entertaining. The two-story great room with a fireplace opens to a spacious

Mary Ann Hebert

BHGRE Gaetano Marra Homes

67 Abbott Farms, Middlebury, CT 06762
/25
$585,000
- 4 Beds
- 3.5 Baths
- 2,691 Sq Ft
66 Artillery Rd, Middlebury, CT 06762

Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The

Maria Taylor Klemm Real Estate Inc

66 Artillery 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
/40
$819,000

Open Sun 12PM - 2PM
- 4 Beds
- 2.5 Baths
- 2,700 Sq Ft
18 Hunting Ridge Rd, Middlebury, CT 06762

Welcome to Hunting Ridge Estates! This stunning 2,700 sq. ft. Colonial, built in 2025 and just 14 months young, is located in a desirable 23-home Middlebury subdivision. Offering the ease and feel of new construction, this 4-bedroom, 4-bath home features an open floor plan and hardwood flooring throughout both levels. The bright, stylish kitchen showcases white shaker cabinetry, off-white quartz

Robert Disapio Dave Jones Realty, LLC

18 Hunting Ridge Rd, Middlebury, CT 06762
/37
$749,900
- 4 Beds
- 3.5 Baths
- 2,674 Sq Ft
77 Crest Rd, Middlebury, CT 06762

Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters,

Michael Vartolone William Raveis Real Estate

77 Crest Rd, Middlebury, CT 06762
/40
$649,900

$115K 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
/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
/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
/39
$675,000
- 4 Beds
- 3.5 Baths
- 1,940 Sq Ft
46 Washington Dr, Middlebury, CT 06762

Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional

Sabrina Janco Century 21 Bay-Mar Realty

46 Washington Dr, Middlebury, CT 06762
/3
$229,000
- Land
- 1.48 Acres
- $154,730 per Acre
500 Watertown Rd, Middlebury, CT 06762

A RARE FIND IN MIDDLEBURY- BEAUTIFUL LEVEL 1.48 AC APPROVED BUILDING LOT FOR A 3 BDRM HOME WITH 112' OF ROAD FRONTAGE- PERC TESTS & SOIL TESTS DONE- PLOT PLAN DONE- CALL LISTING AGENT FOR DETAILS

Michael Vitale Vitale Realty

500 Watertown 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

Connecticut New Haven County

Home Prices in Middlebury, CT

The median home sale price in Middlebury, CT is $565,000, up 2% year-over-year. Homes in Middlebury sell in 76 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $565,000	Median Single Family Sale Price $575,000
Median Townhouse Sale Price $565,000	Median 2 Bedroom Sale Price $457,450
Median 1 Bedroom Sale Price $231,200	Average Price Per Sq Ft $282
Number of Homes for Sale 28	Last 12 months Home Sales 106
Months of Supply 3.20	Median List Price $575,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 2%

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

In Middlebury, there are currently 15 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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