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Recently Sold Middlebury, CT Homes

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  • 94 Upper Whittemore Rd, 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
  • 203 Lake Shore 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
  • 18 Hunting Ridge 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
  • 69 Nick 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
  • 58 Chesham 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
  • 64 Joy Rd, 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
  • 180 Ridgewood Dr Unit 219, 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
  • 15 Brookside Dr Unit 15, 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
  • 259 White Ave, 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
  • 400 Long Meadow 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 Bannon & Hebert

    400 Long Meadow Rd, Middlebury, CT 06762
  • 43 Ridgewood Dr Unit 43, 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 Bannon & Hebert

    43 Ridgewood Dr Unit 43, Middlebury, CT 06762
  • 593 Park Road Extension, Middlebury, CT 06762

    $950,000 Sold Jun 05, 2025

    • 4,496 Sq Ft
    • $211/SF
    • 51 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
  • 7 Highridge Rd Unit 7, 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
  • 138 Skyline Dr, 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
  • 110 Glenwood Ave, Middlebury, CT 06762

    $525,000 Sold Jun 02, 2025

    • 2,160 Sq Ft
    • $243/SF
    • 33 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2006

    110 Glenwood Ave, Middlebury, CT 06762

    Nestled on a private, set-back lot surrounded by beautifully landscaped gardens, this classic 3-bedroom Colonial offers timeless appeal and modern comfort. A welcoming country-style front porch invites you inside, where a dramatic two-story foyer sets the tone. To your right, a flexible formal living room or a convenient spot for a home office, complete with elegant French doors leading to the

    Christina Zainc BHGRE Bannon & Hebert

    110 Glenwood Ave, Middlebury, CT 06762
  • 713 Whittemore Rd, Middlebury, CT 06762

    $505,000 Sold May 23, 2025

    • 1,476 Sq Ft
    • $342/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1916

    713 Whittemore Rd, Middlebury, CT 06762

    Welcome to this wonderful classic Cape Cod home. Situated on over an acre of land, this house exudes character and craftsmanship. The home sits on a sloping lot with panoramic views. Stone walls border the property and a 900 sq foot pole barn await its next owners. The spacious yard has a water feature in the back yard. The detached garage at the end of the driveway offers 400 sq ft of space. The

    Robert Vignola Coldwell Banker Realty

    713 Whittemore Rd, Middlebury, CT 06762
  • 460 Lake Shore Dr, Middlebury, CT 06762

    $415,000 Sold May 23, 2025

    • 1,288 Sq Ft
    • $322/SF
    • 68 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    460 Lake Shore Dr, Middlebury, CT 06762

    Price Improvement!! DIRECT WATER FRONT PROPERTY with water access and rights just waiting for new owners right in time for Spring! This 3 bed, 2 full bath recently remodeled home boasts custom cabinets, granite counters & island with a breakfast bar, stainless steel appliances, custom built-ins and views of the private Long Meadow Pond. Hiking trails abound with Larkin State Park as your backdrop

    Blair Patterson William Raveis Real Estate

    460 Lake Shore Dr, Middlebury, CT 06762
  • 835 Whittemore Rd, Middlebury, CT 06762

    $479,000 Sold May 21, 2025

    • 3,016 Sq Ft
    • $159/SF
    • 60 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1963

    835 Whittemore Rd, Middlebury, CT 06762

    Come see this Westside 4-bedroom beauty boasting over 1,800 sq. ft. of classic Colonial elegance. You'll fall in love with the charming wrap-around front porch, perfect for relaxing afternoons! Inside, you'll find a formal living and dining room with stunning natural woodwork and gleaming hardwood floors throughout. The bright, eat-in kitchen features tile flooring and comes fully equipped with

    Mike Albert RE/MAX RISE

    835 Whittemore Rd, Middlebury, CT 06762
  • 45 E Farms Rd, Middlebury, CT 06762

    $1,100,000 Sold May 19, 2025

    • 5,054 Sq Ft
    • $218/SF
    • 48 Days On Market
    • 4 Beds
    • 6 Baths
    • Built 2000

    45 E Farms Rd, Middlebury, CT 06762

    Over 5000 total finished sqft in this gorgeous custom colonial with 3 car garage situated on 1.84 acres in a neighborhood of like homes. Grand entry foyer and 9ft ceilings throughout the main level. Eat-in-kitchen with hard wood floors, island, breakfast bar, pantry, granite countertops, and high end stainless steel appliances including double oven, propane cooktop, and Sub Zero refrigerator.

    John Donato Jr Showcase Realty, Inc.

    45 E Farms Rd, Middlebury, CT 06762
  • 66 White Ave, Middlebury, CT 06762

    $385,000 Sold May 16, 2025

    • 2,568 Sq Ft
    • $150/SF
    • 139 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1938

    66 White Ave, Middlebury, CT 06762

    Start your new chapter here in the desirable town of Middlebury. All the charming appointments you would expect from an early 1900's home. Generous sized bedrooms & closets including one bedroom on the main floor. Hardwood flooring throughout. There is 1600 sq feet plus an ADDITIONAL 200+ heated square feet in the enclosed rear porch which has a full view of the expansive backyard. Lower level

    Gina Jacobs Gina Jacobs Real Estate

    66 White Ave, Middlebury, CT 06762
  • 129 Periwinkle Dr, Middlebury, CT 06762

    $625,000 Sold May 15, 2025

    • 2,476 Sq Ft
    • $252/SF
    • 45 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2005

    129 Periwinkle Dr, Middlebury, CT 06762

    Come live your best life at 129 Periwinkle Dr. This 2/3 Bedrm home offers apprx 2500 sqft of understated elegance & easy living PLUS the Unfinished Daylight Walkout Lower Level boasts apprx 1000 Sqft (ready to customize). You'll be captivated upon approach with its wonderful setting perched on a premium lot offering curb appeal & privacy yet is not secluded. At first glance it may appear more

    Lisa Gallagher William Raveis Real Estate

    129 Periwinkle Dr, Middlebury, CT 06762
  • 7 Arrowwood Ct Unit 7, Middlebury, CT 06762

    $630,000 Sold May 15, 2025

    • 3,465 Sq Ft
    • $182/SF
    • 77 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2019

    7 Arrowwood Ct Unit 7, Middlebury, CT 06762

    Discover luxury living in this beautifully upgraded end-unit condo located in the sought-after Ridgewood of Middlebury community. With 3,465 sq. ft., this spacious home offers 3 bedrooms, 3 full baths, and 1 half bath, providing ample space and comfort. Step inside to a traditional open floor plan featuring a gourmet kitchen with an over sized island, granite countertops, a gas stove, and

    Jonna Dibble BHGRE Bannon & Hebert

    7 Arrowwood Ct Unit 7, Middlebury, CT 06762
  • 679 Christian Rd, Middlebury, CT 06762

    $454,000 Sold May 08, 2025

    • 2,312 Sq Ft
    • $196/SF
    • 47 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1967

    679 Christian Rd, Middlebury, CT 06762

    Charming custom home with a barn on a flat lot! This spacious, custom-built home offers character, functionality, and endless potential. Situated on a beautiful level lot, the property includes a barn with a loft-perfect for storage, a workshop, or creative possibilities. Inside, you'll find a living room with a stone fireplace, a first-floor office, an eat-in kitchen, and a formal dining room. A

    Chloe White KW Legacy Partners

    679 Christian Rd, Middlebury, CT 06762
  • 43 Merideth Rd, Middlebury, CT 06762

    $385,000 Sold May 05, 2025

    • 1,576 Sq Ft
    • $244/SF
    • 51 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1957

    43 Merideth Rd, Middlebury, CT 06762

    This one-level home is nestled on a quiet, walkable street, backs up to a peaceful, wooded setting and is located in a sought-after neighborhood. The bright eat-in kitchen boasts a breakfast bar, plus a large window overlooking the backyard, providing a serene view. The spacious living room features hardwood floors and another large window, filling the space with natural light. This home offers

    Christina Zainc BHGRE Bannon & Hebert

    43 Merideth Rd, Middlebury, CT 06762
  • 34 Breakneck Hill Rd, Middlebury, CT 06762

    $799,000 Sold May 02, 2025

    • 4,551 Sq Ft
    • $176/SF
    • 19 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2006

    34 Breakneck Hill Rd, Middlebury, CT 06762

    Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT! Home features 5 bedrooms with 3 full bathrooms. Features include a spacious Great room with over 800 sq feet of space, which is perfect to host any special occasion. The heart of this home, the eat-in kitchen which connects to Great room and Dining room, comes with wine cooler, granite countertops

    Arben Belica William Raveis Real Estate

    34 Breakneck Hill Rd, Middlebury, CT 06762
  • 130 Christian Rd, Middlebury, CT 06762

    $461,500 Sold Apr 30, 2025

    • 1,958 Sq Ft
    • $236/SF
    • 139 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1940

    130 Christian Rd, Middlebury, CT 06762

    Welcome to this beautiful Cape Cod home, offering 1,958 square feet of living space with a traditional layout and classic charm. Nestled in a peaceful neighborhood in Middlebury, this home is perfect for those seeking comfort and functionality. The home features two spacious bedrooms located upstairs and two additional bedrooms on the main level, providing flexible living options. Two full

    Joseph Conforti BHGRE Bannon & Hebert

    130 Christian Rd, Middlebury, CT 06762
  • 36 Aveline Ave, Middlebury, CT 06762

    $480,000 Sold Apr 25, 2025

    • 1,782 Sq Ft
    • $269/SF
    • 44 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1952

    36 Aveline Ave, Middlebury, CT 06762

    Discover this charming stucco ranch, nestled on a spacious 0.66-acre lot just five minutes from Route 84. This inviting home features four bedrooms and two full, fully remodeled bathrooms. Enjoy modern comforts with central air conditioning, making it an ideal retreat in any season. The property boasts a convenient horseshoe driveway and is situated on a peaceful dead-end road, offering privacy

    Wayne Watt Jr. THE CONNECTICUT AGENCY LLC

    36 Aveline Ave, Middlebury, CT 06762
  • 10 Stonington Ct, Middlebury, CT 06762

    $640,000 Sold Apr 17, 2025

    • 2,812 Sq Ft
    • $228/SF
    • 209 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    10 Stonington Ct, Middlebury, CT 06762

    Come see this immaculate Colonial in Brookside of Middlebury. The main floor provides an open floor plan with a formal living room and dining room, family room with gas fireplace, and large eat in kitchen with granite counter tops, stainless steel appliances, and hardwood throughout. The main primary suite upstairs opens through double doors, with vaulted ceiling, dual walking closets, and full

    Scott Hellriegel Berkshire Hathaway NE Prop.

    10 Stonington Ct, Middlebury, CT 06762
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    • 3,935 Sq Ft
    • $201/SF
    • 64 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    396 Watertown Rd, Middlebury, CT 06762

    Charming Colonial with In-Law Suite - A Must-See! Welcome to this stunning colonial home situated on 1.4 acres, boasting 3 bedrooms and 2.5 baths in the main living space, perfectly designed for modern living with timeless elegance. The main level impresses with soaring 9+ ft ceilings, an open floor plan, and oversized windows that fill every corner with natural light. The heart of the home is

    Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
  • 396 Watertown Rd, Middlebury, CT 06762

    $790,000 Sold Mar 31, 2025

    • 3,935 Sq Ft
    • $201/SF
    • 64 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    396 Watertown Rd, Middlebury, CT 06762

    Charming Colonial with In-Law Suite - A Must-See! Welcome to this stunning colonial home situated on 1.4 acres, boasting 3 bedrooms and 2.5 baths in the main living space, perfectly designed for modern living with timeless elegance. The main level impresses with soaring 9+ ft ceilings, an open floor plan, and oversized windows that fill every corner with natural light. The heart of the home is

    Beth Santos Showcase Realty, Inc.

    396 Watertown Rd, Middlebury, CT 06762
  • 197 White Ave, Middlebury, CT 06762

    $410,000 Sold Mar 28, 2025

    • 1,494 Sq Ft
    • $274/SF
    • 55 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1928

    197 White Ave, Middlebury, CT 06762

    Charming 1920's 3 bedroom, 2 bath Cape nestled in a desirable Middlebury neighborhood. This home boasts modern mechanical updates, including split systems air conditioning for year-round comfort. Hardwood floors flow throughout the inviting living space. Outdoors, you'll find beautifully maintained perennial gardens and a private patio, perfect for relaxation or entertaining. Conveniently located

    Beth Santos Showcase Realty, Inc.

    197 White Ave, Middlebury, CT 06762
  • 191 Ridgewood Dr Unit 191, Middlebury, CT 06762

    $620,000 Sold Mar 28, 2025

    • 2,658 Sq Ft
    • $233/SF
    • 79 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2022

    191 Ridgewood Dr Unit 191, Middlebury, CT 06762

    Priced to Sell! Welcome to this rare new luxury home nestled in sought after Ridgewood community, perfectly situated on a cul-de-sac. This stunning newer built unit offers 3 spacious bedrooms, 2.5 bath & 2,658 SQFT w/ endless upgrades! Barely lived in, only 2 yrs old! Step inside & greeted by a beautiful open flr plan on the 1st flr, w/ upgraded wide hardwood flrs that flow seamlessly. Dining

    Jay Irvine Serhant Connecticut, LLC

    191 Ridgewood Dr Unit 191, Middlebury, CT 06762
  • 111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    $585,000 Sold Mar 28, 2025

    • 2,476 Sq Ft
    • $236/SF
    • 131 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2005

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762

    This bright and sunny home in the desirable 55+ community of Benson Woods combines country living with modern convenience. Located just minutes from shopping, town, and I-84, offering easy access for both relaxation and commuting. The spacious living room features cathedral ceilings, hardwood floors, and a cozy gas fireplace. The chef's kitchen includes granite countertops, ceiling-height

    Marvin and Laura Beninson Keller Williams Realty

    111 Periwinkle Dr Unit 111, Middlebury, CT 06762
  • 23 Hunting Ridge Rd, Middlebury, CT 06762

    $800,000 Sold Mar 26, 2025

    • 2,700 Sq Ft
    • $296/SF
    • 350 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2023

    23 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates.23 Hunting Ridge Road (aka Lot 6) is under construction and will be a 2600+ sq ft 4 bedroom colonial. 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

    23 Hunting Ridge Rd, Middlebury, CT 06762
  • 28 Yale Ave, Middlebury, CT 06762

    $342,000 Sold Mar 21, 2025

    • 1,434 Sq Ft
    • $238/SF
    • 6 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 1923

    28 Yale Ave, Middlebury, CT 06762

    Welcome to this charming 1-bedroom house with incredible potential! This home is ready for you to move right in, featuring lots of new updates. The main living areas include an inviting living room, a dining area, and kitchen which features all-new appliances, perfect for cooking your favorite meals. With 2 full bathrooms, this home offers plenty of space for comfort and convenience. There are 2

    Lysa Napoli Showcase Realty, Inc.

    28 Yale Ave, Middlebury, CT 06762
  • 115 Periwinkle Dr Unit 115, Middlebury, CT 06762

    $620,000 Sold Mar 21, 2025

    • 3,276 Sq Ft
    • $189/SF
    • 108 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2005

    115 Periwinkle Dr Unit 115, Middlebury, CT 06762

    Enjoy a lifestyle of relaxed sophistication in this captivating home located in an adult community (Age 55+). Picture perfect home amidst a conveniently located country landscape. Enter through the marble foyer. The Llving room offers a vaulted ceiling, hardwood flooring and fireplace. French doors lead to the light and bright dining room. The kitchen will please the most exceptional cookwith

    Lawren Hubal RE/MAX Right Choice

    115 Periwinkle Dr Unit 115, Middlebury, CT 06762
  • 81 Sandy Beach Rd, Middlebury, CT 06762

    $410,000 Sold Mar 14, 2025

    • 972 Sq Ft
    • $422/SF
    • 61 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    81 Sandy Beach Rd, Middlebury, CT 06762

    Set among the trees offering a tranquil, waterfront setting! Single family ranch style home at Tyler's Cove. Galley kitchen with an abundance of cabinets. Enjoy your morning coffee in this lovely dining room with wall of windows affording you natural light and scenic views of the lake! Cozy living room with French doors to dining room. 2 bedrooms & bathroom. All on main level with hardwood

    Wilson Lamas Realty Group of New England, LLC

    81 Sandy Beach Rd, Middlebury, CT 06762
  • 81 Sandy Beach Rd, Middlebury, CT 06762

    $410,000 Sold Mar 14, 2025

    • 972 Sq Ft
    • $422/SF
    • 61 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    81 Sandy Beach Rd, Middlebury, CT 06762

    Set among the trees offering a tranquil, waterfront setting! Single family condo at Tyler's Cove. Galley kitchen with an abundance of cabinets. Enjoy your morning coffee in this lovely dining room with wall of windows affording you natural light and scenic views of the lake! Cozy living room with French doors to dining room. 2 bedrooms & bathroom. All on main level with hardwood flooring

    Wilson Lamas Realty Group of New England, LLC

    81 Sandy Beach Rd, Middlebury, CT 06762
  • 6 Ridgewood Dr, Middlebury, CT 06762

    $600,000 Sold Mar 13, 2025

    • 3,071 Sq Ft
    • $195/SF
    • 71 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2007

    6 Ridgewood Dr, Middlebury, CT 06762

    Stunning Luxury Townhome in the Desirable Ridgewood Community. Beautifully upgraded 3/4-bedroom, 3.5-bathroom end-unit townhome with a 2-car garage, offering approximately 3,000 sq. ft. of luxurious living space. Enjoy the private yard, walk-out deck with all the enhancements, this home has more space than you can imagine. The main floor features an open-concept layout with oak floors, a

    Jay Irvine Serhant Connecticut, LLC

    6 Ridgewood Dr, Middlebury, CT 06762
  • 377 Porter Ave, Middlebury, CT 06762

    $432,500 Sold Mar 11, 2025

    • 1,545 Sq Ft
    • $280/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1935

    377 Porter Ave, Middlebury, CT 06762

    Step into this charming Cape brimming with character and modern updates! Nestled in the highly desirable town of Middlebury, renowned for its award-winning schools, this home offers unique charm and stands out as one of a kind. As you enter through the front door, you're welcomed by a warm and inviting living area featuring a cozy fireplace with a woodstove insert and custom built-ins. The

    Jane Crooke RE/MAX One

    377 Porter Ave, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 4

Connecticut Middlebury

Recently Sold Real Estate & Homes in Middlebury, CT

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $636,557.
What is the average time to sell a house in Middlebury, CT?
The houses for sale in Middlebury, CT spend an average of 92 days on the market.
What is the number of active homes for sale in Middlebury, CT?
There are 39 active homes for sale in Middlebury, CT.
How many homes have sold over the last 12 months in Middlebury, CT?
112 homes have sold in Middlebury, CT over the last 12 months.

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 92 days on the market compared to the national average of 50 days. The median sale price for homes in Middlebury, CT over the last 12 months is $567,500, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$567,500
Median Single Family Sale Price
$559,900
Median Townhouse Sale Price
$565,000
Median 2 Bedroom Sale Price
$609,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
39
Last 12 months Home Sales
112
Months of Supply
4.20
Median List Price
$600,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
6%
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