Middlefield Real Estate

Welcome to Middlefield, Connecticut – a charming town nestled in the heart of Middlesex County, where small-town charm meets natural beauty. With its picturesque landscapes and friendly community, Middlefield offers a unique blend of tranquility and accessibility, making it an ideal place to call home.

Rich in history and character, Middlefield boasts a vibrant community that celebrates its roots while embracing modern living. The town is dotted with quaint shops, local eateries, and beautiful parks, providing residents with ample opportunities for leisure and recreation. Whether you're strolling through the serene trails of the nearby Cockaponset State Forest or enjoying a picnic at the scenic Lake Beseck, nature enthusiasts will find plenty to explore.

Education is a cornerstone of Middlefield, with a strong emphasis on quality schooling and community involvement. The town is served by the highly regarded Regional School District 13, ensuring that families have access to excellent educational resources.

Middlefield is also conveniently located just a short drive from major cities like New Haven and Hartford, offering residents the perfect balance of suburban living with easy access to urban amenities. Enjoy a day of shopping at local boutiques or take advantage of the diverse dining options in the surrounding areas.

For those seeking a peaceful yet engaging lifestyle, Middlefield is a hidden gem that promises a warm community, beautiful surroundings, and a place to create lasting memories. Come discover the charm of Middlefield – where every day feels like a breath of fresh air!

Newest Listings in Middlefield

$299,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194605 MLS

Handyman special. This home has good bones, hardwood floors throught, it needs exterior pain, interior paint, updating and remodeling but will be a really nice solid home when its done. Located in Middlefield! Large private yard. Being sold as is.

2 Ballfall Rd, Middlefield

$625,000

4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24192216 MLS

Nestled back from the road in a serene, private setting, this impeccably maintained and professionally landscaped 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of comfort, elegance, and privacy. The sunken living room features a stunning stone fireplace with a majestic mantel, creating a warm focal point that can also be enjoyed from the kitchen and breakfast nook. The beautifully appointed kitchen boasts granite countertops, stainless steel appliances, a center island, and plenty of space for cooking and entertaining. The formal dining room and cozy den showcase beautiful hardwood flooring, adding warmth and character throughout the main level. The expansive primary suite is a true retreat, complete with a spa-like bath featuring a hydro tub, double-sink vanity, and separate shower. Just off the primary bedroom is a versatile bonus room with conveniently located laundry, ideal as a dressing room, sitting area, home office, or nursery. The private fourth bedroom, located on the third floor, makes an excellent guest suite, offering separation from the main living areas. Step outside to enjoy the Trex deck with a pergola, perfect for entertaining family and friends or simply relaxing while overlooking the fully fenced in backyard designed for both fun and tranquility. Conveniently located just minutes from shopping, dining, and everyday amenities, yet tucked away in its own peaceful oasis. Don't miss the opportunity to make it yours!

41 Harvest Wood Rd, Middlefield

$750,000

4 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24193789 MLS

Exceptional custom built home tucked away at the end of a private enclave of only four custom homes. This thoughtfully designed residence offers over an acre of privacy, oversized living spaces, handcrafted millwork, solid six-panel doors, hardwood floors, and insulated interior walls. Designed for both everyday living and elegant entertaining, the open floor plan is spacious, bright and cheerful; including a large kitchen with abundant cabinetry and counter space and an expansive island that naturally becomes the heart of the home. Two wall ovens make preparing meals for large gatherings a breeze. The kitchen flows into a dining nook with bay windows and a fireplaced family room with double-french doors opening to a 60' x 16' deck overlooking the spacious yard which is framed with trees in summer and provides expansive horizon views in the winter. Once the leaves fall, you can see all the way to the Portland Bridge and beyond! Enjoy the breathtaking sunrises/moonrises from this east-facing deck. Desirable feature is the presence of 2 private primary suites. Huge first floor primary suite w/12' tray ceiling includes a cozy fireplace, 2 double French doors to huge deck TWO WALK-IN CLOSETS!, plus two additional linen closets in a hall leading to the oversized spa bathroom complete with jacuzzi tub, walk-in shower, two extra-long sink vanities with mirrored cabinets, and a separate doored toilet room. The first floor also includes formal & living rooms for all your lifestyle &

29 Jackson Hill Rd, Middlefield

$199,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24190359 MLS ⋅ Bittersweet Ridge BLDG.

Rare Opportunity in Bittersweet Ridge! Seldom available 1-bedroom unit in the desirable Bittersweet Ridge 55+ community. This charming home has been thoughtfully updated and offers comfortable, low-maintenance living in a small, welcoming neighborhood. Step inside to find new flooring throughout, high ceilings that create a bright and spacious feel, a beautifully remodeled bathroom, and newer appliances, including a new dishwasher. A new water heater provides added peace of mind. Enjoy your morning coffee or relax with a good book in the screened porch featuring new windows and screens, overlooking a private backyard that offers a peaceful setting. The full basement provides exceptional storage and flexibility, complete with a workbench and a separate finished room that's perfect for crafts, hobbies, a workshop, or a home office. Conveniently located near shopping, restaurants, parks, walking trails, golf courses, and major highways, Bittersweet Ridge offers the perfect combination of a quiet community and easy access to everyday conveniences. This move-in ready home is a rare find-don't miss your chance to own one of the few 1-bedroom units available in this sought-after 55+ community.

6 Bittersweet Rdg Unit B, Middlefield

$749,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

ACTIVE Status ⋅ 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

$600,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24188626 MLS

Every weekend you wait is another weekend someone else gets to spend here. Wake up to spectacular sunrises over Lake Beseck, spend the day boating, swimming, kayaking or fishing, and end the evening relaxing on your private deck as the water sparkles just steps away. This direct waterfront cottage offers the lake lifestyle so many dream about, yet so few ever find. With private docks and a floating dock, you'll enjoy instant access to the lake where motorboats are welcome. Paddle the shoreline, cast a line from your dock, or take a short stroll to the town beach for another day in the sun. Inside, the charming open floor plan is filled with natural light and flows into a beautiful sunroom wrapped in walls of windows that keep the breathtaking views front and center. The Trex deck is the perfect place for morning coffee, summer gatherings, and unforgettable sunrises. Thoughtfully maintained with central air and a new roof in 2024, this home is ready to enjoy from day one. Because Lake Beseck is managed by DEEP, no flood insurance is required. Looking ahead? The home offers the potential to build up to 35 feet (subject to approvals), creating the opportunity for an even more spectacular waterfront retreat. Conveniently located just minutes from I-91 and in the heart of Connecticut's recreation corridor, you'll enjoy easy access to Powder Ridge, Lyman Orchards, and four nearby golf courses. Lake homes are more than real estate. They're where summers become tradition.

18-A Lake Shore Dr, Middlefield

$250,000

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24182051 MLS

ATTENTION ALL INVESTORS AND RENOVATION SPECIALISTS- Being sold "AS IS". This is a Year-round ranch in the desirable Beseck Lake community offering water views and access to the lake, beach, and boat launch. The town shows this as a one bedroom home that features an eat-in kitchen, living room with fireplace, primary bedroom, den/possible 2nd bedroom, and a new updated full bath with Washer/Dryer combo unit. Additional laundry hookup available in the partial basement. Enjoy outdoor living from the large deck overlooking the peaceful setting. Additional features include a 1-car garage, whole-house generator, propane for cooking and generator, oil-fired hot air heat. Located near Lyman Orchard Golf Course and Powder Ridge Ski Resort so this could be a great Air B&B for an investor. It has great potential for year-round living, weekend getaways, or investment opportunity. New roof, and new full bath all done in the last year. Rehab financing options may be available through Total Mortgage for qualified buyers.

28 Kickapoo Rd, Middlefield

$165,000

ACTIVE Status ⋅ 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

$749,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24144604 MLS

Prepare to be mesmerized with this Middlefield masterpiece set on 5-acre park like grounds at the end of a private road cul-de-sac epitomizes an exceptional residence which combines refined elegance with unparalleled privacy. Sunlight floods the living room through a southeast-facing Palladian window, highlighting tailored built-in cabinetry with exquisite craftsmanship, exposed beams and a cathedral ceiling. The chef's kitchen, fully transformed in 2012, features a panel-ready Sub-Zero refrigerator, panel-ready Bosch dishwasher, Wolf double oven and built-in cooktop, granite island with seating and secondary sink. Outdoor living is what you've dreamt of with a gunite pool and expansive 900 sq ft composite deck overlooking manicured grounds. Additional amenities include a finished lower level, second-floor crafts room, new 3-season porch sliders and Generac 10kW generator automatic. Perfectly located with easy access to Route 66, Middletown and four nearby public golf courses.

30 Cherry Ridge Rd, Middlefield

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