Middlefield Homes for Sale

Welcome to Middlefield, a charming town located in Middlesex County, Connecticut. Known for its picturesque landscapes and tight-knit community, Middlefield offers a peaceful retreat while still being conveniently located near major cities like Hartford and New Haven.

If you're considering making Middlefield your home, you'll be delighted to find a variety of homes for sale in this area. From historic colonial-style houses to modern single-family homes, Middlefield has something to offer for every taste and budget. Whether you're looking for a cozy starter home or a spacious property for your growing family, you're sure to find the perfect fit in Middlefield.

With top-rated schools, beautiful parks, and a thriving local economy, Middlefield is an ideal place to settle down and enjoy a high quality of life. Whether you're a nature lover, a history buff, or a foodie, Middlefield has something to offer everyone.

Let us help you find your dream home in Middlefield. Contact us today to learn more about the homes for sale in this charming town and start your journey towards homeownership in this lovely community.

Newest Middlefield Homes for Sale

$625,000

4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 from this east-facing deck. A desirable feature is the presence of two private primary suites. The sizable first floor primary suite includes a cozy gas fireplace, double French doors to the huge deck, coffered ceilings, 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

29 Jackson Hill Rd, Middlefield

$499,900

4 Beds ⋅ 3 Baths ⋅ 24191258 MLS

Rarely Available Multi-Generational Home with Private Accessory Apartment. Welcome to this exceptional and meticulously maintained property offering the perfect blend of privacy, flexibility, and modern comfort. Nestled in a quiet, desirable neighborhood, this unique home features a spacious main residence & a fully independent accessory apartment, thoughtfully designed with side-by-side, single-level living & completely separate utilities. The accessory apartment offers approximately 1,000 square feet of comfortable living space with three bedrooms, a full bathroom, hardwood floors throughout, a beautifully updated kitchen with granite countertops, & a partially finished walk-out lower level, making it ideal for extended family, guests, or additional living space. The stunning 2,000-square-foot main residence has been tastefully updated & showcases an open, inviting layout with hardwood floors throughout, central air, a cozy gas fireplace, & a beautifully appointed kitchen featuring granite countertops and abundant cabinetry. A dedicated home office provides the perfect work-from-home space, while the spacious primary suite offers a walk-in closet and a luxurious bathroom complete with a soaking tub & separate walk-in shower. The finished walk-out lower level expands the living space with a large family room, an additional flexible room, a full bathroom with laundry & an oversized storage area. French doors lead directly to the beautifully maintained, level backyard.

23 Wildwood Acres, 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

$600,000

2 Beds ⋅ 1 Baths ⋅ 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

$385,000

3 Beds ⋅ 2 Baths ⋅ 24180014 MLS

Charming and versatile Cape offering 3 bedrooms, 2 full baths, and a 1-car garage. The flexible floor plan features a first-floor bedroom and full bath, perfect for guests, a home office, or one-level living. Upstairs you'll find two additional bedrooms and a second full bath. The updated kitchen is designed for both function and style, featuring an open pantry area that is ideal for a coffee bar, additional cabinetry, or extra storage. Laundry hookups are conveniently located on the main level, with a second hookup available in the lower level. Just off the dining room, a bright and inviting sunroom provides the perfect spot to relax with your morning coffee, read a book, or enjoy additional living space throughout the seasons. Step outside to enjoy the large, fully fenced backyard-perfect for entertaining, gardening, or giving your four-legged friends plenty of room to run and play. Located in the desirable Rockfall section of Middlefield, this home offers easy access to year-round recreation. Enjoy nearby golf courses, boating on Lake Beseck, hiking and outdoor adventures, and skiing, snowboarding, concerts, and seasonal events at Powder Ridge Mountain Park. Whether you're looking for outdoor fun, relaxation, or a convenient location, this home offers something for everyone. OFFER DEADLINE 6/28 BY NOON.

32 Maple St, Middlefield

$250,000

1 Beds ⋅ 1 Baths ⋅ 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

$749,900

4 Beds ⋅ 4 Baths ⋅ 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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