Homes in ZIP Code 06412

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  /25

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 3,788 Sq Ft

  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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  /52

  $2,600 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  82 Goose Hill Rd Unit 82 Goose Hill #A, Chester, CT 06412

  LOVELY CHESTER APARTMENT – 20 MINUTES TO MDSXHosp. Life’s wonderful in Chester, a beautiful town with a storybook village of unique shops, restaurants, and numerous wooded trails all right down the road! Enjoy the Chester Sunday market as well as local attractions including the historic Chester Hadlyme Ferry, Norma Terris and Goodspeed Theaters, Gillette Castle and Pattaconk Nature Preserve.

  82 Goose Hill Rd Unit 82 Goose Hill #A, Chester, CT 06412
• 

  $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
• 

  Est $492,292 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
• 

  

  

  /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
• 

  

  /13

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft
  • Apartment for Rent

  6 Main St, Chester, CT 06412

  Fantastic Chester Village location. One bedroom apartment, open floor plan, shared laundry on premises. Live in the heart of Chester Village with shops, restaurants, live theater, and the amazing in season Chester Village Farmers Market.

  Susan Malan William Pitt Sotheby's Int'l

  6 Main St, Chester, CT 06412
• 

  $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
• 

  Est $406,667 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  51 Bokum Rd, Chester, CT 06412

  51 Bokum Rd, Chester, CT 06412
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  /40

  $1,299,000

  • 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 farmhouse 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 gem

  Colette Harron William Pitt Sotheby's Int'l

  7 Old Depot Rd, Chester, CT 06412
• 

  $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
• 

  Est $376,871 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
• 

  

  /30

  $1,100,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,351 Sq Ft

  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
• 

  $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
• 

  Est $430,032 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
• 

  

  /38

  $819,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,054 Sq Ft

  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
• 

  $1,250,000 Sold May 02, 2025

  • 4,661 Sq Ft
  • $268/SF
  • 24 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1988

  16 Waterhouse Ln, Chester, CT 06412

  Discover the essence of elegance and tranquility in this exquisite Chester estate, boasting a host of 2024 upgrades including a new roof, furnace, and a tastefully renovated half bath. This property also comes with an approved separate building lot, enhancing your privacy and offering potential investment opportunities. The home is perfectly oriented to capture the morning sunrises, providing

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

  16 Waterhouse Ln, Chester, CT 06412
• 

  Est $611,517 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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  /37

  $895,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,206 Sq Ft

  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
• 

  $675,000 Sold May 01, 2025

  • 4,056 Sq Ft
  • $166/SF
  • 65 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2002

  108 Middlesex Ave, Chester, CT 06412

  Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to

  Trever Smith Chiarito Real Estate LLC

  108 Middlesex Ave, Chester, CT 06412
• 

  Est $522,672 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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  /24

  $895,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,164 Sq Ft

  25 Spring St, Chester, CT 06412

  The "Mill House", built in 1860 is sited on a hill overlooking the town of Chester and a string of waterfalls that once powered the mill and continues through the town square. The Mill House itself is a handsome example of period New England colonials of the era. Dating to colonial times, Chester was founded alongside the Connecticut River around 1672. Today the central square is a hub for an

  Tim Boyd William Pitt Sotheby's Int'l

  25 Spring St, Chester, CT 06412
• 

  $975,000 Sold Apr 30, 2025

  • 2,680 Sq Ft
  • $364/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2002

  6 Old County Rd, Chester, CT 06412

  Private, pristine, and with proximity to the Connecticut River, many wonderful restaurants, and boutiques. This meticulously maintained four bedroom 2 1/2 bath home is less than 2 miles from fabulous Chester Village. Set on over 2 acres this beautiful home has been carefully updated and enhanced. The meandering driveway takes you to a perfectly sited home with an amazing heated barn which also

  Susan Malan William Pitt Sotheby's Int'l

  6 Old County Rd, Chester, CT 06412
• 

  Est $643,602 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
• 

  

  /39

  $764,900

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

  43 N Main St, Chester, CT 06412

  Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Surrounded by Chester Creek and across the street from a beautiful waterfall sits 43 North Main Street Chester. 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 fireplace,

  Susan Malan William Pitt Sotheby's Int'l

  43 N Main St, Chester, CT 06412
• 

  $1,363,500 Sold Apr 15, 2025

  • 4,205 Sq Ft
  • $324/SF
  • 136 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  19 W Main St, Chester, CT 06412

  Welcome to the Waterfall House, an iconic custom home perched above the scenic Pattaconk Brook in the heart of historic Chester Village. Overlooking a picturesque 15-foot waterfall and offering sweeping views of the serene Jennings Pond from every room, this home is a masterpiece. Meticulously renovated in 2021, it blends modern luxury with timeless historic charm. Just a 5-minute stroll from

  Michael Marsden Compass Connecticut, LLC

  19 W Main St, Chester, CT 06412
• 

  Est $794,786 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
• 

  

  /40

  $694,000

  • 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
• 

  $285,000 Sold Apr 09, 2025

  • 1,519 Sq Ft
  • $188/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1702

  14 Straits Rd, Chester, CT 06412

  **Incredible Opportunity Awaits!** Discover the potential of this charming three-bedroom colonial, ideally situated in the heart of Chester Village. With a new septic system, roof, and windows already installed, the groundwork is laid for your dream home. The interior is completely gutted down to the studs, offering a blank canvas for a full rehab or the perfect opportunity to build your own

  Kelly Puorro Puorro Realty Group

  14 Straits Rd, Chester, CT 06412
• 

  Est $694,106 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
• 

  

  /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
• 

  $350,000 Sold Apr 07, 2025

  • 1,188 Sq Ft
  • $295/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1964

  11 Bishop Rd, Chester, CT 06412

  Enjoy one-level living with protected year -round views of Cedar Lake in this 2-3 bedroom ranch. The smaller bedroom features convenient laundry access. A spacious living room with a fireplace and bay window offers a perfect spot to take in the scenic view. The home boasts hardwood floors throughout. The full basement is partially finished and offers plenty of potential. Located next to

  Craig Milton Re/Max Valley Shore

  11 Bishop Rd, Chester, CT 06412
• 

  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
• 

  /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
• 

  $900,000 Sold Mar 24, 2025

  • 2,755 Sq Ft
  • $327/SF
  • 26 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1998

  10 Old County Rd, Chester, CT 06412

  Private and peaceful with seasonal views of the Connecticut River yet less than two miles to fabulous Chester Village with shops, restaurants, art galleries, spectacular (in season) farmers market and more. This 4-bedroom custom built home has a wonderful floor plan consisting of 4 bedrooms, 3 1/2 baths, 9' ceilings, huge primary bedroom with cathedral ceilings, oversized ensuite full bath and

  Susan Malan William Pitt Sotheby's Int'l

  10 Old County Rd, Chester, CT 06412
• 

  Est $485,589 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft

  16 Middlesex Ave, Chester, CT 06412

  16 Middlesex Ave, Chester, CT 06412
• 

  

  /40

  $3,495,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,727 Sq Ft

  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
• 

  $540,000 Sold Mar 20, 2025

  • 2,144 Sq Ft
  • $252/SF
  • 172 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1980

  71 Maple St, Chester, CT 06412

  Close to the town center, yet on a two acre tree shaded lot set back from the street. Gambrel colonial with a two car attached garage and three car detached garage. Garden area with in-ground pool feature. Possible in-law apartment on first floor. Furnace is oil with optional wood burning capability. Living room fireplace has a wood burning stove. New washer and dryer. Newer septic tank. Wide

  Louisa Ketron Berkshire Hathaway NE Prop.

  71 Maple St, Chester, CT 06412
• 

  Est $566,791 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  8 Hickory Hill Dr, Chester, CT 06412

  8 Hickory Hill Dr, Chester, CT 06412
• 

  

  /40

  $600,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  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
• 

  $280,000 Sold Mar 07, 2025

  • 1,170 Sq Ft
  • $239/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1951

  15 Kirtland Terrace, Chester, CT 06412

  Nestled at the end of a quiet street, this 3-bedroom, 1.5-bath ranch offers a rare chance to create your dream home in historic Chester. Overlooking the serene Chester Fairgrounds fields, this property features stunning views and a spacious lot, making it ideal for renovation or a fresh new build. With easy one-floor living and central air, this home offers comfort and convenience. Whether you

  Kristina Quinones William Pitt Sotheby's Int'l

  15 Kirtland Terrace, Chester, CT 06412

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