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Middlebury, CT Homes for Sale

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  • 33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
    /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

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (203) 871-0910

    33 Ridgewood Dr Unit 33, Middlebury, CT 06762
  • 1 Stevens Rd, Middlebury, CT 06762
    1 Stevens Rd, Middlebury, CT 06762
    1 Stevens Rd, Middlebury, CT 06762
    /32

    $524,900 Pending

    • 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

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 265-6768

    1 Stevens Rd, Middlebury, CT 06762
  • 0 Ferndale Ave, Middlebury, CT 06762
    0 Ferndale Ave, Middlebury, CT 06762
    0 Ferndale Ave, 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

    Agent Photo

    Ken Demirs

    Regency Real Estate, LLC

    (475) 258-7617

    0 Ferndale Ave, Middlebury, CT 06762
  • 1440 Straits Turnpike, Middlebury, CT 06762

    $505,000 Sold Jul 30, 2025

    • 2,046 Sq Ft
    • $247/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1940

    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

    1440 Straits Turnpike, Middlebury, CT 06762
  • 1 Yale Ave, Middlebury, CT 06762

    $425,000 Sold Jul 25, 2025

    • 1,788 Sq Ft
    • $238/SF
    • 40 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1935

    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
  • 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
  • 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
  • 7 E Farm Rd, Middlebury, CT 06762

    $1,300,000 Sold Dec 04, 2024

    • 9,981 Sq Ft
    • $130/SF
    • 372 Days On Market
    • 4 Beds
    • 7 Baths
    • Built 1999

    7 E Farm Rd, Middlebury, CT 06762

    Come enjoy a unique, elegant, old-world experience designed with artful accents and architectural accentuations throughout. The grand sweeping foyer with porcelain & marble tile flooring, the curved custom stairway, and the 20’ ceiling mirrors that of the grande European Manors. The authentic reproduction of the French porcelain flooring, coupled with multiple French & English influences elevates

    Your Home Group Keller Williams Realty

    7 E Farm Rd, Middlebury, CT 06762
  • 8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    /40

    $565,500 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,147 Sq Ft

    8 Kimberwick Ct, Middlebury, CT 06762

    Welcome to Steeplechase of Middlebury! Enjoy low-maintenance living in this well-maintained free-standing Osborn 2 model located in a sought-after planned community. Steeplechase offers the ease of natural gas from the street as well as public water and public sewer. This home features two primary bedrooms-one on the main level and one upstairs-each with an en-suite bath, offering flexible living

    Kate Willoughby Gina Jacobs Real Estate

    8 Kimberwick Ct, Middlebury, CT 06762
  • 2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    /40

    $575,000

    • 3 Beds
    • 3.5 Baths
    • 3,103 Sq Ft

    2 Dogwood Ct, Middlebury, CT 06762

    Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the best best private streets in the highly sought-after Ridgewood community. The resort style complex people are raving about! This spacious home offers a flexible layout perfect for modern living. The main level features hardwood floors, a half bath, a bright living room, a dining area, and an eat-in kitchen

    Jay Irvine Serhant Connecticut, LLC

    2 Dogwood Ct, Middlebury, CT 06762
  • 111 Dwyer Rd, Middlebury, CT 06762
    111 Dwyer Rd, Middlebury, CT 06762
    111 Dwyer Rd, 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 Gaetano Marra Homes

    111 Dwyer Rd, Middlebury, CT 06762
  • 39 Independence Cir, Middlebury, CT 06762
    39 Independence Cir, Middlebury, CT 06762
    39 Independence Cir, Middlebury, CT 06762
    /26

    $624,900 Open Sun 11AM - 1:30PM

    • 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
  • 1 Independence Cir, Middlebury, CT 06762
    1 Independence Cir, Middlebury, CT 06762
    1 Independence Cir, Middlebury, CT 06762
    /38

    $630,000

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

    1 Independence Cir, Middlebury, CT 06762

    Welcome to this beautiful 4 bedroom, 2.5 bath colonial in the highly sought after complex at Brookside of Middlebury. As you enter, the main floor boasts 9' ceilings. There is a large office, bright living room and formal dining room perfect for entertaining with its great flow. Kitchen continues that flow with granite covered island and countertops, gas stovetop with overhead microwave, and wall

    Carol D'Amato Regency Real Estate, LLC

    1 Independence Cir, Middlebury, CT 06762
  • 1 Dogwood Ct Unit 1, Middlebury, CT 06762
    1 Dogwood Ct Unit 1, Middlebury, CT 06762
    1 Dogwood Ct Unit 1, Middlebury, CT 06762
    /34

    $630,000

    • 3 Beds
    • 3.5 Baths
    • 3,477 Sq Ft

    1 Dogwood Ct Unit 1, Middlebury, CT 06762

    Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features

    Joyce Drakeley Drakeley Real Estate, Inc.

    1 Dogwood Ct Unit 1, Middlebury, CT 06762
  • 1 Winding Trail Unit 1, Middlebury, CT 06762
    1 Winding Trail Unit 1, Middlebury, CT 06762
    1 Winding Trail Unit 1, Middlebury, CT 06762
    /40

    $659,000

    • 4 Beds
    • 3.5 Baths
    • 3,195 Sq Ft

    1 Winding Trail Unit 1, Middlebury, CT 06762

    Don't wait to see this turn key home in the desirable Ridgewood of Middlebury, one of the areas newest and most picturesque communities. This is a unique end unit, The Emerson Model, situated in a private, quiet cornet lot. As you enter the home, you'll view the open living room/dining room, with a gas fireplace and plenty of light. The attached kitchen includes granite countertops, large cherry

    Scott Hellriegel Berkshire Hathaway NE Prop.

    1 Winding Trail Unit 1, Middlebury, CT 06762
  • 66 Artillery Rd, Middlebury, CT 06762
    66 Artillery Rd, Middlebury, CT 06762
    66 Artillery Rd, Middlebury, CT 06762
    /39

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 2,691 Sq Ft

    66 Artillery Rd, Middlebury, CT 06762

    Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls,

    Mary Helen Levine Mary Helen Levine Real Estate LLC

    66 Artillery Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 59 24116892, Middlebury, CT 06762
    0 N Benson Rd Unit 59 24116892, Middlebury, CT 06762
    0 N Benson Rd Unit 59 24116892, Middlebury, CT 06762
    /9

    $568,564 Pending

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

    0 N Benson Rd Unit 59 24116892, 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 59 24116892, Middlebury, CT 06762
  • 76 Three Mile Hill Rd, Middlebury, CT 06762
    76 Three Mile Hill Rd, Middlebury, CT 06762
    76 Three Mile Hill Rd, Middlebury, CT 06762
    /38

    $549,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,088 Sq Ft

    76 Three Mile Hill Rd, Middlebury, CT 06762

    Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middlebury's most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, you feel the warmth and coziness of the home combined with the ease of modern living. The updated kitchen boasts

    Lisa Clarke Dave Jones Realty, LLC

    76 Three Mile Hill Rd, Middlebury, CT 06762
  • 0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
    /9

    $555,888 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762

    Only 3 Units Remaining! 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 44 24109951, Middlebury, CT 06762
  • 0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
    /9

    $560,753 Pending

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

    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762

    5 Units Remaining! 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 52 24100213, Middlebury, CT 06762
  • 0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762
    0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762
    0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762
    /9

    $548,828 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,462 Sq Ft

    0 N Benson Rd Unit 55 24086408, 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 55 24086408, Middlebury, CT 06762
  • 0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762
    0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762
    0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762
    /9

    $545,400 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 Meuse Lovley Century 21 AllPoints Realty

    0 N Benson Rd Unit 64 24077175, Middlebury, CT 06762
  • 0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
    0 N Benson Rd Unit 43 24071892, Middlebury, CT 06762
    /9

    $546,936 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    0 N Benson Rd Unit 43 24071892, 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 43 24071892, Middlebury, CT 06762
  • 0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762
    0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762
    0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762
    /9

    $591,251 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,923 Sq Ft

    0 N Benson Rd Unit 35 24070506, 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 35 24070506, Middlebury, CT 06762
  • 116 Bronson Dr, 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
  • 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
  • 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
  • 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
  • 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
  • 428 Benson Rd, Middlebury, CT 06762

    $570,000 Sold Feb 28, 2025

    • 3,106 Sq Ft
    • $184/SF
    • 55 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1962

    428 Benson Rd, Middlebury, CT 06762

    Grand, 5-bedroom, 4 bathroom, 3100sf+, fully updated, well maintained Middlebury Cape. This prodigious has been updated with a new heating system, central air, split systems, a new roof, well components and filtration and wood flooring throughout. The spacious, recently renovated kitchen adorns custom cabinetry, breath taking granite countertops and new stainless steel appliance package. Stately,

    Jason Malagutti Regency Real Estate, LLC

    428 Benson Rd, Middlebury, CT 06762
  • 89 Tyler Crossing, Middlebury, CT 06762

    $585,000 Sold Feb 14, 2025

    • 2,704 Sq Ft
    • $216/SF
    • 99 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    89 Tyler Crossing, Middlebury, CT 06762

    Discover this elegant colonial-style home in Middlebury, set on 1.4 serene acres. With 4 bedrooms plus 2.5 baths, this residence offers a sun room for relaxation and a kitchen with abundant counter space for culinary adventures. The upper level features spacious bedrooms, with vaulted ceilings in the primary suite. En-suite bath is beautifully updated Laundry located on the main floor just off

    Matt Rose Keller Williams Realty

    89 Tyler Crossing, Middlebury, CT 06762
  • 203 Tower Rd, Middlebury, CT 06762

    $555,000 Sold Jan 22, 2025

    • 2,572 Sq Ft
    • $216/SF
    • 86 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    203 Tower Rd, Middlebury, CT 06762

    Great New Price! Discover the perfect blend of timeless charm and serene natural beauty in this elegant colonial home, set on a private 2.7 acre parcel, on a cul-de-sac. This home has been designed with a classic, functional layout, that flows effortlessly from room to room, wonderful for both living and entertaining! The living and dining rooms provide generous space to spend time with guests.

    Nancy Lydell Calcagni Real Estate

    203 Tower Rd, Middlebury, CT 06762
  • 107 Periwinkle Dr, Middlebury, CT 06762

    $610,000 Sold Jan 03, 2025

    • 3,676 Sq Ft
    • $166/SF
    • 52 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2005

    107 Periwinkle Dr, Middlebury, CT 06762

    Benson Woods is the perfect place for active adults seeking a serene and carefree lifestyle. The blend of condo and single-family living offers the best of both worlds. This home, offered by the original owner, boasts many custom features and a premium location that is both private and convenient. The open floor plan with hardwood floors throughout creates a warm and inviting atmosphere. The

    Mary Ann Hebert BHGRE Gaetano Marra Homes

    107 Periwinkle Dr, Middlebury, CT 06762
  • 93 Fenn Rd, Middlebury, CT 06762
    93 Fenn Rd, Middlebury, CT 06762
    93 Fenn Rd, Middlebury, CT 06762
    /31

    $425,000

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

    93 Fenn Rd, Middlebury, CT 06762

    Charming Corner-Lot Home in a Great Location. Welcome to this well-maintained 3-bedroom, 1.1-bath home, perfectly situated on a beautiful, level corner lot in a sought-after neighborhood with top-rated school systems. Step inside to find gleaming hardwood floors and a spacious great room that's perfect for relaxing or entertaining. Enjoy the convenience of nearby amenities including a local

    Robert Marucci Better Living Realty, LLC

    93 Fenn Rd, Middlebury, CT 06762
  • 119 Christian Rd, Middlebury, CT 06762
    119 Christian Rd, Middlebury, CT 06762
    119 Christian Rd, Middlebury, CT 06762
    /38

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 866 Sq Ft

    119 Christian Rd, Middlebury, CT 06762

    Nestled in one of Middlebury's most sought-after neighborhoods, this well-maintained two-bedroom ranch blends comfort, convenience, and charm. Step inside through the inviting enclosed front porch-perfect for morning coffee or evening relaxation-into a warm and welcoming living room complete with a cozy wood stove. The bright, airy kitchen flows seamlessly from the living space, making it ideal

    David Aurigemma Regency Real Estate, LLC

    119 Christian Rd, Middlebury, CT 06762
  • 225 Whittemore Rd, Middlebury, CT 06762
    225 Whittemore Rd, Middlebury, CT 06762
    225 Whittemore Rd, Middlebury, CT 06762
    /24

    $399,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 1 Bath
    • 1,630 Sq Ft

    225 Whittemore Rd, Middlebury, CT 06762

    Welcome to 225 Whittemore Road in Middlebury, CT, where charm meets convenience in this cozy solid 3-bedroom, 2-bathroom brick cape. Situated with easy access to Route 8 and I-84, this home is a perfect retreat close to 3 parks and the greenway for outdoor recreation enthusiasts. Step inside to discover an inviting living room featuring a gas stove, creating a warm and welcoming ambiance. The

    Adelia Santos William Pitt Sotheby's Int'l

    225 Whittemore Rd, Middlebury, CT 06762
  • 1996 Straits Turnpike, Middlebury, CT 06762
    1996 Straits Turnpike, Middlebury, CT 06762
    1996 Straits Turnpike, Middlebury, CT 06762
    /24

    $480,000

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

    1996 Straits Turnpike, Middlebury, CT 06762

    Welcome home to this turn key entertainers dream in highly desirable Middlebury CT. Set far back on a secluded and expansive peaceful fenced in lot, outdoor living is private and tranquil. From the moment you enter this home your attention will be drawn to the high end kitchen and bathroom finishes, custom railings and lighting, and shiplap accent wall, noting every detail has been curated.

    Devon O'Neill Litchfield Hills Properties LLC

    1996 Straits Turnpike, Middlebury, CT 06762
  • 30 Nick Rd, Middlebury, CT 06762
    30 Nick Rd, Middlebury, CT 06762
    30 Nick Rd, Middlebury, CT 06762
    /21

    $495,000

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft

    30 Nick Rd, Middlebury, CT 06762

    Wake up with a smile in this spacious 2-3 bedroom cape style home in a quiet neighborhood. Originally built in 1950, it was re built and expanded in 2011, and it has a great deal to offer, including an expansive 17' X 9' entry that leads to the 26' X 16' living room. In addition the eat in kitchen has access to the deck overlooking the private yard. This home also features a dining room, a

    Donna Bannon BHGRE Gaetano Marra Homes

    30 Nick Rd, Middlebury, CT 06762
  • 87 Falcon Crest Rd, Middlebury, CT 06762
    87 Falcon Crest Rd, Middlebury, CT 06762
    87 Falcon Crest 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
  • 190 Allerton Farms Rd, Middlebury, CT 06762
    190 Allerton Farms Rd, Middlebury, CT 06762
    190 Allerton Farms Rd, Middlebury, CT 06762
    /40

    $499,900

    • 2 Beds
    • 2.5 Baths
    • 1,744 Sq Ft

    190 Allerton Farms Rd, Middlebury, CT 06762

    Custom-Built Ranch - A Rare Find in Middlebury! Discover this exceptional custom-built ranch featuring 2 bedrooms and 2.5 baths. A large country kitchen, formal dining room, sunken living room and great room complete the main level of the home. The walk-out lower level is finished, offering a summer kitchen, spacious family room, and convenient laundry area-perfect for entertaining or extended

    Mary Ann Hebert BHGRE Gaetano Marra Homes

    190 Allerton Farms Rd, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 6

Connecticut New Haven County Middlebury

Real Estate & Homes for Sale in Middlebury, CT

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 104 days on the market compared to the national average of 70 days. The median sale price for homes in Middlebury, CT over the last 12 months is $565,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$565,000
Median Single Family Sale Price
$609,000
Median Townhouse Sale Price
$630,000
Median 2 Bedroom Sale Price
$534,900
Average Price Per Sq Ft
$284
Number of Homes for Sale
7
Last 12 months Home Sales
57
Months of Supply
1.50
Median List Price
$575,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-2%
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