Middlebury, CT Homes

• 

  

  

  /40

  $689,900

  • 3 Beds
  • 4 Baths
  • 3,432 Sq Ft

  33 Ridgewood Dr Unit 33, Middlebury, CT 06762

  Walls of windows! Spectacular, light filled end unit at an award-winning townhome community in Middlebury. Turnkey! Primary bedroom on main level with newly renovated en suite bath. Gorgeous updated kitchen with modern appliances. 2 guest bedrooms on 2nd floor with large shared Jack & Jill bath. Spacious loft for bonus space or home office. Finished lower level flex space for playroom, home

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 871-0910

  33 Ridgewood Dr Unit 33, Middlebury, CT 06762
• 

  

  

  /17

  $2,850 per month

  • 2 Beds
  • 1 Bath
  • 1,217 Sq Ft
  • House for Rent

  95 Christian Rd, Middlebury, CT 06762

  Property Id: 1615951Discover your perfect home at 95 Christian Rd, Middlebury, CT! This charming Cape Cod-style house blends character and comfort, making it an ideal rental for those seeking a peaceful retreat. Located in a tranquil residential community, this 2-bedroom, 1-bathroom home offers 1,217 sq. ft. of cozy living space on over an acre of land—plenty of room to

  95 Christian Rd, 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
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762
• 

  

  

  /32

  $524,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  1 Stevens Rd, Middlebury, CT 06762

  First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 265-6768

  1 Stevens Rd, Middlebury, CT 06762
• 

  

  /9

  $950 per month

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • House for Rent

  10 Old Waterbury Rd Unit 3, Middlebury, CT 06762

  Cozy studio for lease. Spacious living room. Kitchenette with ample cabinet space, Full bathroom w/ stand-up shower. Private in-ground pool with deck. Set in close proximity to schools, shopping & highway(s).

  Jeffrey Corcoran Corcoran Properties, LLC

  10 Old Waterbury Rd Unit 3, 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
• 

  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, Middlebury, CT 06762
• 

  

  /4

  $75,000 Pending

  • Land
  • 1.64 Acres
  • $45,732 per Acre

  0 Ferndale Ave, Middlebury, CT 06762

  For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
• 

  

  /10

  $1,250 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  10 Old Waterbury Rd Unit 1, Middlebury, CT 06762

  Cozy one bedroom unit for lease. Spacious living room with wood burning fireplace. Kitchenette with amble counter space. Full bathroom w/ stand-up shower. Private in-ground pool with deck. One car detached garage. Set in close proximity to schools, shopping & highway(s).

  Jeffrey Corcoran Corcoran Properties, LLC

  10 Old Waterbury Rd Unit 1, 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 $1,496,859 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  397 White Deer Rock Rd, Middlebury, CT 06762
• 

  

  /40

  $499,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  1440 Straits Turnpike, Middlebury, CT 06762

  Pride of ownership abounds in this custom built cape! Main level offers living room with fireplace and pellet insert, crown moldings and hardwood flooring with open flow into the dining room appointed with French doors with transom, crown moldings and hardwood flooring, eating space kitchen boasting vaulted ceiling heights, skylights, ceiling fan, maple cabinets, granite counter tops, pantry,

  

  Linda Mayfield

  RE/MAX RISE

  (203) 349-8926

  1440 Straits Turnpike, Middlebury, CT 06762
• 

  

  /13

  $2,500 per month

  • 3 Beds
  • 1 Bath
  • 1,774 Sq Ft
  • House for Rent

  1395 West St, Middlebury, CT 06762

  Colonial style home set close to town green. Kitchen leads to a separate dining area. Living room has a wood burning fireplace & original moldings. Primary bedrooms with his & her closets. Hardwood floors throughout. Bright sunroom opens out to an oversized deck. Two car garage. Conveniently located on town walking trail, schools & restaurants. A must see!

  Jeffrey Corcoran Corcoran Properties, LLC

  1395 West St, 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 $418,039 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,434 Sq Ft

  23 Atwood St, Middlebury, CT 06762

  23 Atwood St, Middlebury, CT 06762
• 

  

  /38

  $449,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1 Yale Ave, Middlebury, CT 06762

  Charming Cape in prime neighborhood location. Ideally set just off the Middlebury Greenway Trail, this beautiful home offers comfort, space, and convenience. The updated kitchen features granite countertops, stainless steel appliances, white cabinetry, and ample space for cooking and dining. A bright, inviting living room provides the perfect space to relax. The main-level primary suite is

  Elizabeth Newnham William Pitt Sotheby's Int'l

  1 Yale Ave, 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 $681,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,403 Sq Ft

  24 Ridgewood Dr, Middlebury, CT 06762

  24 Ridgewood Dr, Middlebury, CT 06762
• 

  

  /38

  $717,000

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  111 Dwyer Rd, Middlebury, CT 06762

  Elegant Saltbox Colonial in Sought-After Middlebury, Nestled on 2.44 secluded acres, this tasteful saltbox colonial boasts park-like grounds with a private, tree-lined driveway leading to professionally landscaped gardens. Enjoy blooming trees and bushes from spring to fall, creating a picturesque setting. Outdoor living is enhanced with a slate patio, built-in barbecue, and bocce court, perfect

  Mary Ann Hebert BHGRE Bannon & Hebert

  111 Dwyer 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 $547,027 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Judd Rd, Southbury, CT 06488

  436 Judd Rd, Southbury, CT 06488
• 

  

  /40

  $699,900 Open Tue 4:30PM - 6:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,988 Sq Ft

  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
• 

  $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 $627,060 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  740 Whittemore Rd, Middlebury, CT 06762

  740 Whittemore Rd, Middlebury, CT 06762
• 

  

  /26

  $649,900

  • 4 Beds
  • 4 Baths
  • 3,382 Sq Ft

  39 Independence Cir, Middlebury, CT 06762

  Set your eyes on this gorgeous home which features 4 bedrooms, 2 full baths & 2 1/2 baths in Middlebury! This beautifully maintained home boasts classic architecture with modern updates, offering the perfect blend of charm and sophistication. You are welcomed as you enter through the front door by a beautiful family room with charming fireplace and high ceilings. From the family room you have an

  Arben Belica William Raveis Real Estate

  39 Independence Cir, 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 Bannon & Hebert

  64 Joy Rd, Middlebury, CT 06762
• 

  Est $549,255 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,611 Sq Ft

  212 Breakneck Hill Rd, Middlebury, CT 06762

  212 Breakneck Hill Rd, Middlebury, CT 06762
• 

  

  /40

  $899,950

  • 5 Beds
  • 4 Baths
  • 3,700 Sq Ft

  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
• 

  $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 $841,679 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,378 Sq Ft

  126 Burr Hall Rd, Middlebury, CT 06762

  126 Burr Hall Rd, Middlebury, CT 06762
• 

  

  /40

  $900,000

  • 4 Beds
  • 2.5 Baths
  • 3,142 Sq Ft

  87 Falcon Crest Rd, Middlebury, CT 06762

  4 Bedroom home on cul-de-sac road with direct waterfront on Mirey Dam Pond! Gorgeous views from many rooms in the house. Immerse yourself in the serene setting and manicured yard. Eat-in-kitchen with pantry, Corian countertops, custom cherry cabinets, tile floor and backsplash, stainless steel appliances, vaulted ceiling, and pond views! Family room with hardwood floors, gas fireplace, crown

  John Donato Jr Showcase Realty, Inc.

  87 Falcon Crest 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 $598,966 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  108 White Ave, Middlebury, CT 06762

  108 White Ave, Middlebury, CT 06762
• 

  

  /40

  $559,900

  • 2 Beds
  • 2.5 Baths
  • 2,593 Sq Ft

  112 Periwinkle Dr Unit 112, Middlebury, CT 06762

  Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

  Mary Ann Hebert BHGRE Bannon & Hebert

  112 Periwinkle Dr Unit 112, 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 $440,140 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,457 Sq Ft

  456 Whittemore Rd, Middlebury, CT 06762

  456 Whittemore Rd, Middlebury, CT 06762
• 

  

  /40

  $549,900

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  29 Winding Trail Unit 29, Middlebury, CT 06762

  Beautiful luxury Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances,

  Jay Irvine Serhant Connecticut, LLC

  29 Winding Trail Unit 29, 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 Bannon & Hebert

  400 Long Meadow Rd, Middlebury, CT 06762
• 

  Est $574,598 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  84 Anawan Ave, Middlebury, CT 06762

  84 Anawan Ave, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 18