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$1,399,900
4 Beds ⋅ 4 Baths ⋅ 24200152 MLS
This custom-built classic brick colonial sits in one of Middlebury's most desirable neighborhoods. A private drive leads to a circular driveway with Belgian block accents, welcoming you into a gracious foyer with a sweeping staircase, on the left a formal living room and on the right a beautiful dining room-both ideal for entertaining. The two-story great room with a fireplace opens to a spacious kitchen featuring custom wood cabinetry, a breakfast bar, and a dining area. Off the kitchen, an all-season sunporch offers the perfect spot for morning coffee or evening drinks. The main floor primary suite includes a bath with a stall shower, jetted tub, and ample cabinet space, along with a walk-in closet and exercise room. Upstairs, you'll find a charming library, a second fireplace, an additional office, a loft and three more bedrooms-one ensuite and two sharing a bath. Outside, enjoy a new raised patio with a hot tub, surrounded by vibrant perennial flowers and bushes. Walking distance to beautiful Lake Quassapaug, minutes to restaurants and shops. 90 min to NYC.

67 Abbott Farms Rd, Middlebury
$999,000
4 Beds ⋅ 4 Baths ⋅ 24203121 MLS
Exceptional opportunity to build a brand-new Colonial-style home at 135 Washington Drive in desirable Middlebury. This proposed 3,485 sq. ft. residence is thoughtfully designed to feature 10 rooms, 4 bedrooms, 3 full baths and 1 half bath, a dedicated home office, fireplace, and 2-car garage, all situated on a beautiful 0.92-acre lot. Home to be built upon buyer contract, offering the opportunity to personalize select finishes and features in consultation with the builder. Final details and specifications subject to approved plans and buyer selections.

135 Washington Dr, Middlebury
$979,900
4 Beds ⋅ 5 Baths ⋅ 24204911 MLS
Welcome to this extraordinary 4,261-square-foot home, truly one of a kind within the complex. This 4 bedroom, 3 full baths & 2 half baths is thoughtfully designed for both elegant entertaining and comfortable everyday living. This exceptional residence offers a first-floor primary suite and an impressive open-concept layout. The luxurious primary suite is a private retreat, featuring a newly remodeled spa-inspired bathroom with beautiful fixtures & elegant, white marble throughout and a relaxing soaking tub. Dual walk-in closets with custom-built organizers provide exceptional storage and organization. For effortless entertaining, the home features a generously sized kitchen, opened to a spectacular, 2 story great room. A substantial center island creates the perfect gathering space, while an abundance of rich cherry cabinetry provides both warmth and exceptional storage. The seamless connection between the kitchen and great room makes entertaining and everyday life feel effortless. The impressive great room creates a dramatic focal point, filling the home with an abundance of natural light and offering a wonderful sense of openness yet providing warmth with the grand, stone, gas fireplace. A dedicated dining room with French doors, creating an inviting connection to the surrounding living spaces both for family and friends.

9 Whitehall 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
$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
$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
$724,900
4 Beds ⋅ 4 Baths ⋅ 24161366 MLS
Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting dinner parties. The entertaining continues into a well-lit living room and a separate, cozy family room-offering plenty of space for everyone to relax. Upstairs, you'll find the home's private sleeping quarters, featuring three bedrooms and two full bathrooms. Need more room? Then travel downstairs to a highly versatile area that can function as additional bedrooms, a dedicated office space, or even a perfect in-law suite thanks to an additional full bathroom. The partially finished basement is an entertainer's dream, complete with a dedicated media room and storage galore. The unfinished portion offers even more practicality, serving as a workshop for tools and crafts, along with abundant extra storage. Step outside to your private yard, a true outdoor oasis! The landscaped pool area is an entertainer's delight, offering the perfect backdrop for summer barbecues and weekend relaxation. With plenty of parking, hosting friends and family is always a breeze. This distinctive property truly is a must-see!

80 Pine Hollow Dr, Middlebury
$675,000
4 Beds ⋅ 4 Baths ⋅ 24202816 MLS
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 bedrooms, a full bath, and a huge bonus room with endless possibilities for a home office, recreation room, or additional living space. The finished lower level includes an in-law setup with a walkout, providing excellent flexibility for extended family, guests, or additional living space. Enjoy beautiful views across to Long Meadow Pond from the covered rear deck off the great room, or relax and entertain on the expansive patio area. A three-car garage provides plenty of room for vehicles, storage, and hobbies. Additional features include a whole-house propane generator and newer roofs on both the house and shed, installed in 2023. Ideally located in a great setting, this meticulously maintained custom home offers comfort, space, versatility, and beautiful views-truly a special property you'll want to see!

46 Washington Dr, 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
$660,000
4 Beds ⋅ 4 Baths ⋅ 24167501 MLS
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.

90 Fenn Rd, Middlebury
$649,900
4 Beds ⋅ 4 Baths ⋅ 24178550 MLS
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.

168 N Farm Rd, Middlebury
$599,900
4 Beds ⋅ 4 Baths ⋅ 24146182 MLS
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 !!! AS IS SALE (INSPECTIONS ARE INFOMATIONAL PURPOSES ONLY )

3 Brookside Dr Unit 3, Middlebury
$599,900
4 Beds ⋅ 4 Baths ⋅ 24145711 MLS ⋅ Brookside Of Middlebury BLDG.
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. AS IS SALE (INSPECTIONS ARE INFOMATIONAL PURPOSES ONLY )

3 Brookside Dr Unit 3, 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
$585,000
4 Beds ⋅ 4 Baths ⋅ 24164662 MLS
Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The charming sunroom opens to a stone patio, ideal for enjoying the serene setting of mature trees, gardens, stone walls and rolling and level lawns. The property is surrounded by Middlebury Land Trust land, including the preserved Brookdale farm across the street. Additional features include an attached 2-bay garage and a 20kW Generac generator.Pool is being sold "as-is." Middlebury offers an extensive variety of outdoor enjoyment such as the Middlebury Rec Area, Quassy Amusement Park, Lake Quassapaug, the 4.5 paved Greenway walking trail, Meadowview Park and the John Largay Preserve. Come take a look!

66 Artillery Rd, 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
$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
$479,900
4 Beds ⋅ 2 Baths ⋅ 24200006 MLS
Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy access to the large deck, and back yard-perfect for all your outdoor entertaining. Two bedrooms, and recently renovated full bath and hardwood floors complete the main level. As you walk upstairs you will find a Full remodeled bathroom, A bedroom and A large primary bedroom, with vaulted ceilings, slider to balcony overlooking your landscaped back yard, A large closet, hardwood floors and fresh paint finish out this fabulous space. Added bonuses include full walk out basement into one car garage, ample storage, large shed and parking for the whole family. Don't miss out on the chance to make this move-in ready home yours! It is close to Route 84 and Middlebury walking trail. Welcome to Middlebury and their award- winning region 15 school.

106 Steinmann Ave, Middlebury

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