Middlebury Homes under $750,000

Welcome to Middlebury, Connecticut, a charming town nestled in the heart of New Haven County. Known for its picturesque landscapes and vibrant community spirit, Middlebury offers a perfect blend of suburban tranquility and modern conveniences. With its rich history, beautiful parks, and top-rated schools, it’s no wonder that families and professionals alike are drawn to this delightful town.

Middlebury boasts a variety of homes under $750,000, making it an attractive option for first-time buyers, growing families, and those looking to downsize without compromising on quality of life. From cozy single-family residences to spacious contemporary designs, the real estate market here caters to diverse tastes and budgets. Many of these homes feature charming architectural details, large backyards, and proximity to local amenities, ensuring a comfortable lifestyle for all residents.

The town’s welcoming atmosphere is complemented by its numerous recreational opportunities. Enjoy a leisurely stroll through the scenic parks, partake in community events, or explore the nearby hiking trails that showcase the stunning natural beauty of the region. With easy access to major highways and the vibrant city of Waterbury just a short drive away, Middlebury offers the perfect balance of peaceful living and urban accessibility.

Whether you’re looking to settle down in a friendly community or invest in a property that promises both comfort and value, Middlebury is an exceptional choice. Discover your dream home today in this charming Connecticut gem, where every day feels like a retreat!

Newest Middlebury Homes under $750,000

$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

$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

$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

$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

$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

$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

$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

$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

$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

$409,900

2 Beds ⋅ 1 Baths ⋅ 24203525 MLS

Rare opportunity to own direct waterfront on beautiful Lake Quassapaug! Located in the desirable Tylers Cove community, this charming two-bedroom cottage sits just 50 feet from the water and features its own private dock and yard with direct lake frontage. The cottage is ready for a new owner to bring their ideas and updates-renovate the existing home, explore the possibilities of rebuilding, or simply enjoy it as a classic summer retreat. A special opportunity to experience lakefront living, boating, swimming, and relaxing by the water on one of the area's most beautiful lakes.

89 Sandy Beach Road Unit 89, 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

$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

Start Your Search

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.