Moving to Middlebury CT | real estate for sale in Middlebury Connecticut | Property Statistics of living in Middlebury
Middlebury is an affluent suburban community characterized by large residential lots, executive homes, and attractive natural surroundings. The housing market consists primarily of owner-occupied single-family residences. Property values benefit from excellent schools, limited development, and proximity to Waterbury and New Haven County employment centers. The town remains highly desirable among families seeking upscale suburban living.
24 Yale Avenue
Middlebury, Connecticut 06762
$349,900 | Active
3 Beds | 2 Baths | 1469 Sqft | 0.23 Acres | 18 Days on Market
Property Type: Single Family For Sale
Nestled on a quiet, picturesque street in one of Middleburys classic New England neighborhoods, this warm and inviting Cape Cod offers a rare opportunity to own a move-in ready home in this highly sought-after community, at an exceptional price point. Built in 1982, this charming...
625 Charcoal Avenue
Middlebury, Connecticut 06762
$945,000 | Active
3 Beds | 3 Baths | 4236 Sqft | 20.51 Acres | 1 Days on Market
Property Type: Single Family For Sale
Rare 20+ acres with 1920s house and 3 outbuildings in Middlebury estate area near Lake Quassapaug and the Highfield Club. Very private settling up long driveway with mature landscaping. 3 bedroom main house with multiple entertainment rooms and 2 kitchens. 3 bay car barn with lar...
80 Pine Hollow Drive
Middlebury, Connecticut 06762
$724,900 | Active
4 Beds | 4 Baths | 2806 Sqft | 1.65 Acres | 132 Days on Market
Property Type: Single Family For Sale
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 ...
85 Blueberry Knolls
Middlebury, Connecticut 06762
$550,000 | Coming Soon
3 Beds | 2 Baths | 2156 Sqft | 0.92 Acres | Days on Market
Property Type: Single Family For Sale
Welcome to a truly special property! This beautifully updated 7-room ranch is tucked away at the end of a private cul-de-sac and set on stunning, parklike grounds that offer exceptional privacy and tranquility. Meticulously maintained and thoughtfully updated, this home features ...
10 Curtis Road
Middlebury, Connecticut 06762
$670,000 | Active
4 Beds | 3 Baths | 2484 Sqft | 0.46 Acres | 32 Days on Market
Property Type: Single Family For Sale
Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-...
12 Yale Avenue
Middlebury, Connecticut 06762
$339,900 | Active
2 Beds | 1 Baths | 836 Sqft | 0.23 Acres | 18 Days on Market
Property Type: Single Family For Sale
Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middleburys ...
213 Acme Drive
Middlebury, Connecticut 06762
$499,000 | Active
4 Beds | 3 Baths | 1833 Sqft | 0.32 Acres | 40 Days on Market
Property Type: Single Family For Sale
Welcome to this meticulously maintained and exceptional 4-bedroom, 2.5-bathroom Colonial that perfectly blends classic comfort with wonderful living space. ADDED BONUS - Solar panels that have no monthly fee and very low usage expense! Winter months around $60 month, Summer bill ...
552 Breakneck Hill Road
Middlebury, Connecticut 06762
$950,000 | Active
5 Beds | 4 Baths | 4114 Sqft | 3.21 Acres | 7 Days on Market
Property Type: Single Family For Sale
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, ston...
77 Crest Road
Middlebury, Connecticut 06762
$749,900 | Active
4 Beds | 4 Baths | 2674 Sqft | 1.5 Acres | 9 Days on Market
Property Type: Single Family For Sale
Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middleburys 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 wi...
70 Pine Hollow Drive
Middlebury, Connecticut 06762
$649,900 | Active
3 Beds | 3 Baths | 3174 Sqft | 1.22 Acres | 61 Days on Market
Property Type: Single Family For Sale
SELLER MOTIVATED! Nestled on 1.22 acres of park-like grounds, this large contemporary offers privacy & serenity youve 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...
90 Fenn Road
Middlebury, Connecticut 06762
$660,000 | Active
4 Beds | 4 Baths | 3162 Sqft | 1.67 Acres | 111 Days on Market
Property Type: Single Family For Sale
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 l...
700 Watertown Road
Middlebury, Connecticut 06762
$590,000 | Active
4 Beds | 3 Baths | 2528 Sqft | 1.25 Acres | 64 Days on Market
Property Type: Single Family For Sale
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 fin...
168 Farm Road
Middlebury, Connecticut 06762
$699,900 | Active
4 Beds | 4 Baths | 3302 Sqft | 2.34 Acres | 74 Days on Market
Property Type: Single Family For Sale
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 h...
123 Northwood Drive
Middlebury, Connecticut 06762
$539,000 | Active
3 Beds | 3 Baths | 1552 Sqft | 0.67 Acres | 19 Days on Market
Property Type: Single Family For Sale
Step into this beautifully maintained 3-bedroom, 2.5-bath split-level home where comfort and functionality come together. Gleaming hardwood floors extend throughout the entire home. The living room features a cozy fireplace, creating the perfect space to relax. The bright kitchen...
130 Fairhaven Drive
Middlebury, Connecticut 06762
$649,900 | Under Contract
3 Beds | 3 Baths | 2654 Sqft | 2.73 Acres | 8 Days on Market
Property Type: Single Family For Sale
Ideal location! Beautiful 3-bedroom, 3.5-bath colonial situated at the end of a private cul-de-sac in desirable Middlebury, just minutes from the highway. This bright, sun-filled home features hardwood floors throughout, a spacious family room, custom kitchen with quartz countert...
117 Crest Road
Middlebury, Connecticut 06762
$750,000 | Under Contract - Continue
4 Beds | 3 Baths | 2753 Sqft | 1.7 Acres | 207 Days on Market
Property Type: Single Family For Sale
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, ...
4 Kimberwick Court
Middlebury, Connecticut 06762
$539,900 | Active
3 Beds | 3 Baths | 2181 Sqft | 0 Acres | 42 Days on Market
Property Type: Single Family For Sale
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middleburys most sought after communities. Boasting nearly 2,200 square feet, this spacious home f...
66 Artillery Road
Middlebury, Connecticut 06762
$585,000 | Active
4 Beds | 4 Baths | 2691 Sqft | 1.02 Acres | 51 Days on Market
Property Type: Single Family For Sale
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 fir...
47 Middlebury Terrace
Middlebury, Connecticut 06762
$485,000 | Active
2 Beds | 2 Baths | 1953 Sqft | 0.38 Acres | 21 Days on Market
Property Type: Single Family For Sale
Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood fl...
555 Whittemore Road
Middlebury, Connecticut 06762
$449,000 | Under Contract
4 Beds | 3 Baths | 1855 Sqft | 0.34 Acres | 53 Days on Market
Property Type: Single Family For Sale
Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, w...
25 Avalon Drive
Middlebury, Connecticut 06762
$879,900 | Under Contract - Continue
3 Beds | 4 Baths | 3494 Sqft | 0.69 Acres | 44 Days on Market
Property Type: Single Family For Sale
Located in one of Middleburys most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premiu...
200 Northridge Drive
Middlebury, Connecticut 06762
$650,000 | Under Contract - Continue
3 Beds | 3 Baths | 2360 Sqft | 2.03 Acres | 16 Days on Market
Property Type: Single Family For Sale
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 wo...
880 Whittemore Road
Middlebury, Connecticut 06762
$499,000 | Under Contract - Continue
4 Beds | 3 Baths | 2157 Sqft | 1.4 Acres | 16 Days on Market
Property Type: Single Family For Sale
Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, incl...
24 Steinmann Avenue
Middlebury, Connecticut 06762
$449,000 | Under Contract
3 Beds | 2 Baths | 1378 Sqft | 0.43 Acres | 4 Days on Market
Property Type: Single Family For Sale
*Please submit your offers by Monday July 20th at 2:00pm.* Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middleburys most desirable locations. This inviting Cape offers a flexible layout that lives larger t...
1252 Straits Turnpike
Middlebury, Connecticut 06762
$299,900 | Under Contract - Continue
4 Beds | 1 Baths | 1848 Sqft | 0.28 Acres | 51 Days on Market
Property Type: Single Family For Sale
SUBJECT TO PROBATE APPROVAL, AS-IS, WHERE-IS CONDITION NO FHA, CHFA OR VA LENDING AVAILABLE. NEEDS WORK. LOTS OF HARDWOOD FLOORS, DETACHED 2 CAR GARAGE WORKSHOP AND STORAGE LOFT. LARGE ROOMS, SHARED DRIVEWAY,...
420 Charcoal Avenue
Middlebury, Connecticut 06762
$485,000 | Under Contract
3 Beds | 2 Baths | 1575 Sqft | 1.7 Acres | 10 Days on Market
Property Type: Single Family For Sale
Not Your Typical Cape Style Home! This Beautifully Maintained 3 BD Home in Middlebury is Situated on 1.70 Acres and Exemplifies all the Love and Care Taken by its Owner! Surrounded by Lush Mature Landscaping, This Home Offers a Serenity Inspired Outdoor Living Spaces! Enjoy the S...
326 Lake Shore Drive
Middlebury, Connecticut 06762
$520,000 | Active
3 Beds | 2 Baths | 1568 Sqft | 0.39 Acres | 33 Days on Market
Property Type: Single Family For Sale
Experience the beauty of waterfront living in this charming 3-bedroom, 2-bath Cape Cod-style home nestled along Long Meadow Pond. Combining timeless character with thoughtful updates, this inviting home offers the perfect balance of comfort, convenience, and year-round recreation...
2 Northwood Drive
Middlebury, Connecticut 06762
$575,000 | Active
3 Beds | 3 Baths | 1700 Sqft | 0.42 Acres | 33 Days on Market
Property Type: Single Family For Sale
Tucked into Middleburys desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the homes two floor-to-ce...
397 White Deer Rock Road
Middlebury, Connecticut 06762
$2,195,000 | Under Contract - Continue
3 Beds | 3 Baths | 3863 Sqft | 14.85 Acres | 90 Days on Market
Property Type: Single Family For Sale
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 owners many updates and improvements and timeless materials, the h...
413 Watertown Road
Middlebury, Connecticut 06762
$485,000 | Under Contract
4 Beds | 3 Baths | 2251 Sqft | 0.69 Acres | 6 Days on Market
Property Type: Single Family For Sale
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit todays evolving lifestyle. The main home features ex...
8 Deer Run Road
Middlebury, Connecticut 06762
$839,900 | Under Contract
3 Beds | 3 Baths | 2450 Sqft | 1.5 Acres | 16 Days on Market
Property Type: Single Family For Sale
Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run Road (aka Lot 16) is just beginning construction. There are several other lots and plans to choose from or will build to suit! City water and sewer....
321 Artillery Road
Middlebury, Connecticut 06762
$699,990 | Under Contract - Continue
4 Beds | 3 Baths | 3300 Sqft | 4 Acres | 142 Days on Market
Property Type: Single Family For Sale
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...
3 Brookside Drive
Middlebury, Connecticut 06762
$599,900 | Under Contract - Continue
4 Beds | 4 Baths | 4200 Sqft | 1 Acres | 209 Days on Market
Property Type: Single Family For Sale
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 inst...
Lot 41 Somerset Drive
Middlebury, Connecticut 06762
$939,000 | Under Contract
3 Beds | 3 Baths | 2878 Sqft | 0.8 Acres | 63 Days on Market
Property Type: Single Family For Sale
Under Construction in One of Middleburys 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 wi...
36 Highridge Road
Middlebury, Connecticut 06762
$585,000 | Under Contract
3 Beds | 3 Baths | 1997 Sqft | 0 Acres | 18 Days on Market
Property Type: Condo/Co-Op For Sale
Welcome to 36 Highridge Road, a beautifully maintained home in one of Middleburys most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-mainten...
19 Deer Run Road
Middlebury, Connecticut 06762
$900,000 | Under Contract
4 Beds | 3 Baths | 3100 Sqft | 3.33 Acres | 24 Days on Market
Property Type: Single Family For Sale
Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 19 Deer Run Road (aka Lot 21) is to be built. It is a 3100 sq ft colonial with 2 car attached garage with bonus room. Features includes hardwood floors throughout, gas fireplace with stone surround, gour...
6 Deer Run Road
Middlebury, Connecticut 06762
$849,900 | Active
3 Beds | 3 Baths | 2190 Sqft | 2.2 Acres | 330 Days on Market
Property Type: Single Family For Sale
Welcome Home to Middleburys 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 ...
15 Hunting Ridge Road
Middlebury, Connecticut 06762
$834,900 | Active
3 Beds | 3 Baths | 2190 Sqft | 0.92 Acres | 525 Days on Market
Property Type: Single Family For Sale
Welcome Home to Middleburys 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 wil...
20 Hunting Ridge Road
Middlebury, Connecticut 06762
$774,900 | Active
3 Beds | 2 Baths | 1877 Sqft | 0.98 Acres | 155 Days on Market
Property Type: Single Family For Sale
Welcome Home to Middleburys 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...
775 South Street
Middlebury, Connecticut 06762
$2,850,000 | Active
8 Beds | 8 Baths | 9619 Sqft | 12.6 Acres | 182 Days on Market
Property Type: Single Family For Sale
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 ...
Benson Road
Middlebury, Connecticut 06762
$561,271 | Under Contract
3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...
Benson Road
Middlebury, Connecticut 06762
$573,584 | Under Contract
3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
Last remaining unit! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offerin...
3 Pine Ridge
Middlebury, Connecticut 06762
$721,000 | Under Contract
2 Beds | 3 Baths | 2290 Sqft | 0 Acres | 211 Days on Market
Property Type: Condo/Co-Op For Sale
Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with n...
Benson Road
Middlebury, Connecticut 06762
$555,888 | Under Contract
3 Beds | 3 Baths | 2252 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
Only 3 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offe...
Benson Road
Middlebury, Connecticut 06762
$560,753 | Under Contract
3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
5 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering ...
Benson Road
Middlebury, Connecticut 06762
$522,128 | Under Contract
3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...
Benson Road
Middlebury, Connecticut 06762
$525,438 | Under Contract
3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...
Benson Road
Middlebury, Connecticut 06762
$519,900 | Under Contract
3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...
Benson Road
Middlebury, Connecticut 06762
$548,828 | Under Contract
3 Beds | 3 Baths | 2462 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...
Benson Road
Middlebury, Connecticut 06762
$545,400 | Under Contract
3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market
Property Type: Condo/Co-Op For Sale
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design ...