Middlebury, CT Homes for Sale under $900,000

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

Jodi Dawley Real Estate Two

Welcome to Hunting Ridge Estates! This stunning 2,700 sq. ft. Colonial, built in 2025 and just 14 months young, is located in a desirable 23-home Middlebury subdivision. Offering the ease and feel of new construction, this 4-bedroom, 4-bath home features an open floor plan and hardwood flooring throughout both levels. The bright, stylish kitchen showcases white shaker cabinetry, off-white quartz

Robert Disapio Dave Jones Realty, LLC

Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters,

Michael Vartolone William Raveis Real Estate

Welcome to 182 Green Hill Road, where space, privacy, and an exceptional Curtis Farms setting come together. Set at the end of a long private driveway on nearly 3 acres, this spacious 4-bedroom, 2.5-bath Colonial offers over 3,000 square feet of living space with an incredible grand living-room with fireplace and vaulted ceiling, perfect for entertaining or relaxing with the family. The main

Chris Jahn Showcase Realty, Inc.

Luxury Toll Brothers built townhome in sought after Ridgewood at Middlebury! This exquisite Denton Elite end unit was customized in 2018 and offers 3 bedrooms, 2.5 baths and over 2,643 sqft of beautifully designed living space. The main level welcomes you with a spacious foyer, double storage closet, private study with garden doors and powder room. The custom kitchen features upgraded cabinetry,

Jay Irvine Serhant Connecticut, LLC

Welcome to this beautifully maintained ranch, ideally situated on a quiet cul-de-sac in one of Middlebury's desirable neighborhoods. Set on a private, level 1 acre lot, this 3 bedroom, 3.5 bath home offers comfort, character, and exceptional space for everyday living and entertaining. The inviting open floor plan features a stunning sunken living room, three fireplaces, and a spacious family

Tina Tanushi Regency Real Estate, LLC

Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional

Sabrina Janco Century 21 Bay-Mar Realty

Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building

Judith Caputo Advantage Realty Group, Inc.

Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry.

Heather Dever Showcase Realty, Inc.

Welcome to 285 Southford Rd, a beautiful spacious ranch which checks off all the boxes. Main level living with Open foyer leading into family room w/ gas fireplace, vaulted ceilings, dimmer controlled recessed lighting, and atrium door opening to stone patio. Formal dining room w/ 9 foot ceilings and plenty of natural sunlight. Eat in kitchen has a bow window and table nook area, an abundance of

Nancy Addessio Showcase Realty, Inc.

Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The

Heather Dever Showcase Realty, Inc.

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.

Jodi Dawley Real Estate Two

Welcome to this beautifully updated 9-room Georgetown Dr. Colonial, offering 4 upper level bedrooms with a practical laundry room, a dedicated office, 3 bathrooms, a 2 car garage, and a landscaped .46-acre lot with the convenience of public water and sewer. This exceptional Strachan built home combines timeless architectural details with modern updates and everyday comfort. Inside, you'll find

Stephen Briotti Lamacchia Realty