3,777

Middlebury, CT Homes

Section Image
  • /9

    $523,920 Pending

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

    0 N Benson Rd Unit 51 24117506, 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 51 24117506, Middlebury, CT 06762
  • 405 Chestnut Cir Unit 77, Middlebury, CT 06762

    $649,500 Sold Jul 25, 2025

    405 Chestnut Cir Unit 77, Middlebury, CT 06762

    • 2 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 99 Days On Market

    Current Estimated Value $652,368

    Last Listing Agent Jodi Dawley Real Estate Two

    405 Chestnut Cir Unit 77, 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
  • 288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    $225,000 Sold Sep 24, 2025

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762

    • Land
    • 3.32 Acres
    • $67,771 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 330 Days On Market

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    288 Watertown Rd Unit Lot 4, Middlebury, CT 06762
  • /39

    $574,000

    • 3 Beds
    • 3.5 Baths
    • 2,879 Sq Ft

    24 Ridgewood Dr, Middlebury, CT 06762

    Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • 1 Independence Cir, Middlebury, CT 06762

    $615,000 Sold Oct 30, 2025

    1 Independence Cir, Middlebury, CT 06762

    • 4 Beds
    • 2.5 Baths
    • 3,224 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $191/SF
    • 120 Days On Market

    Last Listing Agent Carol D'Amato Regency Real Estate, LLC

    1 Independence Cir, Middlebury, CT 06762
  • /40

    $1,085,000

    • 3 Beds
    • 4 Baths
    • 4,138 Sq Ft

    225 Crest Rd, Middlebury, CT 06762

    Exquisite French Provincial MANOR HOUSE In the heart of Middlebury Ct. On a 3.21 acre private corner lot with mature plantings, English Boxwoods, fenced and tree lined. Pool and stone seating area. Double car oversized garage. Circular drive and designated parking for family and guests lined with stone pavers. This stately house 4,138 sq. ft. (not including basement with access to the garden),

    Wilson Lamas Realty Group of New England, LLC

    225 Crest Rd, Middlebury, CT 06762
  • 45 E Farms Rd, Middlebury, CT 06762

    $1,100,000 Sold May 19, 2025

    45 E Farms Rd, Middlebury, CT 06762

    • 4 Beds
    • 6 Baths
    • 5,054 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 48 Days On Market

    Current Estimated Value $1,122,428

    Last Listing Agent John Donato Jr Showcase Realty, Inc.

    45 E Farms 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
  • 89 Tyler Crossing, Middlebury, CT 06762

    $585,000 Sold Feb 14, 2025

    89 Tyler Crossing, Middlebury, CT 06762

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

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 99 Days On Market

    Current Estimated Value $629,620

    Last Listing Agent Matt Rose Keller Williams Realty

    89 Tyler Crossing, Middlebury, CT 06762
  • /2

    $529,900

    • 3 Beds
    • 1.5 Baths
    • 1,811 Sq Ft

    61 Sandy Hill Rd, Middlebury, CT 06762

    Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

    Arben Belica William Raveis Real Estate

    61 Sandy Hill Rd, Middlebury, CT 06762
  • 0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    $63,250 Sold Dec 05, 2025

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770

    • Land
    • 0.76 Acre
    • $83,224 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 80 Days On Market

    Last Listing Agent Rebecca Zandvliet Coldwell Banker Realty 2000

    0 Evelyn Dr Unit 24124911, Naugatuck, CT 06770
  • /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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 46 24097231, Middlebury, CT 06762
  • 0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

    $593,360 Sold Oct 10, 2025

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762

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

    Last Sold Summary

    • 17% Above List Price
    • $304/SF
    • 0 Days On Market

    Last Listing Agent Renee Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 40 24066786, Middlebury, CT 06762
  • /40

    $599,900

    • 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
  • 240 Carriage Dr, Middlebury, CT 06762

    $500,000 Sold Feb 21, 2025

    240 Carriage Dr, Middlebury, CT 06762

    • 4 Beds
    • 2 Baths
    • 2,351 Sq Ft
    • Built 1964

    Last Sold Summary

    • 9% Below List Price
    • $213/SF
    • 243 Days On Market

    Current Estimated Value $539,444

    Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

    240 Carriage Dr, Middlebury, CT 06762
  • /40

    $524,900

    • 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
  • 116 Yale Ave, Middlebury, CT 06762

    $495,000 Sold Dec 04, 2025

    116 Yale Ave, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,311 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Above List Price
    • $214/SF
    • 51 Days On Market

    Last Listing Agent Dave Jones Dave Jones Realty, LLC

    116 Yale Ave, Middlebury, CT 06762
  • /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 Meuse Lovley Century 21 AllPoints Realty

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

    $790,000 Sold Mar 31, 2025

    396 Watertown Rd, Middlebury, CT 06762

    • 4 Beds
    • 3.5 Baths
    • 3,935 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Below List Price
    • $201/SF
    • 64 Days On Market

    Current Estimated Value $810,572

    Last Listing Agent Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
  • /38

    $659,900

    • 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
  • 29 Winding Trail Unit 29, Middlebury, CT 06762

    $520,000 Sold Aug 08, 2025

    29 Winding Trail Unit 29, Middlebury, CT 06762

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $244/SF
    • 117 Days On Market

    Last Listing Agent Jay Irvine Serhant Connecticut, LLC

    29 Winding Trail Unit 29, Middlebury, CT 06762
  • /40

    $889,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,220 Sq Ft

    383 Leonard Rd, Middlebury, CT 06762

    Welcome to your dream home...just for holidays-a beautifully designed 3220 sq ft NEW CONSTRUCTION offering warmth, space and flexibility for today's modern family. With 4 generous bedrooms and 3.5 bathrooms, this home invites you to live, laugh and grow in comfort. You have to see in person to appreciate the design of each of the bedrooms with their one full bath and double closet space. The

    Koco Pela William Raveis Real Estate

    383 Leonard Rd, Middlebury, CT 06762
  • 64 Joy Rd, Middlebury, CT 06762

    $422,000 Sold Jun 18, 2025

    64 Joy Rd, Middlebury, CT 06762

    • 3 Beds
    • 1 Bath
    • 1,688 Sq Ft
    • Built 1959

    Last Sold Summary

    • 6% Above List Price
    • $250/SF
    • 58 Days On Market

    Current Estimated Value $414,636

    Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

    64 Joy Rd, Middlebury, CT 06762
  • /40

    $629,900 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,244 Sq Ft

    51 Cross Rd, Middlebury, CT 06762

    Highest and Best by Wednesday, 12/10, 6pm. Welcome to this beautifully maintained Colonial nestled in the highly sought-after Curtis Farms neighborhood. Thoughtfully designed, this home blends classic charm with modern comfort. The gorgeous kitchen offers abundant cabinetry, granite countertops, and a gas cooktop overlooking the breakfast bar, which enjoys a view of the stone-faced fireplace. A

    Christina Zainc BHGRE Gaetano Marra Homes

    51 Cross Rd, Middlebury, CT 06762
  • 93 Fenn Rd, Middlebury, CT 06762

    $420,000 Sold Oct 09, 2025

    93 Fenn Rd, Middlebury, CT 06762

    • 3 Beds
    • 1.5 Baths
    • 1,636 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $257/SF
    • 62 Days On Market

    Current Estimated Value $420,985

    Last Listing Agent Robert Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
  • /40

    $709,000

    • 4 Beds
    • 5 Baths
    • 3,254 Sq Ft

    84 Munson Rd, Middlebury, CT 06762

    Experience comfort, space, and scenic surroundings at 84 Munson Road, Middlebury, CT 06762, a well-situated home set in a peaceful and desirable community. This inviting property offers a thoughtfully designed layout with generous living areas filled with natural light, creating a bright and welcoming atmosphere. The main level provides ideal flow for everyday living and entertaining, while the

    Thomas Mele Dorrance Realty

    84 Munson Rd, Middlebury, CT 06762

Showing Results 81 - 120, Page 3 of 18

How to Buy a Home How to Finance a Home How to Sell a Home