Middlesex County, CT Homes

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  $479,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,188 Sq Ft

  31 N Maple St, East Hampton, CT 06424

  Welcome to 31 N Maple Rd, East Hampton - where space, updates, and lifestyle come together in one of the area's most desirable settings. Well maintained and thoughtfully improved, this 4-bedroom, 2.5-bath home offers the kind of room and functionality today's buyers are searching for. From everyday living to hosting family and friends, the layout provides a comfortable flow with plenty of space

  

  James Harrington

  Carl Guild & Associates

  (860) 735-4661

  31 N Maple St, East Hampton, CT 06424
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  $1,500 Per Month

  • 1 Bath
  • 4,060 Sq Ft
  • House for Rent

  184 Middlesex Ave Unit 6, Chester, CT 06412

  Well-maintained studio apartment in a prime Chester location. Bright, open layout with good natural light and efficient use of space. Kitchen includes modern appliances with dishwasher, updated countertops, and solid cabinet storage. In-unit washer and dryer. Quiet setting with landscaped grounds and off-street parking, just minutes to Chester Village shops, restaurants, and local amenities.

  

  Anthony Velez

  VC Property Group, LLC

  (860) 847-7480

  184 Middlesex Ave Unit 6, Chester, CT 06412
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  $452,000 Sold Apr 30, 2026

  1 Steepleview Dr, East Hampton, CT 06424

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1968

  Last Sold Summary

  • 21% Above List Price
  • $285/SF
  • 4 Days On Market

  Current Estimated Value $371,721

  Last Listing Agent Cheryl Zalewski eXp Realty

  1 Steepleview Dr, East Hampton, CT 06424
• 

  Est $405,682 Not Listed For Sale

  32 Old Nod Rd, Clinton, CT 06413

  • 3 Beds
  • 1.5 Baths
  • 1,638 Sq Ft
  • Built 1870

  32 Old Nod Rd, Clinton, CT 06413

  Last Sold Summary

  • 5% Below List Price
  • $259/SF
  • 104 Days On Market

  • Last Sold Price $425,000
  • May 09, 2025

  Last Listing Agent Leslie Timmons Berkshire Hathaway Home Services
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  $1,000,000 Under Contract

  • 6 Beds
  • 3 Baths
  • 2,522 Sq Ft

  176 Shore Rd, Clinton, CT 06413

  Unprecedented Investment or Family Compound with Private Beach Rights This is a rare and unparalleled opportunity to own a piece of paradise, featuring deeded rights to a private beach on the Long Island Sound and three distinct residences, making it an ideal family compound or a high-yield investment property. The Main Residence has been an Airbnb $500 per night. Completely updated and boasting

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 507-9240

  176 Shore Rd, Clinton, CT 06413
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  Starting at $1,710

  Total Monthly Price

  • Studio - 2 Beds

  75 Marlborough St, Portland, CT 06480

  Experience the perfect blend of history and modern elegance at Brainerd Place, a luxury apartment community built in historic Portland, CT. Where the charm of the past meets the sophistication of the present, our thoughtfully designed residences offer unparalleled comfort, state-of-the-art amenities, and timeless style. Immerse yourself in a setting that honors its heritage while providing the

  Brainerd Place

  (860) 854-3101

  75 Marlborough St, Portland, CT 06480
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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

  Current Estimated Value $650,347

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  41 Day School Dr, Middlefield, CT 06455
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  Est $404,347 Not Listed For Sale

  37 Bashan Rd, East Haddam, CT 06423

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 1960

  37 Bashan Rd, East Haddam, CT 06423

  Last Sold Summary

  • 6% Above List Price
  • $254/SF
  • 3 Days On Market

  • Last Sold Price $381,727
  • Apr 25, 2025

  Last Listing Agent Deborah Pepin Coldwell Banker Realty
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  $399,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,776 Sq Ft

  156 Wopowog Rd, East Hampton, CT 06424

  Tucked away on a quiet country road, 156 Wopowog Rd feels less like a home and more like a setting-something straight out of a Van Morrison song where nature, craftsmanship, and soul come together in perfect harmony.This is a property that invites you to slow down and listen-to the gentle rhythm of a stunning stream that winds through the back, complete with a picturesque waterfall and a hidden

  

  James Harrington

  Carl Guild & Associates

  (860) 792-3791

  156 Wopowog Rd, East Hampton, CT 06424
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  $2,500 Per Month

  • 3 Beds
  • 1 Bath
  • 1,800 Sq Ft
  • House for Rent

  18 Old Young St, East Hampton, CT 06424

  Welcome to easy living in the town of East Hampton! This classic 3-bedroom, 1-bath split-level ranch offers the perfect blend of comfort, convenience, and a desirable neighborhood setting. Well maintained and in exceptionally clean, move-in ready condition, this home provides a warm and inviting atmosphere from the moment you arrive. Enjoy a functional layout with bright, well-proportioned rooms

  

  James Harrington

  Carl Guild & Associates

  (860) 650-1833

  18 Old Young St, East Hampton, CT 06424
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  $340,000 Sold Mar 12, 2026

  38 Old Middletown Ave, East Hampton, CT 06424

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft
  • Built 1974

  Last Sold Summary

  • $244/SF
  • 51 Days On Market

  Current Estimated Value $336,681

  Last Listing Agent Mark Reyher Reyher Real Estate

  38 Old Middletown Ave, East Hampton, CT 06424
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  Est $485,887 Not Listed For Sale

  223 Middletown Ave, East Hampton, CT 06424

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft
  • Built 1996

  223 Middletown Ave, East Hampton, CT 06424

  Last Sold Summary

  • 4% Above List Price
  • $247/SF
  • 4 Days On Market

  • Last Sold Price $465,000
  • Apr 30, 2025

  Last Listing Agent Alexis Trzcinski Berkshire Hathaway Home Services
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  $850,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 8,382 Sq Ft

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this residential 2 Family property presents a rare opportunity to acquire a multifamily property in one of Connecticut's most desirable markets. The property consists of two 2-bedroom residential apartments. The improvements are situated on over 2 acres of land. Waterhouse Brook flows directly through the site, creating a tranquil backdrop, while the property

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
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  Starting at $2,286

  Total Monthly Price

  • 1 - 3 Beds

  1100 Springside Ln, Middletown, CT 06457

  "Connecticut's Best New Rental Community" as awarded by the CT Home Builder and Remodeler's Association. Discover Springside Middletown, a brand-new apartment community that features a one-of-a-kind central amenity village, as well as a choice of multi-story rental townhomes and traditional single-level apartment homes.

  Springside Middletown

  (860) 854-3267

  

  1100 Springside Ln, Middletown, CT 06457
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  $1,725,000 Sold Dec 15, 2025

  20 Hemlock Dr, Essex, CT 06426

  • 4 Beds
  • 3.5 Baths
  • 4,162 Sq Ft
  • Built 1962

  Last Sold Summary

  • 22% Below List Price
  • $414/SF
  • 156 Days On Market

  Current Estimated Value $1,796,277

  Last Listing Agent Dee Hasuly KW Legacy Partners

  20 Hemlock Dr, Essex, CT 06426
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  Est $553,331 Not Listed For Sale

  7 Windsor Oval, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,856 Sq Ft
  • Built 1961

  7 Windsor Oval, Old Saybrook, CT 06475

  Last Sold Summary

  • 8% Above List Price
  • $276/SF
  • 55 Days On Market

  • Last Sold Price $513,000
  • May 06, 2025

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  $1,350,000

  • 7 Beds
  • 6 Baths
  • 3,787 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a two-parcel assemblage in Deep River, Connecticut, offering stabilized mixed-use income with residential value and land optionality. The assemblage includes: 87 Main Street - a parcel improved with: a Newer Construction Single Family Residence and a 5-unit mixed-use building (four residential apartments and one retail unit) 55 Prospect Street - a contiguous

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1057

  87 Main St, Deep River, CT 06417
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  $6,500 Per Month

  • 4 Beds
  • 4.5 Baths
  • 2,850 Sq Ft
  • House for Rent

  6 Fennwood Dr, Cromwell, CT 06416

  Spacious and rarely available, this 4-bedroom, 4-full bath home with a 3-car garage is ready for lease. The generous main bedroom boasts a walk-in closet and a stunning bath. This pristine property features an above-ground saltwater pool and a sprawling deck. The finished walk-out lower level with a full bath offers extra living space, while the fully equipped kitchen and fireplaced family room

  

  Patricia Deperry

  Berkshire Hathaway NE Prop.

  (860) 831-3617

  6 Fennwood Dr, Cromwell, CT 06416
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  $1,450,000 Sold Nov 17, 2025

  55 Main St, East Haddam, CT 06423

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $630/SF
  • 147 Days On Market

  Current Estimated Value $1,424,406

  Last Listing Agent Sacha Armstrong William Pitt Sotheby's International Realty

  55 Main St, East Haddam, CT 06423
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  Est $411,560 Not Listed For Sale

  16 Waverly Ave, Portland, CT 06480

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1930

  16 Waverly Ave, Portland, CT 06480

  Last Sold Summary

  • 2% Above List Price
  • $256/SF
  • 5 Days On Market

  • Last Sold Price $405,000
  • May 09, 2025

  Last Listing Agent Kadji Anderson Berkshire Hathaway Home Services
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  $675,000 Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  2 Pequot Trail, Old Saybrook, CT 06475

  Welcome to 2 Pequot Trail, perfectly positioned within Old Saybrook's desirable Indian Town Association, this beautifully maintained coastal ranch offers a rare opportunity to enjoy shoreline living in one of the area's most established waterfront neighborhoods. This stunning home captures the relaxed charm and lifestyle that make Indian Town and Old Saybrook at large, so sought after. Completely

  

  Dylan Walter

  William Raveis Real Estate

  (860) 909-8203

  2 Pequot Trail, Old Saybrook, CT 06475
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  Starting at $1,726

  Total Monthly Price

  • 1 - 2 Beds

  100 Town Brooke, Middletown, CT 06457

  At Middletown Brook Apartment Homes, you'll be greeted by modern interiors and breathtaking views of the surrounding neighborhood. With high-end finishes and sophisticated design, your apartment is the perfect place to relax and unwind after a long day. Curl up on your cozy couch with a glass of wine or enjoy a romantic dinner for two in your spacious dining area. With a beautiful swimming pool

  Middletown Brooke Apartments

  (860) 846-4439

  

  100 Town Brooke, Middletown, CT 06457
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  $406,000 Sold Jan 06, 2026

  55 Lorelei Cir, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1966

  Last Sold Summary

  • 3% Above List Price
  • $251/SF
  • 9 Days On Market

  Current Estimated Value $409,549

  Last Listing Agent Michelle Pirruccio Carl Guild & Associates

  55 Lorelei Cir, Middletown, CT 06457
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  Est $286,677 Not Listed For Sale

  92 Main St Unit 203, Deep River, CT 06417

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1985

  92 Main St Unit 203, Deep River, CT 06417

  Last Sold Summary

  • 4% Above List Price
  • $238/SF
  • 123 Days On Market

  • Last Sold Price $275,000
  • Apr 25, 2025

  Last Listing Agent George Sznaj DB Associates of CT, LLC
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  $519,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  56 Coles Rd, Middletown, CT 06457

  Come see this beautiful 4 bedroom, 2.5 bathroom Colonial with a 2-car garage, built in 1996 and ideally located on .41 acres in a quiet cul-de-sac setting before it is SOLD! The remodeled kitchen features granite countertops, a large center island with breakfast bar, and opens seamlessly to a cozy fireplaced family room with sliders to the back deck and a bright living room with hardwood

  

  Cheryl Zalewski

  eXp Realty

  (860) 579-1457

  56 Coles Rd, Middletown, CT 06457
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  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • House for Rent

  6 Stevens Rd, Clinton, CT 06413

  Beautifully remodeled rental just minutes from Clinton Harbor and downtown! Recently expanded and completely updated, this 1,488 sq. ft. home offers a bright, open floor plan with 2 large second-floor bedrooms and 2 full bathrooms. The main level features a spacious, sun-filled living area with fresh flooring, recessed lighting, sliders to the yard, and a clean modern layout that flows

  

  Dylan Walter

  William Raveis Real Estate

  (860) 979-5440

  6 Stevens Rd, Clinton, CT 06413
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  $174,000 Sold Aug 21, 2025

  1 Brush Pasture Ln Unit 109, Portland, CT 06480

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $209/SF
  • 50 Days On Market

  Current Estimated Value $178,267

  Last Listing Agent Maria Phillips William Raveis Real Estate

  1 Brush Pasture Ln Unit 109, Portland, CT 06480
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  Est $662,691 Not Listed For Sale

  6 Tucker Rd, Old Saybrook, CT 06475

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft
  • Built 1954

  6 Tucker Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 5% Above List Price
  • $808/SF
  • 4 Days On Market

  • Last Sold Price $630,250
  • May 02, 2025

  Last Listing Agent Terry McDonald McDonald Real Estate, LLC
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  $375,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,169 Sq Ft

  31 Grandview Terrace, Portland, CT 06480

  Welcome home to this well-built brick ranch offering exceptional space, comfort, and flexibility, set on over an acre in the heart of Portland. With 1272 sq ft on the main level and an additional 897 sq ft of finished walkout lower-level space, this home is ideal for today's lifestyle and multi-generational living. Step inside to a spacious, light-filled living rm centered around a cozy

  

  Cheryl Zalewski

  eXp Realty

  (860) 850-2433

  31 Grandview Terrace, Portland, CT 06480
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  Starting at $1,380

  Total Monthly Price

  • Studio - 2 Beds

  131 Ridgefield Dr, Middletown, CT 06457

  ***Maintenance Team On-site*** At Ridgefield Apartments we offer studios, lofts, and one and two bedroom apartments. We invite you to take advantage of our quality apartment homes. We offer value, comfort, and convenience to our residents, We are located in the esteemed Westlake neighborhood nestled among the trees. Our features include a pleasant, professional, and accommodating maintenance and

  Ridgefield Apartments

  (475) 255-0337

  

  131 Ridgefield Dr, Middletown, CT 06457
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  $749,900 Sold Jul 16, 2025

  17 Partridge Hill Ln, Essex, CT 06426

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft
  • Built 1967

  Last Sold Summary

  • $252/SF
  • 27 Days On Market

  Current Estimated Value $829,462

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  17 Partridge Hill Ln, Essex, CT 06426
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  Est $393,768 Not Listed For Sale

  188 Newfield St, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • Built 1890

  188 Newfield St, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $195/SF
  • 39 Days On Market

  • Last Sold Price $372,609
  • Apr 30, 2025

  Last Listing Agent Keith Murphy Innovative Properties
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  $325,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft

  11 Winter Ave, Deep River, CT 06417

  Check out this gorgeous home completely rebuilt from top to bottom! Imagine... brand new Roof, Siding, Windows, Mechanicals... no hassles for years to come!! This Deep River gem offers all new electrical, heating, and on-demand hot water systems for modern efficiency. Enjoy the stunning new kitchen with soft-close cabinets, stainless steel appliances, and quality finishes throughout. Unique

  

  Amber Jones

  KW Legacy Partners

  (860) 378-8016

  11 Winter Ave, Deep River, CT 06417
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  $2,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,328 Sq Ft
  • House for Rent

  55 Liberty St, Chester, CT 06412

  Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

  

  Janet Cronin-Rumanoff

  William Pitt Sotheby's Int'l

  (860) 981-0835

  55 Liberty St, Chester, CT 06412
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  $675,000 Sold Feb 20, 2026

  99 Maple Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Above List Price
  • $577/SF
  • 34 Days On Market

  Current Estimated Value $672,977

  Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

  99 Maple Ave, Old Saybrook, CT 06475
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  Est $433,824 Not Listed For Sale

  415 Ridge Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,615 Sq Ft
  • Built 1949

  415 Ridge Rd, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $253/SF
  • 6 Days On Market

  • Last Sold Price $408,000
  • Apr 28, 2025

  Last Listing Agent Levi Judqin Brass Moon Realty
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  $799,000

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  6 Cedar Island Ave, Clinton, CT 06413

  Just a short walk from Clinton's downtown shopping, marinas, and waterfront dining, this charming, remodeled 1940s ranch/cape offers a true coastal life style. The home features easy one-level living with hardwood floors throughout, three bedrooms, two full and one half baths, a bright year-round sunroom, living and dining rooms, and a den. The existing layout would work well for someone needing

  

  Dana Weinstein

  Coldwell Banker Realty

  (860) 891-6639

  6 Cedar Island Ave, Clinton, CT 06413
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  Starting at $1,624

  Total Monthly Price

  • 1 - 3 Beds

  100 Town Ridge, Middletown, CT 06457

  Middletown Ridge Apartments is a pet-friendly community located in the Town Ridge neighborhood near Cromwell, CT, within close proximity to Hartford. Our community offers the perfect blend of comfort and convenience, with spacious floor plans, modern amenities, and a prime location just minutes from everything you need.Each of our one, two, and three-bedroom apartments are designed with your

  Middletown Ridge Apartments

  (475) 255-2858

  

  100 Town Ridge, Middletown, CT 06457
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  $300,000 Sold Sep 19, 2025

  23 Lexington Place S, Durham, CT 06422

  • 2 Beds
  • 2.5 Baths
  • 1,686 Sq Ft
  • Built 1997

  Last Sold Summary

  • $178/SF
  • 174 Days On Market

  Current Estimated Value $308,847

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  23 Lexington Place S, Durham, CT 06422
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  Est $572,629 Not Listed For Sale

  10 Black Walnut Dr, Middletown, CT 06457

  • 3 Beds
  • 3 Baths
  • 3,027 Sq Ft
  • Built 1986

  10 Black Walnut Dr, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $178/SF
  • 2 Days On Market

  • Last Sold Price $539,000
  • May 02, 2025

  Last Listing Agent Jamie Bell Berkshire Hathaway Home Services

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