Middlebury, CT Homes

• 

  Est $623,998

  Not Listed For Sale

  82 Northwood Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,729 Sq Ft
  • Built 1960

  82 Northwood Dr, Middlebury, CT 06762

  Last Sold Summary

  • 230 Days On Market

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
• 

  

  

  /40

  $485,000

  • 2 Beds
  • 1.5 Baths
  • 1,953 Sq Ft

  47 Middlebury Terrace, Middlebury, CT 06762

  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 flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood

  RuthAnne Salvatore Coldwell Banker Realty

  47 Middlebury Terrace, Middlebury, CT 06762
• 

  $560,000

  Sold Jun 19, 2026

  24 Highridge Rd Unit 24, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,802 Sq Ft
  • Built 2017

  Last Sold Summary

  • $311/SF
  • 58 Days On Market

  Last Listing Agent Jay Irvine Serhant Connecticut, LLC

  24 Highridge Rd Unit 24, Middlebury, CT 06762
• 

  Est $526,545

  Not Listed For Sale

  835 Whittemore Rd, Middlebury, CT 06762

  • 4 Beds
  • 3.5 Baths
  • 3,016 Sq Ft
  • Built 1963

  835 Whittemore Rd, Middlebury, CT 06762

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Mike Albert RE/MAX RISE
• 

  

  

  /9

  $559,250

  New Construction Pending

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

  0 N Benson Rd Unit 44, 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 44, Middlebury, CT 06762
• 

  $345,000

  Sold Sep 10, 2025

  119 Christian Rd, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 866 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Below List Price
  • $398/SF
  • 11 Days On Market

  Current Estimated Value $347,052

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  119 Christian Rd, Middlebury, CT 06762
• 

  Est $617,290

  Not Listed For Sale

  61 Carriage Dr, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft
  • Built 1966

  61 Carriage Dr, Middlebury, CT 06762

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Colleen Burne Coldwell Banker Realty
• 

  

  /3

  $229,000

  • Land
  • 1.48 Acres
  • $154,730 per Acre

  500 Watertown Rd, Middlebury, CT 06762

  A RARE FIND IN MIDDLEBURY- BEAUTIFUL LEVEL 1.48 AC APPROVED BUILDING LOT FOR A 3 BDRM HOME WITH 112' OF ROAD FRONTAGE- PERC TESTS & SOIL TESTS DONE- PLOT PLAN DONE- CALL LISTING AGENT FOR DETAILS

  Michael Vitale Vitale Realty

  500 Watertown Rd, Middlebury, CT 06762
• 

  $875,000

  Sold Jun 15, 2026

  245 Upper Whittemore Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,990 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Above List Price
  • $293/SF
  • 0 Days On Market

  Current Estimated Value $868,942

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  245 Upper Whittemore Rd, Middlebury, CT 06762
• 

  Est $579,071

  Not Listed For Sale

  141 Camp Rd, Middlebury, CT 06762

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1988

  141 Camp Rd, Middlebury, CT 06762

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Olivia Hardt Berkshire Hathaway NE Prop.
• 

  

  /9

  $545,400

  New Construction Pending

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

  0 N Benson Rd Unit 64 24077175, 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 64 24077175, Middlebury, CT 06762
• 

  $456,000

  Sold Nov 17, 2025

  18 E Ridge Dr, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,340 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Above List Price
  • $340/SF
  • 54 Days On Market

  Current Estimated Value $461,541

  Last Listing Agent Beth Santos Showcase Realty, Inc.

  18 E Ridge Dr, Middlebury, CT 06762
• 

  Est $529,492

  Not Listed For Sale

  1 Stevens Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1937

  1 Stevens Rd, Middlebury, CT 06762

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
• 

  

  /9

  $603,780

  New Construction 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 Lovley Century 21 AllPoints Realty

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

  $530,328

  Sold Oct 30, 2025

  0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762

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

  Last Sold Summary

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

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 36 24058145, Middlebury, CT 06762
• 

  Est $629,093

  Not Listed For Sale

  129 Periwinkle Dr, Middlebury, CT 06762

  • 2 Beds
  • 2.5 Baths
  • 2,476 Sq Ft
  • Built 2005

  129 Periwinkle Dr, Middlebury, CT 06762

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Lisa Gallagher William Raveis Real Estate
• 

  

  /24

  $324,900

  Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  125 Shadduck Rd, Middlebury, CT 06762

  Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

  Ed Vayan BHGRE Gaetano Marra Homes

  125 Shadduck Rd, Middlebury, CT 06762
• 

  $409,000

  Sold Nov 25, 2025

  115 Porter Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 39 Days On Market

  Current Estimated Value $432,394

  Last Listing Agent Judith Caputo Advantage Realty Group, Inc.

  115 Porter Ave, Middlebury, CT 06762
• 

  Est $418,039

  Not Listed For Sale

  43 Merideth Rd, Middlebury, CT 06762

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

  43 Merideth Rd, Middlebury, CT 06762

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
• 

  

  /25

  $499,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  112 Joy Rd, Middlebury, CT 06762

  Welcome home to this beautifully updated property located in one of Middlebury's quiet and sought after neighborhoods. This move in ready home features a stylish kitchen with granite countertops, a gas range, and smart appliances, including a refrigerator, washer and dryer. Gleaming hardwood floors in living room, hallway and bedrooms. Enjoy year-round comfort with central air conditioning and

  Rob Marucci Better Living Realty, LLC

  112 Joy Rd, Middlebury, CT 06762
• 

  $706,000

  Sold Jun 30, 2026

  15 Central Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,870 Sq Ft
  • Built 1941

  Last Sold Summary

  • 2% Above List Price
  • $246/SF
  • 60 Days On Market

  Current Estimated Value $683,417

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes

  15 Central Rd, Middlebury, CT 06762
• 

  Est $641,323

  Not Listed For Sale

  89 Tyler Crossing, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 2,704 Sq Ft
  • Built 1998

  89 Tyler Crossing, Middlebury, CT 06762

  Last Sold Summary

  • 99 Days On Market

  Last Listing Agent Matt Rose Keller Williams Realty
• 

  

  /34

  $2,195,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,863 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  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 owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point

  Peter Klemm Klemm Real Estate Inc

  397 White Deer Rock Rd, Middlebury, CT 06762
• 

  $70,000

  Sold Jun 29, 2026

  0 Ferndale Ave, Middlebury, CT 06762

  • Land
  • 1.64 Acres
  • $42,683 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 54 Days On Market

  Last Listing Agent Ken Demirs Regency Real Estate, LLC

  0 Ferndale Ave, Middlebury, CT 06762
• 

  Est $508,994

  Not Listed For Sale

  1440 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft
  • Built 1940

  1440 Straits Turnpike, Middlebury, CT 06762

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Linda Mayfield RE/MAX RISE
• 

  /2

  $900,000

  New Construction Pending

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  19 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's 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, gourmet kitchen with large center island, convenient office. The primary bedroom boasts walk-in closet with custom

  Jodi Dawley Real Estate Two

  19 Deer Run Rd, Middlebury, CT 06762
• 

  $465,000

  Sold Oct 03, 2025

  1996 Straits Turnpike, Middlebury, CT 06762

  • 3 Beds
  • 3 Baths
  • 1,768 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $263/SF
  • 47 Days On Market

  Current Estimated Value $464,574

  Last Listing Agent Devon O'Neill Litchfield Hills Properties LLC

  1996 Straits Turnpike, Middlebury, CT 06762
• 

  Est $501,969

  Not Listed For Sale

  115 Marney Dr, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 1971

  115 Marney Dr, Middlebury, CT 06762

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Allysa DeRosa Mapleridge Realty
• 

  

  /9

  $573,572

  New Construction Pending

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

  0 N Benson Rd Unit 65, 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 65, Middlebury, CT 06762
• 

  $850,000

  Sold Jul 07, 2026

  122 Crest Rd, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 3,253 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Above List Price
  • $261/SF
  • 75 Days On Market

  Current Estimated Value $825,221

  Last Listing Agent Heather Dever Showcase Realty, Inc.

  122 Crest Rd, Middlebury, CT 06762
• 

  Est $992,760

  Not Listed For Sale

  593 Park Road Extension, Middlebury, CT 06762

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

  593 Park Road Extension, Middlebury, CT 06762

  Last Sold Summary

  • 428 Days On Market

  Last Listing Agent Jackie Desmarais Showcase Realty, Inc.
• 

  

  /9

  $533,416

  New Construction Pending

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

  0 N Benson Rd Unit 49 24096137, 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 49 24096137, Middlebury, CT 06762
• 

  $574,900

  Sold May 04, 2026

  292 Park Road Extension, Middlebury, CT 06762

  • 5 Beds
  • 2 Baths
  • 1,924 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $299/SF
  • 136 Days On Market

  Current Estimated Value $563,043

  Last Listing Agent Tammy Ferrauola Eagle Eye Realty PLLC

  292 Park Road Extension, Middlebury, CT 06762
• 

  Est $384,812

  Not Listed For Sale

  44 Middlebury Terrace, Middlebury, CT 06762

  • 2 Beds
  • 1.5 Baths
  • 1,229 Sq Ft
  • Built 1937

  44 Middlebury Terrace, Middlebury, CT 06762

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
• 

  

  /32

  $670,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,484 Sq Ft

  10 Curtis Rd, Middlebury, CT 06762

  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-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The

  Heather Dever Showcase Realty, Inc.

  10 Curtis Rd, Middlebury, CT 06762
• 

  $495,000

  Sold Dec 22, 2025

  182 Bayberry Terrace, Middlebury, CT 06762

  • 4 Beds
  • 2 Baths
  • 2,302 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 34 Days On Market

  Current Estimated Value $508,951

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  182 Bayberry Terrace, Middlebury, CT 06762
• 

  Est $690,133

  Not Listed For Sale

  150 Burr Hall Rd, Middlebury, CT 06762

  • 4 Beds
  • 2.5 Baths
  • 3,895 Sq Ft
  • Built 1979

  150 Burr Hall Rd, Middlebury, CT 06762

  Last Sold Summary

  • 186 Days On Market

  Last Listing Agent Heather Dever Showcase Realty, Inc.
• 

  

  /37

  $2,850,000

  • 8 Beds
  • 8 Baths
  • 9,619 Sq Ft

  775 South St Unit 777, Middlebury, CT 06762

  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 details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the

  Kary Apanovitch Coldwell Banker Realty

  775 South St Unit 777, Middlebury, CT 06762
• 

  $541,566

  Sold Oct 06, 2025

  0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762

  • 3 Beds
  • 2.5 Baths
  • 2,206 Sq Ft
  • Built 2025

  Last Sold Summary

  • $245/SF
  • 0 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
• 

  Est $451,882

  Not Listed For Sale

  110 Yale Ave, Middlebury, CT 06762

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1926

  110 Yale Ave, Middlebury, CT 06762

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Heather Dever Showcase Realty, Inc.

Showing Results 161 - 200, Page 5 of 18