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

$520,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24203910 MLS

The tax record may say 1935, but this is far from your typical 1935 home. The original footprint represents just a small portion of the home you see today, thoughtfully renovated and expanded over the decades by its builder-owner to create a home designed for the way we live now. The spacious kitchen features a center island, abundant cabinetry, pantry and breakfast area, flowing easily into the dining room and inviting living spaces. A true standout is the impressive family room addition with vaulted ceiling, walls of windows, its own front entrance and access to the deck, creating flexible space for entertaining, relaxing, a game room, studio or whatever fits your lifestyle. The main level offers two bedrooms and an updated full bath, while upstairs, the private primary suite features a walk-in closet and spa-like bath with freestanding soaking tub and beautifully tiled glass shower. A dedicated lower-level office provides quiet work-from-home space. Outside, enjoy multiple areas to gather and unwind, including a paver patio and a fenced-in retreat with above-ground pool, spacious deck and pool clubhouse. Located in Rockfall, you're close to Lake Beseck, Powder Ridge, Lyman Orchards and Wadsworth Falls, with convenient access to shopping and highways. 1935 may be where the story started, but this home has evolved beautifully for today's lifestyle.

12 Ross Rd, Middlefield

$699,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24202689 MLS

Keep your boat in the backyard! Rare opportunity to own a beautifully updated Multi family property with waterfront, exceptional outdoor spaces, and outstanding income potential. Whether you're looking for an owner-occupied investment, multigenerational living, or an income-producing property, this home offers incredible versatility. Recent improvements include a brand-new roof, new siding, a beautifully renovated second floor, and brand-new fencing, giving the property a fresh, updated feel while taking care of many of the major improvements a new owner would typically face. The main two-family residence features beautiful balconies overlooking the lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing and enjoying the view. Outside, you'll find a charming courtyard area, landscaped grounds, and inviting spaces for entertaining. Brand new Metal Dock.

157 Baileyville Rd, Middlefield

$749,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$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

$168,000

ACTIVE Status ⋅ 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

$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

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