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$2,195,000
3 Beds ⋅ 3 Baths ⋅ 24169624 MLS
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.

397 White Deer Rock Rd, Middlebury
$849,900
3 Beds ⋅ 3 Baths ⋅ 24128666 MLS
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.

6 Deer Run Rd, Middlebury
$829,900
3 Beds ⋅ 3 Baths ⋅ 24200862 MLS
Welcome to Avalon Farms community. This home is located in Middlebury's most desirable and beautifully maintained subdivision, which is known for its unique Cotswold inspired architecture and beautifully preserved and manicured settings. This turnkey home has been so lovingly cared for. There is nothing you need to do but make this space yours. Everything feels fresh and new! Walk in the door and feel instantly relaxed by the neutral colors carefully chosen throughout the home which showcase all the many updates this home provides with beautifully maintained hardwood floors throughout the first floor. The convenience of having a first-floor primary suite with so many added touches, such as tray ceiling, 2 spacious walk-in closets, and a beautifully updated master bath with towel warmers complete this bedroom oasis. The kitchen truly serves as the heart of the home, featuring an oversized center island with granite countertops that complement the updated Jenn Air stainless steel appliances. This kitchen is an entertainer's dream for everything from casual mornings to hosting holidays with family and friends. First floor laundry adds everyday convenience, while soaring cathedral ceilings create an open, airy feeling throughout the living room. Step outside to the expansive 18x30 mahogany rear deck where privacy and serenity await as you enjoy views of Avalon Farm Pond from afar throughout much of the year.

29 Cambridge Ct, Middlebury
$819,000
4 Beds ⋅ 3 Baths ⋅ 24203733 MLS
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 countertops, stainless steel appliances, a large center island, and walk-in pantry. It opens to the dining area and spacious family room with gas fireplace and sliders to the 17' x 15' rear patio. A formal dining room and flexible main-level bedroom/half bath add versatility. Upstairs, the spacious primary suite is a true retreat, featuring a beautifully finished ensuite with dual quartz-topped vanities, elegant oval sinks, and a 4' x 5' glass-enclosed walk-in shower. The suite includes two walk-in closets, highlighted by an impressive 12' x 14' dream closet/changing room-perfect for anyone who has always wanted exceptional wardrobe space. An upper-level laundry closet and additional full bath with double vanity, granite, tile flooring, and glass-enclosed tub/shower complete the second floor. Enjoy all that Middlebury and the surrounding area have to offer, from parks, trails, recreation, dining, and shopping to convenient access to neighboring communities. Beautifully designed, thoughtfully finished, and ideally situated, this is a home designed for modern living and enjoying life

18 Hunting Ridge Rd, Middlebury
$779,900
4 Beds ⋅ 3 Baths ⋅ 24206538 MLS
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 and an incredible great living-room with fireplace-perfect for entertaining or relaxing with family. The main level features hardwood flooring, generous formal living and dining areas, a private office, and a spacious eat-in kitchen with granite countertops and stainless appliances. The primary suite includes a private en-suite bath with Jacuzzi tub, while three additional bedrooms provide plenty of room for family and guests. Enjoy the privacy of the expansive grounds from the large deck, along with a two-car garage, large unfinished basement space, generator hookup, and brand-new central air system. The rooftop solar system also offers a favorable locked-in lease rate with for transfer to the next owner. Located in one of Middlebury's most sought-after residential neighborhoods, this home offers the space and privacy of an acreage property while remaining convenient to local amenities, , and surrounding communities plus its within the Region 15 school district.

182 Green Hill Rd, Middlebury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24147892 MLS
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.

117 Crest Rd, Middlebury
$670,000
4 Beds ⋅ 3 Baths ⋅ 24191383 MLS
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 kitchen opens to the family room with a fireplace, creating a comfortable gathering space. A half bath completes the first floor. Upstairs you'll find 4 bedrooms, including a primary suite with two walk-in closets and a full bath with a corner tub. The second-floor laundry adds everyday convenience. The unfinished walk-out basement offers excellent storage and future expansion potential. Outside, enjoy the deck, patio, and private backyard. Conveniently located in the award-winning Region 15 school district and close to parks, schools, the library, shopping, restaurants, and major commuter routes. A move-in ready home in a sought-after neighborhood.

10 Curtis Rd, Middlebury
$649,900
3 Beds ⋅ 3 Baths ⋅ 24185515 MLS
MAKE OFFER! Nestled on 1.22 acres of park-like grounds, this large custom designed home offers 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.

70 Pine Hollow Dr, Middlebury
$600,000
3 Beds ⋅ 3 Baths ⋅ 24191400 MLS ⋅ Steeplechase BLDG.
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. The primary suite features two walk-in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury
$600,000
3 Beds ⋅ 3 Baths ⋅ 24202542 MLS
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. The primary suite features two walk- in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury
$599,900
3 Beds ⋅ 3 Baths ⋅ 24203901 MLS
Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

58 Shadduck Rd, Middlebury
$590,000
4 Beds ⋅ 3 Baths ⋅ 24184437 MLS
This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates. Built-in equity! Recent appraisal values this home at $715,000. Set on 1.25 meticulously landscaped acres, this 4-bedroom, 3-bath home offers warmth, space, and versatility with a huge finished attic space. 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

700 Watertown Rd, Middlebury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24190906 MLS
Tucked into Middlebury's desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the home's two floor-to-ceiling fireplaces - a warm focal point for gatherings large and small. Just off the living space, the generous eat-in kitchen showcases updated stainless steel appliances and flows through sliding glass doors to a spacious back deck, an effortless setting for morning coffee, summer grilling, or weekend entertaining. Upstairs, two well-proportioned bedrooms provide a quiet retreat, served by two full baths newly remodeled with a clean, contemporary finish. The primary is located on its own level and provides all the area you ever wished for. Additional highlights include the convenience of city water and city sewer, recessed lighting throughout, and thoughtful updates that make this home genuinely move-in ready. All of this in one of Middlebury's most established neighborhoods, with quick access to Route 64 and I-84 for an easy commute toward Waterbury, Southbury, and beyond, plus shopping, dining, and everyday amenities close at hand. A rare opportunity to own a turnkey home in a location that truly delivers. Schedule your private showing today. Porch is now painted black.

2 Northwood Dr, Middlebury
$539,000
3 Beds ⋅ 3 Baths ⋅ 24191913 MLS
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.

123 Northwood Dr, Middlebury
$539,000
4 Beds ⋅ 3 Baths ⋅ 24194559 MLS
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.)

323 Watertown Rd, Middlebury
$534,900
3 Beds ⋅ 3 Baths ⋅ 24189888 MLS
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury
$534,900
3 Beds ⋅ 3 Baths ⋅ 24188488 MLS ⋅ Steeplechase BLDG.
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury
$529,900
3 Beds ⋅ 3 Baths ⋅ 24186753 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to 10 Ridgewood Drive in Middlebury, located in the highly sought-after Ridgewood community, offering exceptional amenities including a clubhouse, swimming pool & tennis courts. This beautifully maintained townhouse is being offered for sale by its original owner and has been extensively remodeled throughout. The main level features an open-concept floor plan designed for today's lifestyle, with gleaming hardwood floors and a convenient first-floor half bath. The updated eat-in kitchen boasts granite countertops, stainless steel appliances and direct access to a private deck perfect for relaxing or entertaining. The second floor offers 3 generously sized bedrooms and 2 full baths. The spacious primary suite features a walk-in closet, double vanity, soaking tub, and separate shower. A conveniently located second-floor laundry area with washer and dryer adds to the home's functionality. Need even more living space? The finished third-floor loft provides endless possibilities as a home office, fitness area, or guest suite. Additional features includes a 1-car garage, full basement offering abundant storage, and an efficient three-zone heating and cooling system, allowing you to maximizing energy efficiency. Ideally situated near the community clubhouse and pool, and just minutes from shopping, restaurants, walking trails and major highways, this exceptional home offers the perfect combination of comfort, style, and convenience in one of Middlebury's premier communities.

10 Ridgewood Dr Unit 10, Middlebury
$499,000
4 Beds ⋅ 3 Baths ⋅ 24188724 MLS
Welcome to this meticulously maintained and exceptional 4-bedroom, 2.5-bathroom Colonial that perfectly blends classic comfort with wonderful living space. ADDED BONUS - Solar panels that have no monthly fee and very low usage expense! Winter months around $60 month, Summer bill typically no more than $180. Annual average $1530!! Step inside to find a warm, welcoming interior defined by beautiful hardwood flooring. The main floor features a cozy living room anchored by a traditional wood-burning fireplace, creating the perfect focal point for quiet evenings, as well as two comfortable bedrooms and a full bathroom. Upstairs, you will find two more generously sized bedrooms and a second full bathroom, offering a highly functional layout for family or guests. The lower level expands your options significantly, boasting a spacious family room equipped with a wood-burning stove to keep the space warm and inviting. Step outside to find a fantastic, large backyard featuring a level lawn and a handy storage shed to keep tools organized. Tucked away in a peaceful Middlebury neighborhood, this home offers an exceptional location where you are just minutes away from local outdoor recreation at the Middlebury Greenway and Meadowview Park, as well as convenient neighborhood dining, shopping, and everyday amenities right down the road. This beautiful, turnkey property is ready for you to move right in and make it your own!

213 Acme Dr, Middlebury
$474,900
3 Beds ⋅ 3 Baths ⋅ 24200565 MLS
Move-in ready and thoughtfully renovated this 7-room, 3-bedroom, 2.5-bath home offers 1,357 sq ft of stylish living space plus an additional 480 sq ft finished walkout lower level, set on a quiet cul-de-sac. The open-concept main level features a spacious Living Room and Dining Room flowing into an expansive Eat-In Kitchen, with direct access to a large deck overlooking a private backyard-ideal for outdoor dining, entertaining, or relaxing. Three bedrooms and two fully renovated full baths complete the main level. The finished walkout lower level adds valuable flexibility with a large Family/Recreation Room, laundry room with half bath, and abundant storage. Additional highlights include Central Air Conditioning, attached 2-car garage, maintenance-free vinyl siding, and convenient access to shopping, dining, recreation, and major commuter routes. Beautifully updated and ready to enjoy, this home offers the perfect blend of comfort, functionality, and lifestyle convenience. A wonderful opportunity to make this inviting property your own and enjoy a place to call home.

133 Algin Dr, Middlebury
$449,900
3 Beds ⋅ 3 Baths ⋅ 24191937 MLS
Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. A cozy fireplace, central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system was installed on 7/14/26, adding to peace of mind.

42 White Ave, Middlebury

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