3,784

New Haven, CT Homes

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  • 100 Fairhaven Dr, Middlebury, CT 06762
    100 Fairhaven Dr, Middlebury, CT 06762
    100 Fairhaven Dr, Middlebury, CT 06762
    /40

    $679,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,988 Sq Ft

    100 Fairhaven Dr, Middlebury, CT 06762

    Welcome home to this beautiful 4-bedroom, 2.5-bath colonial located at the end of a private cul-de-sac in a desirable neighborhood, just minutes from the highway. Inside, you'll find a bright and welcoming layout filled with natural light and hardwood floors throughout. The family room features custom built-ins and a cozy gas fireplace, while the formal living room offers a classic brick

    Tom Dorso Mapleridge Realty

    100 Fairhaven 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
  • 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
  • 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
  • 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
  • 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
  • 0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
    0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
    0 N Benson Rd Unit 41 24061449, Middlebury, CT 06762
    /9

    $541,566 Pending

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

    0 N Benson Rd Unit 41 24061449, 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 41 24061449, 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
  • 55 Westwood Dr, Middlebury, CT 06762
    55 Westwood Dr, Middlebury, CT 06762
    55 Westwood Dr, Middlebury, CT 06762
    /26

    $695,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    55 Westwood Dr, Middlebury, CT 06762

    Middlebury Modern. Authentic c.1962 Mid-Century Modern Designed by Noted Architect Andrew S Cohen as his Personal Residence. This Largely Untouched Modernist is Set Quietly on Nearly 1-Acre. Walls of Glass & Dark Stone Floors Showcase the Signature Elements of the Era. 4 Bedrooms, 2.5 Baths Include an en-suite Primary Bedroom with Dressing Room & Balcony. Large Eat-in Kitchen Adjacent to Family

    Graham Klemm Klemm Real Estate Inc

    55 Westwood Dr, 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
  • 14 Deer Run Rd, Middlebury, CT 06762
    14 Deer Run Rd, Middlebury, CT 06762
    /2

    $699,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,877 Sq Ft

    14 Deer Run Rd, Middlebury, CT 06762

    Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) 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

    14 Deer Run Rd, 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 Gaetano Marra Homes

    64 Joy 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
  • 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
  • 8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    8 Kimberwick Ct, Middlebury, CT 06762
    /40

    $565,500

    • 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
  • 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
  • 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
  • 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
  • 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
  • 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 Gaetano Marra Homes

    400 Long Meadow 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
  • 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 Gaetano Marra Homes

    43 Ridgewood Dr Unit 43, 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
  • 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
  • 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
  • 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
  • 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

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