Moving to Middlefield CT | real estate for sale in Middlefield Connecticut | Property Statistics of living in Middlefield

Middlefield offers a blend of rural charm and accessibility, with housing ranging from modest single-family homes to larger custom-built residences. The town remains relatively small and retains a distinctly residential character. Real estate values benefit from limited inventory and proximity to both Middletown and major transportation corridors. Buyers are often attracted by the combination of affordability, scenic surroundings, and community stability.

Current Real Estate Statistics for Homes in Middlefield CT as of Friday, October 16, 2026
10 Active Homes Listed
42 Avg. DOM
$217 Avg. $ / Sq.Ft.
$499900 Med. List Price
8/19/2026 1:37:50 PM
Active
19 High Street Middlefield CT
19 High Street

Middlefield, Connecticut 06455

$749,000 | Active

2 Beds | 2 Baths | 4073 Sqft | 1.2 Acres | 5 Days on Market

Property Type: Single Family For Sale

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 beautifully designed 2008 addition. The original 1750 home is not currently livable and is ready for renovation, provid...

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8/19/2026 4:05:02 AM
Active
75 Main Street Middlefield CT
75 Main Street

Middlefield, Connecticut 06481

$380,000 | Active

3 Beds | 2 Baths | 1264 Sqft | 0.44 Acres | 0 Days on Market

Property Type: Single Family For Sale

Classic 1906 Colonial charm meets thoughtful updates in the storybook village of Rockfall. A window-wrapped front sun porch welcomes you home, while to the side of the home a screened porch with exposed timber rafters feels like a treehouse over the yard, an outdoor living room f...

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7/24/2026 11:41:05 PM
Under Contract CTS
23 Wildwood Acres Middlefield CT
23 Wildwood Acres

Middlefield, Connecticut 06481

$499,900 | Under Contract - Continue

4 Beds | 3 Baths | 3425 Sqft | 0.47 Acres | 18 Days on Market

Property Type: Single Family For Sale

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 feature...

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7/10/2026 12:30:38 PM
Active
88 Powder Hill Road Middlefield CT
88 Powder Hill Road

Middlefield, Connecticut 06455

$749,900 | Active

4 Beds | 3 Baths | 2458 Sqft | 1 Acres | 40 Days on Market

Property Type: Single Family For Sale

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...

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6/29/2026 12:13:43 AM
Under Contract CTS
32 Maple Street Middlefield CT
32 Maple Street

Middlefield, Connecticut 06481

$385,000 | Under Contract - Continue

3 Beds | 2 Baths | 1335 Sqft | 0.46 Acres | 38 Days on Market

Property Type: Single Family For Sale

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 youll find two additional bedrooms and a second full bath. Th...

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6/21/2026 12:52:57 PM
Active
30 Cherry Ridge Road Middlefield CT
30 Cherry Ridge Road

Middlefield, Connecticut 06455

$749,900 | Active

4 Beds | 4 Baths | 3355 Sqft | 5.01 Acres | 243 Days on Market

Property Type: Single Family For Sale

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-fa...

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6/12/2026 12:05:45 AM
Under Contract
169 Cedar Street Middlefield CT
169 Cedar Street

Middlefield, Connecticut 06481

$296,000 | Under Contract

2 Beds | 1 Baths | 1591 Sqft | 0.46 Acres | 5 Days on Market

Property Type: Single Family For Sale

Under $300K in Middlefield - a rare opportunity to own, update, and build real equity. Located in the desirable Rockfall section, this one-level ranch offers comfortable living today with the chance to personalize and enhance over time. While cosmetic updates will unlock the home...

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5/29/2026 11:18:07 AM
Under Contract
170 Ross Road Middlefield CT
170 Ross Road

Middlefield, Connecticut 06481

$249,900 | Under Contract

2 Beds | 1 Baths | 1100 Sqft | 0.92 Acres | 13 Days on Market

Property Type: Single Family For Sale

Attention investors and builders! This oversized lot with two structures offers exceptional potential. This property is located in a desirable location in Middlefield and is ready for a full renovation. This home is being sold as-is and requires extensive rehab. A great opportuni...

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6/6/2022 3:51:00 PM
Under Contract
31 High Street & Baileyville Road  Middlefield CT
31 High Street & Baileyville Road

Middlefield, Connecticut 06455

$499,900 | Under Contract

4 Beds | 3 Baths | 2272 Sqft | 1.127 Acres | 43 Days on Market

Property Type: Single Family For Sale

A beautiful subdivision to be built with 4 lots to choose from, and 3 different house plans. The Ashwood model consists of 2,614 sq ft, 4 bedrooms, 2.5 bathrooms, 2 car attached garage. The Aspen model is 2,272 sq ft, 4 bedrooms, 2.5 bathrooms and a 2 car attached garage. Lastly,...

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5/3/2022 7:34:00 PM
Under Contract
31 High Street & Baileyville Road  Middlefield CT
31 High Street & Baileyville Road

Middlefield, Connecticut 06455

$524,900 | Under Contract

3 Beds | 3 Baths | 2063 Sqft | 1.627 Acres | 10 Days on Market

Property Type: Single Family For Sale

A beautiful subdivision to be built with 4 lots to choose from, and 3 different house plans. The Ashwood model consists of 2,614 sq ft, 4 bedrooms, 2.5 bathrooms, 2 car attached garage. The Aspen model is 2,272 sq ft, 4 bedrooms, 2.5 bathrooms and a 2 car attached garage. Lastly,...

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