Middlefield Real Estate

Welcome to Middlefield, a charming town nestled in Middlesex County, Connecticut. Known for its picturesque landscapes and tight-knit community, Middlefield offers residents a peaceful and idyllic setting to call home.

Middlefield boasts a rich history dating back to the 17th century when it was first settled. Today, the town seamlessly blends its historical roots with modern amenities, making it a desirable place to live for individuals and families alike.

Nature enthusiasts will appreciate Middlefield's proximity to the stunning Wadsworth Falls State Park, where hiking trails, picnic areas, and a picturesque waterfall await exploration. For those who enjoy outdoor activities, the town also offers ample opportunities for fishing, boating, and golfing.

In addition to its natural beauty, Middlefield is home to a vibrant community with a strong sense of camaraderie. Residents can partake in local events, farmers' markets, and community gatherings throughout the year, fostering connections and friendships that last a lifetime.

With its convenient location in Middlesex County, Middlefield provides easy access to neighboring towns and cities, ensuring that residents have access to a range of shopping, dining, and entertainment options.

Whether you're looking for a peaceful retreat or a close-knit community to call home, Middlefield offers the perfect blend of small-town charm and modern conveniences. Come discover all that this lovely town has to offer!

Newest Listings in 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 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

$219,900

1 Beds ⋅ 1 Baths ⋅ 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

$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

$309,925

2 Beds ⋅ 2 Baths ⋅ 24188622 MLS ⋅ Bittersweet Ridge BLDG.

Welcome to Bittersweet Ridge, a beautifully maintained 2-bedroom, 2-bath condo in a desirable 55+ community. This move-in ready home features a tiled entry, engineered flooring throughout, an updated kitchen with modern cabinetry, propane cooking, included appliances, and convenient main-level laundry. The spacious primary bedroom offers a custom-designed wardrobe system with built-in drawers, hanging space, shoe storage, and upper cabinetry. Both bathrooms have been updated, with one featuring removable ADA-style accessibility upgrades. A standout feature is the stunning enclosed sunroom by Patio Enclosures, a recent approximately $30,000 improvement with insulated panels, new windows, and double-locking doors, creating the perfect space to relax and enjoy every season. The full, dry basement offers exceptional storage with extensive shelving and the potential to be finished for additional living space. Additional highlights include central vacuum, a whole-house fan, pull-down attic access with an insulated cover, digital keypad entry locks, 200-amp electrical service, and a newer hot water heater, as well as a new roof. Ideally located across from Peckham Park and close to walking trails and seasonal ice skating, this home offers peaceful, low-maintenance living with easy access to local amenities. Don't miss this opportunity to own in one of Middlefield's most sought-after communities.

12 Bittersweet Rdg Unit 12, 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

$168,000

24181732 MLS

Imagine waking up every day in a town where orchards bloom, ski slopes come alive in winter, golf courses stretch across rolling hills, and hiking trails, waterfalls, and lakes are just minutes from your front door. This beautiful level, cleared lot on Cherry Hill offers the opportunity to build more than a home-it offers a lifestyle. Nestled in one of Middlefield's most convenient locations, you'll enjoy easy access to Lyman Orchards, Powder Ridge, Lake Beseck, and all the small-town charm that makes this community so special, while remaining close to major commuting routes. Bring your vision and create the home you've always dreamed of in a place where adventure, recreation, and New England beauty surround you year-round. There are no perc tests on file, and buyers are responsible for conducting their own due diligence regarding building suitability and approvals.

Cherry Hill Rd, Middlefield

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