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23 Caveson Court, Unit 23, Middlebury
$565,000
3 Beds ⋅ 3 Baths ⋅ 24135107 MLS ⋅ Steeplechase Of Middlebury BLDG.
Come discover this beautifully maintained 3-bedroom, 2.5-bathroom detached condo, ideally situated on a quiet cul-de-sac in the highly sought-after Steeplechase complex in Middlebury! This rare standalone unit offers the privacy of a single-family home with the convenience of condo living-no shared walls and minimal exterior maintenance. Inside, you'll find a spacious and open floor plan with abundant natural light, a modern kitchen, and a comfortable living area perfect for entertaining. Living room features beautiful fireplace with a gorgeous mantle. The primary bedroom features an en-suite bathroom and walk-in closet with additional space perfect for home office. Enjoy outdoor living with a private patio or backyard area, ideal for relaxing evenings or weekend gatherings. Located close to parks, schools, shopping, and major commuting routes, this home combines comfort, privacy, and convenience. Additional 500+ sq feet of living space in basement with wet bar and beautiful gas fireplace. New HVAC system was just installed last month! Not Age Restricted! This gorgeous home is a must see!

23 Caveson Court, Unit 23, Middlebury
27 Winding Trail, Unit 27, Middlebury
$565,000
3 Beds ⋅ 3 Baths ⋅ 24133988 MLS ⋅ Ridgewood At Middlebury BLDG.
Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-bed, 2.5-bath home by Toll Brothers is perfectly situated on a private cul-de-sac in one of Ridgewood's most desirable and unique locations. Offering over 2,680 SqFt of beautifully designed living space, this residence includes a rare 4-ft bump-out for added size plus a finished walk-out basement. The main level features an open floor plan with gleaming hardwood floors, custom cabinetry, stainless steel appliances, and marble countertops-perfect for modern entertaining. An upgraded skylight fills the kitchen with natural light, while sliding doors lead to a private deck with tranquil wooded views. The spacious living room highlights a gas fireplace with a stone veneer surround and rich wood mantle. Upstairs, entire 2nd level has upgraded designer hardwood flrs. Primary suite impresses with a walk-in closet and a spa-like bath w/ a double vanity, soaking tub, and separate shower. Two additional bedrooms include generous closets & soaring ceilings. The remodeled finished walk out basement is great for a media/ entertainment room. Enjoy the rare privacy of a wooded backdrop and direct access to the expansive "Great Meadow Lawn" next door-ideal for gatherings, games, or a peaceful stroll. Resort-style amenities include an outdoor pool, gym, tennis and basketball courts, movie theater, and clubhouse-all within walking distance. You can't build this home for the price, an absolute must-see!

27 Winding Trail, Unit 27, Middlebury
24 Highridge Road Unit 24, Middlebury
$560,000
3 Beds ⋅ 3 Baths ⋅ 24169215 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to luxury condo living in one of Middlebury's most sought-after communities, RIDGEWOOD. Built in 2018, this stunning 2-3 bedroom, 2.5 bath home offers over 2,600 SqFt of beautifully designed living space, plus an additional ~800 sq ft in a newly remodeled walkout lower level. Step inside to soaring cathedral ceilings, gleaming hardwood floors, and an open-concept layout filled with natural light. The kitchen seamlessly flows into the dining & living areas, highlighted by a gas fireplace and expansive windows overlooking serene wooded views. Step out onto your private deck, perfect for entertaining or relaxing in a peaceful setting. The main-level primary suite features 9+ ft ceilings, a spacious walk-in closet, a well-appointed en-suite bath. Upstairs, a versatile loft overlooks the main living space, accompanied by two additional bedrooms & a full bath... ideal for guests, a home office, or additional lounge space. The finished walkout lower level adds incredible flexibility, perfect for a media room, gym, or extended living area, w/ potential to create your own outdoor patio retreat. Enjoy resort-style amenities including a heated outdoor pool with pool house, tennis courts, indoor basketball court, fitness center, private movie theater, and a clubhouse complete with full kitchen, bar, and gathering spaces. This is a rare opportunity to own newer construction in an established luxury community, without the wait. Schedule your private showing today. 1.5 hours fr

24 Highridge Road Unit 24, Middlebury
3 Winding Trl Unit 3, Middlebury
$559,900
3 Beds ⋅ 3 Baths ⋅ 24177196 MLS ⋅ Ridgewood At Middlebury BLDG.
Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.

3 Winding Trl Unit 3, Middlebury
49 N Benson Rd Unit 49, Middlebury
$555,423
3 Beds ⋅ 3 Baths ⋅ 24096137 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 55 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.

49 N Benson Rd Unit 49, Middlebury
24 Ridgewood Dr Unit 24, Middlebury
$554,000
3 Beds ⋅ 4 Baths ⋅ 24147226 MLS ⋅ Ridgewood At Middlebury BLDG.
Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops, custom backsplash, and updated flooring. The glass sliders flood the space with natural light and lead to a private deck with tranquil wooded views. The second level offers three generously proportioned bedrooms, all with walk-in closets, including an elegant primary suite with a spa-like bath complete with soaking tub and separate shower. A third-floor loft with skylights provides flexible space ideal for a home office or lounge, while the newly finished walk-out lower level features a spacious recreation room, full bath, abundant storage, and direct access to a private patio. Fresh paint, crown molding, recessed lighting, and upscale finishes add warmth and sophistication throughout. Ideally positioned near the pool and clubhouse and conveniently located close to shopping, highways, parks, and walking trails, this exceptional home delivers comfort, style, and convenience in one of Middlebury's premier communities.

24 Ridgewood Dr Unit 24, Middlebury
North Benson Rd Unit 64, Middlebury
$545,400
3 Beds ⋅ 3 Baths ⋅ 24077175 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 64 is an End Unit. Phase 1 occupancy starting Summer 2025. Now taking deposits on Phase 2. Model unit coming Spring 2025! A Planned Unit Development (PUD) - Built by Lovley Development, Inc. / Developed by Newport Realty Group. Agent related.

North Benson Rd Unit 64, Middlebury
2 Dogwood Ct Unit 2, Middlebury
$545,000
3 Beds ⋅ 4 Baths ⋅ 24111129 MLS ⋅ Ridgewood At Middlebury BLDG.
Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the best best private streets in the highly sought-after Ridgewood community. The resort style complex people are raving about! This spacious home offers a flexible layout perfect for modern living. The main level features hardwood floors, a half bath, a bright living room, a dining area, and an eat-in kitchen with granite countertops and space for a breakfast nook. Step out from the kitchen to a private deck overlooking a serene, wooded setting, ideal for relaxing or entertaining. Upstairs, you'll find three generously sized bedrooms, including a primary suite with vaulted ceilings, a walk-in closet, and an en-suite bath. A full bath and convenient laundry area complete this level. Basement & Bedroom floors recently remodeled 2.5 yrs ago. The top floor features a large finished loft-perfect as a home office, guest room, or playroom. The fully finished walk-out lower level includes a full bath and can serve as a media room, gym, or additional primary bedroom or potential in law. walk out basement has a patio w/ private backyard. Enjoy resort-style living with access to a clubhouse offering a fitness center, indoor basketball court, party room with kitchen, billiards, and more. Outdoor amenities include a pool, tennis court, and playground. Ideally situated across from Middlebury's Greenway Trail and park. Don't miss this rare rental opportunity in a premier community with top-tier amenities!

2 Dogwood Ct Unit 2, Middlebury
323 Watertown Rd, Middlebury
$540,000
4 Beds ⋅ 3 Baths ⋅ 24194559 MLS
Looking for a 4 bedroom home in a prime location? Here it is. This classic home sits on just over one acre of property with gorgeous gardens and a lush lawn. On the interior, a spacious updated kitchen with granite counters, an island, plenty of room for dining and wonderful storage. For easy entertaining, the living room and dining room adjoin and allow for a great flow. Enjoy a cozy family room with fireplace, oak flooring and access to a 15 x 12 deck with awning overlooking the private rear yard. In addition, there are 2.5 baths, a partially finished walk out basement and an outbuilding, perfect for storage. (Needs a bit of work.)

323 Watertown Rd, Middlebury
123 Northwood Dr, Middlebury
$535,000
3 Beds ⋅ 3 Baths ⋅ 24191913 MLS
Step into this beautifully maintained 3-bedroom, 2.5-bath split-level home where comfort and functionality come together. Gleaming hardwood floors extend throughout the entire home. The living room features a cozy fireplace, creating the perfect space to relax. The bright kitchen opens seamlessly into the dining room, making everyday living and entertaining a breeze. From the kitchen, step out onto the backyard deck overlooking the spacious backyard-ideal for summer barbecues, morning coffee, or simply enjoying the outdoors. The finished lower level offers valuable additional living space and features a walkout to a beautiful patio, providing even more room for entertaining, a family room, home office, or recreation area. With expansive front and back yards, this home offers plenty of outdoor space for gardening, play, or relaxing. Thoughtfully designed with inviting indoor and outdoor living spaces, this home is ready for its next chapter.

123 Northwood Dr, Middlebury
13 Caveson Court, Unit 13, Middlebury
$530,000
2 Beds ⋅ 2 Baths ⋅ 24137483 MLS
Welcome to this beautifully updated Osborn 2 model located in the highly desirable Steeplechase community, offering the convenience of natural gas, public water, and public sewer. This versatile home features two spacious primary suites-one on the main level and one upstairs-each with its own en-suite bath, providing flexible living arrangements. The main level boasts an open-concept layout with hardwood floors throughout, a cozy family room with a gas fireplace, and a custom-built maple storage wall. The bright eat-in kitchen is a standout, featuring white shaker cabinets, granite countertops, and stainless-steel appliances. Upstairs, you'll find the second primary suite complete with a walk-in closet and full bath, along with a loft area and a separate office space, ideal for remote work or creative pursuits. Outside, the manageable yard includes a charming slate patio bordered by a stone wall, perfect for relaxing or entertaining. Situated just minutes from Lake Quassapaug, parks, shopping, dining, and schools, this home offers a perfect blend of comfort, convenience, and a welcoming neighborhood lifestyle

13 Caveson Court, Unit 13, Middlebury
51 N Benson Rd Unit 51, Middlebury
$523,920
3 Beds ⋅ 3 Baths ⋅ 24117506 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 July 2025. A Planned Unit Development (PUD). Developed by Newport Realty Group. Agent related.

51 N Benson Rd Unit 51, Middlebury
4 Kimberwick Ct Unit 4, Middlebury
$520,000
3 Beds ⋅ 3 Baths ⋅ 24188488 MLS ⋅ Steeplechase BLDG.
Rare Stand-Alone Home in Desirable Steeplechase Complex. Experience the perfect combination of elegance, privacy and convenience in this exceptional stand alone residence in one of Middlebury's most sought after communities. Boasting nearly 2,200 square feet, this spacious home features 3 generously sized bedrooms upstairs, 2.5 baths, and an inviting open concept floor plan designed for both everyday living and entertaining. The bright living and dining area showcase soaring ceilings, beautiful hardwood floors, and an abundance of natural light. The comfortable family room is centered around a cozy gas fireplace and opens directly to a relaxing screened in porch-perfect for enjoying your morning coffee or unwinding at the end of the day. The spacious eat-in kitchen is all white and offers ample cabinet storage, newer countertops & backsplash and tile flooring. It's nice! Additional features include a 2 car garage, a full unfinished basement with lots of space , natural gas heat, city water & sewer. Also, enjoy peace of mind with a newer roof & furnace. Conveniently located near I84 and Rte 8 for easy access and commuting. Enjoy everything this turnkey home has to offer located in a quiet, walkable community.

4 Kimberwick Ct Unit 4, Middlebury
566 Benson 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
880 Whittemore 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
133 Algin Dr, Middlebury
$510,000
3 Beds ⋅ 3 Baths ⋅ 24200565 MLS
Move-in ready and thoughtfully renovated this 7-room, 3-bedroom, 2.5-bath home offers 1,357 sq ft of stylish living space plus an additional 480 sq ft finished walkout lower level, set on a quiet cul-de-sac. The open-concept main level features a spacious Living Room and Dining Room flowing into an expansive Eat-In Kitchen, with direct access to a large deck overlooking a private backyard-ideal for outdoor dining, entertaining, or relaxing. Three bedrooms and two fully renovated full baths complete the main level. The finished walkout lower level adds valuable flexibility with a large Family/Recreation Room, laundry room with half bath, and abundant storage. Additional highlights include Central Air Conditioning, attached 2-car garage, maintenance-free vinyl siding, and convenient access to shopping, dining, recreation, and major commuter routes. Beautifully updated and ready to enjoy, this home offers the perfect blend of comfort, functionality, and lifestyle convenience. A wonderful opportunity to make this inviting property your own and enjoy a place to call home.

133 Algin Dr, Middlebury
80 Anawan Ave, 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
38 E Ridge Dr, 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
50 N Benson Road Unit 50, Middlebury
$509,900
3 Beds ⋅ 3 Baths ⋅ 24118969 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 July 2025. A Planned Unit Development (PUD). Developed by Newport Realty Group. Agent related.

50 N Benson Road Unit 50, Middlebury
251 Lake Shore Dr, Middlebury
$505,000
3 Beds ⋅ 2 Baths ⋅ 24193863 MLS
Completely renovated and thoughtfully designed, this stunning 3-bedroom Cape offers modern style, quality craftsmanship, and a glimpse of lake views. The open floor plan is perfect for today's lifestyle, featuring newly refinished hardwood floors, detailed custom woodwork, wood ceilings, and a spacious living area that flows seamlessly into the beautifully updated kitchen. The kitchen is a cook's dream, showcasing a large center island, stylish finishes, and two sliding doors that open to an expansive wraparound slate patio, creating the ideal indoor/outdoor entertaining space. The flexible floor plan includes a bonus room that can serve as a formal dining room, home office, or cozy den. The spacious primary suite overlooks the professionally landscaped backyard and features a large walk-in closet with a custom California Closet organization system. Renovated bathrooms, propane heat, central air, a tankless hot water heater, and a high efficiency furnace provide comfort and efficiency. The home is also whole house generator ready for added peace of mind. The finished lower level offers additional living space with a fireplace, perfect for a family room, game room, or home gym. Outside, enjoy a beautifully landscaped yard, a one car garage, a large storage shed, and the added value of an included extra lot, providing exceptional outdoor space and privacy.

251 Lake Shore Dr, Middlebury
283 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
112 Joy Rd, Middlebury
$499,900
3 Beds ⋅ 2 Baths ⋅ 24195720 MLS
Welcome home to this beautifully updated property located in one of Middlebury's quiet and sought after neighborhoods. This move in ready home features a stylish kitchen with granite countertops, a gas range, and smart appliances, including a refrigerator, washer and dryer. Gleaming hardwood floors in living room, hallway and bedrooms. Enjoy year-round comfort with central air conditioning and peace of mind with a generator hookup and included generator. Fresh paint throughout and a completely renovated lower level provide modern, versatile living space. Step outside to a low-maintenance Trex deck and almost a half acre yard, perfect for relaxing or entertaining. Conveniently located near schools, parks, walking trails, and major highways, with local vineyards, fine dining, and all that Middlebury has to offer just minutes away.

112 Joy Rd, Middlebury
18 Freedom Rd, Middlebury
$495,650
3 Beds ⋅ 2 Baths ⋅ 24163920 MLS
Welcome to this charming and beautifully maintained 3BR ranch, perfectly situated on a quiet cul-de-sac. Offering the ease of one-level living, this inviting home features an open living room and dining room layout enhanced by gleaming hardwood floors, a cozy fireplace and abundant natural light. The updated kitchen boasts a large granite center island that is ideal for cooking gathering and entertaining. Just off the main living space is bright four season room that provides the perfect place to relax year-round. Step outside to a spacious two-tiered deck over-looking private rear yard, offering a peaceful setting for outdoor dining, entertaining or simply unwinding. The lower level has excellent potential for future expansion and is perfect for creating additional living space, a home office or recreation area. The homes low maintenance exterior and two-car garage add to its overall appeal and convenience. A wonderful combination of comfort and style, this home is ready to welcome its next owner! Seller requests highest and best by Wed 4/15 @12:00 pm

18 Freedom Rd, Middlebury
116 Yale Ave, Middlebury
$495,000
3 Beds ⋅ 3 Baths ⋅ 24131737 MLS
Tucked on a quiet street in the heart of Middlebury, this beautifully maintained Cape is where comfort meets craftsmanship. Step inside to a sunlit living room anchored by gleaming hardwood floors and a cozy gas fireplace-the perfect place to unwind after a long day. The thoughtfully designed first-floor primary suite offers a serene escape, complete with a full bath and walk-in closet. The granite-topped eat-in kitchen blends function and style, ideal for both everyday meals and weekend gatherings. Upstairs, you'll be pleasantly surprised by the spacious landing-no tight ceilings here-and two generous bedrooms flanking a well-appointed full bath. Downstairs, a partially finished basement provides room for hobbies, workouts, or movie nights. With central air, a brand-new roof, and public sewer, this home is as practical as it is inviting. Outside, lush landscaping and a maintenance-free exterior make enjoying your surroundings effortless. Timeless design, modern updates, and that unmistakable feeling of "home"-you'll find it all at 116 Yale Avenue, Middlebury.

116 Yale Ave, Middlebury
182 Bayberry Ter, Middlebury
$495,000
4 Beds ⋅ 2 Baths ⋅ 24129568 MLS
Welcome to this stunning Colonial that's full of charm and curb appeal! Step inside to a spacious kitchen with abundant storage, a cozy breakfast nook, and an adjoining dining room perfect for gatherings. The kitchen flows seamlessly into a bright, sun-filled living room and out to a two-tier deck (upper deck is trex & the lower level is pressure treated wood) is overlooking a peaceful wooded backyard-an ideal spot to relax or entertain. The main level also features hardwood floors throughout, a full bath, dining room and a dedicated laundry area for everyday convenience. Upstairs, you'll find four comfortable bedrooms, a full bath with an attractive soaker tub, and a private primary suite with its own balcony. Beautiful crown moulding throughout the home. The partially finished basement offers flexible, light-filled space for play, hobbies, or a home office, along with a well-appointed utility and workshop area that walks out to the backyard. Recent updates include: Central air (upstairs, 2021), refinished kitchen hardwood floors, roof replaced with a 50-year warranty (transferable by DiGiorgi), newer Marvin windows, newer boiler, trex decking and a generator hookup. With a two-car detached garage and plenty of parking, this home blends beauty, comfort, and practicality. Public water & sewer! Don't miss your chance to make it yours!

182 Bayberry Ter, Middlebury
413 Watertown Rd, Middlebury
$485,000
4 Beds ⋅ 3 Baths ⋅ 24185992 MLS
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!

413 Watertown Rd, Middlebury
30 Nick Rd, Middlebury
$480,000
3 Beds ⋅ 3 Baths ⋅ 24104870 MLS
Wake up with a smile in this spacious 2-3 bedroom cape style home in a quiet neighborhood. Originally built in 1950, it was re built and expanded in 2011, and it has a great deal to offer, including an expansive 17' X 9' entry that leads to the 26' X 16' living room. In addition the eat in kitchen has access to the deck overlooking the private yard. This home also features a dining room, a sunroom as well as a possible first floor bedroom. On the second level, there is a spacious, bright loft area as well as 2 bedrooms and a full bath. There are oak floors throughout the living area and tile in kitchen and baths. Plenty of space to enjoy life and to entertain. Public water and sewer. All this on a quiet street in a convenient location. (Sale is subject to Probate Court approval.)

30 Nick Rd, Middlebury
420 Charcoal Ave, Middlebury
$475,000
3 Beds ⋅ 2 Baths ⋅ 24167472 MLS
Not Your Typical Cape Style Home! This Beautifully Maintained 3 BD Home in Middlebury is Situated on 1.70 Acres and Exemplifies all the Love and Care Taken by its Owner! Surrounded by Lush Mature Landscaping, This Home Offers a Serenity Inspired Outdoor Living Spaces! Enjoy the Sounds of Birds while Sitting on Your Rear Patio. Or Host Dinner Parties in the Enclosed Sunroom on a Cool Summer evening. Enjoy the Beautiful Mixture of Gorgeous Modern Updates Seamlessly Intergraded with Stunning Hardwood floors, and Beautiful Built-Ins. Impressive Fully Appliance Eat-in Kitchen with Stainless Steel Gas Oven range, Dishwasher and Refrigerator, Updated Cabinetry with Crown Molding and Relaxing Breakfast Bar to Sit and Have Morning Coffee with Friends. Host Dinner Parties in the Formal Dining room or Holiday Celebrations in the Oversized Fireplaced Living room Featuring Large Picture Windows Overlooking Beautiful Side Yard with Babbling Brook. Foyer Entry Allows Ample room for Coats, Shoes and Storage Closet, Plus Convenient First Floor Full Bath with Soaking Tub. Second Floor Offers 3 Beautiful Bedrooms, Full Bath, Built-in Shelving, Walk-in Closet in Primary Bedroom. Additional Amenities: Over Sized 2 car Detached garage with walkup to Oversized Storage area (or Convert to Media room or Office). Home Offers Whole House Generac Generator, Ductwork in Place...Could Add CA. Do not walk property or drive on Driveway(s) without an appointment!

420 Charcoal Ave, Middlebury
637 Watertown Rd, Middlebury
$475,000
3 Beds ⋅ 4 Baths ⋅ 24145459 MLS
Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home. Recent updates include a brand new furnace, offering added comfort and peace of mind. Step outside to a large, private, slightly wooded backyard-perfect for relaxing, entertaining, or enjoying peaceful outdoor living. Conveniently located close to town shopping, restaurants, and everyday amenities, with easy access to Route 8 and I-84, this home offers an ideal blend of privacy, comfort, and convenience. A must-see opportunity.

637 Watertown Rd, Middlebury
24 Steinmann Ave, Middlebury
$467,000
3 Beds ⋅ 2 Baths ⋅ 24189880 MLS
*Please submit your offers by Monday July 20th at 2:00pm.* Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middlebury's most desirable locations. This inviting Cape offers a flexible layout that lives larger than expected. The renovated kitchen features butcher block countertops, updated appliances, hardwood floors, recessed lighting, a breakfast bar, and a GE Kitchen Hub, flowing seamlessly into the dining room. The cozy living room boasts refinished hardwood floors, custom built-ins, a wood plank ceiling, recessed lighting, and an energy-efficient pellet stove. A spacious first-floor primary suite with an en-suite bath and convenient laundry offers easy one-level living, while two bright bedrooms and a full bath complete the second floor. Recent improvements include refinished hardwood floors, updated electrical, security cameras, and a new electric pool heater. Outside, enjoy your own private retreat with a heated in-ground pool, patio, firepit space, and pool room - perfect for relaxing or entertaining. The oversized fenced driveway provides ample parking and direct access to the Middlebury Greenway for walking, running, and biking. Combining timeless character, modern updates, and outstanding outdoor amenities, this move-in ready home is one you won't want to miss! 1-Year home warranty included with sale.

24 Steinmann Ave, Middlebury

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