Refine Search
Map
Sort by
$525,000
3 Beds ⋅ 3 Baths ⋅ 170614150 MLS
Welcome to 58 Shadduck Road! This home has been beautifully and completely renovated from top to bottom. Interior renovations feature a new kitchen, new bathrooms, closet systems, blinds, fresh paint, and gorgeous hardwood floors throughout both levels. Exterior improvements include a new roof, gutters, windows, siding, driveway, patio, shed, and three car detached garage. Electric, plumbing, central air, propane-powered heating system and the well pump have all been updated. A unique opportunity to move into a beautifully designed home where all the work has been done! The open main level living space includes the light and bright kitchen with a center island, a dining room, seating/office area, and a living room with sliders to the wraparound patio. Upstairs is the primary bedroom with an en-suite bath and walk-in closet as well as two additional bedrooms and a full hall bath. The spacious lower level provides ample storage space. The large and level lot offers a private back yard bordered by trees and a charming brook, and the patio with a privacy fence is the perfect place for outdoor living and entertaining. The property is currently using a private well, but public water is on the road and can easily be connected if desired. Convenient location with easy access to I-84 and Route 8, and beautiful walking trails are just two blocks away. This home is an incredible opportunity not to be missed!

58 Shadduck Rd, Middlebury
$525,000
3 Beds ⋅ 3 Baths ⋅ 170613381 MLS
This unique home has been custom-designed with elegance. The formal living room is adjoining the formal dining room, with a butler's pantry and ample space for storage or a bar area, giving this the perfect home to entertain. The tastefully decorated dining room opens up to the back deck. The eat-in kitchen features vaulted ceilings, earthy tones, a walk-in pantry, granite countertops, a generous island, gas stove range, double ovens, and a large window overlooking the outdoor greenery, which will make all of your meal prep enjoyable. The first-floor den offers a cozy fireplace to snuggle up on cold evenings. The upper level hosts a sizable primary suite complete with a walk-in closet, renovated full bath, vaulted ceilings, and plenty of windows to soak in the light. The second bedroom is the perfect retreat for guests or children. The study doubles as an entryway to the great room, which will quickly draw you in, with the gas-burning fireplace, cathedral ceilings, and plenty of windows including a custom stained glass window. The whole house generator, central air, and a two-car attached garage are some of the many features this home offers. Conveniently located 90 miles from NYC, enjoy the beautiful town of Middlebury has to offer.

169 Sandy Hill Rd, Middlebury
$525,000
2 Beds ⋅ 3 Baths ⋅ 24113719 MLS
Thank you for touring, all highest and best offers are due on Wednesday the 13th, by 6pm. Charming Single-Family Home in a Peaceful, Non-Age-Restricted Community! Welcome to your new home in a serene and beautifully maintained community, nestled at the end of a quiet cul-de-sac. Surrounded by lush landscaping and tranquil sounds of nature, this single-family, detached residence offers both comfort and convenience-with no age restrictions. Step inside to a soaring two-story living and dining area featuring gleaming hardwood floors and an abundance of natural light. A cozy loft space overlooks the main living area, ideal for a home office or reading nook. The open-concept kitchen is bright and functional, flowing seamlessly into the inviting family room with a warm gas fireplace-perfect for gatherings or relaxing evenings. The first-floor primary suite offers privacy and ease, complete with a walk-in shower and generous closet space. A discreetly placed half bath is perfect for guests. Upstairs, the second bedroom suite includes a full en-suite bathroom and sits just off the loft, providing a private and comfortable space for visitors or family. Enjoy your morning coffee or unwind in the evening on your private backyard patio, surrounded by a peaceful and secluded setting. Low maintenance with public water, public sewer and gas hookup. Conveniently located near I-84 and Route 8, this home provides easy access for commuting, shopping, and dining.

6 Pommel Ln Unit 6, Middlebury
$525,000
3 Beds ⋅ 3 Baths ⋅ 170612796 MLS ⋅ Ridgewood At Middlebury BLDG.
Like new construction but without the wait, Welcome to 4 Arrowwood Ct! First occupied in late 2020. Masterfully built by Toll Brothers consisting of many upgrades throughout the 2,380 SF of living space. Set on a lot premium location on a quiet circular street. Fall in love w/ the open floor plan & abundance of natural light flowing through oversized windows/transoms. Gourmet kitchen w/ upgraded cabinetry & 7' island. The open concept of the main level sets this home apart from the rest- dark flooring complimented by a modern color pallet & complete w/ a high-end trim package. Main level features: gas insert fireplace focal point and access to the backyard paver patio. 2nd floor consists of a primary suite & 2 additional bedrooms, each w/ a custom closet. You will appreciate the architectural interest of the vaulted ceilings on the 2nd level as well as the hardwood hallway. The lower level offers 572 SF of living space. Home office/playroom- a versatile space that is finished w/ the same quality as the rest of the home. Enjoy the Ridgewood at Middlebury lifestyle: Tennis & basketball courts, playground, clubhouse gym, movie theatre & pools (kiddie pool too!). Nat. gas for heating & cooking. High-efficiency heating system. At just a few years old and meticulously cared for; opportunities like this are hard to find. Forgo the wait & ‘risk’ of a new build and avoid having to remodel an older property – 4 Arrowwood Ct is an incredible opportunity, Welcome Home!

4 Arrowwood Ct Unit 4, Middlebury
$525,000
3 Beds ⋅ 3 Baths ⋅ 24091640 MLS
Nestled on a private, set-back lot surrounded by beautifully landscaped gardens, this classic 3-bedroom Colonial offers timeless appeal and modern comfort. A welcoming country-style front porch invites you inside, where a dramatic two-story foyer sets the tone. To your right, a flexible formal living room or a convenient spot for a home office, complete with elegant French doors leading to the formal dining room-ideal for entertaining. The heart of the home is the eat-in kitchen, with sliding glass doors opening to the backyard. Just off the kitchen, the spacious family room features soaring cathedral ceilings and a cozy gas fireplace-perfect for relaxing evenings at home. Upstairs, you'll find three bedrooms, including a serene primary suite with a walk-in closet and a private full bath. The finished lower level includes a tucked-away office space, laundry area, and direct access to the two-car garage. Enjoy gleaming hardwood floors throughout, central air, city water and sewer for peace of mind in this move-in-ready gem. Located in the highly desirable Region 15 school district, just minutes to town center, I-84, and Route 8-this home truly has it all!

110 Glenwood Ave, Middlebury
$525,000
5 Beds ⋅ 3 Baths ⋅ 170615928 MLS
It's your chance to move in to a stunning home in a wonderful Middlebury neighborhood! With 5 BR's & 3 FBA's there is plenty of room for everyone. If you don't need to use all 5 bedrooms these rooms are large enough for a spacious home office! Beautifully refinished hardwood floors, a large living room with built ins & an amazing fireplace with an updated insert. The dining room has a large slider to the beautiful low maintenance patio. The kitchen features granite counters, SS appliances & plenty of counter space for the cook! As you walk up the stairs you will find a full bath that has been totally updated with a full shower & custom glass doors & 2 oversized bedrooms. The Primary bedroom has a walk in closet, a full bathroom & newly refinished floors. There is a third level with a full bath & 1 extra large bedroom with a walk-in closet & another spacious bedroom with a built in work space. On the lower level you will find a the large family room/play room with newer bamboo flooring, a laundry area & a great workshop area! A 2 car garage, public water, public sewer, whole house fan, a newer roof and all this in this great location!

95 Woodland Rd, Middlebury
$520,000
4 Beds ⋅ 3 Baths ⋅ 24185547 MLS
Before you enter this charming oversized cape, take a look beyond the covered deck at 2.5 parklike acres that just happen to sit adjacent to 19 acres of Middlebury Land Trust. Imagine yourself relaxing there ... and then enter the house. The kitchen was remodeled with white cabinets, matching appliances, and Corian countertops that have a drainboard scored into the top by the sink, and a metal trivet next to the stove that allows you to put hot pots & pans on the counter without damaging it. Between the dining and living rooms is a fireplace with a propane insert to supplement the hot water baseboard heat. Mini splits provide a/c as well as an additional heat source for the first floor. The town card says 4 bedrooms, but a small room on the main level, currently used as a laundry room offers many options to fit your needs. The first floor includes a primary with a walk-in closet, and full bath with a jetted tub/shower, plus a 2nd bedroom currently used as a music room. Upstairs, 2 huge bedrooms with built-ins, large closets, & storage in the eaves are separated by a generously sized landing for max privacy, and share the 2nd full bath with its updated Fiberglass surround tub/shower and a skylight that provides natural light no matter the time of day. A full basement provides access to the 2 car garage, and lots of storage. Schedule your showing and come fall in love with this well loved and well maintained home in Middlebury.

566 Benson Rd, Middlebury
$520,000
3 Beds ⋅ 3 Baths ⋅ 24113730 MLS ⋅ Steeplechase BLDG.
Welcome to Steeplechase of Middlebury! Enjoy low-maintenance living in this well-maintained free-standing Osborn 2 model located in a sought-after planned community. Steeplechase offers the ease of natural gas from the street as well as public water and public sewer. This home features two primary bedrooms-one on the main level and one upstairs-each with an en-suite bath, offering flexible living arrangements. The main level includes an open-concept family room with a gas fireplace, an eat-in kitchen with breakfast bar, and a spacious living and dining area with hardwood floors throughout the house. Upstairs, you'll find another primary bedroom with full bath and a third smaller bedroom or office, plus ample closet space throughout. Mechanical updates include a hot water heater (2020) and newer Furnace and AC condenser (2015). The yard is manageable and private, ideal for enjoying the outdoors or creating your own garden space. Conveniently located near Lake Quassapaug, parks, shopping, schools, and dining. A great opportunity to own in a peaceful, walkable community!

8 Kimberwick Ct Unit 8, Middlebury
$520,000
3 Beds ⋅ 3 Baths ⋅ 24085206 MLS ⋅ Ridgewood At Middlebury BLDG.
Beautiful luxury Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath 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 resort style must-see property! Can't build for this price!

29 Winding Trail, Unit 29, Middlebury
$520,000
3 Beds ⋅ 3 Baths ⋅ 24098549 MLS
First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming hardwood floors, a formal dining room perfect for entertaining, a cozy eat-in kitchen, and a thoughtfully added family room providing extra space for everyday living. Upstairs, you'll find three generously sized bedrooms, two full baths, and a bright second-floor landing with additional built-ins. A walk-up attic offers abundant storage or potential future expansion. Set in a hidden gem of a neighborhood, this home sits along the historic trolley bed trail, offering direct access to local shops, restaurants, and all the amenities of in-town living.

1 Stevens Rd, Middlebury
$515,000
4 Beds ⋅ 3 Baths ⋅ 24189438 MLS
Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler. Inside, a classic center hall foyer with a graceful staircase welcomes you. The spacious eat-in kitchen is ideal for everyday living, while the formal dining room, complete with a charming swinging door, and is perfect for entertaining. The front-to-back living room features a cozy wood-burning fireplace and new sliding glass doors that open to the backyard, creating a seamless connection to outdoor living. A tucked-away office or den with built-ins provides the perfect space for working from home, reading, or relaxing. Upstairs, the generous primary suite offers a private full-bath along with his-and-hers closets. Three additional bedrooms provide ample space for family, guests, or hobbies. Hardwood floors run throughout the home, enhancing its warmth and classic appeal. Completing the property is an attached two-car garage and a private setting that offers both tranquility and convenience. This charming Colonial is the perfect blend of traditional elegance, thoughtful updates, and comfortable living.

880 Whittemore Rd, Middlebury
$515,000
4 Beds ⋅ 3 Baths ⋅ 24046817 MLS
Purchasers default puts this great home back on market. Ideal Middlebury location, this spacious home showcases a legal in-law apartment, an easy commuter location offering a 4 Bedroom, 3 Bath open plan with hardwood floors, walls of windows, 2 fireplaces and more. A grand main level family room/game room with plank floors. The lower-level provides a 3 room in-law apartment with vinyl plank floors, full bath and kitchen, bedroom, living room and an additional family room with fireplace. The main level consists of L- shaped living room with dining room and a 30 x 30 family room. This home showcases great space for entertaining and relaxing family lifestyle. New stainless appliances, large dining area, built-in pantry cabinets and plank floors lead through sliders to the multi-level pressure treated deck and private yard. Amenities include; New geothermal heat and solar panels installed in 2023 keeps heating, cooling and overall electric costs to only $391 dollars per month. Additionally, new water heater (2023), roof (2018), blown in insulation, siding (2022), freshly painted in and out plus supplemental wood heat. Easy access to town, great schools, restaurants and parks. Easy commute to New York or down county.

1053 Middlebury Rd, Middlebury
$515,000
3 Beds ⋅ 3 Baths ⋅ 24042835 MLS
Welcome to Middlebury and this well-maintained Oversized Cape. This house is full of charm. It has all of the timeless appeals such as multi arches and hardwood floors but with modern updates. The formal living room, complete with a gas fireplace has access to an arched portico. The perfect place to relax. The kitchen has granite counters and stainless-steel appliances with access to both the formal dining room and the den. There is also a mud room on the main level. The upper level has the primary bedroom with cathedral ceiling, full bath (with jacuzzi tub) and sliders to a private deck. Two additional bedrooms upstairs (one with an adjoining dressing room/office). All of this with newer windows, brand new roof and newer furnace. The oversized two car detached garage has a large unfinished area above with walk-up stairs (already has electricity and plumbing) perfect for an in-law apartment, au-par or guest area. The property is at the end of the cul-de-sac and sits in a very serene setting. There is also a stone fireplace in the yard. It is close to Route 84 and the Middlebury Walking Trail. Welcome to Middlebury and their award-winning Region 15 schools.

133 1/2 Steinmann Ave, Middlebury
$515,000
3 Beds ⋅ 3 Baths ⋅ 24096094 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area, and cozy family room, making it perfect for both everyday living and entertaining. Vaulted ceilings add an airy, welcoming feel, while large windows bring in even more light. The main-level primary suite provides a peaceful retreat with plenty of space to relax and unwind. Upstairs, you'll find two additional bedrooms and a full bathroom, ideal for family, guests, or a home office. The unfinished basement offers a fantastic opportunity to create even more living space-whether you envision a rec room, home gym, or a media lounge, the possibilities are endless. A two-car attached garage and a thoughtfully designed layout add to the home's comfort and convenience. Located in a vibrant community that features a basketball court, multiple pools, and a playground, you'll have plenty of opportunities to enjoy the outdoors and stay active close to home. Don't miss your chance to experience everything this lovely townhome and neighborhood have to offer!

17 Highridge Road Unit 17, Middlebury
$515,000
4 Beds ⋅ 3 Baths ⋅ 24094842 MLS
Over $60,000 Price Improvement - Now is the Time! Whether you're discovering it for the first time or coming back for another look, don't miss the chance to own this distinctive contemporary ranch at 61 Stonybrook Road. Tucked away on 1.38 private, wooded acres in picturesque Middlebury, this light-filled retreat offers over 2,800 square feet of thoughtfully designed living space. Inside, you'll find soaring vaulted ceilings, gleaming hardwood floors, and a seamless connection to nature through expansive windows and a wraparound deck-perfect for soaking in the peaceful surroundings. The open-concept layout is ideal for both easy everyday living and lively entertaining. The inviting living room features a cozy fireplace, while the spacious primary suite offers a tranquil escape with its ensuite bath and calming views. With four bedrooms, 2.5 baths, and nine versatile rooms, you'll have all the space you need for family, guests, work-from-home setups, or creative pursuits. Outside, the oversized detached 2-car garage provides room for your vehicles, tools, and extra storage. All of this nestled in a welcoming community known for its highly rated schools, small-town charm, and easy access to shopping, dining, and major commuter routes. If you're looking for the perfect blend of comfort, space, and serenity-this is the one to see!

61 Stony Brook Rd, Middlebury
$511,000
3 Beds ⋅ 3 Baths ⋅ 24064329 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Unit 38 is an End Unit. Phase 1 occupancy starting Summer 2025. Model unit coming soon! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 38, Middlebury
$510,000
2 Beds ⋅ 2 Baths ⋅ 24174618 MLS
Beautifully updated ranch in ultra-convenient Middlebury location offering nearly 2000 sq ft of stunning living space! This meticulously maintained home features hdwd floors throughout excluding kitchen, an incredible open, sun-filled layout w/ oversized windows & skylight bringing in natural light from every angle. The massive living room w/ gas fireplace flows seamlessly into living room & dining area that are anchored by wrap around windows & access to the wraparound deck, perfect for entertaining. The chef's kitchen is truly spectacular w/ large granite center island, custom tile backsplash, gas cooktop, abundant cabinetry, double wall oven, eat-in space, & endless counter space. The absolutely stunning primary suite is a true retreat featuring a huge bedroom w/ hardwood floor, walk-in closet w/ custom built-ins, private screened in porch overlooking backyard, & luxurious spa-inspired bath that feels straight out of a high-end resort. Incredible primary bathroom showcases a custom tiled oversized glass shower, deep free-standing soaking tub, double granite vanity, elegant finishes, & exceptional attention to detail throughout. Spacious 2nd bedroom & beautifully updated hall bath w/ stall shower & separate tub complete the main level. Lower level offers incredible flexibility w/ finished bonus space perfect for home office, playroom, gym, plus wine closet, walk-in cedar closet & massive laundry room. 1 car garage, incredible yard space w/ 2 sheds, truly turnkey, mint!

80 Anawan Ave, Middlebury
$510,000
3 Beds ⋅ 2 Baths ⋅ 24158643 MLS
Highest & Best due Tuesday 3/31 @5:00 pm. Welcome to 38 E Ridge Drive - Move-In Ready & Fully Updated. This beautifully renovated home is located in one of the most sought-after areas of town. With an open floor plan and hardwood floors throughout, it offers a seamless blend of comfort and style. Inside, you'll find a large living and dining room combo. The kitchen has been thoughtfully updated with granite countertops, a lovely backsplash, and stainless-steel appliances. There are 3 spacious bedrooms and two full bathrooms. The primary bedroom includes its own private bath for added convenience. The home features two gorgeous fireplaces, one of which is propane, adding warmth and charm to the living spaces. Downstairs, the finished basement provides excellent additional living space, perfect for a gym, office, or recreation room. There's also a dedicated laundry and utility room, plus a two-car garage for added storage and convenience. The property features an upgraded heating system, converted from electric to oil, with an on-demand water heater to ensure maximum efficiency. Additionally, the home offers central air conditioning for year-round comfort. Outside, enjoy summer days by the above-ground pool, complete with composite decking, and a beautiful, large yard! This home truly has it all-modern updates, functional spaces, and a prime location. Schedule your showing today!

38 E Ridge Dr, Middlebury
$510,000
2 Beds ⋅ 3 Baths ⋅ 24085335 MLS ⋅ Benson Woods BLDG.
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. Roof, exterior siding and driveways are also covered. 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.

112 Periwinkle Dr Unit 112, Middlebury
$508,500
5 Beds ⋅ 3 Baths ⋅ 170567806 MLS
Lovely, level lot with luscious gardens. Well maintained home with so much room for everyone. You'll love the open floor plan, quality and condition combine to make this 3030 s.f. home a great value. The spacious living room is open to the dining room overlooking the professionally landscaped rear yard. The family room, with mahogany paneling and oak flooring, offers a beautiful stone fireplace and Andersen sliders for easy access to the lovely bluestone patio. Very comfortable kitchen with generous cabinets, large dining area, fully applianced and access to the bluestone patio. In addition, there are 3 bedrooms on the main level and 2 bedrooms on the 2nd level. One of these can be the primary bedroom with its custom built ins and closets. You'll enjoy the lovely terrace overlooking the beautiful property with lush gardens and very mature trees. Very convenient location, close to highway, schools, excellent restaurants and many conveniences. Region 15 has excellent schools. Less than an hour commute to Hartford and New Haven. New York approximately 1 hour away.

312 Three Mile Hill Rd, Middlebury
$507,500
2 Beds ⋅ 2 Baths ⋅ 24001705 MLS
Welcome home to 71 Acme Dr. Don't miss the opportunity to live in the sought after town of Middlebury Ct, Sitting on a 1 acre lot. Inside you'll find a bright and airy recently remodeled home with over 1,600 square ft....This charming ranch has 2 bedrooms, 2 Baths, extra large family room with vaulted ceilings. The kitchen is updated with quartz counters, subway tiles, GE cafe series appliances (brushed bronze ), double refrigerator.,,, Both bathrooms are completely remodeled.... This cozy ranch has so many updates including, New furnace, hot water heater, soffits and gutters which include leaf guards. A new Hot Springs Prodigy Hot Tub, with reinforced Trex Decking over looking the garden and trees aligned for your privacy. Newer garage doors and treated flooring, newer roof , 2 propane tanks (owned). Remote controlled blinds in the primary. Newer tinted windows in the family room overlooking a beautiful yard with flourishing landscaping, gorgeous perennial's throughout, for lots of added color for all seasons. A full house security system with four hardwired cameras. Two large flat screen TV'S with soundbars. A propane white birch fireplace with a Honed Black granite facade. An adorable front entrance for major curb appeal!!!! This home has so much to offer, you can tell how well maintained and cared for this home was by its previous owner. Don't wait this home will not last long. Make your appointment today and get ready to FALL IN LOVE. COMING SOON MORE PHOTO"S.

71 Acme Dr, Middlebury
$505,834
3 Beds ⋅ 3 Baths ⋅ 24076410 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming Spring 2025. Now accepting deposits on Phase 2! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 39, Middlebury
$505,000
3 Beds ⋅ 3 Baths ⋅ 24092716 MLS
Pride of ownership abounds in this custom built cape! Main level offers living room with fireplace and pellet insert, crown moldings and hardwood flooring with open flow into the dining room appointed with French doors with transom, crown moldings and hardwood flooring, eating space kitchen boasting vaulted ceiling heights, skylights, ceiling fan, maple cabinets, granite counter tops, pantry, abundance of windows and sliding glass doors to patio, 2 bedrooms both offering hardwood flooring, full remodeled bath and powder room complete this level. The upper level features primary bedroom suite complete with office space, sitting area, skylights, crown molding, walk in closet, hardwood flooring and luxurious full bath adorned with soaking tub, walk in shower, skylight and granite counter tops. This treasure as offers spacious outbuilding with electric and garage, tasteful landscaping complete with custom rock walls, slate patio and full covered front porch! Additional amenities include central air conditioning, custom trim throughout, newer siding, thermopane windows, roof and oil tank! This home is conveniently located just minutes to Interstates 84 & 8, Metro North and an abundance of restaurants, shopping and medical facilities!

1440 Straits Tpke, Middlebury
$505,000
3 Beds ⋅ 2 Baths ⋅ 24081256 MLS
Welcome to this wonderful classic Cape Cod home. Situated on over an acre of land, this house exudes character and craftsmanship. The home sits on a sloping lot with panoramic views. Stone walls border the property and a 900 sq foot pole barn await its next owners. The spacious yard has a water feature in the back yard. The detached garage at the end of the driveway offers 400 sq ft of space. The house offers 3 or 4 bedrooms on the upper level. The 4'th space is currently used as an office. Each bedroom has softwood pine floors in excellent shape. a full bathroom for the upstairs. A walk up attic from a bedroom has abundant storage. The main level has a rear entry breezeway into the eat in kitchen, with Hickory cabinets. Off one side of the kitchen is a dining room with a slider to an incredible 3 season porch. The porch has an eat in area, pine softwood flooring, large screened windows and ceiling fans. Large timbers were used to frame the porch area. The living room has a fireplace (propane log) and the family room sits off the living room, and has a false wall separating the dining room from it. You can take this wall down to create an open floor plan. All rooms with carpeting have pine softwood flooring underneath the carpet. The covered front porch with center stairway provides a warm entry or sitting area with those wonderful views. The basement is stone with dry lock paint and basement system to keep the area dry all year round. A full bath is off of the kitchen.

713 Whittemore Rd, Middlebury
$500,000
3 Beds ⋅ 3 Baths ⋅ 24169230 MLS
Thoughtful updates, versatile living space, and an unbeatable location come together at this gorgeous, meticulously maintained Middlebury home which offers the perfect blend of comfort and functionality and a layout designed for both everyday living and gracious entertaining. Freshly painted throughout, the home feels bright, clean, and move-in ready from the moment you step inside. The heart of the home flows from the kitchen and dining area out to a spacious bi-level deck, overlooking a large, flat backyard, ideal for gatherings, play, or simply enjoying peaceful time outdoors. A lovely lower patio creates an additional outdoor living space that feels like your own private retreat. Downstairs, the recently renovated lower level adds exceptional value and flexibility. Finished with upscale touches, this space features a comfortable living area with a luxurious fireplace, a private bedroom, full bathroom, and direct access to both the oversized 2-car garage and the backyard patio through sliding doors. Practical upgrades provide peace of mind and long-term efficiency, including: New roof and leaf guards (2020), Upgraded 200-amp electrical service, New Furnace (2024), Generator hookup (2020), New double-wall 300-gallon oil tank (2020), New well pump and water softener (2025), and hot and cold water supply in garage (2025).

283 Whittemore Rd, Middlebury
$500,000
3 Beds ⋅ 2 Baths ⋅ 24008500 MLS
Welcome to your dream colonial! This charming 3-bedroom, 2-bathroom home boasts a timeless appeal, complete with modern updates and classic features. Step onto the inviting front porch, where relaxation and curb appeal meet. Enter the living room adorned with a cozy fireplace and elegant built-ins, creating a warm and welcoming atmosphere. The dining room is where gatherings happen and hardwood floors flow throughout this area of the home, adding to its allure. The large eat in kitchen features stainless steel appliances, granite counters, durable tile flooring and is open to the light filled office/den/playroom with access to the rear deck. Feel secure and comfortable with new Harvey replacement windows, ensuring energy efficiency and peace of mind for years to come. Newly installed custom window shades in every room, providing both style and privacy. The new roof (2021) and just paved driveway (2024) add to the home's appeal. The front to back lot is one of the larger ones is the neighborhood. You will have fantastic sunset views from your deck, patio and rear yard. Don't miss the opportunity to own this exquisite home, where modern comforts blend seamlessly with timeless charm and award winning Region 15 schools. City water and sewer. Easy to show.

110 Yale Ave, Middlebury
$500,000
4 Beds ⋅ 2 Baths ⋅ 24024756 MLS
This sprawling cape sits majestically on nearly an acre of property on Carriage Drive, one of Middlebury's most desirable neighborhoods. With its flexible layout, it lends itself to a variety of living situations to coincide with today's need for a variety of lifestyles. On the interior, an eat in kitchen overlooks the private rear yard. The formal dining room is adjacent to the kitchen and is the perfect spot for hosting special meals with friends & family. A formal living room with fireplace, oak flooring and access to the screened porch is a great space for entertaining or quiet enjoyment. In addition, the main level offers 2 bedrooms, a full bath and a family room/den with access to the rear yard. On the second level, 2 additional bedrooms and a full bath. You can create a home office on either level because there is plenty of space, or you can utilize the full basement. Please note that there are beautiful oak floors throughout.

240 Carriage Dr, Middlebury
$499,900
3 Beds ⋅ 3 Baths ⋅ 24083738 MLS
PRICED TO SELL! DO NOT MISS YOUR OPPORTUNITY TO LIVE IN THE AMAZING TOWN OF MIDDLEBURY IN THIS BEAUTIFUL COLONIAL THAT NEEDS NOTHING BUT TO MOVE RIGHT IN! ACT QUICK! 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!

58 Shadduck Rd, Middlebury
$499,900
3 Beds ⋅ 3 Baths ⋅ 24076140 MLS ⋅ Aberdeen Estates At Benson Woods BLDG.
An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming Spring 2025. Now accepting deposits on Phase 2! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 42, Middlebury
$499,000
2 Beds ⋅ 2 Baths ⋅ 170527688 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham Elite style is our single level attached home with the loft option. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

108 Periwinkle Dr Unit 18, Middlebury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.