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961 Middlebury Rd, Middlebury
$479,900
3 Beds ⋅ 2 Baths ⋅ 24211870 MLS
Welcome to this inviting Middlebury home, beautifully situated on 1.6 private acres directly along the Greenway and across from picturesque Fenn's Pond. Offering a wonderful combination of privacy, natural beauty, and convenient living, this property is ideal for those who enjoy walking, outdoor activities, and entertaining. A long private driveway leads to the home, providing plenty of parking for family and guests. The fenced backyard features a dedicated play area, creating a wonderful outdoor space for children, pets, or simply enjoying the peaceful surroundings. Inside, the home is filled with natural light, and well-proportioned living spaces. The upper level features a spacious primary bedroom with a private full bath, along with two additional generously sized bedrooms, all with hardwood flooring. A second full bath includes both a tub and separate shower stall. The formal dining room is perfect for hosting and features hardwood flooring and a fireplace, while the oversized Great Room makes an impressive everyday gathering space with its cathedral ceiling and abundance of windows overlooking the private, natural setting. The home's open and light-filled perfect for entertaining. The eat-in kitchen features warm wood cabinetry, granite countertops, tile backsplash, and stainless-steel appliances. Lower level provides additional space, laundry room, garage, and unfinished space for storage. Recent updates include Newer Roof, Septic, Windows, and hot water heater.

961 Middlebury Rd, Middlebury

314 Porter Ave, Middlebury
$485,000
3 Beds ⋅ 2 Baths ⋅ 24209861 MLS
Step inside and the first thing you notice is the light: sun pouring through the kitchen's bay window onto warm new bamboo floors, which give way to the original hardwood, refinished, in the living and dining rooms. This 1941 Cape has been renovated top to bottom with high-end materials and a designer's eye, while keeping the original character that makes an older home feel like home. The kitchen and both bathrooms share a thread of rich black stone, and the primary bath is a retreat vanity, warm wood and soft, glowing floor lighting. Custom details show up wherever you look, custom kitchen cabinetry, lots of built-in storage, extra space tucked into the attic. Downstairs, the finished lower level gives you room to spread out - a second living room, a compact gym, and office fit comfortably. The mechanical room adds more storage alongside a dedicated laundry area. The big-ticket items are handled. A brand-new multi-zone AC+Heat system keeps every room comfortable, and a second independent heating systems (oil) means you are never left in the cold. The roof is just ten years old, and the garage has been refinished and waterproofed. Appliances and systems are covered by a one-year warranty, extendable up to three years. Final renovation details are still being finalized. Turnkey finished property at closing.

314 Porter Ave, Middlebury

802 Charcoal Ave, Middlebury
$550,000
4 Beds ⋅ 3 Baths ⋅ 24209000 MLS
For the antique lover, the one with vision and a desire to bring this fabulous home back to its original glory, this is the place for you. Set on over 2 acres within walking distance to Lake Quassapaug, this is a fabulous property. It offers a main house with approximately 1900 s.f.. You'll love the wide board floors, plaster walls and so many details that reflect a fabulous past. In addition to the main house, there is a detached, oversized 2 car garage with a workshop and a finished artist's loft. Enjoy the opportunity for gardens, more fruit trees and a lovely enclosed screened porch. So many original features. This is a spot for the artist, antique lover, the ones who appreciate history and have a desire to own a piece of history. The house is not air conditioned, but the area over the garage has a split system for heat and air conditioning.

802 Charcoal Ave, Middlebury

85 Ridgewood Dr Unit 85, Middlebury
$650,000
3 Beds ⋅ 3 Baths ⋅ 24209236 MLS ⋅ Ridgewood At Middlebury BLDG.
Luxury Toll Brothers built townhome in sought after Ridgewood at Middlebury! This exquisite Denton Elite end unit was customized in 2018 and offers 3 bedrooms, 2.5 baths and over 2,643 sqft of beautifully designed living space. The main level welcomes you with a spacious foyer, double storage closet, private study with garden doors and powder room. The custom kitchen features upgraded cabinetry, granite counters, stainless steel appliances, gas cooktop, hood, subway tile backsplash, oversized island and breakfast nook/ eat in kitchen. This opens to a composite deck, perfect for morning coffee or entertaining with a peaceful backyard. The living room features hardwood floors, gas fireplace and mantle, while the dining area showcases an octagonal tray ceiling and chandelier. Soaring 9 ft ceilings & upgraded lighting complete the main level. Upstairs you'll find 3 oversized bedrooms, full hall bath, laundry and a versatile loft ideal for a den, office or potential 4th bedroom. The primary suite features cathedral ceilings, massive walk in closet & luxurious bath with glass enclosed tiled shower, built in seat, double vanity & granite counters. Large basement offers potential for nearly 1,000 additional sqft. Two car garage. Upgraded location for private back and side yard, great for entertaining. Enjoy resort style amenities including heated pool, clubhouse, fitness center, tennis and indoor basketball. Enjoy the middlebury greenway! Approximately 1.3 hours to NYC! TURN KEY!

85 Ridgewood Dr Unit 85, Middlebury

25 Juniper Rd, Middlebury
$895,000
3 Beds ⋅ 4 Baths ⋅ 24209325 MLS
Welcome to this beautifully maintained ranch, ideally situated on a quiet cul-de-sac in one of Middlebury's desirable neighborhoods. Set on a private, level 1 acre lot, this 3 bedroom, 3.5 bath home offers comfort, character, and exceptional space for everyday living and entertaining. The inviting open floor plan features a stunning sunken living room, three fireplaces, and a spacious family room. The kitchen and living spaces flow seamlessly to a screened-in porch and newly remodeled deck, creating a wonderful indoor-outdoor entertaining experience. Additional highlights include an attached 3 car garage, partially finished basement, central air, city water and sewer, oil and electric heat, and an auto-start Generac generator. This home is conveniently located minutes from shopping, grocery stores, and major highways. A special home offering privacy, space, and convenience-don't miss it!

25 Juniper Rd, Middlebury

10 Old Waterbury Rd, Middlebury
$699,900
5 Beds ⋅ 4 Baths ⋅ 24207437 MLS
Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building consists of an adorable, detached single-family RANCH STYLE house-3 rooms/1 bedroom w/oversize fireplace living room & oil heat. Separate heat and utilities. Public water & sewer. Enjoy Middlebury's Greenway trails, hop brook lake for swimming, picnicking, hiking, biking and so much more-all within walking distance! The SUBURBAN town of MIDDLEBURY, is HIGHLY SOUGHT AFTER, rated on TOP, for it's schools and LOW, RENTAL VACANCY. Perfect opportunity for OWNER OCCUPANT to live in one unit and collect rent from other 3 units. INVESTORS...be proud to add this one to your portfolio while growing "SWEET EQUITY" . PLEASE REFER TO AGENT COMMENTS!

10 Old Waterbury Rd, Middlebury

294 Christian Rd, Middlebury
$995,000
3 Beds ⋅ 3 Baths ⋅ 24206798 MLS
New construction designed to impress! The Cambridge Model offers 2,878 sq. ft. of thoughtfully designed living space. A grand two-story foyer leads to the stunning great room with soaring ceilings, fireplace and beautiful windows creating a light and airy feel. The heart of the home is the spacious kitchen featuring an expansive island, granite countertops, stainless steel appliances and white shaker-style cabinetry. A breakfast nook with French doors opens to the back deck, while the formal dining room is perfect for entertaining. The first-floor primary suite offers two walk-in closets and a luxurious bath with oversized shower and double vanities. A private first-floor den provides the ideal space for a home office, homeschooling or quiet retreat. Hardwood floors run throughout the main level, which also includes laundry and a mudroom. Upstairs, two generously sized bedrooms share a Jack-and-Jill bath. Additional features include a 2-car attached garage, central air, underground utilities and sprinklers, private well and public sewer. Set on just over an acre in the desirable Avalon Farms community with limited seasonal views of the pond. Photos are of similar construction; pictured lighting is not included. Floor plans, elevations and proposed site plan are attached.

294 Christian Rd, Middlebury

182 Green Hill Rd, Middlebury
$749,000
4 Beds ⋅ 3 Baths ⋅ 24206538 MLS
Looking for a quiet, secluded location? No street noise, no close neighbors? Welcome to 182 Green Hill Road, where space, privacy, and an exceptional Curtis Farms setting come together. Set at the end of a long private driveway on nearly 3 acres, this spacious 4-bedroom, 2.5-bath Colonial offers over 3,000 square feet of living space with an incredible grand living-room with fireplace and vaulted ceiling, perfect for entertaining or relaxing with the family. The main level features hardwood flooring, generous formal living and dining areas, a private office, and a spacious eat-in kitchen with granite countertops and stainless appliances. The primary suite includes a private en-suite bath with Whirlpool tub, separate shower and double vanity. Three additional bedrooms provide plenty of room for family and guests. Enjoy the privacy of the expansive grounds from the large deck, along with a two-car garage, large unfinished basement space, generator hookup, and brand-new central air system. The rooftop solar system also offers a favorable locked-in lease rate with for transfer to the next owner. Located in one of Middlebury's most sought-after residential neighborhoods, this home offers the space and privacy of an acreage property while remaining convenient to local amenities, and surrounding communities plus the property is within the desirable Region 15 school district. MOTIVATED SELLER!

182 Green Hill Rd, Middlebury

9 Whitehall Ct, Middlebury
$979,900
4 Beds ⋅ 5 Baths ⋅ 24204911 MLS
Welcome to this extraordinary 4,261-square-foot home, truly one of a kind within the complex. This 4 bedroom, 3 full baths & 2 half baths is thoughtfully designed for both elegant entertaining and comfortable everyday living. This exceptional residence offers a first-floor primary suite and an impressive open-concept layout. The luxurious primary suite is a private retreat, featuring a newly remodeled spa-inspired bathroom with beautiful fixtures & elegant, white marble throughout and a relaxing soaking tub. Dual walk-in closets with custom-built organizers provide exceptional storage and organization. For effortless entertaining, the home features a generously sized kitchen, opened to a spectacular, 2 story great room. A substantial center island creates the perfect gathering space, while an abundance of rich cherry cabinetry provides both warmth and exceptional storage. The seamless connection between the kitchen and great room makes entertaining and everyday life feel effortless. The impressive great room creates a dramatic focal point, filling the home with an abundance of natural light and offering a wonderful sense of openness yet providing warmth with the grand, stone, gas fireplace. A dedicated dining room with French doors, creating an inviting connection to the surrounding living spaces both for family and friends.

9 Whitehall Ct, Middlebury

327 Steinmann Ave, Middlebury
$280,000
2 Beds ⋅ 1 Baths ⋅ 24205239 MLS
REDUCED AND PRICED FOR IMMEDIATE SALE! Totally renovated and completely move-in ready! This charming Cape is located in the wonderful town of Middlebury and offers a fantastic alternative to condo living-without the monthly HOA fees. Step inside to a bright, fresh interior where all the work has already been done for you. The updated kitchen features stainless steel appliances, modern finishes, and plenty of natural light. Thoughtfully renovated throughout, this home offers the perfect blend of comfort, style, and low-maintenance living. Whether you're a first-time buyer, looking to downsize, or simply searching for a beautifully updated home in a desirable community, this Middlebury gem is ready for you to move right in and enjoy!

327 Steinmann Ave, Middlebury

138 Steinmann Ave, Middlebury
$350,000
3 Beds ⋅ 2 Baths ⋅ 24203915 MLS
This charming 3-bedroom, 2-full-bath home offers 1,466 square feet of comfortable living space on nearly half an acre, tucked away in a peaceful neighborhood in one of Connecticut's most sought-after communities. Step inside to a welcoming living room featuring hardwood flooring and a generous 6'x3' walk-in closet. The main-level primary bedroom offers the same warmth of hardwood flooring, along with an impressive 6'x5' walk-in closet. A full bathroom with a convenient shower stall is also included on the main level. The eat-in kitchen features hardwood flooring and recessed lighting and flows naturally into a spacious family room designed for relaxing and entertaining. Here, an impressive stone fireplace creates a warm focal point, while brand-new carpeting and two skylights add comfort and natural light. Just beyond the family room, enjoy two covered outdoor spaces-an expansive 19'x16' covered patio on one side and a 17'x7' covered patio on the other-providing plenty of room for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The second level offers two additional bedrooms, each featuring hardwood flooring, along with another full bathroom enhanced by a skylight that brings in wonderful natural light. A full walk-out basement provides excellent additional space and flexibility, with a newer water heater already in place. This home offers charm, functionality, generous living spaces, and an opportunity to make it your own in beautiful Middlebury!

138 Steinmann Ave, Middlebury

58 Shadduck Rd, Middlebury
$574,900
3 Beds ⋅ 3 Baths ⋅ 24203901 MLS
Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

58 Shadduck Rd, Middlebury

18 Hunting Ridge Rd, Middlebury
$799,900
4 Beds ⋅ 3 Baths ⋅ 24203733 MLS
Welcome to Hunting Ridge Estates! This stunning 2,700 sq. ft. Colonial, built in 2025 and just 14 months young, is located in a desirable 23-home Middlebury subdivision. Offering the ease and feel of new construction, this 4-bedroom, 4-bath home features an open floor plan and hardwood flooring throughout both levels. The bright, stylish kitchen showcases white shaker cabinetry, off-white quartz countertops, stainless steel appliances, a large center island, and walk-in pantry. It opens to the dining area and spacious family room with gas fireplace and sliders to the 17' x 15' rear patio. A formal dining room and flexible main-level bedroom/half bath add versatility. Upstairs, the spacious primary suite is a true retreat, featuring a beautifully finished ensuite with dual quartz-topped vanities, elegant oval sinks, and a 4' x 5' glass-enclosed walk-in shower. The suite includes two walk-in closets, highlighted by an impressive 12' x 14' dream closet/changing room-perfect for anyone who has always wanted exceptional wardrobe space. An upper-level laundry closet and additional full bath with double vanity, granite, tile flooring, and glass-enclosed tub/shower complete the second floor. Enjoy all that Middlebury and the surrounding area have to offer, from parks, trails, recreation, dining, and shopping to convenient access to neighboring communities. Beautifully designed, thoughtfully finished, and ideally situated, this is a home designed for modern living and enjoying life

18 Hunting Ridge Rd, Middlebury

285 Southford Rd, Middlebury
$650,000
3 Beds ⋅ 2 Baths ⋅ 24201753 MLS
Welcome to 285 Southford Rd, a beautiful spacious ranch which checks off all the boxes. Main level living with Open foyer leading into family room w/ gas fireplace, vaulted ceilings, dimmer controlled recessed lighting, and atrium door opening to stone patio. Formal dining room w/ 9 foot ceilings and plenty of natural sunlight. Eat in kitchen has a bow window and table nook area, an abundance of cabinets, granite countertops, built in oven and counter cooktop stove. Hardwood flooring flowing through to Primary bedroom suite complete with trey ceiling, walk in closet, full bath compliments the soaking tub and separate shower stall. 2 bedrooms, full bath and laundry area complete this great floor plan. An added bonus is the office, exercise room or study on the upper level. Full basement and walk in attic commands plenty of storage. Manicured level private lot with heated in the ground pool and hot tub and offering 2 car garage .

285 Southford Rd, Middlebury

46 Washington Dr, Middlebury
$645,000
4 Beds ⋅ 4 Baths ⋅ 24202816 MLS
Welcome to this fabulous one-owner custom-built Cape Cod offering 4 bedrooms, 3.5 baths, and exceptional living space throughout. Beautiful tile and hardwood floors, vaulted ceilings, and a spacious great room with a fireplace and pellet stove create a warm and inviting atmosphere. The first-floor primary suite features a private ensuite bath, while the second floor offers two additional bedrooms, a full bath, and a huge bonus room with endless possibilities for a home office, recreation room, or additional living space. The finished lower level includes an in-law setup with a walkout, providing excellent flexibility for extended family, guests, or additional living space. Enjoy beautiful views across to Long Meadow Pond from the covered rear deck off the great room, or relax and entertain on the expansive patio area. A three-car garage provides plenty of room for vehicles, storage, and hobbies. Additional features include a whole-house propane generator and newer roofs on both the house and shed, installed in 2023. Ideally located in a great setting, this meticulously maintained custom home offers comfort, space, versatility, and beautiful views-truly a special property you'll want to see!

46 Washington Dr, Middlebury

16 Caveson Court, Unit 16, Middlebury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24191400 MLS ⋅ Steeplechase BLDG.
Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk-in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury

16 Caveson Court, Unit 16, Middlebury
$575,000
3 Beds ⋅ 3 Baths ⋅ 24202542 MLS
Welcome to this beautifully updated three-bedroom Cape in the desirable Steeplechase community. Hardwood flooring flows throughout the home, complemented by custom plantation shutters and window treatments in most rooms. The flexible floor plan includes an additional room off the eat-in kitchen. Upstairs, you'll find three spacious bedrooms, two updated baths, and conveniently located laundry. The primary suite features two walk- in closets, while the additional bedrooms offer built-in closet systems. Enjoy the private deck and backyard, plus a full unfinished walkout basement with plenty of potential. Additional highlights include an automatic whole-house Generac generator, natural gas heat, central air, public water and sewer, and a total of 2.5 updated baths. Ideally located on a quiet cul-de-sac, this lovely home is ready for its next owner. Schedule your appointment today!

16 Caveson Court, Unit 16, Middlebury

106 Steinmann Ave, Middlebury
$439,900
4 Beds ⋅ 2 Baths ⋅ 24200006 MLS
Welcome Home to this nicely updated New England Cape style home with a comfortable and convenient layout. This move-in ready home offers 4 bedrooms and 2 full bathrooms. An inviting living room showcases a fireplace creating a warm and cozy gathering space for the whole family, adjoining dining area leads to The large kitchen includes ample workspace, lots of cabinets and tile flooring, with easy access to the large deck, and back yard-perfect for all your outdoor entertaining. Two bedrooms, and recently renovated full bath and hardwood floors complete the main level. As you walk upstairs you will find a Full remodeled bathroom, A bedroom and A large primary bedroom, with vaulted ceilings, slider to balcony overlooking your landscaped back yard, A large closet, hardwood floors and fresh paint finish out this fabulous space. Added bonuses include full walk out basement into one car garage, ample storage, large shed and parking for the whole family. Don't miss out on the chance to make this move-in ready home yours! It is close to Route 84 and Middlebury walking trail. Welcome to Middlebury and their award- winning region 15 school.

106 Steinmann Ave, Middlebury

552 Breakneck Hill Rd, Middlebury
$950,000
5 Beds ⋅ 4 Baths ⋅ 24198521 MLS
Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home includes wide-board floors, three fireplaces and a remarkable series of covered porches and "piazzas" capturing the romance of 19th-century country living. There is effortless flow from the gorgeous sunroom, with walls of windows, into the formal living room, dining room and large entertaining kitchen. A main-floor laundry room, enormous utility room, pantry and powder room add convenience. The primary suite offers a private retreat, with an en-suite bath and adjoining sitting room or study, flanked by two covered porches. Outside, a charming secluded wading pool with fountain provides a wonderfully relaxed setting for summer gatherings, cocktails and afternoons spent enjoying the gardens. A detached 2-car garage with bonus unfinished loft space invites a future artist studio. An exceptional opportunity to bring this distinctive home to the next level. 2 hrs to NYC. Subject to Probate.

552 Breakneck Hill Rd, Middlebury

77 Crest Rd, Middlebury
$749,900
4 Beds ⋅ 4 Baths ⋅ 24193938 MLS
Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.

77 Crest 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

47 Middlebury Ter, Middlebury
$474,500
2 Beds ⋅ 2 Baths ⋅ 24194436 MLS
Cottage Colonial close to town center, parks and more in beautiful Middlebury CT! This 1929 build charmer has stunning details both inside and out. Lovingly cared for, the pride of ownership of this property is evident upon arrival. Note the unique features including: Hardwood flooring throughout main and upper levels, sunken family room w/wood panel vaulted ceiling and slider to deck, wood burning fireplace in the Parlor/Living room. Kitchen boasts granite countertops, stainless appliances (newer Dishwasher & Range) and breakfast bar. Stunning Dining room with corner built ins reminiscent of bygone days offers a special gathering spot. Combo Laundry/Powder room and Office also on main level. Upstairs there are 2 good sized bedrooms with hall bath. Then a surprise 3rd level finished room w/electric heat. Ideal extra space to enjoy (play room, music room, reading room, you choose!). Step outside to enjoy the lovely wraparound deck with Pergola and Garage/Shed for lawn equipment, tools or even a possible gardening shed! Generator hook-up in place. City water and sewer too. Book your appt. and see this gem of a home for yourself soon!

47 Middlebury Ter, Middlebury

12 Yale Ave, Middlebury
$339,900
2 Beds ⋅ 1 Baths ⋅ 24113785 MLS
Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

12 Yale Ave, Middlebury

42 White Ave, Middlebury
$449,900
3 Beds ⋅ 3 Baths ⋅ 24191937 MLS
Set on nearly half an acre in one of Middlebury's most desirable neighborhoods, this 3-bedroom, 2.5-bath Colonial blends timeless character with everyday comfort. Gleaming hardwood floors run throughout the home, anchoring an open, inviting layout built for both daily living and entertaining. The heart of the home is a spacious family room crowned by a dramatic cathedral ceiling and ceiling fan, a bright and airy retreat that flows naturally into the rest of the main level. The kitchen is ready to cook in and gather around, featuring granite countertops, a breakfast bar, and stainless appliances including a gas cooktop. Generous living and dining rooms round out the main floor, each finished in warm hardwood. Upstairs, the primary bedroom suite offers a private full bath and walk-in closet, with two additional well-sized bedrooms, one with its own walk-in closet. A cozy fireplace, central air, thermopane windows, and zoned heating add year-round comfort and efficiency. Outside, enjoy a level, open lot with plenty of room to play, garden, or relax. A full unfinished basement with garage access and a one-car under-house garage provide ample storage and expansion potential. A brand new basement system was installed on 7/14/26, adding to peace of mind.

42 White Ave, Middlebury

10 Curtis Rd, Middlebury
$670,000
4 Beds ⋅ 3 Baths ⋅ 24191383 MLS
Well-maintained, single-owner Center Hall Colonial located on a corner lot in an established neighborhood. This 4-bedroom, 2.5-bath home offers a functional floor plan, a 2-car garage and central air. The main level features a formal living room and dining room, an updated eat-in kitchen with new granite counters, tile backsplash, new stainless steel appliances, and a slider to the deck. The kitchen opens to the family room with a fireplace, creating a comfortable gathering space. A half bath completes the first floor. Upstairs you'll find 4 bedrooms, including a primary suite with two walk-in closets and a full bath with a corner tub. The second-floor laundry adds everyday convenience. The unfinished walk-out basement offers excellent storage and future expansion potential. Outside, enjoy the deck, patio, and private backyard. Conveniently located in the award-winning Region 15 school district and close to parks, schools, the library, shopping, restaurants, and major commuter routes. A move-in ready home in a sought-after neighborhood.

10 Curtis Rd, Middlebury

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