New Haven, CT Homes

• 

  

  

  /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

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 265-6768

  1 Stevens Rd, Middlebury, CT 06762
• 

  Explore Middlebury

• 

  

  

  /17

  $2,850 per month

  • 2 Beds
  • 1 Bath
  • 1,217 Sq Ft
  • House for Rent

  95 Christian Rd, Middlebury, CT 06762

  Property Id: 1615951Discover your perfect home at 95 Christian Rd, Middlebury, CT! This charming Cape Cod-style house blends character and comfort, making it an ideal rental for those seeking a peaceful retreat. Located in a tranquil residential community, this 2-bedroom, 1-bathroom home offers 1,217 sq. ft. of cozy living space on over an acre of land—plenty of room to

  95 Christian Rd, Middlebury, CT 06762
• 

  $690,000 Sold Aug 01, 2025

  • 2,850 Sq Ft
  • $242/SF
  • 54 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  190 Bronson Dr, Middlebury, CT 06762

  Welcome to this beautifully maintained 4 bedroom 2.5 bath colonial home offering space and style in a sought after location! Enter from the oversized 2 car garage into the mudroom with ample storage. Beyond the large eat-in kitchen and formal dining room is the family room that stretches from the front to the back of the house. A gas insert in the family room fireplace provides a cozy setting

  Jackie Desmarais Showcase Realty, Inc.

  190 Bronson Dr, Middlebury, CT 06762
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  47 Ridgewood Dr Unit 47, 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

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 871-0910

  33 Ridgewood Dr Unit 33, Middlebury, CT 06762
• 

  

  /9

  $950 per month

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • House for Rent

  10 Old Waterbury Rd Unit 3, Middlebury, CT 06762

  Cozy studio for lease. Spacious living room. Kitchenette with ample cabinet space, Full bathroom w/ stand-up shower. Private in-ground pool with deck. Set in close proximity to schools, shopping & highway(s).

  Jeffrey Corcoran Corcoran Properties, LLC

  10 Old Waterbury Rd Unit 3, Middlebury, CT 06762
• 

  $515,000 Sold Jul 31, 2025

  • 2,804 Sq Ft
  • $184/SF
  • 75 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1971

  61 Stony Brook Rd, Middlebury, CT 06762

  Over $60,000 Price Improvement - Now is the Time! Whether you're discovering it for the first time or coming back for another look, don't miss the chance to own this distinctive contemporary ranch at 61 Stonybrook Road. Tucked away on 1.38 private, wooded acres in picturesque Middlebury, this light-filled retreat offers over 2,800 square feet of thoughtfully designed living space. Inside, you'll

  Maria Cohen William Raveis Real Estate

  61 Stony Brook Rd, Middlebury, CT 06762
• 

  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, 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

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
• 

  

  /11

  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  173 Christian Rd, Middlebury, CT 06762

  Property Id: 2064532Perfect year round residence or weekend retreat. This newly renovated 1b/1ba cottage offers plenty of storage and a large covered carport. Vaulted ceilings, ductless heating/cooling, washer & dryer and room for the grill behind the house.Walk to the lake for day fun and enjoy all water sports or experience a magical sunset... an abundance of peaceful country

  173 Christian Rd, Middlebury, CT 06762
• 

  $730,000 Sold Jul 30, 2025

  • 2,442 Sq Ft
  • $299/SF
  • 51 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1941

  222 Crest Rd, Middlebury, CT 06762

  Step in to timeless elegance with this beautifully restored 5 bedroom, 2.5 bath home with solid oak flooring throughout, and a 2 car detached garage nestled on a lush, landscaped 1 acre lot just a short walk to the town green, the Middlebury Library and the scenic Middlebury Greenway. Built in 1941, this classic residence blends vintage charm with modern comforts, offering generous living spaces,

  Jackie Desmarais Showcase Realty, Inc.

  222 Crest Rd, Middlebury, CT 06762
• 

  Est $1,496,859 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  397 White Deer Rock Rd, 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
• 

  

  /10

  $1,250 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  10 Old Waterbury Rd Unit 1, Middlebury, CT 06762

  Cozy one bedroom unit for lease. Spacious living room with wood burning fireplace. Kitchenette with amble counter space. Full bathroom w/ stand-up shower. Private in-ground pool with deck. One car detached garage. Set in close proximity to schools, shopping & highway(s).

  Jeffrey Corcoran Corcoran Properties, LLC

  10 Old Waterbury Rd Unit 1, Middlebury, CT 06762
• 

  $620,000 Sold Jul 30, 2025

  • 2,950 Sq Ft
  • $210/SF
  • 45 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  1 Chatham Ct, Middlebury, CT 06762

  Discover timeless grace and style in this stunning 4 -bedroom home, nestled in the highly sought-after Brookside of Middlebury. From the moment you step inside, you will be captivated by its graceful open floor plan and refined finishes. The beautiful two-story foyer seamlessly flows into an elegant dining room and a fabulous kitchen featuring SS appliances, granite countertops and high bar area

  Norinne Byrne Calcagni Real Estate

  1 Chatham Ct, Middlebury, CT 06762
• 

  Est $418,039 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,434 Sq Ft

  23 Atwood St, Middlebury, CT 06762

  23 Atwood St, Middlebury, CT 06762
• 

  

  /38

  $717,000 Open Thu 4PM - 6PM

  • 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
• 

  $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
• 

  Est $681,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,403 Sq Ft

  24 Ridgewood Dr, Middlebury, CT 06762

  24 Ridgewood Dr, Middlebury, CT 06762
• 

  

  /26

  $649,900

  • 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
• 

  $490,000 Sold Jul 28, 2025

  • 1,682 Sq Ft
  • $291/SF
  • 86 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1971

  115 Marney Dr, Middlebury, CT 06762

  Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter

  Allysa DeRosa Mapleridge Realty

  115 Marney Dr, Middlebury, CT 06762
• 

  Est $547,027 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Judd Rd, Southbury, CT 06488

  436 Judd Rd, Southbury, CT 06488
• 

  

  /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
• 

  $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
• 

  Est $627,060 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  740 Whittemore Rd, Middlebury, CT 06762

  740 Whittemore Rd, Middlebury, CT 06762
• 

  

  /40

  $939,000

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

  383 Leonard Rd, Middlebury, CT 06762

  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 fireplace -

  Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
• 

  $515,000 Sold Jul 24, 2025

  • 1,882 Sq Ft
  • $274/SF
  • 61 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  17 Highridge Rd Unit 17, Middlebury, CT 06762

  Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area,

  Kayla O'Grady William Raveis Real Estate

  17 Highridge Rd Unit 17, Middlebury, CT 06762
• 

  Est $549,255 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,611 Sq Ft

  212 Breakneck Hill Rd, Middlebury, CT 06762

  212 Breakneck Hill Rd, 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
• 

  $750,000 Sold Jul 23, 2025

  • 3,374 Sq Ft
  • $222/SF
  • 62 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2004

  34 Avalon Dr, Middlebury, CT 06762

  Located in a desirable neighborhood setting, this beautifully appointed home offers refined living with the flexibility to suit any stage of life. Step inside to a grand two-story foyer that sets the tone for the home's spacious, light-filled interior. The main-level primary suite features a tray ceiling and spa-inspired bathroom with a double vanity, walk-in shower, and jetted soaking

  Connie Widmann William Raveis Real Estate

  34 Avalon Dr, Middlebury, CT 06762
• 

  Est $598,966 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  108 White Ave, Middlebury, CT 06762

  108 White Ave, 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
• 

  $540,000 Sold Jul 18, 2025

  • 2,122 Sq Ft
  • $254/SF
  • 72 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2014

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762

  Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The

  Jay Irvine Serhant Connecticut, LLC

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762
• 

  Est $574,598 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  84 Anawan Ave, Middlebury, CT 06762

  84 Anawan Ave, 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
• 

  $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
• 

  Est $480,783 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  28 Jensen Dr, Middlebury, CT 06762

  28 Jensen 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
• 

  $950,000 Sold Jul 09, 2025

  • 4,496 Sq Ft
  • $211/SF
  • 428 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  593 Park Road Extension, Middlebury, CT 06762

  This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck.

  Jackie Desmarais Showcase Realty, Inc.

  593 Park Road Extension, Middlebury, CT 06762
• 

  Est $409,414 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  109 Yale Ave, Middlebury, CT 06762

  109 Yale Ave, Middlebury, CT 06762

Showing Results 1 - 40, Page 1 of 18