Middlefield, CT Homes

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  $704,900 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,806 Sq Ft

  5 Race Track Hollow, Middlefield, CT 06455

  Welcome to this four bedroom, three and half bath Colonial beauty with elegant architectural design, and a recently updated versatile in-law suite. The house is filled with the warm allure of cherry hardwood floors that gracefully connect each living space. The large kitchen is a dream for generous hosts and those who love to cook, featuring granite countertops and the latest appliances, enabling

  Paulus Chan eXp Realty

  5 Race Track Hollow, Middlefield, CT 06455
• Explore Middlefield

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  $4,938 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,194 Sq Ft
  • Condo for Rent

  6 Nancy Ln Unit ID1261565P, Middlefield, CT 06455

  The advertised rate of $5,704/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  6 Nancy Ln Unit ID1261565P, Middlefield, CT 06455
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  $645,000 Sold Jan 12, 2026

  41 Day School Dr, Middlefield, CT 06455

  • 3 Beds
  • 2.5 Baths
  • 2,949 Sq Ft
  • Built 1996

  Last Sold Summary

  • 6% Below List Price
  • $219/SF
  • 47 Days On Market

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  41 Day School Dr, Middlefield, CT 06455
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  Est $530,355 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,717 Sq Ft

  8 Crest View Dr, Rockfall, CT 06481

  8 Crest View Dr, Rockfall, CT 06481
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  $524,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,063 Sq Ft

  31 High St Unit Lot 2, Middlefield, CT 06455

  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, the Beechwood model has a first-floor master, 2,063 sq ft, 3 bedroom, 2.5 bathrooms, and 2 car garage attached. This

  Milena Mineri RE/MAX One

  31 High St Unit Lot 2, Middlefield, CT 06455
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  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • House for Rent

  63 Main St, Rockfall, CT 06481

  Spacious and well-maintained 1-bedroom, 1 full-bath apartment featuring a flex room perfect for an office or second bedroom. This apartment includes one garage space, ample parking, and in-unit laundry hookups for added convenience. Enjoy a bright living area, functional kitchen, and a comfortably sized bedroom. Located near Wadsworth Falls, offering easy access to scenic trails, outdoor

  Lauren Reis Carl Guild & Associates

  63 Main St, Rockfall, CT 06481
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  $645,000 Sold Sep 25, 2025

  135 Harvest Woods Rd, Rockfall, CT 06481

  • 4 Beds
  • 3.5 Baths
  • 3,212 Sq Ft
  • Built 1983

  Last Sold Summary

  • 4% Below List Price
  • $201/SF
  • 34 Days On Market

  Current Estimated Value $643,450

  Last Listing Agent Jeff Coleman Hagel & Assoc. Real Estate

  135 Harvest Woods Rd, Rockfall, CT 06481
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  Est $538,072 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,827 Sq Ft

  14 Massasoit Rd, Middlefield, CT 06455

  14 Massasoit Rd, Middlefield, CT 06455
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  $749,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  88 Powder Hill Rd, Middlefield, CT 06455

  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,

  Gary Marino William Raveis Real Estate

  88 Powder Hill Rd, Middlefield, CT 06455
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  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  157 Baileyville Rd Unit Second Floor, Middlefield, CT 06455

  157 Baileyville Rd Unit Second Floor, Middlefield, CT 06455
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  $421,000 Sold Nov 06, 2025

  110 Lake Shore Dr, Middlefield, CT 06455

  • 3 Beds
  • 1 Bath
  • 624 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Above List Price
  • $675/SF
  • 9 Days On Market

  Current Estimated Value $416,151

  Last Listing Agent Lisa Fekete William Raveis Real Estate

  110 Lake Shore Dr, Middlefield, CT 06455
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  Est $438,569 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft

  51 Mack Rd, Middlefield, CT 06455

  51 Mack Rd, Middlefield, CT 06455
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  $349,900 Pending

  • 2 Beds
  • 4 Baths
  • 2,091 Sq Ft

  40 Sylvan Ridge, Rockfall, CT 06481

  Rarely available, desirable end-unit townhouse in Sylvan Ridge Condo Association, tucked away on a cul-de-sac. This three level home offers 2 BRs, 2 full baths and 2 half baths. It has a partially finished and heated walkout basement that provides excellent additional living room or flex space. The beautiful, remodeled kitchen features custom soft close cabinets, under cabinet lighting, SS

  Sandra Cohen William Raveis Real Estate

  40 Sylvan Ridge, Rockfall, CT 06481
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  $404,900 Sold Feb 02, 2026

  4 Lorraine Terrace, Rockfall, CT 06481

  • 3 Beds
  • 1.5 Baths
  • 1,672 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $242/SF
  • 21 Days On Market

  Last Listing Agent rob link Sterling REALTORS

  4 Lorraine Terrace, Rockfall, CT 06481
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  Est $721,717 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,949 Sq Ft

  15 Orchard Ln, Middlefield, CT 06455

  15 Orchard Ln, Middlefield, CT 06455
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  $379,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,760 Sq Ft

  9 Sunset Dr, Rockfall, CT 06481

  Charming All-Brick Ranch in the Heart of Rockfall! Welcome home to this beautiful 1,760 sq. ft. all-brick ranch - a perfect blend of classic charm and comfort! Nestled on a perfectly level .45-acre lot, this home offers easy living inside and out. Step inside to find a bright, spacious living room featuring hardwood floors, built-in hutches, and a cozy gas log fireplace - perfect for relaxing

  Robert Disapio Dave Jones Realty, LLC

  9 Sunset Dr, Rockfall, CT 06481
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  $550,000 Sold Aug 28, 2025

  32 Powder Hill Rd, Middlefield, CT 06455

  • 3 Beds
  • 2.5 Baths
  • 2,812 Sq Ft
  • Built 1981

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 91 Days On Market

  Current Estimated Value $561,557

  Last Listing Agent Margaret Curry William Raveis Real Estate

  32 Powder Hill Rd, Middlefield, CT 06455
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  Est $404,692 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  200 Peters Ln, Rockfall, CT 06481

  200 Peters Ln, Rockfall, CT 06481
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  $399,000

  • Land
  • 7.46 Acres
  • $53,485 per Acre

  0 Baileyville Rd, Middlefield, CT 06455

  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

  Melanie Billie BHGRE Gaetano Marra Homes

  0 Baileyville Rd, Middlefield, CT 06455
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  $375,000 Sold Jul 25, 2025

  38 High St, Middlefield, CT 06455

  • 3 Beds
  • 2 Baths
  • 2,576 Sq Ft
  • Built 1970

  Last Sold Summary

  • $146/SF
  • 116 Days On Market

  Current Estimated Value $388,574

  Last Listing Agent Michelle Pirruccio Carl Guild & Associates

  38 High St, Middlefield, CT 06455
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  Est $343,382 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,194 Sq Ft

  15 Mohican Rd, Middlefield, CT 06455

  15 Mohican Rd, Middlefield, CT 06455
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  $499,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  31 High St Unit Lot 3, Middlefield, CT 06455

  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, the Beechwood model has a first-floor master, 2,063 sq ft, 3 bedroom, 2.5 bathrooms, and 2 car garage attached. This

  Milena Mineri RE/MAX One

  31 High St Unit Lot 3, Middlefield, CT 06455
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  $285,000 Sold Oct 10, 2025

  10 Massasoit Rd, Middlefield, CT 06455

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Above List Price
  • $424/SF
  • 36 Days On Market

  Current Estimated Value $282,466

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  10 Massasoit Rd, Middlefield, CT 06455
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  Est $476,500 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,913 Sq Ft

  95 Main St, Rockfall, CT 06481

  95 Main St, Rockfall, CT 06481
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  $69,000 Under Contract

  • Land
  • 1.9 Acres
  • $36,316 per Acre

  (Map 12, Lot 80A) Hubbard St, Middlefield, CT 06455

  This 1.9 acre lot is level and lightly wooded. Located in a rural setting, close to schools and Wadsworth State Park. Zoned MD (residential), well and septic is required. Land is raw. Seller encourages buyer to do necessary testing to obtain a building permit. Multiple offers received. Highest and best due Monday, Dec 22nd at 5pm

  Marie Padilla Berkshire Hathaway NE Prop.

  (Map 12, Lot 80A) Hubbard St, Middlefield, CT 06455
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  $409,500 Sold Sep 03, 2025

  30 Dwight Rd, Middlefield, CT 06455

  • 3 Beds
  • 1.5 Baths
  • 1,960 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $209/SF
  • 83 Days On Market

  Current Estimated Value $416,323

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  30 Dwight Rd, Middlefield, CT 06455
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  Est $389,164 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft

  17 Dwight Rd, Middlefield, CT 06455

  17 Dwight Rd, Middlefield, CT 06455
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  $799,900

  • 4 Beds
  • 4 Baths
  • 3,355 Sq Ft

  30 Cherry Ridge Rd, Middlefield, CT 06455

  Beat the Spring Market 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

  Matthew Guida Eagle Eye Realty PLLC

  30 Cherry Ridge Rd, Middlefield, CT 06455
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  $120,000 Sold Jan 28, 2026

  80 West St, Middlefield, CT 06455

  • Land
  • 4.24 Acres
  • $28,302 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 26 Days On Market

  Last Listing Agent Casey Meadows William Raveis Real Estate

  80 West St, Middlefield, CT 06455
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  Est $452,122 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,144 Sq Ft

  20 Burt Dr, Middlefield, CT 06455

  20 Burt Dr, Middlefield, CT 06455
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  $285,000 Sold Jul 24, 2025

  10 Bittersweet Ridge Unit 10, Middlefield, CT 06455

  • 2 Beds
  • 1.5 Baths
  • 1,726 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $165/SF
  • 6 Days On Market

  Current Estimated Value $278,822

  Last Listing Agent Jessica Boswell LPT Realty

  10 Bittersweet Ridge Unit 10, Middlefield, CT 06455
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  Est $388,546 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,228 Sq Ft

  12 Valley Heights Dr, Middlefield, CT 06455

  12 Valley Heights Dr, Middlefield, CT 06455
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  $331,000 Sold Jun 26, 2025

  15 Seneca Rd, Middlefield, CT 06455

  • 2 Beds
  • 1 Bath
  • 883 Sq Ft
  • Built 1930

  Last Sold Summary

  • 9% Above List Price
  • $375/SF
  • 6 Days On Market

  Current Estimated Value $331,454

  Last Listing Agent Mikell Foggitt Margaret Bennett Realty

  15 Seneca Rd, Middlefield, CT 06455
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  Est $361,838 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 966 Sq Ft

  9 Wildwood Cir, Rockfall, CT 06481

  9 Wildwood Cir, Rockfall, CT 06481
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  $312,000 Sold Apr 10, 2025

  27 Maryland Dr, Middlefield, CT 06455

  • 4 Beds
  • 1 Bath
  • 1,384 Sq Ft
  • Built 1953

  Last Sold Summary

  • 7% Below List Price
  • $225/SF
  • 134 Days On Market

  Current Estimated Value $328,474

  Last Listing Agent Patrick Lawrence Coldwell Banker Realty

  27 Maryland Dr, Middlefield, CT 06455
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  Est $226,306 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft

  5 Cherokee Rd, Middlefield, CT 06455

  5 Cherokee Rd, Middlefield, CT 06455
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  $960,000 Sold Aug 22, 2025

  22 Lake Shore Dr, Middlefield, CT 06455

  • 4 Beds
  • 3.5 Baths
  • 3,536 Sq Ft
  • Built 1947

  Last Sold Summary

  • 1% Below List Price
  • $271/SF
  • 75 Days On Market

  Current Estimated Value $961,620

  Last Listing Agent Jamie Clark Berkshire Hathaway NE Prop.

  22 Lake Shore Dr, Middlefield, CT 06455
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  Est $570,407 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,084 Sq Ft

  645 Main St, Middlefield, CT 06455

  645 Main St, Middlefield, CT 06455
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  $357,500 Sold Jul 25, 2025

  130 Cherry Hill Rd, Middlefield, CT 06455

  • 3 Beds
  • 1.5 Baths
  • 1,142 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Above List Price
  • $313/SF
  • 6 Days On Market

  Current Estimated Value $355,205

  Last Listing Agent Natalee King Coldwell Banker Realty

  130 Cherry Hill Rd, Middlefield, CT 06455
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  Est $470,346 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,793 Sq Ft

  10 Esther Dr, Middlefield, CT 06455

  10 Esther Dr, Middlefield, CT 06455

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