1,622 properties for sale in Middlebury town, New Haven County Connecticut

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 8 Deer Run Road (aka Lot 16) is just beginning construction. There are several other lots and plans to choose from or will build to suit! City water and sewer

Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher and Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools

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

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. A Planned Unit Development (PUD). Developed by Newport Realty Group. A

Last remaining unit! 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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Devel

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Development (PUD). Develop

Nestled in the highly sought-after North Farm neighborhood, this exceptional 4BR, 3.5 bath Colonial is beautifully situated on 2.34 private acres offering the perfect blend of classic charm and comfortable living. A generous entry foyer welcomes you into a thoughtfully designed home featuring a formal living room with fireplace, elegant formal dining room and a spacious eat-in kitchen complete with pantry and breakfast bar. The inviting family room is the heart of the home, showcasing vaulted ceilings, exposed wood beams, wide plank hardwood floors and a dramatic floor-to ceiling fireplace. A dedicated study/office with built-in bookcases and a versatile bonus room provide flexible space for today's lifestyle needs. Outdoor living is equally impressive with double decks overlooking an expansive pool and serene backyard, ideal for entertaining and relaxing all summer long. This is a rare opportunity to own a beautiful property in one of the area's most desirable neighborhoods

Last remaining unit! 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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Devel

Looking for a 4 bedroom home in a prime location? Here it is. This classic home sits on just over one acre of property with gorgeous gardens and a lush lawn. On the interior, a spacious updated kitchen with granite counters, an island, plenty of room for dining and wonderful storage. For easy entertaining, the living room and dining room adjoin and allow for a great flow. Enjoy a cozy family room with fireplace, oak flooring and access to a 15 x 12 deck with awning overlooking the private rear yard. In addition, there are 2.5 baths, a partially finished walk out basement and an outbuilding, perfect for storage. (Needs a bit of work.)

Located in one of Middlebury's most desirable and beautifully maintained subdivisions Avalon Farms with streetlights and Belgian block lined streets, this impressive 3 bedroom, 3 full and 1 half bath Colonial offers 3,494 square feet of refined and flexible living. Set on a premium, fully usable flat lot surrounded by mature pines for year round privacy, the home features Hardie Plank siding and extensive stone veneer. A grand two story foyer opens to a spacious, light filled interior designed for comfortable main level living. The first floor primary suite offers an oversized closet and spa like bath, complemented by main level laundry, pantry, eat in kitchen, great room, large study with its own fireplace, and attached garage. The soaring great room features a second fireplace and an inviting gathering space. The kitchen includes a Bertazzoni gas cooktop, new under counter ZLINE microwave, new refrigerator, new dishwasher, double oven, and updated hardware. Upstairs are two generous

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Unit 55 is an End Unit. Phase 1 occupancy starting Summer 2025. Model

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Development (PUD). Develop

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Development (PUD). Develop

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. A Planned Unit Development (PUD). Develop

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 townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Phase 1 occupancy starting Summer 2025. Model unit coming soon! A Plan

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

Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the home features a large living room, formal dining room, and an updated kitchen with a butler's pantry. Also on the main level is a sunroom that is an inviting year-round heated with electric, living space. A well-appointed mudroom with laundry sits just off the attached 2 car garage and the kitchen, adding function without sacrificing style. Throughout the home, classic architectural details shine, including custom built-in curios and bookshelves, hardwood floors, and two fireplaces that enhance the home's warmth and character. Four bedrooms in all and set on 1.7 acres with a level yard in a sough

Please submit your offers by Monday July 20th at 2:00pm.* Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middlebury's most desirable locations. This inviting Cape offers a flexible layout that lives larger than expected. The renovated kitchen features butcher block countertops, updated appliances, hardwood floors, recessed lighting, a breakfast bar, and a GE Kitchen Hub, flowing seamlessly into the dining room. The cozy living room boasts refinished hardwood floors, custom built-ins, a wood plank ceiling, recessed lighting, and an energy-efficient pellet stove. A spacious first-floor primary suite with an en-suite bath and convenient laundry offers easy one-level living, while two bright bedrooms and a full bath complete the second floor. Recent improvements include refinished hardwood floors, updated electrical, security cameras, and a new electric pool heater. Outside, enjoy your own private retreat with a heate

Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-maintenance living. Step inside to find a thoughtfully designed interior enhanced with upgraded molding, elegant cabinetry, and high-end appliances that elevate both style and functionality. The inviting living space is truly a showstopper, featuring soaring 30-foot ceilings and a stunning fireplace that creates a warm yet dramatic focal point-perfect for both relaxing and entertaining. Nestled on a highly sought-after cul-de-sac, this home offers both privacy and a true sense of community. Beyond the home itself, residents enjoy access to exceptional, fully loaded amenities including a beautiful clubhouse, resort-style pool, playground, tennis courts, and both indoor and outdoor basketball courts-perfect for an acti

Step into this beautifully maintained 3-bedroom, 2.5-bath split-level home where comfort and functionality come together. Gleaming hardwood floors extend throughout the entire home. The living room features a cozy fireplace, creating the perfect space to relax. The bright kitchen opens seamlessly into the dining room, making everyday living and entertaining a breeze. From the kitchen, step out onto the backyard deck overlooking the spacious backyard-ideal for summer barbecues, morning coffee, or simply enjoying the outdoors. The finished lower level offers valuable additional living space and features a walkout to a beautiful patio, providing even more room for entertaining, a family room, home office, or recreation area. With expansive front and back yards, this home offers plenty of outdoor space for gardening, play, or relaxing. Thoughtfully designed with inviting indoor and outdoor living spaces, this home is ready for its next chapter

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 offers a walkable lifestyle with direct access to restaurants, coffee shops, shopping, and the Middlebury Greenway Trail. Now in Phase Two, Granite Woods showcases five unique home designs built for comfort, style, energy efficiency, and aging in place. Every home is ENERGY STAR certified for exceptional performance offering lower utility costs, improved air quality, and year-round comfort. Designed with your future in mind, all homes feature single-step front and garage entries, wide interior doorways, and access to a private residents-only pavilion. The Spruce is a delightful two-bedroom home

Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting dinner parties. The entertaining continues into a well-lit living room and a separate, cozy family room-offering plenty of space for everyone to relax. Upstairs, you'll find the home's private sleeping quarters, featuring three bedrooms and two full bathrooms. Need more room? Then travel downstairs to a highly versatile area that can function as additional bedrooms, a dedicated office space, or even a perfect in-law suite thanks to an additional full bathroom. The partially finished basement is an entertainer's dream, complete with a dedicated media room and storage galore. The unfinished portion o