Middlebury CT Real Estate & Homes for Sale

16 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,877
Status:
NEW LISTING
MLS#:
24160275
Type:
Single Family
Subdivision:
N/A
Lot size:
0.98 Acres
Year built:
2026
Courtesy: Real Estate Two 203-926-1122
View additional info

ADDITIONAL INFORMATION

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting Ridge Road (aka Lot 11) is to be built. It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms and a 2 car attached garage. The primary bedroom boasts walk-in closet with custom shelving and private full bath. There are several other lots and plans to choose from or will build to suit! City water and sewer. Pictures are of previous house built.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,198
Status:
NEW LISTING
MLS#:
24158517
Type:
Single Family
Subdivision:
N/A
Lot size:
3.34 Acres
Year built:
1998
Courtesy: Weichert REALTORS Briotti Group 203-879-2339
View additional info

ADDITIONAL INFORMATION

This beautiful 9 room colonial has every attention to detail and all the features that a discriminating buyer is looking for. Set on a private 3.34 acre lot with a 10' X 16' shed in a sought-after, very commuter friendly neighborhood, this 3,198 square foot residence boasts 4 bedrooms, 2-1/2 bathrooms, a bright and airy 25' X25' main floor family room with cathedral ceilings, built-ins, a fireplace with pellet stove and atrium doors to a private 14' X 24' deck, plus an additional 480 SF finished lower level with interior access to the 2 car oversize garage, a mudroom and a recreation room. The main floor has an updated eat-in kitchen with granite countertops, newer appliances, and an island. The open foyer leads to a large living room and dining room with wainscoting and a half bath. The upper level has 4 generously sized bedrooms and 2 bathrooms, including a 17' X 20' primary bedroom with a newly remodeled on-suite bathroom. Other amenities include central A/C, central vacuum, security system, Ring doorbells and flood lights, a generator hookup, detailed trim work throughout, built-in shelving galore and hardwood floors. The roof and gutters are only 2 years old. The Thermo-Pride hot air furnace was installed in 2019. This well maintained home will provide buyers with many more years of carefree and very pleasurable living.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,878
Status:
NEW LISTING
MLS#:
24158747
Type:
Single Family
Subdivision:
N/A
Lot size:
0.8 Acres
Year built:
2026
Courtesy: BHGRE Gaetano Marra Homes 203-758-1300
View additional info

ADDITIONAL INFORMATION

Under Construction in One of Middlebury's Most Desirable Neighborhoods! Welcome to the Avalon Farms community-known for its beautiful homes, manicured lawns, and thoughtfully designed landscaping that create a truly picturesque setting. The Cambridge model blends classic design with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious great room features a cathedral ceiling, fireplace, and oversized windows that fill the home with natural light. At the heart of the home is a gourmet kitchen with abundant shaker-style cabinetry and a large center island-ideal for gatherings. A charming breakfast nook with French doors opens to a private deck, perfect for casual dining or relaxing outdoors. For more formal occasions, the home also offers a dedicated dining room for entertaining. The main-level primary suite includes walk-in closets and a luxurious bathroom with a large walk-in shower. This level also features a private den, mudroom, laundry room, and half bath. Hardwood flooring runs throughout the entire first floor. Upstairs, you'll find two generously sized bedrooms connected by a convenient Jack-and-Jill bathroom. Additional highlights include an attached two-car garage, full walk-out basement, central air, natural gas, public water and sewer, and underground utilities. Situated on a cul-de-sac lot, the home will be completed with professional landscaping. Come experience the beauty and comfort of Avalon Farms!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,734
Status:
Active
MLS#:
24158024
Type:
Single Family
Subdivision:
N/A
Lot size:
1.22 Acres
Year built:
1978
Courtesy: Regency Real Estate, LLC 860-945-9868
View additional info

ADDITIONAL INFORMATION

A private hilltop retreat at the end of a quiet cul-de-sac, this stunning 8-room contemporary is set well back from the road on a picturesque knoll, offering exceptional privacy and a peaceful natural setting. Custom built and proudly maintained by its original owner, the home features soaring ceilings, expansive rooms, and walls of windows that flood the interior with natural light. The open, airy design creates an inviting atmosphere perfect for both everyday living and entertaining. Step outside onto the brand-new deck overlooking the beautifully private surroundings-an ideal setting for relaxing, dining, or hosting gatherings. A circular driveway and attached 3-car garage add to the home's impressive presence and convenience. Distinctive architecture, privacy, and space come together to create a truly special property.

Open House:

Sunday, 3/22 1:00-2:30PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
3,300
Status:
Active
MLS#:
24155964
Type:
Single Family
Subdivision:
N/A
Lot size:
4 Acres
Year built:
1955
Courtesy: William Raveis Real Estate 203-426-3429
View additional info

ADDITIONAL INFORMATION

Large Colonial with charm and character ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please. The formal living room complete with a large picture window and marble fireplace will serve as a great place to relax at the end of a long day. The dining room is ready to host any event you plan, and has the space to welcome everyone over for dinner without scrambling for additional space. The eat in kitchen has 3 ovens and plenty of space to meal prep. The home also offers a den/study with a wet bar to gather in a relaxed environment or curl up to a book or cocktail. The Florida Room (Sunroom) is heated and has 2 sliders to the outdoors. Such a fun room to take in the views. Roof is 6 years old, and the chimneys have been lined and repointed in the last 5 years.

Beds:
8
Baths:
8.00
Sq.Ft.:
9,619
Status:
Active
MLS#:
24151632
Type:
Single Family
Subdivision:
N/A
Lot size:
12.6 Acres
Year built:
1939
Courtesy: Coldwell Banker Realty 203-264-1400
View additional info

ADDITIONAL INFORMATION

Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the house and related garden cottages, grounds and surrounding landscapes of fields and woodlands, drape across the gentle hilltops of Middlebury with magnificent vistas east, west and north. It constitutes one of the most beautiful and historically significant properties in the area. The estate encompasses the seventeen room main house and three guest cottages: converted stables with unique industrial accents, classic cape, and pool side studio. The main home features magnificently scaled formal and informal settings, exquisite millwork, hardwood floors. Chefs' quality kitchen with sensational marble, large butler's pantry, breakfast nook, informal dining room, 800 bottle temperature controlled wine room complete this area. This opens to the library and raised paneled great room with vaulted ceilings and stone fireplace. Pass by the sweeping free-standing staircase which leads to the second level and enter the formal dining room and living room both with fireplaces adjacent to a mahogany paneled office. The wonderful conservatory overlooking the beautiful gardens, sauna room, two half baths

Beds:
3
Baths:
2.00
Sq.Ft.:
1,811
Status:
Active
MLS#:
24148828
Type:
Single Family
Subdivision:
N/A
Lot size:
5.26 Acres
Year built:
1782
Courtesy: William Raveis Real Estate 203-264-8180
View additional info

ADDITIONAL INFORMATION

Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added security of a whole-house generator, you can enjoy the serenity of country living with total peace of mind. Truly a unique opportunity to own a great piece of property in Middlebury. More Pics to come.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,753
Status:
Active
MLS#:
24147892
Type:
Single Family
Subdivision:
N/A
Lot size:
1.7 Acres
Year built:
1959
Courtesy: BHGRE Gaetano Marra Homes 203-758-1300
View additional info

ADDITIONAL INFORMATION

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 sought-after Middlebury location, abuts Middlebury Land Trust's Crest Rd. Preserve. Recent improvements include a new roof in 2025. Ideally situated close to dining, parks, library, town amenities, private school, and commuter routes, this home presents a rare blend of quality craftsmanship, location, and lifestyle. Middlebury residents can also join the Middlebury Recreation Association annually for a small fee and have access to a beach on Lake Quassapaug and a pavilion at the park.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,879
Status:
Active
MLS#:
24147226
Type:
Condo
Subdivision:
N/A
Year built:
2008
Courtesy: Real Estate Two 203-926-1122
View additional info

ADDITIONAL INFORMATION

Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops, custom backsplash, and updated flooring. The glass sliders flood the space with natural light and lead to a private deck with tranquil wooded views. The second level offers three generously proportioned bedrooms, all with walk-in closets, including an elegant primary suite with a spa-like bath complete with soaking tub and separate shower. A third-floor loft with skylights provides flexible space ideal for a home office or lounge, while the newly finished walk-out lower level features a spacious recreation room, full bath, abundant storage, and direct access to a private patio. Fresh paint, crown molding, recessed lighting, and upscale finishes add warmth and sophistication throughout. Ideally positioned near the pool and clubhouse and conveniently located close to shopping, highways, parks, and walking trails, this exceptional home delivers comfort, style, and convenience in one of Middlebury's premier communities.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,200
Status:
Active
MLS#:
24145711
Type:
Condo
Subdivision:
N/A
Year built:
2004
Courtesy: S Factor Realty Group LLC 203-302-0672
View additional info

ADDITIONAL INFORMATION

Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the main living areas-perfect for hosting family and friends. First-floor primary suite, complete with a luxurious jacuzzi tub and two spacious walk-in closets. Through elegant glass French doors, you'll find a dream dressing room or home office, outfitted with a PAX wardrobe system, dressing table, and desk. The dramatic two-story foyer leads to the upper level, offering three additional bedrooms and a full bath, all overlooking the stunning two-story living room with a cozy fireplace. The finished walk-out basement expands your living space with endless possibilities-ideal for a home office, gym, media room, or game area. An additional 600+ sq ft of storage with a tool bench provides ample space for hobbies and organization. Enjoy peaceful mornings or relaxing evenings on the expansive deck, taking in tranquil views of the lush, protected preserve. This is more than just a house-it's a place to be a truly home.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,200
Status:
Active
MLS#:
24146182
Type:
Single Family
Subdivision:
N/A
Lot size:
1 Acres
Year built:
2004
Courtesy: S Factor Realty Group LLC 203-302-0672
View additional info

ADDITIONAL INFORMATION

Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the main living areas-perfect for hosting family and friends. First-floor primary suite, complete with a luxurious jacuzzi tub and two spacious walk-in closets. Through elegant glass French doors, you'll find a dream dressing room or home office, outfitted with a PAX wardrobe system, dressing table, and desk. The dramatic two-story foyer leads to the upper level, offering three additional bedrooms and a full bath, all overlooking the stunning two-story living room with a cozy fireplace. The finished walk-out basement expands your living space with endless possibilities-ideal for a home office, gym, media room, or game area. An additional 600+ sq ft of storage with a tool bench provides ample space for hobbies and organization. Enjoy peaceful mornings or relaxing evenings on the expansive deck, taking in tranquil views of the lush, protected preserve. This is more than just a house-it's a place to be a truly HOME !!!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,085
Status:
Active
MLS#:
24146106
Type:
Single Family
Subdivision:
N/A
Lot size:
0.2 Acres
Year built:
1935
Courtesy: West View Properties, LLC 860-274-7838
View additional info

ADDITIONAL INFORMATION

2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your style do not forget Lake Quassapaug, Middlebury Greenway, or Hop Brook Lake. See all that Middlebury Living has to offer. EMD 10% cash 1% Financed or 1k minimum whichever is greater.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,190
Status:
Active
MLS#:
24128666
Type:
Single Family
Subdivision:
N/A
Lot size:
2.2 Acres
Year built:
2025
Courtesy: Real Estate Two 203-926-1122
View additional info

ADDITIONAL INFORMATION

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,360
Status:
Active
MLS#:
24124893
Type:
Single Family
Subdivision:
N/A
Lot size:
2.54 Acres
Year built:
1980
Courtesy: Showcase Realty, Inc. 860-274-7000
View additional info

ADDITIONAL INFORMATION

Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth wall, custom remote blinds, a fabulous wood wet bar area as well as built-in entertainment cabinet. The eat-in kitchen invites you to enjoy meals & coffee looking out at the beautiful backyard or relax on the screened in porch. A formal dining area & living room are perfect for entertaining & enjoying the views through the oversized windows. Upstairs you will find 4 large bedrooms including the Primary suite with sitting area, remote control blinds, custom bathroom cabinets, a walk-in shower, as well as radiant heated floors. You'll find your private oasis in the backyard with an amazing in-ground pool & features an electric pool cover that is walkable for added safety, a large spa with cover, composite deck for low to no maintenance, 2 large resort style sun umbrellas & an electric awning! You'll never want to leave your backyard! Don't miss the walk up attic storage area in the mudroom waiting for your imagination! With a 3 car attached garage & an automatic generator everything has been thoughtfully planned when this home was built by this family!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,190
Status:
Active
MLS#:
24079981
Type:
Single Family
Subdivision:
N/A
Lot size:
0.92 Acres
Year built:
2025
Courtesy: Real Estate Two 203-926-1122
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,466
Status:
Active
MLS#:
24079497
Type:
Single Family
Subdivision:
N/A
Lot size:
2.8 Acres
Year built:
2025
Courtesy: Real Estate Two 203-926-1122
View additional info

ADDITIONAL INFORMATION

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.

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Davis E. Owen, Sr., License REB.0754414, Xome CT LLC, License REB.0790146 , [email protected], 844-400-XOME (9663), 2083 Main Street, Stratford, CT 06615


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Middlebury Real Estate

Middlebury is located in Connecticut. Middlebury, Connecticut has a population of 7,617. Middlebury is more family-centric than the surrounding county with 37.06% of the households containing married families with children. The county average for households married with children is 26.84%.

The median household income in Middlebury, Connecticut is $124,619. The median household income for the surrounding county is $75,043 compared to the national median of $69,021. The median age of people living in Middlebury is 46.2 years.

Middlebury Weather

The average high temperature in July is 83.8 degrees, with an average low temperature in January of 15.2 degrees. The average rainfall is approximately 51.9 inches per year, with 37.8 inches of snow per year.

Middlebury Map

Middlebury Real Estate Market Conditions

  • Median sales price

    $565,000
    13.4%
    change since last quarter
  • # Active listings

    20
    30-day change

Middlebury Schools and Demographics

Education near Middlebury, CT

City County
High School Graduates 96.52 90.32
College Degree - 2 year 11.52 7.33
College Degree - 4 year 54.83 36.65
Graduate Degree 19.79 11.87
Expenditures per Student 23,138 23,138
Students per Teacher 12.7 12.7

Elementary Schools near Middlebury, CT

Grades Students P/T Ratio ZIP
Andrew Avenue School KG - 04 246 15.4 06770
B. W. Tinker School KG - 05 572 16.3 06708
Brass City Charter School PK - 02 150 10.8 06702
Bunker Hill School PK - 05 511 16.5 06708
Carrington School PK - 07 487 13.9 06708
Central Avenue Preschool PK - PK 24 12 06770
Driggs School PK - 05 528 15.5 06710
Duggan School PK - 08 464 13.2 06708
F. J. Kingsbury School PK - 05 513 17.1 06710
Head Start PK - PK 121 252 06770
Hop Brook Elementary School KG - 04 337 15.7 06770
Long Meadow Elementary School PK - 05 521 13.7 06762
Maloney Interdistrict Magnet School PK - 05 592 13.8 06702
Maple Hill School KG - 04 475 15.8 06770
Middlebury Elementary School KG - 05 348 13.5 06762
Salem School KG - 04 249 16.2 06770
Western School KG - 04 265 17.7 06770

Middle Schools near Middlebury, CT

Grades Students P/T Ratio ZIP
City Hill Middle School 07 - 08 680 16.6 06770
Cross Street Intermediate School 05 - 06 346 16.1 06770
Hillside Intermediate School 05 - 06 304 16.9 06770
Memorial Middle School 06 - 08 460 12.6 06762
Waterbury Arts Magnet School (Middle) 06 - 08 330 16.3 06702
West Side Middle School 06 - 08 1,021 11.8 06708

High Schools near Middlebury, CT

Grades Students P/T Ratio ZIP
John F. Kennedy High School 09 - 12 1,304 14.1 06708
Naugatuck High School 09 - 12 1,259 14.1 06770
Waterbury Arts Magnet School (High) 09 - 12 490 12.2 06702

Ungraded Schools near Middlebury, CT

Grades Students P/T Ratio ZIP
Enlightenment School 06 - 12 179 8.5 06702

Demographics near Middlebury, CT

City County
Neighborhood Type Small town
Population 7,617 864,751
Population Density 429 1,431
Median Age 46.2 40.4
People per Household 2.6 2.5
Median Household Income 124,619 75,043
Average Income per Capita 55,242 41,192

Real estate near Middlebury