Middlebury CT Real Estate & Homes for Sale

9 Properties Found

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Beds:
3
Baths:
3.00
Sq.Ft.:
2,734
Status:
Active
MLS#:
24185515
Type:
Single Family
Subdivision:
N/A
Lot size:
1.22 Acres
Year built:
1978
Courtesy: KW Legacy Partners 860-313-0700
View additional info

ADDITIONAL INFORMATION

Nestled on 1.22 acres of park-like grounds, this 2,734 sq ft contemporary offers the privacy & serenity you've been searching for, lovingly maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors or gather in the huge family room- another fireplace and generous proportions make it the heart of the home. The eat-in kitchen features a breakfast bar, perfect for casual mornings. Three bedrooms, 2.5 baths, and 3 fireplaces offer the comfort and warmth your family deserves. And, when you want to escape, a finished mancave with wet bar is all yours. Outside, a 54-foot deck provides the ultimate backdrop for outdoor entertaining, overlooking your own private retreat. Three oversized garages and newly paved driveway add convenience and curb appeal alike. Oh, and by the way, please do not forget to walk up a couple of steps behind the deck to a beautiful level lot adjacent to a tree lined area. Perfect for incorporating your very own fire pit or gazebo, for further relaxation and enjoyment. Peace of mind comes built-in with recent updates including a new whole-house generator (1 yr), deck (3 yrs), electric hot water heater (3 yrs), paved driveway (2 yr), and a 15-year roof. Located in the New England town of Middlebury, known for its small-town character and top-rated schools.

Beds:
3
Baths:
4.00
Sq.Ft.:
3,494
Status:
Active
MLS#:
24184419
Type:
Single Family
Subdivision:
N/A
Lot size:
0.69 Acres
Year built:
2002
Courtesy: William Raveis Real Estate 203-426-3429
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ADDITIONAL INFORMATION

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 bedrooms with full bath access and a spacious loft that could easily serve as a fourth bedroom, office, or additional living area. Updates include refinished hardwood floors, fresh interior paint, updated hardware, select new lighting, and many more chic updates. A paver patio, established gardens, landscape lighting, central vacuum, generator plug, EV charging capability, and unfinished lower level, ready for you to finish for additional living space, complete this exceptional home.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,528
Status:
Active
MLS#:
24184437
Type:
Single Family
Subdivision:
N/A
Lot size:
1.25 Acres
Year built:
1790
Courtesy: Regall Realty, LLC 860-966-3804
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ADDITIONAL INFORMATION

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates throughout. Set on 1.25 meticulously landscaped acres, this 5-bedroom, 3-bath home offers warmth, space, and versatility. Built-in equity is an added bonus, with a recent appraisal valuing the home at $715,000. The stunning grounds feature mature plantings, classic New England stone walls, and inviting patio spaces that create a private outdoor retreat ideal for relaxing or entertaining. Easily accessed from the kitchen, the outdoor living areas offer seamless flow for gatherings, dining, and enjoying the peaceful setting. Inside, the updated eat-in kitchen features a fireplace with pellet stove insert, while the formal living room offers a second fireplace and the bright sunroom provides flexible living space. A separate outbuilding/studio expands the possibilities-perfect for an artist, home office, workshop, guest space, or easily converted into a detached in-law setup. Extensive updates include newer windows, updated plumbing, replaced well pump and pressure tank, newer oil tank, furnace burner replacement, exterior painting, new appliances, renovated studio/office, and a full first-floor bath. The main level has been updated with sheetrock replacing original plaster walls and ceilings, while the upper level retains its original plaster craftsmanship and antique character. A rare opportunity to own historic beauty, modern function, and value-without historic district restrictions.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,302
Status:
Active
MLS#:
24178550
Type:
Single Family
Subdivision:
N/A
Lot size:
2.34 Acres
Year built:
1981
Courtesy: Showcase Realty, Inc. 860-274-7000
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,863
Status:
Active
MLS#:
24169624
Type:
Single Family
Subdivision:
N/A
Lot size:
14.85 Acres
Year built:
2008
Courtesy: Klemm Real Estate Inc 860-868-7313
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ADDITIONAL INFORMATION

Tucked along Big Cove on Lake Quassapaug, this custom architect designed Arts & Crafts bungalow is privately set on 14.85 serene acres with a path to your own cove frontage. Thoughtfully designed with the current owner's many updates and improvements and timeless materials, the home features a living room with a stone fireplace crafted from the property, a well-appointed kitchen with Custom Point cabinetry, honed granite, Wolf and Bosch appliances, and a Sub-Zero refrigerator, all opening to terraces, gardens, and a conservatory. The main-level primary suite offers two walk-in closets, a full bath, and terrace access. Upstairs includes a family room, office nook, two bedrooms, and full bath. Additional highlights include quarter-sawn white oak floors, 9' ceilings, radiant heat (kitchen, conservatory, baths), a walk-out lower-level heated recreation space, wine room and gym, plus Viessmann mechanicals and Unico A/C (5 zones). Outbuildings include two garages --one heated and cooled with epoxy floors, an equipment barn with greenhouse, and potting and wood sheds. Gated drive, magnificent stone outdoor fireplace and shower, electric awnings, and buried cistern irrigation complete this turnkey offering. Rarely does a property balance artistry, privacy, and livability so gracefully. This is a place to slow down, to gather, and to stay.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,162
Status:
Active
MLS#:
24167501
Type:
Single Family
Subdivision:
N/A
Lot size:
1.67 Acres
Year built:
1989
Courtesy: BHGRE Gaetano Marra Homes 203-758-1300
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ADDITIONAL INFORMATION

The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both rooms. You can then make your wy to the oversized kitchen with separate dining area, featuring updated quartz counters and newer appliances. The kitchen is open to the family room and on cool nights you can enjoy the fireplace from both rooms. Upstairs the four bedrooms and two full baths create comfortable living quarters. In addition, an unfinished 21'x22 over the office is a fabulous opportunity for the new owner to add more space to this already spacious home. There is more than enough storage area provided by the walk up attic and the full basement that offers an overhead garage door for easy access. The current owner had converted the former 600 sq. ft garage as a dentist office after acquiring a certificate of zoning compliance.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,877
Status:
Active
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:
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:
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.

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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


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.



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

    N/A
  • # Active listings

    12
    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