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7-11 Sandy Beach Rd, Middlebury
$4,050,000
6 Beds ⋅ 4 Baths ⋅ 24131596 MLS
SUPERB LAKE PROPERTY. First time on the market, this 4,811 sf shingle-style home on 6.99 acres in Lake Quassapaug's estate area offers 195 feet of direct waterfront with a private dock and small beach. Designed by renowned architect Rick Moisan and built in 2000, the residence blends timeless design with modern comfort, enjoying complete privacy and pastoral views of permanently protected neighboring hayfields and vineyards. This rare offering combines architectural pedigree, serene natural beauty, and versatile living spaces-a true sanctuary for lakefront living. TWO PARCELS. Includes the main residence and a charming two-bedroom cottage sold together. MAIN RESIDENCE. Classic shingle-style architecture with a bright, open layout for today's lifestyle. The living room, dining area, and kitchen flow together beautifully; the kitchen features high-end appliances and opens to an inviting sunroom capturing passive solar warmth. Every room enjoys a full or partial landscape view. A deep covered porch spans the lake side for gracious entertaining, sunsets, and al fresco dining. Large Doric columns frame the space, and a majestic oak anchors the open lawn. COTTAGE. Originally the caretaker's residence for historic Tranquillity Farm, this two-bedroom, 1,005 sf cottage on a separate parcel offers wonderful flexibility as a guesthouse, writer's retreat, or rental.

7-11 Sandy Beach Rd, Middlebury
397 White Deer Rock Rd, Middlebury
$1,925,000
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
82 Mirey Dam Rd, Middlebury
$975,000
4 Beds ⋅ 3 Baths ⋅ 24131272 MLS
Welcome to 82 Mirey Dam Road, Middlebury, CT, a stunning colonial oasis tucked away on 2.74 acres of mature, peaceful landscaping in one of the area's most sought-after neighborhoods. From the moment you arrive, you'll feel the sense of calm this property conveys. Lush landscaping, mature trees, and careful design grant privacy and serenity. The heated saltwater inground pool and outdoor spaces invite you to relax, entertain, and savor every season in your own personal retreat. Inside, the flow is effortless. The freshly painted interior, upgraded windows, and modern lighting set an elevated tone. The fully renovated bathrooms blend style and practicality. Bedrooms are generous with stunning views and light-filled; common rooms are versatile and ideal for both daily living and special occasions. Every major system and feature of this home has been thoughtfully updated, creating a move in ready property with style and reliability. A detailed list of all upgrades is attached to the listing highlighting the extensive improvements that make this property truly move-in ready.

82 Mirey Dam Rd, Middlebury
Lot 41 Somerset, Middlebury
$949,417
3 Beds ⋅ 3 Baths ⋅ 24158747 MLS
Under Construction in One of Middlebury's Most Desirable Neighborhoods! Welcome to the Avalon Farms community-known for its beautiful homes, manicured lawns, and thoughtfully designed landscaping that create a truly picturesque setting. The Cambridge model blends classic design with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious great room features a cathedral ceiling, fireplace, and oversized windows that fill the home with natural light. At the heart of the home is a gourmet kitchen with abundant shaker-style cabinetry and a large center island-ideal for gatherings. A charming breakfast nook with French doors opens to a private deck, perfect for casual dining or relaxing outdoors. For more formal occasions, the home also offers a dedicated dining room for entertaining. The main-level primary suite includes walk-in closets and a luxurious bathroom with a large walk-in shower. This level also features a private den, mudroom, laundry room, and half bath. Hardwood flooring runs throughout the entire first floor. Upstairs, you'll find two generously sized bedrooms connected by a convenient Jack-and-Jill bathroom. Additional highlights include an attached two-car garage, full walk-out basement, central air, natural gas, public water and sewer, and underground utilities. Situated on a cul-de-sac lot, the home will be completed with professional landscaping. Come experience the beauty and comfort of Avalon Farms!

Lot 41 Somerset, Middlebury
851 South St, Middlebury
$937,500
5 Beds ⋅ 3 Baths ⋅ 24167191 MLS
Welcome to this beautifully updated home which offers modern comfort, high-end finishes & peace of mind with several upgrades already completed! Located in Middlebury's South Street neighborhood this Colonial is 3300 sq ft on a 1.85 acre lot. Step in to a bright & inviting foyer feat. a high ceiling, a custom wood & glass front door & a stunning custom handrail leading the expansive 4 bedrooms. On the main level you will find a formal living room with coffered ceilings, French doors & a large dining room with plenty of room for gathering to enjoy a meal.The spacious great room offers a gas fire place, gleaming HW floors & French doors leading out to an oversized deck as well as a custom stone patio w/a built-in fire pit surrounded by a stone wall & beautiful gardens. The chef's kitchen is the heart of the home where everyone gathers around d the kitchen island. Seating around the breakfast bar with quartzite counters is the perfect spot to enjoy a cup of coffee in the morning. Included in the dream kitchen is a 6 Burner Thermador, range/oven, a SS Subzero side by side refrigerator, a SS microwave tucked neatly in the island, a SS dishwasher & a large farm sink. An oversized powder room & nice sized office finish off the first floor. Upstairs the Primary Suite features a tray ceiling, walk-in California Closet w/plenty of storage & new tile flooring. The on Suite to the Primary has heated Calcutta Gold Marble flooring, custom vanity, walk-in, extra large shower & soaking tub.

851 South St, Middlebury
625 Charcoal Ave, Middlebury
$900,000
3 Beds ⋅ 3 Baths ⋅ 24199862 MLS
Rare 20+ acres with 1920's house and 3 outbuildings in Middlebury estate area near Lake Quassapaug and the Highfield Club. Very private settling up long driveway with mature landscaping. 3 bedroom main house with multiple entertainment rooms and 2 kitchens. 3 bay car barn with large storage area and loft. 2 other small outbuildings. Great opportunity for someone with vision to bring property to life.

625 Charcoal Ave, Middlebury
286 Mirey Dam Rd, Middlebury
$900,000
4 Beds ⋅ 3 Baths ⋅ 24179200 MLS
Set in one of Middlebury's most desirable neighborhoods, this lovingly maintained 4,450 sq. ft. Colonial welcomes you with a beautiful paver driveway, manicured lawn, and timeless curb appeal. Step inside the sunny two-story foyer and feel right at home. The spacious eat-in kitchen is designed for gathering, featuring granite counters, a center island, breakfast bar, and generous dining area. For more intimate occasions, enjoy the formal dining room and living room with fireplace. The grand first-floor cathedral family room offers a second cozy fireplace and atrium doors leading to an expansive paver patio with firepit, perfect for outdoor entertaining The main level also includes a welcoming sunroom, office or optional bedroom, full bath, and spacious laundry room with abundant storage. Upstairs, you'll find four generously sized bedrooms and a full hall bath, including a primary suite with private bath, jetted tub, shower, double sinks, and a walk-through closet. A 25' x 16' great room with separate access to the 3-car garage offers excellent flexibility for a home office, gym, recreation space, or potential in-law setup. A wonderful opportunity to enjoy space, comfort, and versatility in a sought-after Middlebury setting.

286 Mirey Dam Rd, Middlebury
383 Leonard Rd, Middlebury
$895,000
4 Beds ⋅ 5 Baths ⋅ 24141215 MLS
Welcome to your dream home...a beautifully designed 3220 sq ft NEW CONSTRUCTION offering warmth, space and flexibility for today's modern family. With 4 generous bedrooms and 4.5 bathrooms, this home invites you to live, laugh and grow in comfort. You have to see in person to appreciate the design of each of the bedrooms with their one full bath and double closet space. The heart of the home is the open concept main level, where the kitchen, dining and living areas come together around a cozy electric fireplace- perfect for family dinners, holiday gatherings, or quiet evenings in. The chef's kitchen is as functional as it is stunning, featuring granite countertops, tiled backsplash, double ovens, a large island ideal for casual meals and an abundance of cabinets for all your kitchen treasures. Step through the sliding doors to a spacious trex deck(16x12), perfect for morning coffee or weekend barbecues. Stairs led you down to a charming patio and walkway the wraps around the home- an entertainer's dream and safe place to play and explore. The lower level is designed with versatility in mind- a warm family room, a private bedroom with half bath (easy convertible to full) for guests or possible in law setup and another full bathroom with a second laundry hook-up for more convenience. Upstairs, the peaceful oversized primary suite is your personal retreat complete with a large walk-in closet and a spa-like bathroom featuring a soaking tub, glass shower and double vanities

383 Leonard Rd, Middlebury
245 Upper Whittemore, Middlebury
$875,000
3 Beds ⋅ 3 Baths ⋅ 24167463 MLS
Enjoy magnificent sunsets from this exceptional home, privately set on just over three acres in one of the area's most desirable locations. The beautifully landscaped grounds offer both open space and a wooded backdrop for added privacy, along with views of a neighboring stone wall. An in-ground heated saltwater pool is surrounded by an expansive patio and charming pergola-perfect for outdoor entertaining. Three garages are conveniently accessible from both the upper and lower driveways. Inside, the home features 2,990 square feet of thoughtfully designed living space with custom touches throughout. The spacious kitchen includes a dining area, breakfast bar, and a 36" GE Monogram dual-fuel range, offering ample space for cooking and gathering. The adjoining 23' x 20' family room provides a welcoming setting, a propane fired custom fireplace and overlooks the scenic rear property. The primary suite features a walk-in closet, an additional closet, and an updated full bath. The main level is completed by a formal dining room, private office/library, powder room, and laundry area. Upstairs, you'll find two additional bedrooms, a full bath, and a flexible guest area and lots of room for expansion. Additional highlights include the lush grounds, patio, heated saltwater pool, pergola, and more.

245 Upper Whittemore, Middlebury
25 Avalon Dr, Middlebury
$865,000
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
122 Crest Rd, Middlebury
$850,000
3 Beds ⋅ 3 Baths ⋅ 24168079 MLS
Welcome to your own private retreat at 122 Crest Road-where timeless charm meets thoughtful modern updates. This beautifully maintained 3-bedroom, 2.5-bath Cape Cod-style home is just moments from town, the library, green, and local dining. Designed with both everyday living and entertaining in mind, the home features a custom sunken great room with a dramatic wall of windows that floods the space with natural light and showcases the surrounding landscape. Sliding doors lead seamlessly to a bluestone patio, creating indoor-outdoor flow. The kitchen has new appliances and opens nicely to the great room, enhancing the home's open feel. For more formal gatherings, enjoy the elegant dining room with French doors leading to a charming screened porch, as well as a separate formal living room featuring a fireplace and custom built-ins. Wide plank hardwood flooring adds warmth and character throughout much of the home. A dedicated study offers a cozy fireplace and built-ins-perfect for a home office or quiet retreat. The main-level primary suite is a very nice convenience. Extensive recent upgrades include a new roof, new Hardie board siding, new gutters, new central air system (including air handler), new boiler, new windows, and a security system. Professionally landscaped grounds, mature trees, stone walls and bluestone create a serene setting, yet remains close to everything. Includes a whole house generator. A full list of improvements is available. 90 miles to NYC.

122 Crest Rd, Middlebury
29 Cambridge Ct, Middlebury
$844,760
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
11 Hunting Ridge Rd, Middlebury
$820,000
4 Beds ⋅ 3 Baths ⋅ 24055021 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting Ridge Road (aka Lot 3) is to be built. It is a 2700 sq ft colonial with 2 car attached garage.Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office. 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 !!

11 Hunting Ridge Rd, Middlebury
38 Avalon Dr, Middlebury
$815,000
3 Beds ⋅ 3 Baths ⋅ 24180471 MLS
Welcome to Avalon Farms community, located in one of Middlebury's distinctive residential communities, known for its beautifully built, upscale homes. The home is known for its European inspired architecture, beautifully preserved, natural surroundings, at the end of a cul-de-sac, which suits any stage of life you're in. Step inside to a grand two-story foyer that sets the tone for the homes spacious, filled with natural light. This 3 bedroom, 2.5 bath home has an open floor plan great for entertaining. The primary bedroom situated on the first floor, features a coffered ceiling, a generous walk-in closet, with a spacious bathroom complete with a walk-in shower & whirlpool tub. Directly off the primary bedroom there are endless opportunities, whether that space may serve as a nursey, office space or play area. The kitchen serves as the heart of the home, featuring a spacious granite island, abundant cabinetry, and plenty of storage perfect for everyday living, entertaining, and gathering with family & friends. Conveniently off the kitchen you have first floor laundry in its own dedicated space with a utility sink and tons of storage space. Two spacious bedrooms & a full bathroom complete the upstairs and if you needed more space you will find a heated finished basement as well.

38 Avalon Dr, Middlebury
18 Deer Run Rd, Middlebury
$810,000
3 Beds ⋅ 3 Baths ⋅ 24099002 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 18 Deer Run Road (aka Lot 20) 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.

18 Deer Run Rd, Middlebury
1 Hampshire Ct, Middlebury
$800,000
4 Beds ⋅ 4 Baths ⋅ 24124736 MLS
Welcome to Avalon Farms in Middlebury, one of the area's most desirable single-family home communities. This exceptional residence offers 4 bedrooms, 3.5 baths, and 3,711 sq. ft. of living space, perfectly combining comfort, style, and functionality. Set on one of the few lots overlooking the serene community pond, this home invites you in with a dramatic two-story foyer. The spacious first-floor primary suite provides a private retreat, while the second level boasts three generously sized bedrooms, one with its own en-suite bath and the other two access to a full bathroom. Designed for everyday living and entertaining, the main floor features a well-appointed kitchen and dining area that opens to a deck with tranquil water views. A mudroom and laundry room add convenience, and the two-car garage provides ample storage. The walkout basement offers an abundance of natural light and endless possibilities to create a recreation room, gym, or additional living space. Don't miss the opportunity to own a rare pond-front property in Avalon Farms-where comfort meets community.

1 Hampshire Ct, Middlebury
64 Watertown Rd, Middlebury
$759,900
3 Beds ⋅ 4 Baths ⋅ 24166543 MLS
Spacious and meticulously maintained Cape offering 3 bedrooms and 3.5 baths with a flexible layout designed for today's lifestyle. The main level features a stunning home office with custom built-ins and fireplace, and a kitchen with a Wolf gas range/oven, Sub-Zero refrigerator, and center island with beverage cooler. Upstairs, you'll find generously sized bedrooms, including a spacious primary suite with two walk-in closets, along with a versatile flex room. The walkout lower level offers additional finished space with flexible use potential, ideal for extended living. Step outside to your private outdoor oasis featuring a saltwater, in-ground heated pool with LED lighting, hot tub, outdoor shower, and an expansive deck with built-in speakers throughout-extending to the pool and patio-perfect for entertaining or relaxing. A brand-new pool liner and steps complete the space. Additional highlights include a 2-car attached garage with EV charging, a newer roof, full property irrigation, and numerous upgrades throughout. Don't miss out on this beautiful home!

64 Watertown Rd, Middlebury
366 Charcoal Ave, Middlebury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24158517 MLS
This beautiful 9 room colonial has every attention to detail and all the features that a discriminating buyer is looking for. Set on a private 3.34 acre lot with a 10' X 16' shed in a sought-after, very commuter friendly neighborhood, this 3,198 square foot residence boasts 4 bedrooms, 2-1/2 bathrooms, a bright and airy 25' X25' main floor family room with cathedral ceilings, built-ins, a fireplace with pellet stove and atrium doors to a private 14' X 24' deck, plus an additional 480 SF finished lower level with interior access to the 2 car oversize garage, a mudroom and a recreation room. The main floor has an updated eat-in kitchen with granite countertops, newer appliances, and an island. The open foyer leads to a large living room and dining room with wainscoting and a half bath. The upper level has 4 generously sized bedrooms and 2 bathrooms, including a 17' X 20' primary bedroom with a newly remodeled on-suite bathroom. Other amenities include central A/C, central vacuum, security system, Ring doorbells and flood lights, a generator hookup, detailed trim work throughout, built-in shelving galore and hardwood floors. The roof and gutters are only 2 years old. The Thermo-Pride hot air furnace was installed in 2019. This well maintained home will provide buyers with many more years of carefree and very pleasurable living.

366 Charcoal Ave, Middlebury
28 Hunting Ridge Rd, Middlebury
$740,000
4 Beds ⋅ 3 Baths ⋅ 24079497 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. 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.

28 Hunting Ridge Rd, Middlebury
117 Crest Rd, Middlebury
$735,000
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
179 Burr Hall Rd, Middlebury
$730,000
4 Beds ⋅ 3 Baths ⋅ 24196075 MLS
This stunning ranch blends contemporary style with effortless one-level living. The open floor plan is filled with natural light, highlighted by dramatic floor-to-ceiling windows that create a bright and inviting atmosphere throughout. The beautifully updated interior features a luxurious primary suite and stylish, high-quality finishes at every turn. Designed for both everyday living and entertaining, the seamless indoor-outdoor flow leads to an expansive deck that spans the entire length of the home, overlooking the spectacular backyard. This exceptional home offers the perfect balance of luxury, comfort, and timeless appeal-an opportunity not to be missed. Your private outdoor oasis includes an inground pool, multiple patios, a hot tub, and beautifully landscaped grounds that offer exceptional privacy. Located in a premier neighborhood, this home combines sophisticated design, abundant natural light, and resort-style amenities in an unparalleled setting.

179 Burr Hall Rd, Middlebury
200 N Farm Rd, Middlebury
$728,000
4 Beds ⋅ 4 Baths ⋅ 24163117 MLS
Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth wall, custom remote blinds, a fabulous wood wet bar area as well as built-in entertainment cabinet. The eat-in kitchen invites you to enjoy meals & coffee looking out at the beautiful backyard or relax on the screened in porch. A formal dining area & living room are perfect for entertaining & enjoying the views through the oversized windows. Upstairs you will find 4 large bedrooms including the Primary suite with sitting area, remote control blinds, custom bathroom cabinets, a walk-in shower, as well as radiant heated floors. You'll find your private oasis in the backyard with an amazing in-ground pool & features an electric pool cover that is walkable for added safety, a large spa with cover, composite deck for low to no maintenance, 2 large resort style sun umbrellas & an electric awning! You'll never want to leave your backyard! Don't miss the walk up attic storage area in the mudroom waiting for your imagination! With a 3 car attached garage & an automatic generator everything has been thoughtfully planned when this home was built by this family!

200 N Farm Rd, Middlebury
80 Pine Hollow Dr, Middlebury
$715,000
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
111 Dwyer Rd, Middlebury
$710,000
3 Beds ⋅ 3 Baths ⋅ 24101389 MLS
Elegant Saltbox Colonial in Sought-After Middlebury, Nestled on 2.44 secluded acres, this tasteful saltbox colonial boasts park-like grounds with a private, tree-lined driveway leading to professionally landscaped gardens. Enjoy blooming trees and bushes from spring to fall, creating a picturesque setting. Outdoor living is enhanced with a slate patio, built-in barbecue, and bocce court, perfect for entertaining. The chef's kitchen features an island and opens to a bright family room for effortless gatherings. The expansive living and dining room combination provides elegant space for hosting. The primary bedroom suite offers a walk-in closet and dressing area, and a remodeled bath with steam shower while two additional bedrooms share a full bath. A finished lower-level bonus room provides extra living space and abundant storage. Never worry about storms this home features a whole house generator. Experience refined country living in this desirable Middlebury location!

111 Dwyer Rd, Middlebury
2 Deer Run Rd, Middlebury
$709,900
3 Beds ⋅ 3 Baths ⋅ 24110714 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) 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.

2 Deer Run Rd, Middlebury
15 Central Rd, Middlebury
$706,000
3 Beds ⋅ 3 Baths ⋅ 24160065 MLS
Gracious, comfortable, and exceptionally well cared for, this home offers a thoughtful layout ideal for both everyday living and entertaining. The large, updated kitchen opens to a bright great room overlooking the private, parklike backyard-an inviting setting with an expansive patio and outdoor kitchen perfect for gatherings. Hardwood floors run throughout, complementing the formal front to back living room with its newly designed fireplace and access to a charming covered side patio. A standout feature is the spacious bonus room over the garage, offering true flexibility. With its private entrance potential and generous footprint, it can serve as a dedicated home office, guest suite, inlaw or au pair apartment, or a fourth bedroom-an exceptional option for multigenerational living or today's work from home needs. The two car attached garage is fully finished including walls, ceiling and apoxy floor. The home has been meticulously updated with all major mechanicals improved, including roof, gutters, windows, skylights, a Buderus high efficiency boiler, and a newer hot water tank. Enjoy the best of both worlds with a private well paired with public sewer. Set on nearly an acre, this property combines comfort, functionality, and long term value in a truly beautiful setting. Walking distance to Middlebury Town Green, Walking trails and restaurants all on a quiet street. 90 min to NYC this could be your perfect forever home or a great getaway.

15 Central Rd, Middlebury
14 Deer Run Rd, Middlebury
$699,900
3 Beds ⋅ 2 Baths ⋅ 24088127 MLS
Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) 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.

14 Deer Run Rd, Middlebury
18 Winding Trail, Unit 18, Middlebury
$695,000
3 Beds ⋅ 5 Baths ⋅ 24119886 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light. Beautiful curves staircase, formal living & dining rooms set the stage for entertaining. The gourmet kitchen boasts granite counters, beautiful cabinets, stainless steel appliances, gas cooktop, tile backsplash, large island for ample prep space, a chefs dream. The family room has vaulted ceilings & gas fireplace creates the ultimate gathering space. Rare floor plan features three bedroom suites: a main-level primary with tray ceiling, dual walk-in closets, spa-like ensuite with soaking tub & shower, plus two additional suites upstairs that each have THEIR OWN BATHROOM. Oversized loft overlooks the main floor. Finished walkout basement adds a rec/play room with a custom wet bar w/ granite counters & white cabinets, media area or office, half bath (potential for lower in law/ 4th bedroom). Highlights: laundry w/ sink, additional gas hookup in basement for fireplace, finished lower patio, upper deck & full wheelchair accessibility. Largest backyard in community, great for entertaining or playing sports. Clubhouse w/ bar, pool, gym, tennis crt, indoor basketball court! This is a MUST see!

18 Winding Trail, Unit 18, Middlebury
84 Munson Rd, Middlebury
$675,000
4 Beds ⋅ 5 Baths ⋅ 24145916 MLS
Experience comfort, space, and scenic surroundings at 84 Munson Road, Middlebury, CT 06762, a well-situated home set in a peaceful and desirable community. This inviting property offers a thoughtfully designed layout with generous living areas filled with natural light, creating a bright and welcoming atmosphere. The main level provides ideal flow for everyday living and entertaining, while the kitchen delivers ample cabinetry, abundant counter space, and a practical configuration suited for daily meal preparation. Bedrooms are comfortably sized and offer flexibility for restful retreats, home offices, or guest accommodations. Bathrooms are arranged for functionality with classic finishes and efficient use of space. Step outside to enjoy a spacious yard surrounded by natural beauty, perfect for outdoor gatherings, gardening, or quiet relaxation. The setting offers a balance of privacy and convenience, with easy access to schools, shopping, dining, recreational areas, and major routes. Whether you are searching for a primary residence or a long-term investment, 84 Munson Road presents a wonderful opportunity to enjoy suburban living with strong potential in one of Middlebury's appealing residential areas.

84 Munson Rd, Middlebury
36 Independence Cir, Middlebury
$670,000
4 Beds ⋅ 4 Baths ⋅ 24183278 MLS ⋅ Brookside Of Middlebury BLDG.
Welcome to this impressive 3,512-square-foot Colonial offering 10 spacious rooms 4 bedrooms 3.5 baths and a 2 car attached garage. Thoughtfully maintained and updated this home features newer mechanicals installed in 2023 including a furnace and water heater. Large deck for convenient outdoor grilling The elegant interior showcases hardwood flooring throughout crown molding and chair rail detailing throughout much of the main level The formal dining room is enhanced by a beautiful tray ceiling and leading off to a serving bar while the stunning kitchen features granite countertops, a center island tile backsplash and abundant cabinetry making it ideal for both everyday living and entertaining The inviting family room offers a soaring vaulted ceiling and a cozy gas fireplace creating a warm and welcoming gathering space The luxurious primary suite includes a spacious sitting room or dressing area that could easily be converted into an expansive walk-in closet. The en-suite bath features a Jacuzzi tub, dual vanities, private water closet and a separate glass-enclosed shower. Three additional bedrooms are located on the second floor, including two connected by a convenient Jack-and-Jill bathroom. The home also offers a main level laundry and mudroom Basement features additional cabinetry and excellent storage The large unfinished 1,795-square-foot basement with 8-foot ceilings presents endless possibilities for future expansion recreation space city water/sewer, and 2 car garage

36 Independence Cir, Middlebury

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