Middlebury, CT Homes

• 

  Est $320,609 Not Listed For Sale

  1232 Straits Turnpike, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,708 Sq Ft
  • Built 1920

  1232 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 21% Above List Price
  • $155/SF
  • 144 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.
• 

  

  

  /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
• 

  $365,000 Sold Jul 01, 2025

  203 Lake Shore Dr, Middlebury, CT 06762

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1965

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 69 Days On Market

  Current Estimated Value $369,710

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  203 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $790,522 Not Listed For Sale

  524 Charcoal Ave, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,030 Sq Ft
  • Built 1999

  524 Charcoal Ave, Middlebury, CT 06762

  Last Sold Summary

  • 10% Above List Price
  • $238/SF
  • 84 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Jill Taylor RE/MAX
• 

  

  

  /9

  $522,128 Pending

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

  0 N Benson Rd Unit 46 24097231, 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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
• 

  $790,000 Sold Jun 30, 2025

  18 Hunting Ridge Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $293/SF
  • 298 Days On Market

  Current Estimated Value $798,402

  Last Listing Agent Jodi Dawley Real Estate Two

  18 Hunting Ridge Rd, Middlebury, CT 06762
• 

  Est $604,252 Not Listed For Sale

  695 Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 4.5 Baths
  • 2,813 Sq Ft
  • Built 1978

  695 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 7% Below List Price
  • $231/SF
  • 8 Days On Market

  Last Sold Price $650,000

  Last Listing Agent rob raad Better Living Realty, LLC
• 

  

  /37

  $825,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 3,253 Sq Ft

  122 Crest Rd, Middlebury, CT 06762

  Welcome to your own private retreat at 122 Crest Road-where timeless charm meets thoughtful modern updates. This beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home is just moments from town, the library, green, and local dining. Designed with both everyday living and entertaining in mind, the home features a custom sunken great room with a dramatic wall of windows that floods the

  Heather Dever Showcase Realty, Inc.

  122 Crest Rd, Middlebury, CT 06762
• 

  $505,834 Sold Oct 17, 2025

  0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Built 2025

  Last Sold Summary

  • $259/SF
  • 0 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 39 24076410, Middlebury, CT 06762
• 

  Est $422,328 Not Listed For Sale

  36 Middlebury Terrace, Middlebury, CT 06762

  • 3 Beds
  • 1.5 Baths
  • 1,849 Sq Ft
  • Built 1933

  36 Middlebury Terrace, Middlebury, CT 06762

  Last Sold Summary

  • 1% Below List Price
  • $230/SF
  • 177 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Frank Durante William Raveis Real Estate
• 

  

  /31

  $749,900 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,806 Sq Ft

  80 Pine Hollow Dr, Middlebury, CT 06762

  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 meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting

  Gina Farra Keller Williams Realty

  80 Pine Hollow Dr, Middlebury, CT 06762
• 

  $630,000 Sold May 15, 2025

  7 Arrowwood Ct Unit 7, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,465 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $182/SF
  • 77 Days On Market

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  7 Arrowwood Ct Unit 7, Middlebury, CT 06762
• 

  Est $963,750 Not Listed For Sale

  122 Northridge Dr, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 5,582 Sq Ft
  • Built 1982

  122 Northridge Dr, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $160/SF
  • 80 Days On Market

  Last Sold Price $895,000

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  

  /40

  $574,900 Under Contract

  • 5 Beds
  • 2 Baths
  • 1,924 Sq Ft

  292 Park Road Extension, Middlebury, CT 06762

  Discover this classic 5-bedroom, 2-bath Colonial set on a private 1.67-acre lot in desirable Middlebury. This home features hardwood floors, a bright formal living room, and a spacious dining room that opens to a cozy three-season porch overlooking the yard. The kitchen offers brand-new stainless steel appliances and the convenient first-floor bedroom includes laundry for easy main-level living.

  Tammy Ferrauola Eagle Eye Realty PLLC

  292 Park Road Extension, Middlebury, CT 06762
• 

  $230,000 Sold Jun 19, 2025

  58 Chesham Dr, Middlebury, CT 06762

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

  Last Sold Summary

  • 18% Below List Price
  • 9 Days On Market

  Current Estimated Value $232,551

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  58 Chesham Dr, Middlebury, CT 06762
• 

  Est $467,955 Not Listed For Sale

  2 Northwood Dr, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1962

  2 Northwood Dr, Middlebury, CT 06762

  Last Sold Summary

  • 1% Above List Price
  • $248/SF
  • 54 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Michael Magas BHGRE Gaetano Marra Homes
• 

  

  /30

  $479,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  18 Freedom Rd, Middlebury, CT 06762

  Welcome to this charming and beautifully maintained 3BR ranch, perfectly situated on a quiet cul-de-sac. Offering the ease of one-level living, this inviting home features an open living room and dining room layout enhanced by gleaming hardwood floors, a cozy fireplace and abundant natural light. The updated kitchen boasts a large granite center island that is ideal for cooking gathering and

  Karen Stanco Showcase Realty, Inc.

  18 Freedom Rd, Middlebury, CT 06762
• 

  $385,000 Sold May 05, 2025

  43 Merideth Rd, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 1957

  Last Sold Summary

  • $244/SF
  • 51 Days On Market

  Current Estimated Value $390,815

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  43 Merideth Rd, Middlebury, CT 06762
• 

  Est $445,358 Not Listed For Sale

  106 Glenwood Ave, Middlebury, CT 06762

  • 5 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1926

  106 Glenwood Ave, Middlebury, CT 06762

  Last Sold Summary

  • 2% Above List Price
  • $254/SF
  • 25 Days On Market

  Last Sold Price $438,000

  Last Listing Agent Crosby Middlemass Coldwell Banker Realty
• 

  

  /40

  $450,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 1,918 Sq Ft

  637 Watertown Rd, Middlebury, CT 06762

  Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home.

  Jonna Dibble BHGRE Gaetano Marra Homes

  637 Watertown Rd, Middlebury, CT 06762
• 

  $950,000 Sold Jul 09, 2025

  593 Park Road Extension, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 4,496 Sq Ft
  • Built 1994

  Last Sold Summary

  • 27% Below List Price
  • $211/SF
  • 428 Days On Market

  Current Estimated Value $960,954

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
• 

  Est $353,089 Not Listed For Sale

  185 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • Built 1953

  185 Porter Ave, Middlebury, CT 06762

  Last Sold Summary

  • 6% Above List Price
  • $272/SF
  • 33 Days On Market

  Last Sold Price $331,900

  Last Listing Agent Beth Santos Showcase Realty, Inc.
• 

  

  /9

  $561,271 Pending

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

  0 N Benson Rd Unit 57, 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 Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 57, Middlebury, CT 06762
• 

  $454,000 Sold May 08, 2025

  679 Christian Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 1967

  Last Sold Summary

  • 1% Above List Price
  • $196/SF
  • 47 Days On Market

  Current Estimated Value $485,886

  Last Listing Agent Chloe White KW Legacy Partners

  679 Christian Rd, Middlebury, CT 06762
• 

  Est $462,950 Not Listed For Sale

  31 Stony Brook Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 1969

  31 Stony Brook Rd, Middlebury, CT 06762

  Last Sold Summary

  • 5% Above List Price
  • $220/SF
  • 54 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Deana Daponte Dave Jones Realty, LLC
• 

  

  /36

  $599,900

  • 4 Beds
  • 4 Baths
  • 4,200 Sq Ft

  3 Brookside Dr, Middlebury, CT 06762

  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 instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the

  Shagufta Zahid S Factor Realty Group LLC

  3 Brookside Dr, Middlebury, CT 06762
• 

  $240,000 Sold Oct 14, 2025

  288 Watertown Rd Unit Lot 2, Middlebury, CT 06762

  • Land
  • 4 Acres
  • $60,000 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 330 Days On Market

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 2, Middlebury, CT 06762
• 

  Est $495,234 Not Listed For Sale

  592 Benson Rd, Middlebury, CT 06762

  • 5 Beds
  • 2 Baths
  • 2,289 Sq Ft
  • Built 1978

  592 Benson Rd, Middlebury, CT 06762

  Last Sold Summary

  • 8% Above List Price
  • $200/SF
  • 3 Days On Market

  Last Sold Price $457,000

  Last Listing Agent Linda Andrikis West View Properties, LLC
• 

  

  /9

  $939,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  41 Somerset Dr, Middlebury, CT 06762

  Under Construction in One of Middlebury's 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 with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious

  Jonna Dibble BHGRE Gaetano Marra Homes

  41 Somerset Dr, Middlebury, CT 06762
• 

  $515,000 Sold Jul 31, 2025

  61 Stony Brook Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft
  • Built 1971

  Last Sold Summary

  • 21% Below List Price
  • $184/SF
  • 75 Days On Market

  Current Estimated Value $546,934

  Last Listing Agent Maria Cohen William Raveis Real Estate

  61 Stony Brook Rd, Middlebury, CT 06762
• 

  Est $349,221 Not Listed For Sale

  294 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,109 Sq Ft
  • Built 1949

  294 Porter Ave, Middlebury, CT 06762

  Last Sold Summary

  • 4% Above List Price
  • $302/SF
  • 4 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Michelle Pavia William Raveis Real Estate
• 

  Price To Be Determined New Construction

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

  Right Garage Plan at Aberdeen Estates at Benson Woods, Middlebury, CT 06762

  Lovley Development Builder

  0 N Benson Rd Unit 39341025, Middlebury, CT 06762
• 

  $675,000 Sold Sep 24, 2025

  55 Westwood Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,570 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Below List Price
  • $263/SF
  • 192 Days On Market

  Current Estimated Value $647,599

  Last Listing Agent Graham Klemm Klemm Real Estate Inc

  55 Westwood Dr, Middlebury, CT 06762
• 

  Est $507,654 Not Listed For Sale

  828 Breakneck Hill Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft
  • Built 1951

  828 Breakneck Hill Rd, Middlebury, CT 06762

  Last Sold Summary

  • 33% Above List Price
  • $173/SF
  • 17 Days On Market

  Last Sold Price $383,000

  Last Listing Agent Mary Helen Levine Mary Helen Levine Real Estate LLC
• 

  

  /40

  $485,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  420 Charcoal Ave, Middlebury, CT 06762

  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 Sounds of Birds while Sitting on Your Rear Patio. Or Host Dinner Parties in the Enclosed Sunroom on a Cool Summer

  Bethany Lydem Stone Crest Realty LLC

  420 Charcoal Ave, Middlebury, CT 06762
• 

  $85,000 Sold Jan 07, 2026

  440 Lake Shore Dr, Middlebury, CT 06762

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

  Last Sold Summary

  • 258 Days On Market

  Current Estimated Value $85,545

  Last Listing Agent Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762
• 

  Est $1,031,190 Not Listed For Sale

  Unlisted Address

  • 5 Beds
  • 5 Baths
  • 5,800 Sq Ft
  • Built 1929

  Unlisted Address

  Last Sold Summary

  • 24% Below List Price
  • $234/SF
  • 54 Days On Market

  Last Sold Price $1,360,000

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes
• 

  

  /37

  $759,000

  • 4 Beds
  • 2.5 Baths
  • 2,753 Sq Ft

  117 Crest Rd, Middlebury, CT 06762

  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, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

  Lori Geraci BHGRE Gaetano Marra Homes

  117 Crest Rd, Middlebury, CT 06762
• 

  $510,000 Sold Oct 22, 2025

  112 Periwinkle Dr Unit 112, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2005

  Last Sold Summary

  • 11% Below List Price
  • $197/SF
  • 186 Days On Market

  Current Estimated Value $476,585

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  112 Periwinkle Dr Unit 112, Middlebury, CT 06762
• 

  Est $391,006 Not Listed For Sale

  140 Glenwood Ave, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • Built 1936

  140 Glenwood Ave, Middlebury, CT 06762

  Last Sold Summary

  • 17% Above List Price
  • $205/SF
  • 35 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Karen Dibble-flaherty Keller Williams Realty

Showing Results 121 - 160, Page 4 of 18