Middlesex, CT Homes

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  /40

  $645,000

  • 2 Beds
  • 3 Baths
  • 3,091 Sq Ft

  28 S Wig Hill Rd, Chester, CT 06412

  Step into history with this 1770 Cape, part of "Old Homes of Chester." Nestled on beautiful grounds featuring rolling hills, gardens, and stunning stone walls, the property abuts 8 acres of serene land trust, offering unparalleled privacy and a park-like setting. The main house spans 1303 square feet and includes 2 bedrooms and 2 full baths. Recent upgrades include a new furnace (2023), electric

  Andrew O'Reilly Seaport Real Estate Services

  28 S Wig Hill Rd, Chester, CT 06412
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  Explore Chester

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  /10

  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • House for Rent

  86 Spring St, Chester, CT 06412

  AVAILABLE OCTOBER 2025: Recently renovated unit of a 2 family house in Chester CT. This 850 sq ft living space is heated by propane, has a flexible floor plan, in-unit laundry, new kitchen area floor & new fridge. 2 private entrances and outdoor space with small fire pit. Perfect for a solo renter or couple. WALK TO TOWN - just 8/10 mile to lovely downtown Chester. This charming, quaint town

  86 Spring St, Chester, CT 06412
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  $610,000 Sold Aug 01, 2025

  • 1,570 Sq Ft
  • $389/SF
  • 15 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1915

  137 Main St, Chester, CT 06412

  VILLAGE OF CHESTER- Embrace the perfect blend of modern comfort and serene living in this beautifully upgraded home, nestled just moments from Chester's enchanting village center. With a newer roof and fresh paint both inside and out, this property offers a seamless move-in experience for the discerning buyer. The home's unique position, secluded without immediate neighbors and bordered by a park

  Teri Strain-Lewis William Pitt Sotheby's Int'l

  137 Main St, Chester, CT 06412
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  Est $854,865 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,033 Sq Ft

  75 Pinnacle Ln, Chester, CT 06412

  75 Pinnacle Ln, Chester, CT 06412
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  /37

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,344 Sq Ft

  25 Spring St, Chester, CT 06412

  Tucked away on Spring Street in the heart of Chester village, this stately two-story residence gracefully combines classic farmhouse tradition with all the amenities of modern living. As you enter the home through the foyer, sunlight pours through generous windows, illuminating the living room anchored by an elegant fireplace. Recessed lighting and gleaming wide-plank wood floors lend an

  Susan Malan William Pitt Sotheby's Int'l

  25 Spring St, Chester, CT 06412
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  /6

  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  23 Denlar Dr Unit A, Chester, CT 06412

  Rent is $1350 Plus Utility first, last, and security. Reference required "NO PETS". show contact infoAir Conditioning

  23 Denlar Dr Unit A, Chester, CT 06412
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  $795,000 Sold Jul 31, 2025

  • 2,389 Sq Ft
  • $333/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1835

  80 W Main St, Chester, CT 06412

  Nestled in the storybook town of Chester, Connecticut-renowned for its vibrant arts scene, scenic countryside, and charming village center-this one-of-a-kind historic home lovingly maintained by its current steward,offers a truly inspiring lifestyle. Set on lush, idyllic grounds framed by mature trees, gardens,&stone walls, the property exudes timeless New England beauty.A collection of

  Mary Jean Agostini RE/MAX Right Choice

  80 W Main St, Chester, CT 06412
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  Est $501,587 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  22 Hickory Hill Dr, Chester, CT 06412

  22 Hickory Hill Dr, Chester, CT 06412
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  $774,000

  • 4 Beds
  • 3.5 Baths
  • 3,396 Sq Ft

  28 Hoop Pole Hill Rd, Chester, CT 06412

  Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm,

  Teri Strain-Lewis William Pitt Sotheby's Int'l

  28 Hoop Pole Hill Rd, Chester, CT 06412
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  $525,000 Sold Jul 25, 2025

  • 2,272 Sq Ft
  • $231/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  4 Sypher Rd, Chester, CT 06412

  Discover a rare gem in the picturesque town of Chester, Connecticut, with this charming 3-bedroom, 2.5-bath colonial home. Nestled on a private 2-acre lot, this property is a dream come true for horse lovers, featuring a barn that offers ample space for your equestrian needs and a chicken coop. Enjoy direct access to nearby state forest trails for riding or exploring. As you step inside, you will

  Kelly Puorro Puorro Realty Group

  4 Sypher Rd, Chester, CT 06412
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  Est $378,979 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  8 Winthrop Rd, Chester, CT 06412

  8 Winthrop Rd, Chester, CT 06412
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  /40

  $1,017,000

  • 4 Beds
  • 3.5 Baths
  • 4,341 Sq Ft

  95 Cedar Swamp Rd, Chester, CT 06412

  Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester. Bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning views over Shailer Pond, this home brings the outdoors in from every angle.

  Rachel Welch William Raveis Real Estate

  95 Cedar Swamp Rd, Chester, CT 06412
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  $715,000 Sold Jul 25, 2025

  • 1,702 Sq Ft
  • $420/SF
  • 30 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1883

  69 Spring St, Chester, CT 06412

  *Multiple offers received - offer deadline for 6/9 by noon* Quintessential Modernized Antique in Chester ~ Step into timeless charm with this beautifully updated antique colonial nestled near the heart of Chester. This visually stunning home seamlessly blends classic character with thoughtful modern updates. Offering 3 light and bright bedrooms, beautifully refinished original 1880 pine floors,

  Rachel Welch William Raveis Real Estate

  69 Spring St, Chester, CT 06412
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  Est $1,055,588 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,862 Sq Ft

  248 Middlesex Ave, Chester, CT 06412

  248 Middlesex Ave, Chester, CT 06412
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  /40

  $790,000

  • 2 Beds
  • 3 Baths
  • 1,598 Sq Ft

  6 Spring St, Chester, CT 06412

  Welcome to 6 Spring Street, a residence that transcends the ordinary. Known affectionately as "The Recycle House," this home is a testament to over a decade of meticulous craftsmanship, with the majority of its structure composed of upcycled materials. Its acclaim extends beyond its eco-friendly design, having been rated as one of the top 70 Airbnbs near NYC by the online magazine "Curbed" and

  Amy Graham William Pitt Sotheby's Int'l

  6 Spring St, Chester, CT 06412
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  $875,000 Sold Jul 25, 2025

  • 3,206 Sq Ft
  • $273/SF
  • 83 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  79 Cedar Lake Rd, Chester, CT 06412

  A perfect opportunity for a 'Gentleman's Farm' in this wonderful 3200 Sq/Ft Farmhouse Colonial on 11.8 Acres of Great Equestrian Lands w/ Beautiful Plantings, Custom Gardens & Direct Access to the Riding Trails of the Cockaponset State Forest & a short walk to Cedar Lake. You cannot beat this location! Check out our Virtual Reality Tour & those Pics! The Open & Contemporary Floor Plan has

  Bill Heenan William Raveis Real Estate

  79 Cedar Lake Rd, Chester, CT 06412
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  Est $449,830 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  37 Castle View Dr, Chester, CT 06412

  37 Castle View Dr, Chester, CT 06412
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  /40

  $749,900

  • 3 Beds
  • 1.5 Baths
  • 1,538 Sq Ft

  43 N Main St, Chester, CT 06412

  Fantastic home in wonderful private setting with views of Chester Creek and sounds of the waterfall across the street. Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Beautiful farm porch, detached two car garage, the "glass house" at the edge of Chester Creek to relax and watch nature. 3 bedrooms, 1 1/2 baths, beautiful propane

  Susan Malan William Pitt Sotheby's Int'l

  43 N Main St, Chester, CT 06412
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  $952,397 Sold Jul 10, 2025

  • 3,788 Sq Ft
  • $251/SF
  • 70 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  32 Gilbert Hill Rd, Chester, CT 06412

  Welcome to a one-of-a-kind estate where history meets modern comfort - located within walking distance to Chester's charming downtown area. Built in 1986, this home was crafted using materials from a 1740 barn that were relocated to the stunning 5.31-acre rocky hillside it occupies today. The original timbers frame a breathtaking residence, blending rustic character with a contemporary and

  Steve Q Exclusive Properties

  32 Gilbert Hill Rd, Chester, CT 06412
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  Est $536,095 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  25 Deep Hollow Rd, Chester, CT 06412

  25 Deep Hollow Rd, Chester, CT 06412
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  /4

  $985,000

  • 2 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  88 Winthrop Rd, Chester, CT 06412

  The charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks a lovely 5 acre pond. The home features a large kitchen and 2 1/2 baths with laundry on the second floor. Highlighting the living room is a 30 ft. Cathedral ceiling. Master bedroom includes an interior balcony, overlooking the living area. Generous windows and sliders afford beautiful open views of the

  Peter Walsh Re/Max Valley Shore

  88 Winthrop Rd, Chester, CT 06412
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  $370,000 Sold Jul 09, 2025

  • 642 Sq Ft
  • $576/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2017

  96 Goose Hill Rd, Chester, CT 06412

  A thoughtfully designed home set on four acres in the heart of Chester. With a mix of open land and lightly wooded areas, the property offers both privacy and usable space in a peaceful, natural setting. Inside, the home features a bedroom on the main level, a full bathroom, and a full eat-in kitchen equipped with a stove, refrigerator, microwave, and ample cabinet space. The open living area is

  Jason Archer PMI East Lyme

  96 Goose Hill Rd, Chester, CT 06412
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  Est $600,294 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  16 Ridge Rd, Chester, CT 06412

  16 Ridge Rd, Chester, CT 06412
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  /40

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 3,149 Sq Ft

  7 Old Depot Rd, Chester, CT 06412

  Bella Vista: A Timeless Italianate Treasure on 6 Acres. Step into a piece of history, a magnificent Italianate country villa that has graced the landscape since 1908. First time on the market, this storied estate has been lovingly preserved by the same family for generations, a testament to its enduring allure. Listed on the National Registry of Historic Places, Bella Vista is an architectural

  Colette Harron William Pitt Sotheby's Int'l

  7 Old Depot Rd, Chester, CT 06412
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  $1,135,000 Sold Jun 30, 2025

  • 3,351 Sq Ft
  • $339/SF
  • 16 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1987

  25 Gilbert Hill Rd, Chester, CT 06412

  Experience the stunning views of the Connecticut River, Lyme's hills, and the expansive valley from your heated Gunite in-ground swimming pool. The beautifully manicured grounds reflect years of dedicated care. This home showcases exceptional quality, featuring customized designs and meticulous details throughout, including custom moldings and cabinetry in the kitchen, bathrooms, and closets.

  Robin Linares William Pitt Sotheby's Int'l

  25 Gilbert Hill Rd, Chester, CT 06412
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  Est $515,904 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  4 Turkey Hill Rd, Chester, CT 06412

  4 Turkey Hill Rd, Chester, CT 06412
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  /10

  $232,500

  • Land
  • 1.50 Acres
  • $155,000 per Acre

  11 Kings Hwy, Chester, CT 06412

  1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

  Rachel Welch William Raveis Real Estate

  11 Kings Hwy, Chester, CT 06412
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  $1,000,050 Sold Jun 25, 2025

  • 3,054 Sq Ft
  • $327/SF
  • 18 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1950

  15 Gilbert Hill Rd, Chester, CT 06412

  Mid-Century Modern Private Compound Overlooking the CT River Valley. Discover this exceptional mid-century modern retreat, a private compound set in a park-like setting with distant water views of the Connecticut River Valley. This expanded Cape blends timeless design with modern updates, featuring an open floor plan flooded with natural light from skylights, two fireplaces, and hand-laid terra

  Angela Ruel Berkshire Hathaway NE Prop.

  15 Gilbert Hill Rd, Chester, CT 06412
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  Est $719,702 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,713 Sq Ft

  12 Liberty St, Chester, CT 06412

  12 Liberty St, Chester, CT 06412
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  /2

  $985,000

  • Land
  • 34 Acres
  • $28,996 per Acre

  88 Winthrop Rd, Chester, CT 06412

  The wooded 33.97 acre site has extensive open water views with frontage on Winthrop Road (Rt 145) and Butter Jones Road. The property abuts Deep River and Killingworth with convenient access to charming shopping areas. Also, the Chester Airport is within walking distance. A long driveway winds through the spacious, park-like setting, ideal for a planned unit development.

  Peter Walsh Re/Max Valley Shore

  88 Winthrop Rd, Chester, CT 06412
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  $3,100,000 Sold Jun 10, 2025

  • 4,727 Sq Ft
  • $656/SF
  • 27 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2010

  31 Parkers Point Rd, Chester, CT 06412

  Nestled near the heart of the quaint Chester Village, this exquisite Nantucket-style home offers a serene retreat on the banks of the CT River. Spanning an impressive 4,727sqft, this architectural gem is all enveloped in traditional shingle elegance. As you step inside, you're welcomed by a two-story, paneled living room that exudes drama and sophistication. The space is adorned with beautiful

  Colette Harron William Pitt Sotheby's Int'l

  31 Parkers Point Rd, Chester, CT 06412
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  Est $673,030 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,607 Sq Ft

  7 Pine Knoll Dr, Chester, CT 06412

  7 Pine Knoll Dr, Chester, CT 06412
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  /25

  $399,000 Under Contract

  • 4 Beds
  • 1.5 Baths
  • 2,025 Sq Ft

  14 Ferry Rd, Chester, CT 06412

  Located by the Chester-Hadlyme Ferry, this 4 bedroom, 1.5 bath home is waiting your customization. Built in 1950, this home has original wainscoting in the living room, hardwood floors and built-in cabinets throughout. A large family room with fireplace is the perfect location to enjoy a cold winter night. There are three bedrooms on the main floor and a fourth on the second floor, which is

  Ian Sacks Coldwell Banker Realty

  14 Ferry Rd, Chester, CT 06412
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  $575,000 Sold May 29, 2025

  • 1,803 Sq Ft
  • $319/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  67 Maple St, Chester, CT 06412

  Welcome to this delightful meticulous Cape Cod home, featuring 3 spacious bedrooms, 2.5 baths and a home office. The primary bedroom suite is generous in size with his and her closets, a jacuzzi tub in the primary bathroom and is conveniently located on the first floor. The main level also includes a dedicated home office that has access to the beautiful, huge trex deck. The kitchen has been

  Laura Cariati Coldwell Banker Realty

  67 Maple St, Chester, CT 06412
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  Est $825,445 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,802 Sq Ft

  22 Waterhouse Ln, Chester, CT 06412

  22 Waterhouse Ln, Chester, CT 06412
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  $651,500 Sold May 16, 2025

  • 1,766 Sq Ft
  • $369/SF
  • 35 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1925

  42 W Main St, Chester, CT 06412

  This newly renovated century-old bungalow home offers a harmonious blend of historic charm and modern amenities. The expansive front porch provides an ideal setting for enjoying morning coffee or evening beverages while appreciating the outdoors. The entirely new kitchen features quartz countertops and a marble backsplash, with ample natural light illuminating the space. An adjacent pantry

  Pardi & Zucco Team William Pitt Sotheby's Int'l

  42 W Main St, Chester, CT 06412
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  Est $700,864 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,646 Sq Ft

  19 Hickory Hill Dr, Chester, CT 06412

  19 Hickory Hill Dr, Chester, CT 06412
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  $450,000 Sold May 14, 2025

  • 1,926 Sq Ft
  • $234/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1790

  24 E Liberty St, Chester, CT 06412

  Step back into Chester history! This home sits on over an acre within the town limits of Chester. It's sits on a quiet street with an expansive back yard. Much of structure has the historical details that antique home enthusiasts look for: wide plank chestnut floors, hand forged hardware, exposed beams, stone fireplaces, etc. Practicality also exists with the main house having higher ceilings

  Bonnie Fillion Berkshire Hathaway NE Prop.

  24 E Liberty St, Chester, CT 06412
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  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,970 Sq Ft

  162 W Main St, Chester, CT 06412

  162 W Main St, Chester, CT 06412
• 

  $180,000 Sold May 09, 2025

  • 752 Sq Ft
  • $239/SF
  • 32 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1955

  93 W Main St, Chester, CT 06412

  Charming One-Bedroom Ranch in Chester Village - A Hidden Gem! Discover the perfect investment opportunity with this delightful one-bedroom ranch located within walking distance to the picturesque downtown Chester Village. Known for its charming ambiance, this quaint town serves as a backdrop for Hallmark movies, offering a delightful mix of fantastic restaurants, unique galleries, and boutique

  Kelly Puorro Puorro Realty Group

  93 W Main St, Chester, CT 06412

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