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Middlebury 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
  • 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 Bannon & Hebert

    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

    $649,900 Open Sun 12PM - 2:30PM

    • 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
  • 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

    NEW CONSTRUCTION split level with possible in-law 3220 sqft, 4 bedrooms, 3.5 baths, open floor plan on main level with kitchen, dinning/living room with a electric fireplace. A large size kitchen with granite countertops, plenty of cabinets, tiled backsplash, double oven, a large island for cooking or eating. The dining area next to the kitchen leads to a sliding door to outside trex deck(16x12),

    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 Bannon & Hebert

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

    $729,900 New Construction

    • 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
  • 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
  • 372 Tucker Hill Rd, Middlebury, CT 06762
    372 Tucker Hill Rd, Middlebury, CT 06762
    372 Tucker Hill Rd, Middlebury, CT 06762
    /40

    $1,685,000

    • 5 Beds
    • 7 Baths
    • 6,600 Sq Ft

    372 Tucker Hill Rd, Middlebury, CT 06762

    Phenomenal renovation and redesign by current owners perfectly blends traditional and modern creating an elegant and luxury living. This exceptional 5 bedroom, 4.3-bath home offers over 6600 square feet of luxurious living. Situated on a private 3.5 acres, the property boasts: stone walls, a 60ft in-ground pool and tennis/pickleball court. Upon entering, you'll be captivated by the stunning

    Naima Mazouzi Eagle Eye Realty PLLC

    372 Tucker Hill Rd, Middlebury, CT 06762
  • 2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    2 Dogwood Ct, Middlebury, CT 06762
    /40

    $590,000

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

    $399,000

    • 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 Bannon & Hebert

    30 Nick 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

    $539,900

    • 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 Bannon & Hebert

    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

    $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 gas

    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 Bannon & Hebert

    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 Open Sun 12:30PM - 2PM

    • 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 Bannon & Hebert

    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
  • 126 Colonial Ave, Middlebury, CT 06762
    126 Colonial Ave, Middlebury, CT 06762
    126 Colonial Ave, Middlebury, CT 06762
    /36

    $635,000 Open Sun 12PM - 2PM

    • 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 Bannon & Hebert

    126 Colonial Ave, Middlebury, CT 06762
  • 28 Maple Dr, Middlebury, CT 06762
    28 Maple Dr, Middlebury, CT 06762
    28 Maple Dr, Middlebury, CT 06762
    /33

    $449,000

    • 3 Beds
    • 3.5 Baths
    • 1,596 Sq Ft

    28 Maple Dr, Middlebury, CT 06762

    Now Listed at $449,000 - Motivated Sellers! Don't miss this incredible opportunity to own a standout property in the heart of Middlebury. 28 Maple Drive offers 3 bedrooms, 3.5 bathrooms, and sits on a rare 2.31-acre double lot with potential for subdivision - a true value with room to grow. Inside, you'll find bright, spacious living areas with a great layout, perfect for both everyday living

    Dean Giatas William Raveis Real Estate

    28 Maple Dr, 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
  • 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 Bannon & Hebert

    294 Christian 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 Sun 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
  • 8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    /40

    $565,500 Coming Soon

    • 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
Connecticut New Haven County Naugatuck Middlebury

Real Estate & Homes for Sale in Middlebury, Naugatuck

Why Live in Middlebury
Middlebury, a small town in New Haven County, Connecticut, offers a blend of rural charm and urban accessibility. With a population of 7,500, it is known for its scenic beauty, high-ranking Pomperaug Regional School District No. 15, and the prestigious Westover School. The town is surrounded by lush forests, state parks, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor enthusiasts. Middlebury's most popular outdoor spots include Quassapaug Lake, Meadowview Park, and the Middlebury Greenway, a 7-mile paved trail. Nearby state forests such as Naugatuck, Mattatuck, and Paugussett offer extensive opportunities for hiking, fishing, and camping. The town maintains a tight-knit community with locally owned businesses and hosts events like "Celebrate Middlebury" at Shepardson Community Center. Dining options include Willie’s Wood Smoked BBQ, The Local Gourmet, and Vyne Restaurant. Middlebury's largest employers are Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. The town is safer than the national average, with low violent crime rates. Middlebury is accessible via Interstates 8 and 84, with Tweed New Haven Airport 30 miles away. The housing market features classic New England homes, historic colonials, and lakeside retreats. Middlebury Green, the historic center, is home to antique colonials, churches, and community amenities. Despite its small size, Middlebury offers a rich blend of attractions and a strong sense of community, making it an appealing place for families and retirees alike.
Learn more about living in Middlebury

Frequently Asked Questions

Is Middlebury a good place to live?
Middlebury is a good place to live. Middlebury is considered car-dependent and somewhat bikeable. Middlebury is a suburban neighborhood. Middlebury has 6 parks for recreational activities. It is sparse in population with 0.7 people per acre and a median age of 47. The average household income is $150,167 which is above the national average. College graduates make up 55.6% of residents. A majority of residents in Middlebury are home owners, with 10.9% of residents renting and 89.1% of residents owning their home. A local real estate agent serving Middlebury can help you decide if this neighborhood is the right one for you. Learn more on our Middlebury neighborhood guide.
How much do you need to make to afford a house in Middlebury?
The median home price in Middlebury is $469,900. If you put a 20% down payment of $94,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,440 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $105K a year to afford the median home price in Middlebury. The average household income in Middlebury is $150K.
What are the best public schools in Middlebury?
The best public schools that serve Middlebury are:
What are the best private schools in Middlebury?
The best private schools that serve Middlebury are:
What are the most popular zip codes in Middlebury, Naugatuck, CT?
The most popular zip codes in Middlebury, Naugatuck, CT include 06762, 06708, 06770, 06795 and 06798.
What are the most popular neighborhoods near Middlebury, Naugatuck, CT?
The most popular neighborhood near Middlebury, Naugatuck, CT is Downtown Waterbury.

Home Trends in Middlebury, CT

On average, homes in Middlebury, Naugatuck sell after 93 days on the market compared to the national average of 70 days. The median sale price for homes in Middlebury, Naugatuck over the last 12 months is $477,014, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$477,014
Median Single Family Sale Price
$469,900
Median Townhouse Sale Price
$446,895
Median 2 Bedroom Sale Price
$524,950
Median 1 Bedroom Sale Price
$235,000
Average Price Per Sq Ft
$246
Number of Homes for Sale
4
Last 12 months Home Sales
54
Months of Supply
0.90
Median List Price
$469,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
19%
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