Chester, CT Homes

• 

  $345,000 Sold Aug 20, 2025

  • 1,472 Sq Ft
  • $234/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  6 Ridge Rd, Chester, CT 06412

  Beautifully maintained split-level home just a short walk to town and the elementary school. Featuring 3 bedrooms and 2 full baths, this home offers updated bathrooms, newer siding, and windows throughout. The main level includes an eat-in kitchen and a bright living area, while the lower level boasts a cozy family room with a fireplace and slider leading to a patio. Enjoy outdoor living with a

  Craig Milton Re/Max Valley Shore

  6 Ridge Rd, Chester, CT 06412
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• 

  Est $704,407 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
• 

  

  

  /11

  $232,500

  • Land
  • 1.5 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
• 

  $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 Lewis William Pitt Sotheby's Int'l

  137 Main St, Chester, CT 06412
• 

  Est $859,810 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
• 

  /2

  $200,000

  • Land
  • 2.25 Acres
  • $88,889 per Acre

  43 Bokum Rd, Chester, CT 06412

  Beautiful potential building lot. Access via Private road, 2.25 acres. Undeveloped.

  Nicholas Tomanelli Coldwell Banker Realty

  43 Bokum Rd, Chester, CT 06412
• 

  $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
• 

  Est $738,742 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
• 

  /2

  $985,000

  • Land
  • 33.97 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
• 

  $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
• 

  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
• 

  

  /33

  $469,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,516 Sq Ft

  36 Kings Hwy, Chester, CT 06412

  Charming Stone Home on Nearly 4 Acres! Just minutes from Chester Village, this distinctive home blends character and modern updates. Enjoy an eat-in kitchen with quartz counters, 3-4 bedrooms, and a versatile home office. Recent upgrades include hardwood floors, new roof and gutters, furnace, oil tank, solar panels, and surveillance system. A detached stone 2-car garage completes this rare find!

  Craig Milton Re/Max Valley Shore

  36 Kings Hwy, Chester, CT 06412
• 

  $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
• 

  Est $525,434 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  42 Railroad Ave, Chester, CT 06412

  42 Railroad Ave, Chester, CT 06412
• 

  

  /32

  $229,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 748 Sq Ft

  15 Hazen St, Chester, CT 06412

  Highest & best by Monday 11/17. OH Saturday 11/15. Charming 4-season cottage with views of Cedar Lake! Corner lot with deck, outdoor shower, and parking. Features an eat-in kitchen, open living area, 3 bedrooms, and hardwood floors.

  Dillon Cass eRealty Advisors, Inc.

  15 Hazen St, Chester, CT 06412
• 

  $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
• 

  Est $505,239 Not Listed For Sale

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

  16 Middlesex Ave, Chester, CT 06412

  16 Middlesex Ave, Chester, CT 06412
• 

  $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
• 

  Est $597,404 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
• 

  $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
• 

  Est $369,757 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  47 Winthrop Rd, Chester, CT 06412

  47 Winthrop Rd, Chester, CT 06412
• 

  $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
• 

  Est $769,061 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  17 Kings Hwy, Chester, CT 06412

  17 Kings Hwy, Chester, CT 06412
• 

  $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
• 

  Est $510,734 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,972 Sq Ft

  45 Winthrop Rd, Chester, CT 06412

  45 Winthrop Rd, Chester, CT 06412
• 

  $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
• 

  Est $423,179 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  54 Bokum Rd, Chester, CT 06412

  54 Bokum Rd, 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 $551,188 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,927 Sq Ft

  24 Deep Hollow Rd, Chester, CT 06412

  24 Deep Hollow Rd, 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 $446,546 Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 2,638 Sq Ft

  53 Main St, Deep River, CT 06417

  53 Main St, Deep River, CT 06417
• 

  $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 $266,530 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft

  187 Middlesex Ave, Chester, CT 06412

  187 Middlesex Ave, 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 $476,537 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft

  6 Hickory Hill Dr, Chester, CT 06412

  6 Hickory Hill Dr, 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 Lewis William Pitt Sotheby's Int'l

  16 Waterhouse Ln, Chester, CT 06412
• 

  Est $431,110 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  3 Cross Rd, Chester, CT 06412

  3 Cross 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 $2,203,968 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 3,968 Sq Ft

  49 Parkers Point Rd, Chester, CT 06412

  49 Parkers Point Rd, 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

Showing Results 41 - 80, Page 2 of 18