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$2,850,000
8 Beds ⋅ 8 Baths ⋅ 24151632 MLS
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

775 South St, Middlebury
$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
$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
$950,000
5 Beds ⋅ 4 Baths ⋅ 24198521 MLS
Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home includes wide-board floors, three fireplaces and a remarkable series of covered porches and "piazzas" capturing the romance of 19th-century country living. There is effortless flow from the gorgeous sunroom, with walls of windows, into the formal living room, dining room and large entertaining kitchen. A main-floor laundry room, enormous utility room, pantry and powder room add convenience. The primary suite offers a private retreat, with an en-suite bath and adjoining sitting room or study, flanked by two covered porches. Outside, a charming secluded wading pool with fountain provides a wonderfully relaxed setting for summer gatherings, cocktails and afternoons spent enjoying the gardens. A detached 2-car garage with bonus unfinished loft space invites a future artist studio. An exceptional opportunity to bring this distinctive home to the next level. 2 hrs to NYC. Subject to Probate.

552 Breakneck Hill Rd, Middlebury
$879,900
3 Beds ⋅ 4 Baths ⋅ 24184419 MLS
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.

25 Avalon Dr, 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
$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
$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
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
$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
$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
$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
$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

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