35

Middlebury, CT Homes for Sale

Section Image Section Image
  • 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 Open Sun 11AM - 1PM

    • 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
  • 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
  • 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
  • 383 Leonard Rd, Middlebury, CT 06762
    383 Leonard Rd, Middlebury, CT 06762
    383 Leonard Rd, Middlebury, CT 06762
    /40

    $939,000

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

    383 Leonard Rd, Middlebury, CT 06762

    *HOME WARRANTY* Welcome to your dream home - a beautifully designed 3,220 sq ft new construction offering warmth, space, and flexibility for today's modern family. With 4 generous bedrooms and 3.5 baths, this home invites you to live, laugh, and grow in comfort. The heart of the home is the open-concept main level, where the kitchen, dining, and living areas come together around a cozy electric

    Koco Pela William Raveis Real Estate

    383 Leonard Rd, Middlebury, CT 06762
  • 4 White Birch Ln, Middlebury, CT 06762
    4 White Birch Ln, Middlebury, CT 06762
    4 White Birch Ln, Middlebury, CT 06762
    /10

    $949,500 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    4 White Birch Ln, Middlebury, CT 06762

    Welcome to 4 White Birch Lane, a to-be-built, fully customizable 2,750 SF home offering the perfect blend of luxury, flexibility, and modern design. This 4-bedroom, 3.5-bath home includes a 2-car garage and a spacious walk-out basement ready for future finishing-ideal for added living space, a home office, gym, or media room. Enjoy hardwood flooring throughout, with stylish tile in all bathrooms

    Donna Kennedy Keller Williams Realty

    4 White Birch Ln, Middlebury, CT 06762
  • 11 White Birch Ln, Middlebury, CT 06762
    11 White Birch Ln, Middlebury, CT 06762
    11 White Birch Ln, Middlebury, CT 06762
    /18

    $999,500 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    11 White Birch Ln, Middlebury, CT 06762

    Welcome to 11 White Birch Lane - a rare opportunity to create your ideal home in one of Middlebury's most desirable neighborhoods. This to-be-built, customizable residence will offer 4 spacious bedrooms, 4.1 luxurious baths, a 3-car garage, and an open-concept layout designed for modern living. From the beautiful hardwood floors and stunning kitchen island to the generous allowances for tile &

    Donna Kennedy Keller Williams Realty

    11 White Birch Ln, Middlebury, CT 06762
  • 3 Pine Ridge Unit 23, Middlebury, CT 06762
    3 Pine Ridge Unit 23, Middlebury, CT 06762
    3 Pine Ridge Unit 23, Middlebury, CT 06762
    /28

    $721,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,290 Sq Ft

    3 Pine Ridge Unit 23, Middlebury, CT 06762

    Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

    Robert Michaud Michaud Real Estate

    3 Pine Ridge Unit 23, Middlebury, CT 06762
  • 22 Somerset Dr, Middlebury, CT 06762
    22 Somerset Dr, Middlebury, CT 06762
    22 Somerset Dr, Middlebury, CT 06762
    /7

    $925,000 New Construction

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

    22 Somerset Dr, Middlebury, CT 06762

    TO BE BUILT. One of the most desirable neighborhoods in Middlebury! The Avalon Farms community is comprised of lovely homes, manicured lawns, and beautiful gardens resulting in a unique aesthetic. The Cambridge model showcases a classic design combined with today's "must haves" that will meet all your expectations of an open floor plan. The great room with a cathedral ceiling, fireplace, and

    Ellie Gollenberg BHGRE Gaetano Marra Homes

    22 Somerset Dr, Middlebury, CT 06762
  • 2 Deer Run Rd, Middlebury, CT 06762
    2 Deer Run Rd, Middlebury, CT 06762
    /2

    $729,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,190 Sq Ft

    2 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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

    2 Deer Run Rd, Middlebury, CT 06762
  • 15 Hunting Ridge Rd, Middlebury, CT 06762
    15 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $759,900 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
  • 28 Hunting Ridge Rd, Middlebury, CT 06762
    28 Hunting Ridge Rd, Middlebury, CT 06762
    /2

    $759,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,466 Sq Ft

    28 Hunting Ridge Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ 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

    28 Hunting Ridge Rd, Middlebury, CT 06762
  • 24 Ridgewood Dr, Middlebury, CT 06762
    24 Ridgewood Dr, Middlebury, CT 06762
    24 Ridgewood Dr, Middlebury, CT 06762
    /39

    $649,900 Open Sun 11AM - 1PM

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

    24 Ridgewood Dr, Middlebury, CT 06762

    Truly spectacular remodeled "Cummings" style townhouse in the sought-after Ridgewood at Middlebury community. The reimagined main level showcases a seamless open layout with a refined living and dining area flowing into a designer kitchen featuring a quartz center island, double ovens, granite counters, custom backsplash, and new flooring. Glass sliders invite natural light and open to a private

    Jodi Dawley Real Estate Two

    24 Ridgewood Dr, Middlebury, CT 06762
  • 126 Colonial Ave, Middlebury, CT 06762
    126 Colonial Ave, Middlebury, CT 06762
    126 Colonial Ave, Middlebury, CT 06762
    /36

    $635,000

    • 3 Beds
    • 1.5 Baths
    • 2,531 Sq Ft

    126 Colonial Ave, Middlebury, CT 06762

    Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully

    Donna Bannon BHGRE Gaetano Marra Homes

    126 Colonial Ave, Middlebury, CT 06762
  • 23 Caveson Ct Unit 23, Middlebury, CT 06762
    23 Caveson Ct Unit 23, Middlebury, CT 06762
    23 Caveson Ct Unit 23, Middlebury, CT 06762
    /24

    $579,900

    • 3 Beds
    • 2.5 Baths
    • 2,547 Sq Ft

    23 Caveson Ct Unit 23, Middlebury, CT 06762

    Come discover this beautifully maintained 3-bedroom, 2.5-bathroom detached condo, ideally situated on a quiet cul-de-sac in the highly sought-after Steeplechase complex in Middlebury! This rare standalone unit offers the privacy of a single-family home with the convenience of condo living-no shared walls and minimal exterior maintenance. Inside, you'll find a spacious and open floor plan with

    Arben Belica William Raveis Real Estate

    23 Caveson Ct Unit 23, Middlebury, CT 06762
  • 18 Winding Trail, Middlebury, CT 06762
    18 Winding Trail, Middlebury, CT 06762
    18 Winding Trail, Middlebury, CT 06762
    /40

    $725,000

    • 3 Beds
    • 5 Baths
    • 4,051 Sq Ft

    18 Winding Trail, Middlebury, CT 06762

    Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light.

    Jay Irvine Serhant Connecticut, LLC

    18 Winding Trail, Middlebury, CT 06762
  • 8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    /40

    $545,000

    • 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
  • 39 Independence Cir, Middlebury, CT 06762
    39 Independence Cir, Middlebury, CT 06762
    39 Independence Cir, Middlebury, CT 06762
    /26

    $624,900 Open Sun 1PM - 3PM

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

    $620,000

    • 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
  • 28 Pine Hollow Dr, Middlebury, CT 06762
    28 Pine Hollow Dr, Middlebury, CT 06762
    28 Pine Hollow Dr, Middlebury, CT 06762
    /8

    $216,000

    • Land
    • 1.04 Acres
    • $207,692 per Acre

    28 Pine Hollow Dr, Middlebury, CT 06762

    Non-conforming conforming two Barns on property.

    Derek Greene Derek Greene

    28 Pine Hollow Dr, Middlebury, CT 06762
  • Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
    /2

    $699,900

    • Land
    • 6 Acres
    • $116,070 per Acre

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

    This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

    Mary Ann Hebert BHGRE Gaetano Marra Homes

    Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
  • 440 Lake Shore Dr, Middlebury, CT 06762
    440 Lake Shore Dr, Middlebury, CT 06762
    /2

    $85,000

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

    440 Lake Shore Dr, Middlebury, CT 06762

    Build your dream cottage on this waterfront building lot on the desirable Long Meadow Pond. The lot is located near the end of a low traffic cul-de-sac. It is a great opportunity

    Florence DeDampierre W. Raveis Lifestyles Realty

    440 Lake Shore Dr, 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
  • 112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    112 Periwinkle Dr Unit 112, Middlebury, CT 06762
    /40

    $534,900

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

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

    Mary Ann Hebert BHGRE Gaetano Marra Homes

    112 Periwinkle Dr Unit 112, 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
  • 75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    75 Gleneagle Rd, Middlebury, CT 06762
    /24

    $209,900

    • Land
    • 4.67 Acres
    • $44,946 per Acre

    75 Gleneagle Rd, Middlebury, CT 06762

    LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

    Scott Tedesco Tedesco Real Estate

    75 Gleneagle Rd, Middlebury, CT 06762
  • 19 Deer Run Rd, Middlebury, CT 06762
    19 Deer Run Rd, Middlebury, CT 06762
    /2

    $274,900

    • Land
    • 3.33 Acres
    • $82,553 per Acre

    19 Deer Run Rd, Middlebury, CT 06762

    Welcome to Hunting Ridge Estates, a premier 23-lot subdivision offering the perfect blend of privacy and natural beauty. This spacious 3.33-acre rear lot provides ample space to build your dream home in a peaceful, upscale setting. With multiple lot options available, you can choose the one that best suits your vision. Whether you prefer to bring your own builder or take advantage of our

    Jodi Dawley Real Estate Two

    19 Deer Run Rd, Middlebury, CT 06762
  • 7 White Birch Ln, Middlebury, CT 06762
    7 White Birch Ln, Middlebury, CT 06762
    7 White Birch Ln, Middlebury, CT 06762
    /9

    $1,099,750 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,325 Sq Ft

    7 White Birch Ln, Middlebury, CT 06762

    Here's your chance to build the home you've always dreamed of at 7 White Birch Lane, a to-be-built 3,325 SF custom residence located on one of the most desirable cul-de-sac lots in Middlebury. With 4 bedrooms, 3.5 baths, and a 2-car garage, this home offers both elegance and flexibility-crafted with the quality and attention to detail you deserve. Enjoy hardwood flooring throughout and the tile

    Donna Kennedy Keller Williams Realty

    7 White Birch Ln, Middlebury, CT 06762
  • 6 White Birch Ln, Middlebury, CT 06762
    6 White Birch Ln, Middlebury, CT 06762
    6 White Birch Ln, Middlebury, CT 06762
    /10

    $1,249,500 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    6 White Birch Ln, Middlebury, CT 06762

    Welcome to 6 White Birch Lane in Middlebury, an exceptional 3,700 sq ft custom home set on the largest lot at the end of the cul-de-sac, offering privacy, space and sophistication in one of Middlebury's most sought-after neighborhoods. This stunning 4-bedroom, 3.5-bath residence is designed for modern living with high-end finishes and timeless elegance throughout. Enjoy hardwood flooring in every

    Donna Kennedy Keller Williams Realty

    6 White Birch Ln, Middlebury, CT 06762
  • 1 Richardson Dr, Middlebury, CT 06762
    1 Richardson Dr, Middlebury, CT 06762
    1 Richardson Dr, Middlebury, CT 06762
    /4

    $449,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,924 Sq Ft

    1 Richardson Dr, Middlebury, CT 06762

    * TO BE BUILT * WATERBURY ADDRESS, BUT WITH THE AMBIANCE OF MIDDLEBURY! THIS VERY PRIVATE 1 ACRE REAR LOT YIELDS A SUBURBAN FEEL, BUT W/ THE CONVENIENCES OF PROXIMITY TO HIGHWAYS AND SERVICE OF PUBLIC UTILITIES! TRULY A REAR OFFERING! 3/4 BED, 2.5 BATH RSD RANCH W/ VAULTED CEILING & ALL OF TODAY'S DESIGN FLAIR! LOOKING FOR A FAMILY COMPUND? THERE IS A 3/4 ACRE SISTER LOT ADJACENT TO THIS ONE

    Scott Tedesco Tedesco Real Estate

    1 Richardson Dr, Middlebury, CT 06762
  • 294 Christian Rd, Middlebury, CT 06762
    294 Christian Rd, Middlebury, CT 06762
    294 Christian Rd, Middlebury, CT 06762
    /8

    $899,000 New Construction

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

    294 Christian Rd, Middlebury, CT 06762

    New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style

    Ellie Gollenberg BHGRE Gaetano Marra Homes

    294 Christian Rd, Middlebury, CT 06762
  • 39 Shadduck Rd, Naugatuck, CT 06770
    39 Shadduck Rd, Naugatuck, CT 06770
    39 Shadduck Rd, Naugatuck, CT 06770
    /20

    $120,000

    • 3 Beds
    • 2 Baths
    • 980 Sq Ft

    39 Shadduck Rd, Naugatuck, CT 06770

    Welcome to this well maintained 3 bedrooms, 2 full baths mobile home in ldleview Mobile Home Park which features an open and inviting floor plan, spacious kitchen with plenty of counter space, laundry area, paved parking and storage shed providing extra storage space on a nice level lot. Land lease $507 monthly which includes the well and septic maintenance, recycling and trash pickup and road

    Jessica Critelli William Raveis Real Estate

    39 Shadduck Rd, Naugatuck, CT 06770
  • 45 Michael Ln, Naugatuck, CT 06770
    45 Michael Ln, Naugatuck, CT 06770
    45 Michael Ln, Naugatuck, CT 06770
    /40

    $650,000

    • 4 Beds
    • 3 Baths
    • 3,096 Sq Ft

    45 Michael Ln, Naugatuck, CT 06770

    Stunning Home with Space, Style & Comfort - A Must-See! Welcome to a home you'll fall in love with the moment you step inside! At its heart is a spacious gourmet kitchen - truly the centerpiece of this home - featuring a cathedral ceiling with skylights, a sunny breakfast nook, large island, stainless steel appliances, and endless cabinets and counter space. Perfect for everyday living or

    Rebecca Zandvliet Coldwell Banker Realty 2000

    45 Michael Ln, Naugatuck, CT 06770
Connecticut New Haven County Middlebury

Real Estate & Homes for Sale in Middlebury, CT

Why Live in Middlebury

Middlebury, Connecticut, is a picturesque New England town located in New Haven County, known for its scenic beauty and tight-knit community. With a population of 7,500, Middlebury offers a blend of rural charm and urban accessibility, being a short drive from New Haven. The town is surrounded by lush forests, state parks, rolling hills, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor activities. Residents enjoy local attractions such as Meadowview Park, Quassapaug Lake, and the Middlebury Greenway, as well as nearby state forests like Naugatuck, Mattatuck, and Paugussett, which offer extensive trails and recreational opportunities. Middlebury's educational system is highly regarded, with Pomperaug Regional School District No. 15 and Westover School providing top-notch education. The town's largest employers include Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. Middlebury maintains a low crime rate compared to the national average, contributing to its appeal for families and retirees. The housing market features classic New England homes, historic colonials, Cape Cods, and lakeside retreats, with properties often including antique barns and garden areas. Local businesses thrive in Middlebury, with popular spots like Willie’s Wood Smoked BBQ, The Local Gourmet, Vyne Restaurant, and Pies & Pub. The town's biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks. Middlebury is well-connected via Interstates 8 and 84, State Routes 63 and 64, and is close to Tweed New Haven Airport and Windsor Locks International Airport. Despite recent development proposals, the community remains committed to preserving its small-town charm.

Learn more about living in Middlebury

Frequently Asked Questions

What is the average home price in Middlebury, CT?
Homes for sale in Middlebury, CT have an average home price of $631,280.
How many homes have sold over the last 12 months in Middlebury, CT?
120 homes have sold in Middlebury, CT over the last 12 months.
What are the most popular zip codes in Middlebury, CT?
The most popular zip codes in Middlebury, CT include 06762, 06708, 06770, 06795 and 06798.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $599,450. If you put a 20% down payment of $119,900 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $3,050 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $131K a year to afford the median home price in Middlebury.
How are the schools in Middlebury, CT?
Middlebury, CT has highly rated public and private schools. Some of the best schools in Middlebury based on Niche Grades are Westover School, Pomperaug Regional High School and Oxford High School. Browse all the schools in Middlebury, CT to learn more.

Home Trends in Middlebury, CT

On average, homes in Middlebury, CT sell after 95 days on the market compared to the national average of 52 days. The median sale price for homes in Middlebury, CT over the last 12 months is $555,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$555,000
Median Single Family Sale Price
$555,000
Median Townhouse Sale Price
$556,230
Median 2 Bedroom Sale Price
$629,250
Average Price Per Sq Ft
$270
Number of Homes for Sale
26
Last 12 months Home Sales
120
Months of Supply
2.60
Median List Price
$599,450
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group