Middlebury CT Real Estate & Homes for Sale

Charming Move-In Ready Ranch in the Heart of Middlebury Welcome home to this beautifully updated ranch-style gem, ideally located in the heart of Middlebury. Set on a quiet street just steps from the scenic Middlebury Greenway Trail, this home offers comfort, style, and convenience all in one. The recently renovated eat-in kitchen is a showstopper, featuring granite countertops, subway tile backsplash, wainscoting, and newer Samsung stainless steel appliances-perfect for everyday living and entertaining. The main level boasts freshly painted bedrooms, hardwood floors throughout, a bright and spacious living room with a wood-burning fireplace, and a completely updated full bathroom. Head downstairs to the fully finished lower level, where you'll find a cozy Jtul wood stove, a wet bar, and a half bath-an ideal space for relaxing, hosting, or even a home office. Located minutes from local dining, shopping, and major routes (Rt. 8 and I-84), and nestled in the award-winning Region 15 school district, this home truly has it all. Don't miss your chance to make this Middlebury beauty your own-schedule your private showing today!

Nestled in one of Middlebury's most sought-after neighborhoods, this well-maintained two-bedroom ranch blends comfort, convenience, and charm. Step inside through the inviting enclosed front porch-perfect for morning coffee or evening relaxation-into a warm and welcoming living room complete with a cozy wood stove. The bright, airy kitchen flows seamlessly from the living space, making it ideal for both everyday living and entertaining guests. The primary bedroom features a generous walk-in closet, offering ample storage. A nicely remodeled full bathroom and a separate laundry room add to the home's thoughtful layout. Enjoy peaceful summer evenings on the back deck overlooking a private, serene backyard. Some key updates include a newer 30-year roof with transferable warranty, recently repointed chimney with fresh brickwork, and a new well holding tank. Schedule your showing today!

Welcome to this charming Cape Cod-style home nestled in the heart of Middlebury, CT. Warm hardwood floors flow throughout the main living spaces, adding a timeless touch of elegance. Begin your day-or unwind at the end of it-in the inviting three-season front porch, the perfect spot to curl up with a good book. Step inside through a cozy entryway where you can hang your coat before choosing to head into the spacious living room, dining room, or upstairs to the generously sized bedrooms. The bright kitchen features a tiled floor, ceiling fan, updated appliances, and plenty of room for a table for casual dining. Each bedroom offers ample closet space and ceiling fans for year-round comfort. The home is equipped with updated windows and a roof installed in 2008. Efficient radiator heat powered by an oil-burning furnace and continuous hot water ensure warmth and comfort during the colder months. While the basement remains unfinished, it offers great storage space and features a convenient hatchway leading to the backyard. Outside, you'll find a private deck overlooking a large backyard-perfect for entertaining or simply enjoying the outdoors. Additional highlights include an oversized detached garage offering plenty of space for storage or a workshop.

This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors, loft area & an attached green house! The main house features a grand foyer with granite flooring, a very large, formal dining room & a generous sized formal living room/music room. The eat-in kitchen area is large enough to hold an 8 seat table & chairs & has slider access to the deck. There is an island in the center of the kitchen with additional seating as well stainless steel appliances & a work area. As you walk down the hall to the 3 car garage you will pass another smaller study with builtins & an exceptionally large pantry & mudroom area. There is a separate laundry room & 1/2 bath. The sizable great room has a fireplace, bar area & sliders to the enormous deck! On the deck is where you can relax or entertain by the outdoor fireplace & cook in the custom pizza oven! There is also an oversized main floor office for those who work from home or need a guest area. This office has a fireplace, built-ins & another full bath. Upstairs is the Primary Suite with a walk in closet, full bath featuring a jacuzzi tub, separate shower & 2 sinks. The main bathroom also has double sinks & a tub with shower. There are 3 other large sized bedrooms with hardwood flooring & plenty of closet space. The enormous basement has a rolling garage type door if you need to store anything with easy access! The possibilities are endless!

Enjoy living a relaxing and luxurious lifestyle in a most desirable community. As you step into this beautifully appointed, light filled townhome, you can appreciate the open floorplan. This Portman model offers hardwood flooring on the main level and features an eat-in kitchen open to the living/dining room with a gas fireplace for ambiance and warmth. Accessible from the kitchen dining area, the TREX deck allows for al fresco dining overlooking a peaceful backyard setting. It is complete with stairs to conveniently access the rear community space. The second floor offers 3 bedrooms, 2 full baths and a laundry room. The spacious primary bedroom suite features a luxurious full bath with a vaulted ceiling and an enclosed shower. Its cathedral ceiling gives the primary bedroom volumes of space, and there is plenty of space in the walk-in closet. The two additional bedrooms are spacious with plenty of closet space. The full basement with a full-size window allows for lots of light and storage, or it can be finished for additional living space. And the 2-car garage is attached for ease of entry. Enjoy all the amenities which Ridgewood has to offer while living a carefree, low maintenance lifestyle.

Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter guard, two full bathrooms and a new kitchen. Situated on a quiet cul-de-sac with a beautiful deck and two car garage, this house checks all the boxes.

Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The gourmet kitchen features granite countertops, stainless steel appliances, a gas cooktop, tile backsplash, and an island with breakfast bar seating, flowing seamlessly into the spacious living room with a gas fireplace and access to a private deck and backyard-perfect for entertaining. The luxurious primary suite impresses with vaulted ceilings, a walk-in closet, and a spa-like bath with a double vanity, soaking tub, and shower. Two additional bedrooms, one with vaulted ceilings and a walk-in closet, and a full bath complete the upper level. The unfinished 900+ SqFt basement offers endless potential. Enjoy resort-style amenities, including a clubhouse with an entertainment area, kitchen, gym, pool, indoor basketball court, tennis court, and playground. This home combines elegance, comfort, and convenience. You very rarely get a unit with a large side yard and private flat wooded backyard. If you like to entertain, or engage in yard activities, this is the unit to buy! Private desirable town, 1.3 hrs from NYC, easy access to highways. Schedule your showing today!

Exceptional Craftsmanship & Refined Luxury. Welcome to 76 Three Mile Hill Rd, where modern updates meet timeless elegance. Completely renovated in 2024, this stunning home is a true masterpiece of design, featuring intricate millwork-like coffered ceilings and thoughtful detailing that infuse warmth and character throughout. The craftsmanship and luxury are felt throughout this home featuring 4 bedrooms & 3 full baths-room for family, guests and quiet moments. The upstairs bedrooms are generously sized providing plenty of space for furniture and personal style. Use the 1st floor bedroom as an office or play space. Each bathroom has ample room and stunning finishes that will leave you speechless. The mudroom serves as a seamless transition into the home from the patio, garage, and driveway. Enjoy your morning coffee on the back patio perfect for quiet reflection, or dining outdoors with friends and family. The home has open and sunlit spaces throughout designed for gathering, entertaining, and making lifelong memories. Sophisticated finishes, beautifully crafted details, such as granite countertops, new appliances,(GE cafe and Subzero fridge) and new windows. It feels like home from the moment you step inside. Whether you're raising a family or looking for the perfect place to enjoy your golden years, this home adapts to every stage of life. From lively family celebrations to quiet evenings, 76 Three Mile Hill Rd is the place to see your best moments unfold. Welcome home!

Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features a vaulted breakfast area surrounded by windows, granite countertops, and stainless steel appliances. The first-floor primary suite boasts a generous walk-in closet and a full bath. Upstairs, a beautifully finished loft area offers another full bath, a walk-in closet, and two additional bedrooms. The lower level is a showstopper, featuring a built-in wet bar, plenty of space for entertaining, and direct access to a private outdoor patio. A private library/office and an additional full bath complete this level. Enjoy an unbeatable location just a short walk to the clubhouse, which includes an outdoor pool, gym, indoor basketball court, and tennis courts. With easy access to I-84, top-rated schools, and fantastic restaurants-plus just 30 minutes to the train to NYC-this home truly has it all! Don't miss this rare opportunity to own the original model home!

Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile backsplash. Stainless steel appliances and gleaming hardwood floors extend through the great room and dining room, creating a seamless flow. The main level offers a luxurious primary bedroom suite with an attached spa-like bath, an office, a powder room, and a convenient laundry area. Upstairs, discover a versatile loft, a second bedroom, and a full bath - perfect for guests or additional living space. This home is equipped with a chair lift from the garage and is prepped for a future elevator, ensuring accessibility for years to come. The HOA covers full lawn maintenance and snow removal right up to your front door, providing hassle-free living. Located minutes from Edgewood for tennis or pickleball, and close to scenic Lake Quassapaug - ideal for boating or picnicking at the Middlebury Recreation Area. Enjoy easy access to fine dining, shopping, and I-84, with NYC just 90 miles away and Boston a two-hour drive.

Welcome to this luxury end-unit condo built in 2022 w/ 3-Bed, 2.5-Bath in Sought-After Ridgewood.1882 Sqft w/ 4 extension to floor plan. This beautifully designed living space, offers 1 level living that many look for. Equipped w/ cathedral ceilings and a first-floor primary bedroom suite for ultimate convenience and a very rare unit. The gourmet kitchen boasts quartz countertops, stainless steel appliances, a breakfast bar, and an open layout perfect for entertaining. The premium gas range with a vented microwave, and ultra-quiet dishwasher adding touches of luxury. High end Ceiling fans throughout floors/ rooms. In the living room enjoy a gas fireplace w/ mantle w/ amazing floor & wall space. Enjoy upgraded extra wide sliding doors leading to the patio where you have wooded views, an entertainers dream. The whole floor flows seamlessly! Upstairs is spacious loft for an office or game room, 2 large bedrooms and a full bath. The partially finished basement is framed and plumbed for an additional bathroom, offering future expansion potential. Smart home upgrades include Wi-Fi-enabled Ecobee thermostats, motorized window shades, luxury ceiling fans, Generac generator wired. Home can be voice activated with user friendly systems. Ridgewood has top-tier amenities, including a gym, outdoor pool, tennis court, playground, indoor basketball court, movie theater, and lounge. Located in quiet area, this home is an incredible find. Almost brand new, come schedule your tour! Rare find.

Beautiful Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances, perfect for modern living, an upgraded skylight in kitchen floods the space with natural light. Off the kitchen is a private deck with wooded views & a large living room w/ a gas fireplace. Upstairs the spacious primary suite offers a walk-in closet and a luxurious bath with a double vanity, shower, and tub. The second bedroom also includes a walk-in closet, while the third bedroom showcases custom millwork/ built-ins for both function and style for additional utility and architectural interest. Enjoy the privacy of a wooded backyard and the convenience of a walk-out basement w/ custom storage shelves and two workbenches, woodworkers dream! Right next to the home is the "Great Meadow Lawn" adding a huge yard to play games, entertain or take a scenic stroll. Very rare location, big upgrade here $$$ . Ridgewood amenities include an outdoor pool, gym, indoor basketball court, tennis courts, a movie theater, and a clubhouse lounging area-all within walking distance. Plenty of upgrades, prime location and privacy. Don't miss this must-see property! Can't build for this price!

Don't wait to see this turn key home in the desirable Ridgewood of Middlbury, one of the areas newest and most picturesque communities. This is a unique end unit, The Emerson Model, situated in a private, quiet cornet lot. As you enter the home, you'll view the open living room/dining room, with a gas fireplace and plenty of light. The attached kitchen includes granite countertops, large cherry cabinets, and quality stainless appliances. Upstairs, you'll find the large primary suite, with walk in closet and full bath, including double sinks, hydro tub and shower. Two additional bedrooms are on level, with an additional bedroom on the 4th floor, which could also be used as guest space, playroom, or as an office. The home offers a total of 3,195 square feet, 2,375 above grade, with an additional finished basement that holds a full bath, wet bar, and walkout to backyard. The property has plenty of natural light and is bright and clean, with 9' ceilings, hardwood, central vacuum and crown molding throughout. Ridgewood of Middlebury offers easy living, with an magnificent clubhouse, exercise room, indoor basketball court, pool, and tennis court, perfect for keeping yourself or guests entertained.

This stunning colonial home features a beautifully landscaped level lot with an expansive side yard. As you approach, you are welcomed by a charming covered front porch that leads into a grand two-story foyer with a winding staircase and abundant natural light from the second-story windows. The foyer seamlessly connects to the bright white kitchen, a gas stove, a stylish tile backsplash, a pantry, and a sunlit eating area surrounded by windows. The kitchen flows into a spacious dining room filled with natural light. The impressive two-story great room features a vaulted ceiling, an interior balcony, a cozy fireplace, and access to the deck-perfect for entertaining. The main floor primary suite has a tray ceiling, a generous walk-in closet, and a beautifully remodeled bathroom with a soaking tub, double vanity, and a separate glass-enclosed tile shower. Upstairs, you'll find additional bedrooms along with a den or office space. The approximately 1,000 sq. ft. finished lower level is perfect for a recreation room or gym. Enjoy outdoor living on the Azek deck overlooking the lovely level backyard -truly a picture-perfect setting! All New Items include furnace, water heater, all kitchen appliances, new kitchen cabinets, counters, and backsplash. New washer/dryer, new recessed lighting, paint whole house. New half bath.

Three bedroom Cape Cod style home in the heart of Middlebury, CT! Sitting on a corner lot, this cozy Cape offers a first floor bedroom connected to a half bath, formal living and dining rooms, and spacious eat-in kitchen. Immediately off the living room is an enclosed porch that provides additional space for a future home office. Upstairs find two additional bedrooms with shared full bath. Plenty of room to throw the ball around or host a spring-time barbeque in the level, partially fenced backyard. The full basement has finishing potential and features newer boiler, walk-out and storage space. Located just a few steps away from all major conveniences, award-winning restaurants, town parks, schools, and Middlebury's "Greenway" biking, running and walking route. It's time to jump right into this vibrant community!

This beautifully renovated colonial seamlessly blends classic elegance with modern updates. Featuring gleaming hardwood floors, an open-concept main level, and a bright kitchen with a center island, this home offers a perfect space for entertaining and everyday living. The primary suite includes a luxurious en suite bath and walk-in closets, complemented by two additional spacious bedrooms and a full bath. Work on your cars or hobbies all year long in the oversized detached garage! Enjoy the private backyard with a wraparound patio, ideal for relaxing or hosting gatherings. With a new roof, driveway, siding, windows, and updated systems throughout. Already hardwired with a security system! This home is truly move-in ready. Conveniently located near major highways and scenic walking trails, it's a wonderful opportunity not to be missed!

Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods offers a walkable lifestyle with direct access to restaurants, coffee shops, shopping, and the Middlebury Greenway Trail. Now in Phase Two, Granite Woods showcases five unique home designs built for comfort, style, energy efficiency, and aging in place. Every home is ENERGY STAR certified for exceptional performance offering lower utility costs, improved air quality, and year-round comfort. Designed with your future in mind, all homes feature single-step front and garage entries, wide interior doorways, and access to a private residents-only pavilion. The Spruce is a delightful two-bedroom home featuring a quaint covered porch that sets a warm and welcoming tone. Step through the foyer and discover a private study conveniently located near a powder room. The heart of the home is the spacious and sunlit great room, complete with a cozy gas fireplace ideal for relaxing or entertaining family and friends. The first-floor owner's suite offers serene backyard views, a generous walk-in closet, and a peaceful place to unwind.

Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods offers a walkable lifestyle with direct access to restaurants, coffee shops, shopping, and the Middlebury Greenway Trail. Now in Phase Two, Granite Woods showcases five unique home designs built for comfort, style, energy efficiency, and aging in place. Every home is ENERGY STAR certified for exceptional performance-offering lower utility costs, improved air quality, and year-round comfort. Designed with your future in mind, all homes feature single-step front and garage entries, wide interior doorways, and access to a private residents-only pavilion. The Maple model features an open-concept layout with a sunlit great room, cozy fireplace, and two owner's suites for flexible living. A mudroom with built-in bench seating and a conveniently located laundry room add to the home's thoughtful design. Need more space? Choose the optional second floor with a guest suite and loft or a creative hobby area. And best of all - each home can be customized to your preferences, allowing you to create a space that truly feels like home.

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) 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.

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.

Middlebury Modern. Authentic c.1962 Mid-Century Modern Designed by Noted Architect Andrew S Cohen as his Personal Residence. This Largely Untouched Modernist is Set Quietly on Nearly 1-Acre. Walls of Glass & Dark Stone Floors Showcase the Signature Elements of the Era. 4 Bedrooms, 2.5 Baths Include an en-suite Primary Bedroom with Dressing Room & Balcony. Large Eat-in Kitchen Adjacent to Family Room. Inviting Living & Dining Room Wrap around Stunning Central Fireplace. 1st Time Ever on the Market. Cohen was a Yale Architecture Graduate with a Prominent Career & Served as President of CT Society of Architects Among Numerous Other Accolades.

Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 x 13 heated sunroom overlooking rolling hills and distant views. On the second level, 2 bedrooms and a beautifully remodeled full bath. The third level offers a finished bedroom as well as a spacious storage area. On the exterior, a gorgeous front porch, patio, gardens and a barn with 2 garages, an area for chickens. Beautiful gardens as well as a mini orchard: 4 apple trees, 2 Pear, Peach tree, Plum Tree and Cherry tree. (Some photos are from a previous listing so that the exterior shows the landscape.)Agents and prospective buyers: Please do not drive up the driveway unless you are there for a showing.

Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch-style home with a finished basement and in-law suite! This home offers the perfect blend of comfort, convenience, and versatility. Step inside the main level to find three spacious bedrooms, plus a bedroom and bathroom downstairs, a bright living area, and a well-appointed kitchen. The finished lower level provides a fantastic in-law suite, perfect for extended family or guests. Outside, the large backyard offers endless possibilities whether you're looking to entertain, garden, or simply relax. A two-car garage and a long driveway provide ample parking. Situated in a peaceful neighborhood yet conveniently close to schools, shopping, and major highways, this home is a must-see!

Welcome to 28 Maple Drive, a classic gem in the heart of Middlebury, Connecticut, where charm and comfort meet timeless design. This meticulously maintained single-family home, built in 1950, offers 1,596 square feet of thoughtfully designed living space. With 3 spacious bedrooms, 3.5 bathrooms, and a warm, inviting layout, this home is perfect for both entertaining and everyday living. A fully finished walk out basement offers a full bathroom and a large bedroom with the potential to be set up as an inlaw apartment! Step inside and be greeted by a cozy living room filled with natural light, showcasing beautiful hardwood floors and classic architectural details. The well-appointed kitchen offers a functional layout, ample storage, and a dining area that opens up to the heart of the home. Whether you're hosting dinner parties or enjoying quiet mornings, the space caters to all your needs.The bedrooms are generously sized, two of them being on the main level of the home with ensuite full baths. providing plenty of room for relaxation and personalization. The 3.5 bathrooms are designed with convenience in mind, featuring modern fixtures and classic finishes that blend seamlessly with the home's vintage charm.Outside, the property boasts a serene backyard surrounded by lush greenery, ideal for summer barbecues, gardening, or simply enjoying the peace and quiet of the neighborhood. The home's location on a quiet street adds to its appeal!

Sitting pretty at 4,200 square feet, this exquisite property is designed for those ready to embrace a luxury lifestyle, offering the perfect setting for anyone looking to expand their living space. Crafted with attention to detail, every corner of this 10-room home radiates sophistication and functionality. Here's what you have to look forward to: Gourmet Kitchen: The heart of the home, featuring top-of-the-line appliances and a vast island, setting the stage for culinary creativity and entertaining. Dramatic Great Room: Boasting a two-story ceiling with a floor-to-ceiling stone fireplace, this space is perfect for gathering with loved ones or simply unwinding in style. Private Den & Office: Enjoy dedicated spaces for work and relaxation, tailored to meet the demands of modern living. Luxurious Primary Suite: Retreat to your personal oasis on the upper level, complete with a lavish bathroom and ample closet space. Three additional bedrooms and a spacious recreation room provide room to grow and flourish. Three-Car Garage: Ensures plenty of storage space and security for vehicles and belongings. Middlebury presents a truly enriching lifestyle. Known for its quality schools and safe environment, it provides a superb quality of life. Envision your mornings sipping coffee on the porch and evenings spent cozying up by the fire as you take in the breathtaking sunsets from your expansive windows. This home isn't just a place to live-it's an experience!