Middlebury, CT Homes

• 

  $515,000 Sold Jul 24, 2025

  • 1,882 Sq Ft
  • $274/SF
  • 61 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  17 Highridge Rd Unit 17, Middlebury, CT 06762

  Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area,

  Kayla O'Grady William Raveis Real Estate

  17 Highridge Rd Unit 17, Middlebury, CT 06762
• 

  Est $367,129 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  5 Laurel Rd, Middlebury, CT 06762

  5 Laurel Rd, Middlebury, CT 06762
• 

  

  

  /40

  $565,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  27 Winding Trail Unit 27, Middlebury, CT 06762

  Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-bed, 2.5-bath home by Toll Brothers is perfectly situated on a private cul-de-sac in one of Ridgewood's most desirable and unique locations. Offering over 2,680 SqFt of beautifully designed living space, this residence includes a rare 4-ft bump-out for added size plus a finished walk-out basement. The main

  Jay Irvine Serhant Connecticut, LLC

  27 Winding Trail Unit 27, Middlebury, CT 06762
• 

  $750,000 Sold Jul 23, 2025

  • 3,374 Sq Ft
  • $222/SF
  • 62 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2004

  34 Avalon Dr, Middlebury, CT 06762

  Located in a desirable neighborhood setting, this beautifully appointed home offers refined living with the flexibility to suit any stage of life. Step inside to a grand two-story foyer that sets the tone for the home's spacious, light-filled interior. The main-level primary suite features a tray ceiling and spa-inspired bathroom with a double vanity, walk-in shower, and jetted soaking

  Connie Widmann William Raveis Real Estate

  34 Avalon Dr, Middlebury, CT 06762
• 

  Est $628,780 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,729 Sq Ft

  82 Northwood Dr, Middlebury, CT 06762

  82 Northwood Dr, Middlebury, CT 06762
• 

  

  /39

  $489,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,311 Sq Ft

  116 Yale Ave, Middlebury, CT 06762

  Tucked on a quiet street in the heart of Middlebury, this beautifully maintained Cape is where comfort meets craftsmanship. Step inside to a sunlit living room anchored by gleaming hardwood floors and a cozy gas fireplace-the perfect place to unwind after a long day. The thoughtfully designed first-floor primary suite offers a serene escape, complete with a full bath and walk-in closet. The

  Dave Jones Dave Jones Realty, LLC

  116 Yale Ave, Middlebury, CT 06762
• 

  $540,000 Sold Jul 18, 2025

  • 2,122 Sq Ft
  • $254/SF
  • 72 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2014

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762

  Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The

  Jay Irvine Serhant Connecticut, LLC

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762
• 

  Est $447,485 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,968 Sq Ft

  271 Shadduck Rd, Middlebury, CT 06762

  271 Shadduck Rd, Middlebury, CT 06762
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  $509,900 Under Contract

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

  0 N Benson Rd Unit 47 24099635, 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 47 24099635, Middlebury, CT 06762
• 

  $950,000 Sold Jul 09, 2025

  • 4,496 Sq Ft
  • $211/SF
  • 428 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  593 Park Road Extension, Middlebury, CT 06762

  This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck.

  Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
• 

  Est $451,793 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,874 Sq Ft

  23 Lubec Rd, Middlebury, CT 06762

  23 Lubec Rd, Middlebury, CT 06762
• 

  /2

  $85,000 Under Contract

  • Land
  • 0.45 Acre
  • $188,889 per Acre

  440 Lake Shore Dr, Middlebury, CT 06762

  Build your dream cottage on this waterfront building lot on the desirable Long Meadow Pond. The lot is located near the end of a low traffic cul-de-sac. It is a great opportunity

  Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762
• 

  $610,000 Sold Jul 09, 2025

  • 2,262 Sq Ft
  • $270/SF
  • 85 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1963

  116 Bronson Dr, Middlebury, CT 06762

  Welcome to this beautifully updated home, perfectly located in the heart of Middlebury! This charming single-story property offers 3 spacious bedrooms and 3 full-sized bathrooms, making it an ideal home for those looking for main-level living. Enjoy the vibrant atmosphere of the Memorial Day parade right from your doorstep! The bright and airy open floor plan features stunning grey hardwood

  Tracie Mormile Paiva Higgins Group Real Estate

  116 Bronson Dr, Middlebury, CT 06762
• 

  Est $305,943 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  40 Yale Ave, Middlebury, CT 06762

  40 Yale Ave, Middlebury, CT 06762
• 

  $555,000 Sold Jul 02, 2025

  • 2,024 Sq Ft
  • $274/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1944

  94 Upper Whittemore Rd, Middlebury, CT 06762

  Nestled along a designated scenic route just seconds from Lake Quassapaug, this custom-built Craftsman-style split-level home offers a rare blend of timeless character and modern comfort. The main-level features rich hardwood floors and a luxurious primary suite, complete with an oversized bedroom, generous closets, a private patio, and a spa-like bathroom with a soaking tub that looks out onto

  Gina Williams Preston Gray Real Estate

  94 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $602,053 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft

  61 Carriage Dr, Middlebury, CT 06762

  61 Carriage Dr, Middlebury, CT 06762
• 

  $365,000 Sold Jul 01, 2025

  • 1,344 Sq Ft
  • $272/SF
  • 69 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  203 Lake Shore Dr, Middlebury, CT 06762

  Lake Shore Drive is just a short walk from the beautifully preserved Long Meadow Pond, a 117-plus acre body of water known for its fishing and kayaking. This home is perfectly in keeping with this idyllic setting, as it is a quintessentially charming ranch, a style of home known for its open and inviting floor plan. There is a confidence in your investment that comes with purchasing a newly

  Michael Caporizzo William Pitt Sotheby's Int'l

  203 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $555,732 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  141 Camp Rd, Middlebury, CT 06762

  141 Camp Rd, Middlebury, CT 06762
• 

  $790,000 Sold Jun 30, 2025

  • 2,700 Sq Ft
  • $293/SF
  • 298 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  18 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome home to Middlebury's newest 23 lot subdivision- Hunting Ridge Estates. This home is currently under construction and will be a 2700 four bedroom colonial featuring hardwood flooring throughout, upgraded trim, walk-in pantry and an attached garage. Still time to customize!! City water and sewers. There are several other lots and plans to choose from or will build to suit!

  Jodi Dawley Real Estate Two

  18 Hunting Ridge Rd, Middlebury, CT 06762
• 

  Est $712,655 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,534 Sq Ft

  207 Artillery Rd, Middlebury, CT 06762

  207 Artillery Rd, Middlebury, CT 06762
• 

  $440,000 Sold Jun 24, 2025

  • 1,414 Sq Ft
  • $311/SF
  • 38 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  69 Nick Rd, Middlebury, CT 06762

  Charming, Fully Renovated Cape in Desirable Middlebury Welcome to this stunningly remodeled 1950s Cape, perfectly blending timeless charm with modern finishes. Located in the heart of Middlebury, known for its award-winning schools, scenic Greenway, and proximity to town, shops, and restaurants, this home has been thoughtfully upgraded inside and out. Step into an open-concept main level

  Beth Santos Showcase Realty, Inc.

  69 Nick Rd, Middlebury, CT 06762
• 

  Est $421,964 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft

  121 Allerton Farms Rd, Middlebury, CT 06762

  121 Allerton Farms Rd, Middlebury, CT 06762
• 

  $230,000 Sold Jun 19, 2025

  • Land
  • 1.89 Acres
  • $121,693 per Acre

  • 9 Days On Market

  58 Chesham Dr, Middlebury, CT 06762

  Build your Dream Home in Middlebury! Don't miss this exceptional opportunity to own nearly 2 acres of prime, level land located on a desirable cul-de-sac in one of Middlebury's most sought-after neighborhoods. Enjoy breathtaking views and the perfect blend of privacy and convenience-just minutes from the center of town and the scenic shores of Lake Quassapaug.and the neighboring towns of Woodbury

  Beth Santos Showcase Realty, Inc.

  58 Chesham Dr, Middlebury, CT 06762
• 

  Est $508,471 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,548 Sq Ft

  4 Woodland Rd, Middlebury, CT 06762

  4 Woodland Rd, Middlebury, CT 06762
• 

  $565,000 Sold Jun 18, 2025

  • 1,882 Sq Ft
  • $300/SF
  • 71 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762

  Welcome to this luxury end-unit condo built in 2022 w/ 3-Bed, 2.5-Bath in Sought-After Ridgewood.1882 Sqft w/ 4 extension to floor plan. This beautifully designed living space, offers 1 level living that many look for. Equipped w/ cathedral ceilings and a first-floor primary bedroom suite for ultimate convenience and a very rare unit. The gourmet kitchen boasts quartz countertops, stainless steel

  Jay Irvine Serhant Connecticut, LLC

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762
• 

  Est $444,977 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,340 Sq Ft

  58 Algin Dr, Middlebury, CT 06762

  58 Algin Dr, Middlebury, CT 06762
• 

  $422,000 Sold Jun 18, 2025

  • 1,688 Sq Ft
  • $250/SF
  • 58 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1959

  64 Joy Rd, Middlebury, CT 06762

  Charming Move-In Ready Ranch in the Heart of Middlebury Welcome home to this beautifully updated ranch-style gem, ideally located in the heart of Middlebury. Set on a quiet street just steps from the scenic Middlebury Greenway Trail, this home offers comfort, style, and convenience all in one. The recently renovated eat-in kitchen is a showstopper, featuring granite countertops, subway tile

  Jonna Dibble BHGRE Gaetano Marra Homes

  64 Joy Rd, Middlebury, CT 06762
• 

  Est $885,594 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,582 Sq Ft

  299 Mirey Dam Rd, Middlebury, CT 06762

  299 Mirey Dam Rd, Middlebury, CT 06762
• 

  $670,000 Sold Jun 18, 2025

  • 3,308 Sq Ft
  • $203/SF
  • 50 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  15 Brookside Dr Unit 15, Middlebury, CT 06762

  This stunning colonial home features a beautifully landscaped level lot with an expansive side yard. As you approach, you are welcomed by a charming covered front porch that leads into a grand two-story foyer with a winding staircase and abundant natural light from the second-story windows. The foyer seamlessly connects to the bright white kitchen, a gas stove, a stylish tile backsplash, a

  Ostap Lisowitch Lisowitch Real Estate Group LLC

  15 Brookside Dr Unit 15, Middlebury, CT 06762
• 

  Est $463,212 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,997 Sq Ft

  1346 Middlebury Rd, Middlebury, CT 06762

  1346 Middlebury Rd, Middlebury, CT 06762
• 

  $370,000 Sold Jun 10, 2025

  • 1,050 Sq Ft
  • $352/SF
  • 44 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1942

  259 White Ave, Middlebury, CT 06762

  Welcome to this charming Cape Cod-style home nestled in the heart of Middlebury, CT. Warm hardwood floors flow throughout the main living spaces, adding a timeless touch of elegance. Begin your day-or unwind at the end of it-in the inviting three-season front porch, the perfect spot to curl up with a good book. Step inside through a cozy entryway where you can hang your coat before choosing to

  Elizabeth Tritschler William Raveis Real Estate

  259 White Ave, Middlebury, CT 06762
• 

  Est $468,927 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,006 Sq Ft

  961 Middlebury Rd, Middlebury, CT 06762

  961 Middlebury Rd, Middlebury, CT 06762
• 

  $675,000 Sold Jun 06, 2025

  • 2,778 Sq Ft
  • $243/SF
  • 44 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  400 Long Meadow Rd, Middlebury, CT 06762

  Highest and Best By Saturday, April 26th at midnight. Offers will be reviewed Sunday the 27th. Beautifully maintained by its original owners, this stunning home offers a peaceful retreat with thoughtful design throughout. The bright, open-concept floor plan is perfect for entertaining, spending time with loved ones, or enjoying quiet moments at home. Expansive windows and the back deck offer

  Christina Zainc BHGRE Gaetano Marra Homes

  400 Long Meadow Rd, Middlebury, CT 06762
• 

  Est $380,490 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,220 Sq Ft

  215 Porter Ave, Middlebury, CT 06762

  215 Porter Ave, Middlebury, CT 06762
• 

  $493,000 Sold Jun 06, 2025

  • 1,808 Sq Ft
  • $273/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2014

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762

  Enjoy living a relaxing and luxurious lifestyle in a most desirable community. As you step into this beautifully appointed, light filled townhome, you can appreciate the open floorplan. This Portman model offers hardwood flooring on the main level and features an eat-in kitchen open to the living/dining room with a gas fireplace for ambiance and warmth. Accessible from the kitchen dining area,

  Donna Bannon BHGRE Gaetano Marra Homes

  43 Ridgewood Dr Unit 43, Middlebury, CT 06762
• 

  Est $393,700 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,229 Sq Ft

  44 Middlebury Terrace, Middlebury, CT 06762

  44 Middlebury Terrace, Middlebury, CT 06762
• 

  $590,000 Sold Jun 04, 2025

  • 2,212 Sq Ft
  • $267/SF
  • 59 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  138 Skyline Dr, Middlebury, CT 06762

  Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch-style home with a finished basement and in-law suite! This home offers the perfect blend of comfort, convenience, and versatility. Step inside the main level to find three spacious bedrooms, that include a primary bedroom with ensuite bathroom, plus a bonus office space, a bright living area, and a well-appointed kitchen.

  Diana Mashni RE/MAX One

  138 Skyline Dr, Middlebury, CT 06762
• 

  Est $678,075 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,895 Sq Ft

  150 Burr Hall Rd, Middlebury, CT 06762

  150 Burr Hall Rd, Middlebury, CT 06762
• 

  $595,000 Sold Jun 04, 2025

  • 2,600 Sq Ft
  • $229/SF
  • 93 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2017

  7 Highridge Rd Unit 7, Middlebury, CT 06762

  Hickory Elite End-Unit Townhouse in sought after Ridgewood at Middlebury, nestled on a quiet cul-de-sac.Offering a blend of luxury, convenience, & top-tier amenities, this 3-bdrm, 3-ba home is designed for both comfort & style.As you step inside, rich dark hdwd flooring flows seamlessly thruout the main living areas, setting a tone of elegance.The expansive 2-story living & dining area is bathed

  Tracy Ropa-Lucifora William Raveis Real Estate

  7 Highridge Rd Unit 7, Middlebury, CT 06762
• 

  Est $535,464 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,781 Sq Ft

  463 Watertown Rd, Middlebury, CT 06762

  463 Watertown Rd, Middlebury, CT 06762

Showing Results 161 - 200, Page 5 of 18