3,783

Middlebury, CT Homes

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  • 6 Deer Run Rd, Middlebury, CT 06762
    6 Deer Run Rd, Middlebury, CT 06762
    /2

    $810,000 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
  • 0 N Benson Rd Unit 38 24064329, Middlebury, CT 06762

    $511,000 Sold Oct 01, 2025

    • 1,950 Sq Ft
    • $262/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    0 N Benson Rd Unit 38 24064329, Middlebury, CT 06762

    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 and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 38 24064329, Middlebury, CT 06762
  • 2 Deer Run Rd, Middlebury, CT 06762
    2 Deer Run Rd, Middlebury, CT 06762
    /2

    $729,900 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    2 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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

    2 Deer Run Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

    $499,900 Sold Sep 30, 2025

    • 1,950 Sq Ft
    • $256/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762

    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 and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 42 24076140, Middlebury, CT 06762
  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $794,900 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
  • 225 Whittemore Rd, Middlebury, CT 06762

    $385,000 Sold Sep 29, 2025

    • 1,630 Sq Ft
    • $236/SF
    • 73 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    225 Whittemore Rd, Middlebury, CT 06762

    Welcome to 225 Whittemore Road in Middlebury, CT, where charm meets convenience in this cozy solid 3-bedroom, 2-bathroom brick cape. Situated with easy access to Route 8 and I-84, this home is a perfect retreat close to 3 parks and the greenway for outdoor recreation enthusiasts. Step inside to discover an inviting living room featuring a gas stove, creating a warm and welcoming ambiance. The

    Adelia Santos William Pitt Sotheby's Int'l

    225 Whittemore Rd, Middlebury, CT 06762
  • 28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $759,900 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
  • 171 Judd Hill Rd, Middlebury, CT 06762

    $882,500 Sold Sep 25, 2025

    • 3,700 Sq Ft
    • $239/SF
    • 49 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2015

    171 Judd Hill Rd, Middlebury, CT 06762

    Welcome to 171 Judd Hill Road, a stunning custom built home with high end finishes throughout, nestled in the quiet beauty of Middlebury CT. Built in 2015, this immaculately maintained 5 bed, 4 bath home offers thoughtful design, with a separate in-law suite plus additional 400 SF of unfinished basement for extra storage. The main level features hardwood floors, a sun-filled two-story foyer and

    Donna Kennedy Keller Williams Realty

    171 Judd Hill Rd, Middlebury, CT 06762
  • 0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
    /3

    $75,000 Pending

    • Land
    • 0.76 Acre
    • $98,684 per Acre

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    Great building lot on Middlebury side of Naugatuck. Lot is .76 acres with lovely view. Well and septic required. You'll love this established neighborhood.

    Rebecca Zandvliet Coldwell Banker Realty 2000

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
  • 181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    $565,000 Sold Sep 25, 2025

    • 2,614 Sq Ft
    • $216/SF
    • 90 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2022

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762

    Welcome to 181 Ridgewood Drive, Middlebury - a premier Hickory Elite end-unit in the award-winning, resort-style community of Ridgewood at Middlebury. Set amidst beautifully landscaped, wooded grounds, this nearly new townhome blends modern luxury with timeless New England charm, offering a turnkey living experience in one of the region's most desirable neighborhoods. This thoughtfully upgraded

    Heather Crabtree Coldwell Banker Realty

    181 Ridgewood Dr Unit 181, Middlebury, CT 06762
  • 1 Hampshire Ct, Middlebury, CT 06762
    1 Hampshire Ct, Middlebury, CT 06762
    1 Hampshire Ct, Middlebury, CT 06762
    /40

    $829,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,711 Sq Ft

    1 Hampshire Ct, Middlebury, CT 06762

    Welcome to Avalon Farms in Middlebury, one of the area's most desirable single-family home communities. This exceptional residence offers 4 bedrooms, 3.5 baths, and 3,711 sq. ft. of living space, perfectly combining comfort, style, and functionality. Set on one of the few lots overlooking the serene community pond, this home invites you in with a dramatic two-story foyer. The spacious first-floor

    Patricia Forbes Berkshire Hathaway NE Prop.

    1 Hampshire Ct, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    $225,000 Sold Sep 24, 2025

    • Land
    • 3.32 Acres
    • $67,771 per Acre
    • 330 Days On Market

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    Gorgeous 3.32 acre interior lot in a brand new subdivision. Level and on a private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! 2 existing barns on the property. We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD.

    John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762
  • 7 Sandy Beach Rd, Middlebury, CT 06762
    7 Sandy Beach Rd, Middlebury, CT 06762
    7 Sandy Beach Rd, Middlebury, CT 06762
    /36

    $4,100,000 Pending

    • 6 Beds
    • 4 Baths
    • 5,816 Sq Ft

    7 Sandy Beach Rd, Middlebury, CT 06762

    SUPERB LAKE PROPERTY. First time on the market, this 4,811 sf shingle-style home on 6.99 acres in Lake Quassapaug's estate area offers 195 feet of direct waterfront with a private dock and small beach. Designed by renowned architect Rick Moisan and built in 2000, the residence blends timeless design with modern comfort, enjoying complete privacy and pastoral views of permanently protected

    Beverly Mosch William Pitt Sotheby's Int'l

    7 Sandy Beach Rd, Middlebury, CT 06762
  • 55 Westwood Dr, Middlebury, CT 06762

    $675,000 Sold Sep 24, 2025

    • 2,570 Sq Ft
    • $263/SF
    • 192 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1962

    55 Westwood Dr, Middlebury, CT 06762

    Middlebury Modern. Authentic c.1962 Mid-Century Modern Designed by Noted Architect Andrew S Cohen as his Personal Residence. This Largely Untouched Modernist is Set Quietly on Nearly 1-Acre. Walls of Glass & Dark Stone Floors Showcase the Signature Elements of the Era. 4 Bedrooms, 2.5 Baths Include an en-suite Primary Bedroom with Dressing Room & Balcony. Large Eat-in Kitchen Adjacent to Family

    Graham Klemm Klemm Real Estate Inc

    55 Westwood Dr, Middlebury, CT 06762
  • 182 Bayberry Terrace, Middlebury, CT 06762
    182 Bayberry Terrace, Middlebury, CT 06762
    182 Bayberry Terrace, Middlebury, CT 06762
    /39

    $500,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,302 Sq Ft

    182 Bayberry Terrace, Middlebury, CT 06762

    Welcome to this stunning Colonial that's full of charm and curb appeal! Step inside to a spacious kitchen with abundant storage, a cozy breakfast nook, and an adjoining dining room perfect for gatherings. The kitchen flows seamlessly into a bright, sun-filled living room and out to a two-tier deck (upper deck is trex & the lower level is pressure treated wood) is overlooking a peaceful wooded

    David Aurigemma Regency Real Estate, LLC

    182 Bayberry Terrace, Middlebury, CT 06762
  • 288 Watertown Rd Unit Lot 3, Middlebury, CT 06762

    $225,000 Sold Sep 16, 2025

    • Land
    • 3.07 Acres
    • $73,290 per Acre
    • 330 Days On Market

    288 Watertown Rd Unit Lot 3, Middlebury, CT 06762

    Gorgeous 3.07 acre lot in a brand new subdivision. Level and on the end of the cul de sac private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for

    John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 3, Middlebury, CT 06762
  • 0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    0 N Benson Rd Unit 60, Middlebury, CT 06762
    /9

    $573,584 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft

    0 N Benson Rd Unit 60, Middlebury, CT 06762

    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 offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 60, Middlebury, CT 06762
  • 119 Christian Rd, Middlebury, CT 06762

    $345,000 Sold Sep 10, 2025

    • 866 Sq Ft
    • $398/SF
    • 11 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1936

    119 Christian Rd, Middlebury, CT 06762

    Nestled in one of Middlebury's most sought-after neighborhoods, this well-maintained two-bedroom ranch blends comfort, convenience, and charm. Step inside through the inviting enclosed front porch-perfect for morning coffee or evening relaxation-into a warm and welcoming living room complete with a cozy wood stove. The bright, airy kitchen flows seamlessly from the living space, making it ideal

    David Aurigemma Regency Real Estate, LLC

    119 Christian Rd, Middlebury, CT 06762
  • 23 Caveson Ct Unit 23, Middlebury, CT 06762
    23 Caveson Ct Unit 23, Middlebury, CT 06762
    23 Caveson Ct Unit 23, Middlebury, CT 06762
    /24

    $565,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,547 Sq Ft

    23 Caveson Ct Unit 23, Middlebury, CT 06762

    Come discover this beautifully maintained 3-bedroom, 2.5-bathroom detached condo, ideally situated on a quiet cul-de-sac in the highly sought-after Steeplechase complex in Middlebury! This rare standalone unit offers the privacy of a single-family home with the convenience of condo living-no shared walls and minimal exterior maintenance. Inside, you'll find a spacious and open floor plan with

    Arben Belica William Raveis Real Estate

    23 Caveson Ct Unit 23, Middlebury, CT 06762
  • 122 Mirey Dam Rd, Middlebury, CT 06762

    $1,375,000 Sold Sep 04, 2025

    • 6,175 Sq Ft
    • $223/SF
    • 103 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2001

    122 Mirey Dam Rd, Middlebury, CT 06762

    Welcome to this expansive and exquisitely renovated Colonial estate, where timeless charm meets modern luxury. Boasting 5 spacious bedrooms and 5 elegantly appointed bathrooms, enhanced by a fully finished lower level offering potential for an in-law apartment or guest suite. Designed with flexibility and functionality in mind, the home features multiple flex rooms that can easily serve as

    Jennifer Jones Coldwell Banker Realty

    122 Mirey Dam Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
    /9

    $603,780 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,706 Sq Ft

    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762

    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 offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 48 24129196, Middlebury, CT 06762
  • 76 Three Mile Hill Rd, Middlebury, CT 06762

    $536,000 Sold Aug 28, 2025

    • 2,088 Sq Ft
    • $257/SF
    • 104 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1954

    76 Three Mile Hill Rd, Middlebury, CT 06762

    Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middlebury's most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, you feel the warmth and coziness of the home combined with the ease of modern living. The updated kitchen boasts

    Lisa Clarke Dave Jones Realty, LLC

    76 Three Mile Hill Rd, Middlebury, CT 06762
  • 11 Hunting Ridge Rd, Middlebury, CT 06762
    11 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $799,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting Ridge Road (aka Lot 3) is to be built. It is a 2700 sq ft colonial with 2 car attached garage.Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office. The primary bedroom boasts walk-in closet with custom shelving and private

    Jodi Dawley Real Estate Two

    11 Hunting Ridge Rd, Middlebury, CT 06762
  • 58 Shadduck Rd, Middlebury, CT 06762

    $499,900 Sold Aug 26, 2025

    • 2,360 Sq Ft
    • $212/SF
    • 150 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1934

    58 Shadduck Rd, Middlebury, CT 06762

    PRICED TO SELL! DO NOT MISS YOUR OPPORTUNITY TO LIVE IN THE AMAZING TOWN OF MIDDLEBURY IN THIS BEAUTIFUL COLONIAL THAT NEEDS NOTHING BUT TO MOVE RIGHT IN! ACT QUICK! This beautifully renovated colonial seamlessly blends classic elegance with modern updates. Featuring gleaming hardwood floors, an open-concept main level, and a bright kitchen with a center island, this home offers a perfect space

    Amber Segetti RE/MAX RISE

    58 Shadduck Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
    /9

    $509,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762

    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 and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached

    Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 50 24118969, Middlebury, CT 06762
  • 100 Fairhaven Dr, Middlebury, CT 06762

    $679,000 Sold Aug 21, 2025

    • 2,988 Sq Ft
    • $227/SF
    • 28 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    100 Fairhaven Dr, Middlebury, CT 06762

    Welcome home to this beautiful 4-bedroom, 2.5-bath colonial located at the end of a private cul-de-sac in a desirable neighborhood, just minutes from the highway. Inside, you'll find a bright and welcoming layout filled with natural light and hardwood floors throughout. The family room features custom built-ins and a cozy gas fireplace, while the formal living room offers a classic brick

    Tom Dorso Mapleridge Realty

    100 Fairhaven Dr, Middlebury, CT 06762

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