Middlebury Homes under $1.25 million

Welcome to Middlebury, Connecticut – a charming town nestled in the heart of New Haven County, where picturesque landscapes meet a vibrant community spirit. Known for its serene environment, Middlebury offers residents a perfect blend of suburban comfort and easy access to urban amenities, making it an ideal place to call home.

With its rich history and stunning natural beauty, Middlebury is characterized by lush parks, tranquil lakes, and scenic walking trails. The town boasts a close-knit community that values both tradition and progress, creating a welcoming atmosphere for families, young professionals, and retirees alike. Local events, farmers' markets, and seasonal festivities foster a sense of belonging, ensuring that residents feel connected to their neighbors.

When it comes to real estate, Middlebury shines with a diverse selection of homes available under $1.25 million. Whether you're searching for a charming colonial, a modern ranch, or a cozy cape, you'll find a variety of options that cater to different lifestyles and preferences. Many of these homes feature spacious yards, inviting interiors, and convenient access to local schools, shopping, and dining.

The town’s commitment to maintaining its natural charm while promoting growth makes it an attractive choice for homebuyers. With excellent schools, a low crime rate, and a strong sense of community, Middlebury is not just a place to live; it’s a place to thrive. Explore the opportunities that await you in this delightful Connecticut town, where your dream home may be just around the corner!

Newest Middlebury Homes under $1.25 million

$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, offering both functionality and a welcoming space for casual meals. The lower level provides additional space, laundry room, garage, and unfinished space for storage.

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

$849,900

3 Beds ⋅ 3 Baths ⋅ 24209615 MLS

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

6 Deer Run 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

$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

$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

$749,000

4 Beds ⋅ 3 Baths ⋅ 24206538 MLS

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

$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

$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

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