Refine Search
Map
Sort by
18 Hunting Ridge Rd, Middlebury
$789,900
4 Beds ⋅ 3 Baths ⋅ 24203733 MLS
Experience uncompromised interior luxury with zero yard-maintenance stress at 18 Hunting Ridge Road. Nestled in a quiet Middlebury cul-de-sac with a natural wooded privacy hill out back, this 2025-built custom Colonial trades endless weekend lawn-mowing chores for spectacular, turn-key indoor living. Step inside to a sprawling, open-concept main floor highlighted by dramatic open-beam ceilings and an abundance of natural light. The chef's kitchen is an absolute showstopper, featuring an oversized quartz island, premium finishes, and a seamless flow into the primary family room. Upstairs, the luxury primary suite serves as a true sanctuary, boasting a massive, dedicated 12' x 14' custom dressing room/changing suite that must be seen to be believed. A flexible main-level bedroom and full bath offer the perfect layout for multigenerational living, long-term guests, or a quiet executive home office. Forget spending your weekends managing sprawling acreage-the rear topography creates a magnificent, maintenance-free natural privacy barrier with absolutely no rear neighbors looking in. Enjoy quiet mornings or evening entertaining on your expansive 17' x 15' rear patio, perfectly curated for an upscale outdoor lounge experience. Equipped with public water, public sewer, and an expansive unfinished full basement ready for future expansion. Perfect for busy professionals, downsizers, or anyone seeking premium custom spaces without the upkeep of a massive lawn.

18 Hunting Ridge Rd, Middlebury
20 Hunting Ridge Rd, Middlebury
$774,900
3 Beds ⋅ 2 Baths ⋅ 24160275 MLS
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.

20 Hunting Ridge Rd, Middlebury
77 Crest Rd, Middlebury
$749,900
4 Beds ⋅ 4 Baths ⋅ 24193938 MLS
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, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.

77 Crest Rd, Middlebury
106 Mirey Dam Rd, Middlebury
$725,000
4 Beds ⋅ 3 Baths ⋅ 24213859 MLS
Located on a most desirable street in North Farms neighborhood, this well loved and beautifully tended 4 bedroom colonial offers great opportunities for comfortable living and entertaining. Filled with light, this home will dazzle you with its beautiful interior. You can prep meals and enjoy them in the updated eat in kitchen with access to a deck overlooking lush grounds. The spacious family room features a fireplace and provides a peaceful retreat after a busy day. The living and dining rooms are great spaces for entertaining and enjoying special times. You can easily relax in the primary bedroom with a recently updated spa-like bathroom and 2 walk in closets. The upper level also features 3 additional bedrooms, an updated full bath as well as a laundry area. You will also enjoy bonus space on the walk out level. The lovely landscaping contributes to the calm atmosphere that surrounds this home. Rear of property adjoins Flanders Nature, further enhancing the privacy of this property.

106 Mirey Dam Rd, Middlebury
783 Whittemore Rd, Middlebury
$725,000
5 Beds ⋅ 3 Baths ⋅ 24213699 MLS
At 783 Whittemore Road, beautifully detailed living spaces are paired with something rarely found in a residential property: an expansive garage with room for far more than everyday parking. Extensively rebuilt in 2010, this Middlebury home offers five bedrooms, three full baths, and remarkable flexibility across its living and utility spaces. Beneath the main living level, the multi-vehicle garage offers substantial room for automobile collections, restoration projects, recreational equipment, and a personal workshop. It's a defining feature for a property where practicality and distinctive design share equal billing. Upstairs, vaulted ceilings, exposed beams, skylights, and blue and green zinc paneling lend architectural character throughout. The kitchen features solid wood cabinetry, a professional gas range, French-door wall oven, convection oven, dual Sub-Zero refrigerators, a separate freezer, and two dishwashers, opening to the dining and family rooms. Radiant-heated hardwood floors distinguish the family room. The primary suite includes a sitting area, two walk-in closets, and a bath with heated floors, soaking tub, oversized shower, and heated towel bars. Additional rooms provide flexibility for living or working, complemented by built-in storage and dedicated laundry. A distinctive combination of craftsmanship, comfortable living, and exceptional space for the things that matter beyond the front door.

783 Whittemore Rd, Middlebury

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 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!