Middlefield Real Estate

Welcome to Middlefield, Connecticut—a hidden gem nestled in the heart of Middlesex County. This charming town offers a delightful blend of rural tranquility and suburban convenience, making it an ideal place for families, retirees, and everyone in between. With a rich history dating back to the 18th century, Middlefield is steeped in tradition, yet it boasts modern amenities that cater to today’s lifestyle.

The town is renowned for its picturesque landscapes, featuring rolling hills, lush forests, and serene lakes. Outdoor enthusiasts will find plenty of opportunities for exploration at the nearby Wadsworth Falls State Park, where hiking trails and scenic waterfalls await. The community is also home to a variety of recreational facilities, including sports fields, playgrounds, and picnic areas, perfect for family outings and social gatherings.

Middlefield’s charming downtown area offers a selection of local shops, cafes, and eateries, creating a warm, small-town atmosphere. Residents enjoy a close-knit community with various events throughout the year, from farmers' markets to seasonal festivals, fostering a sense of belonging and connection among neighbors.

Education is a top priority in Middlefield, with access to quality schools that serve the community’s youth, preparing them for a bright future. The town’s strategic location also provides easy access to major highways, making commutes to nearby cities like Hartford and New Haven a breeze.

Whether you’re looking to settle down or invest in a piece of Connecticut’s beautiful landscape, Middlefield offers an inviting community that feels like home. Come discover the charm and warmth of this delightful town!

Newest Listings in Middlefield

$439,900

3 Beds ⋅ 3 Baths ⋅ 24213598 MLS

4 Stowe Street is a 3-bedroom, 2.1 bath raised ranch on a generous 0.78-acre lot in desirable Middlefield. The bright main level offers a fireplaced living room open to the dining area and an eat-in kitchen with abundant cabinetry, a peninsula, and a slider to the back deck. Three bedrooms and one full and one half baths complete the main floor. The finished lower level adds about 504 sq ft of extra space with a second brick fireplace, a full bath, and laundry. Central air, a newer boiler, a water softener, and an under-house garage. Clean, empty, and ready for its next owner. Regional School District 13. Minutes from Lyman Orchards, Powder Ridge, golf, and Routes 66/147/9! This is a beautiful home!

4 Stowe St, Middlefield

$349,900

3 Beds ⋅ 1 Baths ⋅ 24213622 MLS

*** Charming Ranch in the Desirable Rockfall Neighborhood! *** Welcome to 12 Wildwood Acres Road, nestled in an established neighborhood in Middlefield, CT! This inviting 3-bedroom, 1-full-bath Ranch offers 1,352 square feet of comfortable one-level living, featuring charming blue cedar shingle siding and plenty of potential to make it your own. Situated on a .44-acre lot, the property boasts a lovely, level backyard with plenty of space for outdoor entertaining, gardening, recreation, or simply relaxing. Enjoy the added convenience of a main-level laundry, making everyday living that much easier! Notable improvements include 200-amp electrical service upgraded in 2024, a new septic system installed in 2019, and a roof replaced in 2015. The clean, unfinished basement provides abundant storage and exciting possibilities for future finished living space customized to your needs and vision. Whether you're looking to downsize, purchase your first home, or enjoy the ease of single-level living, this home offers a wonderful opportunity in a desirable Rockfall location. Bring your ideas, add your personal touches, and make this charming Ranch your own! *** Note: Property is Under Contract. Sellers are accepting Backup Offers. ***

12 Wildwood Acres, Middlefield

$595,000

2 Beds ⋅ 1 Baths ⋅ 24210670 MLS

Fall on Lake Beseck may just be its best-kept secret. Wake up to spectacular sunrises reflecting off the water, take in the changing colors from your private deck, and enjoy peaceful days kayaking, fishing or simply relaxing lakeside. This charming direct waterfront cottage offers the lake lifestyle buyers dream about, with private docks and a floating dock providing instant access to the water. Motorboats are welcome, so when warmer days return, boating and swimming are right outside your door. Inside, the open floor plan is filled with natural light and flows into a beautiful sunroom wrapped in windows, keeping the lake views front and center in every season. Step outside to the Trex deck, the perfect spot for morning coffee, evening cocktails and a front-row seat to some unforgettable sunrises. Thoughtfully maintained with central air and a new roof in 2024, this home is ready to enjoy from day one. Lake Beseck is managed by DEEP, and no flood insurance is required. Looking to create something more? There is potential to build up to 35 feet, subject to approvals. Just minutes from I-91 and close to Powder Ridge, Lyman Orchards and four golf courses, this is more than a summer escape. It's a place to enjoy every season and start making lake memories now.

18-A Lake Shore Dr, Middlefield

$420,000

4 Beds ⋅ 2 Baths ⋅ 24202534 MLS

Welcome to this inviting ranch in Middlefield, a home that has been lovingly owned and cared for by the same family for many years. Originally a small cottage, the home has grown over the years with thoughtfully added spaces to accommodate a growing family, creating a unique layout filled with character and plenty of room to make it your own. The spacious living area is a true centerpiece of the home, featuring a custom-built stone fireplace. On the kitchen side, a wood-burning stove offers another option to save money on heating costs. A recently renovated sunroom, completed within the past year, sits between the garage and living room and features electric heat, making it a great space for year-round enjoyment. Outside, the property features a large two-bay garage with additional storage space above. Come see what this home has to offer your family.

24 Sunrise Rdg, Middlefield

$699,000

4 Beds ⋅ 3 Baths ⋅ 24196454 MLS

Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield

$729,999

3 Beds ⋅ 3 Baths ⋅ 24195983 MLS

Welcome Home to Middlefield! Experience the perfect blend of modern comfort and timeless farmhouse charm in this stunning new construction ranch, thoughtfully designed for effortless one-level living. Situated on a clear, level, and fully usable one-acre lot just up the hill from beautiful Lake Beseck, this home offers the ideal combination of privacy, convenience, and style. Boasting 2,278 square feet, this spacious home features three bedrooms, 2.5 bathrooms, and an attached two-car garage. The open-concept floor plan is designed for both everyday living and entertaining, with a welcoming great room that serves as the heart of the home. Unwind in the bright and inviting sunroom, or enjoy the ease and accessibility that only single-story living can provide. Located in the thriving town of Middlefield, this property offers the best of both worlds-peaceful rural surroundings with exceptional access to major amenities. Commuters will appreciate the convenient highway access, placing New Haven just 20 minutes away and Hartford approximately 25 minutes away. Outdoor enthusiasts will love being just minutes from Lake Beseck, scenic hiking trails, championship golf courses, and nearby ski areas. Excellent schools, shopping, dining, and a variety of cultural attractions are all within easy reach, making this an exceptional place to call home. There's still time to select your finishes so don't wait long! Please note, pictures and drawings may contain optional fini

123 Way Rd, Middlefield

$749,900

4 Beds ⋅ 3 Baths ⋅ 24190498 MLS

Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office, playroom, or reading nook. A separate living room, complete with a working fireplace, creates a cozy retreat for New England winters or days on the slopes of the nearby Powder Ridge Ski Resort. For the summer, step outside and you will find a stunning in-ground pool surrounded by a spacious brick patio, perfect for lounging and outdoor dining. An attached two-car garage adds everyday convenience and a second private driveway offers access to the rear of the property and the detached barn. The true gem is this fully renovated, detached barn-an inspired space with limitless potential. Featuring whitewashed wood walls and an airy farmhouse aesthetic, the barn offers a dramatic open-plan ground level and a second floor with three rooms and a bathroom. Off of the ground level, french doors lead to a private terrace shaded by mature grapevines, ideal for al fresco dining or sunset cocktails. Whether used as a luxurious art studio, at-home gym or work-from-home suite, this space delivers unmatched versatility with its own entrance and a beautiful walkway connection to the main home and pool.

88 Powder Hill Rd, Middlefield

$399,000

24189290 MLS

Prime Land Opportunity - Baileyville Rd & Route 147, Middlefield, CT Nestled in the heart of scenic Middlefield, this exceptional 7.5 acre parcel (approx.) located at Baileyville Road this property offers a rare opportunity for developers or investors seeking to capitalize on the area's demand for year-round recreational living. Ideal for a custom home, vacation home, or small-scale residential project (subject to zoning/survey/approvals). Perfectly positioned for outdoor enthusiasts and nature lovers, the property is just minutes from two of Connecticut's most cherished destinations - Lake Beseck and Powder Ridge Mountain Park & Resort. Imagine waking up to serene woodland views, spending summer afternoons kayaking or fishing on Lake Beseck, and enjoying winter adventures skiing or snowboarding at Powder Ridge - all within a short drive from your future doorstep. Features: (1) Road frontage on Baileyville Rd Peaceful, wooded surroundings (2) Close proximity to outdoor recreation (3) Easy access to major highways and local dining. Whether you're a builder, investor, or looking to create a private getaway, this parcel offers natural beauty, lake views, and year-round recreation just minutes away. Don't miss this opportunity! NOTE: Buyer/Buyers Agent to perform their due diligence.

Baileyville Road, Middlefield

$165,000

24177245 MLS

Build your vision on this residential parcel offering a great opportunity in a convenient location with easy access to nearby amenities, shopping, dining, and major routes. Public records reflect the parcel as conforming to current zoning and frontage requirements. Buyers and buyers' agents encouraged to exercise their own diligence regarding all property information, zoning, and intended use.

133 Main St, Middlefield

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Middlefield Real Estate

Newest Listings in Middlefield

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