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

$342,000

2 Beds ⋅ 1 Baths ⋅ 24196110 MLS

Welcome home to this charming ranch nestled on a beautifully landscaped, level .52-acre lot in the desirable Rockfall section of Middlefield. Offering the convenience of one-level living with room to grow, this home features gleaming hardwood floors, a welcoming living room with a classic fireplace and custom built-ins, and an updated eat-in kitchen with granite countertops, stainless steel appliances, rich wood cabinetry, tile backsplash, recessed lighting, and plenty of workspace. The screened porch is the perfect spot to enjoy your morning coffee while overlooking the peaceful backyard, while the covered patio creates an ideal space for outdoor dining and entertaining. The fenced yard offers room for pets, gardening, or play, all surrounded by mature trees for added privacy. Two generously sized bedrooms and a full bath complete the main level. Looking for additional space? The walk-up attic offers exciting potential for future expansion, while the partially finished lower level is perfect for a family room, home office, gym, or hobby space. An under-house garage provides additional storage, and the Generac whole-house generator offers year-round peace of mind. Conveniently located just minutes from Lyman Orchards, Powder Ridge, Wadsworth Falls and everything Middlefield has to offer, with easy access Washington St and commuter routes. Whether you're starting out, downsizing, or simply looking for one-level living, this home is ready to welcome you

88 Peters Ln, Middlefield

$625,000

3 Beds ⋅ 2 Baths ⋅ 24195242 MLS

Cavanaugh & Company is proud to present 46 Powder Hill Road, a beautifully maintained Center Hall Colonial home in one of Middlefield's most desirable neighborhoods. Designed for both everyday living and entertaining, this exceptional home features a bright, open first floor with newly refinished hardwood flooring, spacious living areas, and a beautifully appointed kitchen complete with granite countertops, premium stainless steel appliances, and a center island. The family room offers built-ins, a gas fireplace, and access to a back patio equipped with a Weber grill. This level also includes a living room with a large wood-burning fireplace and custom screen, a fully remodeled bathroom with high-end features, and an inviting sunroom with private views of nature and professionally landscaped gardens. The second floor features three generously sized bedrooms and a fully remodeled, luxury bathroom with heated flooring. For your safety and convenience, the property also comes equipped with a generator. This home is conveniently located just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, golf courses, and major highways.

46 Powder Hill Rd, Middlefield

$329,900

3 Beds ⋅ 2 Baths ⋅ 24194676 MLS

Opportunity awaits at 121 Powder Hill Road! This classic Colonial offers 3 bedrooms, 1 full bath, and approximately 1,642 square feet of living space. Situated on a spacious lot in Middlefield, this property is in need of renovation and is being sold strictly as - is. The home offers character and potential for restoration or renovation. Conveniently located near Powder Ridge Mountain Park, Lyman Orchards, hiking trails, shopping, restaurants, and area amenities.

121 Powder Hill Rd, Middlefield

$299,000

3 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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/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

$499,900

4 Beds ⋅ 3 Baths ⋅ 24191260 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

$499,900

4 Beds ⋅ 3 Baths ⋅ 24191258 MLS

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

$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

$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

$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

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