Middlebury CT Real Estate & Homes for Sale

Come live your best life. 129 Periwinkle Dr at Benson Woods offers luxury & easy care-free living. This stunning 2/3 Bdrm w apprx 2500sqft (plus apprx 1000 sqft in the unfinished daylight Walkout Lower Level-ready for you to customize-its plumbed) will captivate you upon approach with its wonderful setting perched on a unique parcel offering curb appeal & privacy without seclusion. At first glance it may appear more like a traditional 2 story Colonial yet it's designed for a relaxed lifestyle & flows like a Ranch offering one level living on the main flr. Enjoy sitting on the Mahogany porch, then enter the expansive foyer only to be captivated by the 2-story light filled Great Rm-the ultimate gathering place. Wall sconces & recessed lights, all on dimmers & a gas frplc lend warmth & ambiance whether Lounging or Dining. Multiple windows & a Retractable Chandelier lend illumination. The spacious Gourmet Eat-In kitchen was a $50k upgrade package to include-Subzero Frig/Wolf Gas Range w 4 burners/griddle-Wolf Convection Wall Oven/Microwave/Asko Dshwr/Insta-hot water/Granite counters & Custom lit cabinetry. Segue to the comfort of your Main level Den/Study or step outside & dine alfresco. A 1st flr Primary Suite with its spa-like Bthrm-Dual vanities/Frameless Shower/Newly added Walk-In tub offers relaxation. Main level Laundry/Half Bth complete this level. The 2nd Flr rounds out this home w a 2nd Bdrm/Full Bth & an airy Open Loft (the perfect lounge),dual closet & Exercise/Craft R

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. 17 Deer Run Road (aka Lot 22) is ready to move in to! It is 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.

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.

Hickory Elite End-Unit Townhouse in sought after Ridgewood at Middlebury, nestled on a quiet cul-de-sac.Offering a blend of luxury, convenience, & top-tier amenities, this 3-bdrm, 3-ba home is designed for both comfort & style.As you step inside, rich dark hdwd flooring flows seamlessly thruout the main living areas, setting a tone of elegance.The expansive 2-story living & dining area is bathed in natural light, enhanced by Hunter Douglas window treatments for privacy & ambiance.At the heart of the home is the gourmet kitchen, featuring pristine white cabinetry, granite countertops, & high-end stainless steel appliances.Designed for both functionality & aesthetics, the kitchen opens to the inviting family rm, complete with a cozy gas fireplace-the perfect space for gatherings. With a 4 ft bumpout, french doors lead to the oversized patio with natural gas line grill, where you can relax and take in stunning sunset views while entertaining guests. The first-floor master bdrm is a serene retreat, boasting a spa-like ensuite bathrm & a spacious walk-in closet.A convenient main-level laundry rm adds to the ease of living along w/ a Generac generator for peace of mind during power outages.Upstairs, the loft area, along w/ 2 add'l bdrms and a full ba, provides privacy & comfort for family members or guests.The fully fin basement w/ sump pump is a standout feature, offering versatile space for a home theater, gym, or recreation room-truly setting this home apart.Schedule your tour!

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.

Discover luxury living in this beautifully upgraded end-unit condo located in the sought-after Ridgewood of Middlebury community. With 3,465 sq. ft., this spacious home offers 3 bedrooms, 3 full baths, and 1 half bath, providing ample space and comfort. Step inside to a traditional open floor plan featuring a gourmet kitchen with an over sized island, granite countertops, a gas stove, and high-end finishes throughout. Both family room with gas fireplace and loft area are equipped with built in stereo speakers with surround sound. The inviting living and dining areas flow seamlessly, perfect for entertaining. The spacious primary suite boasts a large walk in closet, generous master bath with double sinks, soaking tub and remote controlled blinds. A standout feature of this home is the fully finished walk out lower level, complete with a full kitchen, granite countertops, a gorgeous subway tile backsplash, plantation shutters for privacy, full bath, plus an additional washer and dryer-ideal for guests or multi-generational living. Enjoy the privacy of your own outdoor space, perfect for relaxing or entertaining. This home is upgraded throughout and move-in ready, offering both elegance and convenience in a prime Middlebury location. Come explore Ridgewood's amenities including outdoor pool, gym, indoor basketball court, tennis courts and clubhouse. Don't miss this opportunity-schedule your private tour today!

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!

Beautiful Portman Condo in Sought-After Ridgewood Community. Discover this stunning 3-bedroom, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac street in unique location. Boasting over 2,100 sqft of thoughtfully designed living space, this home includes a 3-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!

TO BE BUILT! Thoughtfully designed Sutton Model in Avalon Farms, a community known for its unique aesthetic, beautifully landscaped common areas and well manicured lawns. This lovely model has a first floor master suite with a luxurious bath and two walk-in closets. The two story foyer leads to an open and airy great room with cathedral ceilings, large windows, gas fireplace and hardwood floors enhancing the exceptional floor plan for everyday living. The kitchen is well designed offering shaker style cabinets, granite countertops, stainless steel appliances, breakfast bar and a large center island meeting all your culinary and entertaining expectations while providing abundant storage. A charming breakfast nook for informal dining features french doors to your patio and backyard. For those special occasions there is a spacious formal dining room with access to the kitchen. The main level is complete with a powder room, laundry room and mudroom with access to the attached two-car garage. The upper level has two generously sized bedrooms and a full bath. Avalon Farms is ideally located with easy access to major highways, recreation, dining, shopping and educational opportunites. Put your mind at ease with public water, sewer and natural gas. Additional features include central air, all appliances, hardwood floors on the main level, paved driveway and professional landscaping. Pricing is subject to change. Taxes to be determined upon issuance of CO.

Welcome to this stunning luxury end-unit condo w/ 3-Bed, 2.5-Bath in Sought-After Ridgewood w/ 1,882 Sq w/ a 4 foot bump out floor plan. This beautifully designed living space, features an open floor plan with 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. In the living room enjoy a gas fireplace and mantle with 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, A generator plug with failover switch ensures power security. 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 on a quiet, no-through street, this home is an incredible find-schedule your tour tod

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!

Welcome to our final phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

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!

Discover luxury living in this stunning 2122+ SqFt Portman ELITE END UNIT in the prestigious 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 bring 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

Build your dream home on a brand new Cul-de sac. Home will feature 4 bedrooms, 3.1 baths, 3 car garage, central air, and beautiful hardwood throughout. Generous allowances for granite countertops, appliances , and lighting.

Start your new chapter here in the desirable town of Middlebury. All the charming appointments you would expect from an early 1900's home. Generous sized bedrooms & closets including one bedroom on the main floor. Hardwood flooring throughout. There is 1600 sq feet plus an ADDITIONAL 200+ heated square feet in the enclosed rear porch which has a full view of the expansive backyard. Lower level has a fireplace & the start of a half bath for a foreseeable finished lower level. Within the last 5 years the oil & water tanks have been replaced, the chimneys were extended, a basement system was installed, replacement windows completed, refrigerator & range were replaced, & just 2 months ago a new boiler was installed. A storage shed sits at the back of the property & just beyond is lightly wooded privacy that abuts to town of Middlebury land. A quaint enclave of roads makes for a family friendly neighborhood but still close to shopping, restaurants, & the highway. Middlebury is part of award winning Region 15 schools & home to Lake Quassapaug Amusement Park. Middlebury Recreation Area (MRA) offers seasonal passes to the lake for residents only. What a great place to spend your summers! Previous buyers flailed & then bailed. Their loss can be your gain. Seller to connect house to public water PRIOR to closing.

Build your dream home on a brand new Cul-de sac. Home will feature 4 bedrooms, 3.1 baths, 3 car garage, central air, and beautiful hardwood throughout. Generous allowances for granite countertops, appliances , and lighting. Schedule an appointment now with builder!!

Build your dream home on a brand new Cul-de sac. Home will feature 3 bedrooms, 2.1 baths, 2 car garage, central air, and beautiful hardwood throughout. Generous allowances for granite countertops, appliances , and lighting. Schedule an appointment now with builder!!

Build your dream home on a brand new Cul-de sac. Home will feature 4 bedrooms, 3 full baths, 3 car garage, central air, and beautiful hardwood throughout. Generous allowances for granite countertops, appliances , and lighting. Schedule an appointment now with builder!!

Build your dream home on a brand new Cul-de sac. Home will feature 4 bedrooms, 3 full baths, 3 car garage, central air, and beautiful hardwood throughout. Generous allowances for granite countertops, appliances , and lighting. Schedule an appointment now with builder!!

Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls, professionally maintained grounds, and an in ground swimming pool for a quick dip on hot summer days! How convenient to have an attached 2 car garage with loft, leading to the main floor. Modern upgrades and conveniences haven't been forgotten either - a bright eat in kitchen with a dramatic Palladium window overlooking the beauty of nature, and upgraded bathrooms add modern yet respectful additions to the home. Mechanical elements include an electric panel with extensive circuit breakers, newer roof, connection to public sewer, newer water pump, and a whole house Generac generator! The sun room could be a perfect greenhouse! Own a unique home with extraordinary character and location! This is an estate sale, and is being sold "as is, where is".

Welcome to 6 Brookside Drive, Middlebury, CT, a meticulously designed residence offering 3,745 square feet of refined living space. This property features four bedrooms and four bathrooms, ideal for comfortable family living. The first floor boasts an open-concept layout, highlighted by 9+ foot high ceilings in the living room, providing an airy and spacious atmosphere. The primary suite includes a luxurious ensuite bathroom with a jacuzzi tub, large windows, and a walk-in closet. The kitchen is equipped with top-of-the-line smart appliances, all under a 10-year warranty, ensuring modern convenience and reliability. Additional first-floor amenities include a laundry room, garage access, a powder room, a coat closet, and a pantry. Custom-made blinds and shades adorn the windows, adding a touch of elegance. The second level features two bedrooms, a loft area overlooking the living room, a full bathroom, and a walk-in closet, offering ample space for family or guests. The lower level is designed as an in-law suite, complete with a kitchenette, a new full bathroom, an open-concept living and dining area, a bedroom with a walk-in closet, high ceilings, and abundant storage. Outdoor living is enhanced by a welcoming front porch and a large deck, perfect for relaxation and entertaining. The property also includes gutter guards with a warranty, ensuring low maintenance. Hardwood floors throughout add to the home's charm and durability.

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.