Chester CT Real Estate

Chester, Connecticut is a beautiful, rural town on the banks of the Connecticut River with lots of historic New England character. Main Street features elegant shops, historic and interesting architecture, delicious restaurants, art galleries, and the world-renowned Godspeed Opera House and Norma Terris Theater. In addition to a quaint downtown, Chester also features cascading waterfalls, a number of marinas, lakes, and thousands of acres of State Forest. Chester is a vibrant community with year-round town-wide events and small-town way of life that is dedicated to the preservation of the town’s history while also providing residents with 21st Century convenience. 

Find Chester Homes for Sale

Scroll down to find the latest real estate for sale in Chester, CT. Look through a variety of listings including residential homes, commercial spaces, land lots and more.

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Pending Continue to Show81 Turkey Hill Road Chester CT 06412
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Price$1,299,000

Est. Mortgage: $/month

MLS Number170410397

  • Single Family
  • Square Feet 2,893
  • Bathroom 3
  • Property Style Colonial
  • Bedrooms 3

RESORT like lifestyle available in this spectacular cedar clapboard colonial on 48.6 acres with a salt water pool, pool house with covered patio, stone pizza oven, hot tub, stone patios, 1792 sq ft barn, basketball hoop, & even its own ball field. Situated on an interior lot this stately home offers privacy & plenty of space to enjoy. The 1st floor includes a large family room with stone fireplace & vaulted ceilings, screened porch, dining room, large gourmet kitchen with cherry cabinets, granite countertops, stainless appliances & breakfast nook full of windows. In addition, the 1st floor also includes a living room with fireplace, den, & full bath with laundry. The 2nd floor includes the spacious master suite with walk-in closet, master bath with tiled walk-in shower, the hall bath, & 2 additional bedrooms. The walk-up 3rd floor includes an office area & bonus room. Above the garage there is a walk-up recreation room. Plenty of room for the entire family to spread out. Hike on the trails, shoot some hoops, continue the tradition of the epic ball games on the field of dreams, grill by the pool, cool off with a swim or relax in the hot tub, enjoy an evening beverage by the fire pit, so easy to relax and enjoy, too much to list. The barn is equipped with work bench & shelves, basketball hoop, batting cage set-up, & room for vehicles & toys. 2 hours from New York or Boston make this a spectacular weekend option or a great permanent home. You have to see to truly appreciate!

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Kristian J Cole of Waterhouse Realty LLC

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33 Liberty Street Chester CT 06412
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Price$799,000

Est. Mortgage: $/month

MLS Number170450411

  • Single Family
  • Square Feet 21,433
  • Year Built 1848
  • Bathroom 2
  • Property Style Other

Own a piece of history!!! Rare opportunity to own 21,000 plus sq. Ft. Building situated on the picturesque Great River-Tranquility & Privacy in an area of exquisite Homes. Liberty Street is minutes to the quaint, Historic Town of Chester, CT. M.S. Brooks & Sons built this property in the 1800's and utilized it until the 1980's. Located in a residential area, descendants of the Brooks have been slowly restoring the property, but a lot of work is still needed. Perfect for a retreat/compound. 1.7 acres located in R-1 zoning. Owner has a real estate license in FL.

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Derek Eisenberg of Continental Real Estate

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11 High Field Lane Chester CT 06412
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Price$665,000

Est. Mortgage: $/month

MLS Number170454200

  • Single Family
  • Square Feet 2,812
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1995

This custom built home should check most of your boxes! This home is located on a quiet cul-de-sac lane. Back of property borders 103 acres of watershed property, never to be built on. There are so many options for you on 3 level acres. Enjoy every aspect of your yard with a heated in-ground pool and spa made with granite coping. The interior of the pool is lined with pebble tech and the spa is lined with pebble sheen. The pool and spa have smart features to control temperature and bubblers remotely. Sunsetter awning on the back deck is perfect for shading in the afternoon sun. Other smart features include garage door openers and heat, AC controls. 3 car garage contructed with steel I beams, so no lolly columns! Plenty of storage, utility sink and access to basement. Home is generator ready and comes with the generator. The main floor has beautiful hardwood floors throughout. Custom cabinets in kitchen built by local cabinet maker. Master bedroom offers a walk in closet and full bath with jacuzzi tub and shower. The bonus room off the master bedroom is used as an office. This home has extensive internet and phone lines. This space could be swapped and used as the master bedroom. Custom built in cabinets have been designed to store heavy files and are 3 feet deep. There are 3 other bedrooms and another full bath to finish the upstairs. Full floored walk up attic for storage. There are many more features to discover upon your visit.

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Michelle Macneil of William Raveis Real Estate

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107 West Main Street Chester CT 06412
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Price$549,900

Est. Mortgage: $/month

MLS Number170439447

  • Single Family
  • Square Feet 3,617
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1976

Amazing opportunity to own over 24 acres of private property in Chester set high and dry above a windy babbling brook! Sought after pretty barn style home with open floor plan, country kitchen with antique brick wood-fired oven & 2 car garage. This 4 bedroom home is in need of a small amount of TLC. The property will be clear of engine parts & vehicles before closing. Includes an oversized 4 bay + garage with In-law apartment built to last the rest of time. This property would be suited for many different uses. Walking distance to the highway & quaint Chester Village.

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Jodi Lisitano of KW Legacy Partners

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76 Middlesex Avenue Chester CT 06412
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Price$479,900

Est. Mortgage: $/month

MLS Number170456071

  • Single Family
  • Square Feet 2,000
  • Property Style Colonial, Farm House
  • Bedrooms 5
  • Bathroom 2

So much charm throughout this absolutely stunning, completely remodeled farmhouse/colonial. Home is set back from the road and walking distance to downtown Chester. Home features 4 /5 bedrooms and 2 full baths. Almost everything in this spectacular home is brand new including electrical, plumbing, septic, windows, furnace and central air!! Walk into the grand foyer with a beautiful crystal chandelier and original oak staircase. Hardwood floors through-out which have been completely refinished. Open floor plan. Phenomenal custom mil-work throughout. Oversized combined living room/dining room with high ceilings, lots of large windows and crown molding. Tons of natural lighting. Kitchen is completely remodeled with black stainless steel appliances, stunning quarts counters and recessed lighting. The first floor also features two generous size bedrooms, a mudroom with laundry and an absolutely gorgeous full bath with a huge walk in shower, sliding glass doors and dual shower heads. This area could be a possible in-law suite. Three additional bedrooms upstairs. One of the bedrooms has an extra area that could be a walk-in closet, small nursery or quiet sitting area. Beautifully remodeled full bath (tub & shower). Sit and relax on the front porch and enjoy the beautiful views. Must see!!

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Tracey A Precourt of Century 21 Clemens Group

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56 Goose Hill Road Chester CT 06412
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Price$479,000

Est. Mortgage: $/month

MLS Number170428494

  • Single Family
  • Square Feet 1,964
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1850

Lovely setting on 4.98 acres. This charming antique colonial home sits on a knoll overlooking the quiet road, and rolling lawns. Spacious home, loads of opportunity to decorate to your taste, hardwood floors, open spacious kitchen, Dining room, living room, den and master bedroom on first floor. Come see...it is unique and charming.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Jeanne M Bailey of Berkshire Hathaway NE Prop.

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Pending Continue to Show284 West Main Street Chester CT 06412
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Price$449,000

Est. Mortgage: $/month

MLS Number170454115

  • Single Family
  • Square Feet 1,848
  • Year Built 1998
  • Bathroom 3
  • Bedrooms 3

Own a little slice of heaven! Relax on your deck overlooking the private, stocked lake in quintessential Chester, CT. This three bedroom contemporary ranch is set privately on over 6 acres that borders state forest. Plenty of natural light from oversized windows and an impressive fireplace complete the living room. Possible in-law and finished basement area with full walk out and half bath. Centrally located and only 2.5 hours from Boston and New York. This is an opportunity not to be missed!

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Kelly Puorro and Brandon Puorro of Puorro Realty Group

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Pending Continue to Show104 Oakwood Trail Chester CT 06412
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Price$410,000

Est. Mortgage: $/month

MLS Number170450430

  • Condo
  • Square Feet 2,144
  • Year Built 2006
  • Property Style Townhouse
  • Bedrooms 2

Beautifully maintained condo in the storybook town of Chester! This condo iis bright, sunny, and open. The propane fireplace will keep you warm on those cold winter nights! This home offers two master bedrooms with full baths and plenty of closet space. There is a large finished bonus room on the 2nd floor that can be used as a study, craft room, home gym or whatever else you can dream of. The extra wide stairway is equipped with a chair lift. There is also a very large on demand generator, so you never have to worry about losing power. The Forest Condo Community is a 55+ community, only one person needs to be 55 or older. This condo is completely move in ready and just waiting to be called home!

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Nikki Copeland-Spencer of William Raveis Real Estate

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Liberty Street Chester CT 06412
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Price$325,000

Est. Mortgage: $/month

MLS Number170423336

  • Land
  • MLS Status Active
  • Acreage 1.01
  • Other Amenities Waterfront
  • Waterfront

Beautiful 1.01 acre water front lot. Partially Cleared & Ready to build Your Dream home. Situated on the picturesque Great River-Tranquility & Privacy in an area of exquisite Homes. Liberty Street is minutes to the quaint, Historic Town of Chester, CT. Owner has a real estate license in FL.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Derek Eisenberg of Continental Real Estate

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44 Castle View Drive Chester CT 06412
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Price$309,000

Est. Mortgage: $/month

MLS Number170460655

  • Single Family
  • Square Feet 1,304
  • Year Built 1987
  • Bathroom 2
  • Property Style Cape Cod

DELIGHTFUL CAPE COD with a modern flair. This home sits on a .4-acre corner lot and offers 2/3 bedrooms, 1 full & 1 half bathrooms, and a 2-car garage. Recently refinished hardwood floors on main level, updated kitchen with granite counter tops and stainless appliances. Living room features a high, vaulted ceiling, built-in bookcase, and a cozy wood-burning fireplace with insert; perfect for those colder winter months. The bedrooms are on the second level, with the master bedroom offering French doors that open to a balcony overlooking the living room space below. Additional amenities, newer roof (2017), full unfinished basement, new carpets in the bedrooms, new furnace and oil tank. Conveniently located, minutes from Route 9 and charming downtown Chester, where you'll enjoy an array of restaurants and boutique shops. Why rent when you can own!

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Rose Ciardiello of William Raveis Real Estate

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11 Kings Highway Chester CT 06412
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Price$215,000

Est. Mortgage: $/month

MLS Number170443615

  • Land
  • MLS Status Active
  • Acreage 1.5
  • Other Amenities Golf, Waterfront
  • Zoning R-1

Building lot 1.5 acres in Chester w excellent CT. River water and river valley views. Driveway installed w crushed stone. Septic approved, City water at street.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Mark Reyher of Reyher Real Estate

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Pending Continue to Show278 West Main Street Chester CT 06412
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Price$199,000

Est. Mortgage: $/month

MLS Number170438812

  • Land
  • Acreage 6.36
  • Zoning R-2
  • Subdividable Unknown

Bring your horses and your kayak!! Incredible opportunity to own over 6 acres in the quaint town of Chester. This private land boarders state forest, and has views of a lake that is shared with only three other houses. Don't miss this opportunity to build your dream home! Underground utilities available.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Kelly Puorro and Brandon Puorro of Puorro Realty Group

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Bokum Road Chester CT 06412
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Price$99,000

Est. Mortgage: $/month

MLS Number170435801

  • Land
  • MLS Status Active
  • Acreage 2.47
  • Other Amenities Golf, Waterfront
  • Zoning R-2

Fully-approved and ready to go...2.74 acre Building Lot within walking distance to Chester Village. Lightly wooded and gently sloping with southwestern exposure and light. Chester is a Connecticut River Valley Town with a vibrant village center that offers year-round activities and events, award-winning gourmet restaurants, boutiques, art galleries, and casual eateries.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Listed by Ellen Henderson of William Pitt Sotheby's Int'l

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2022 SmartMLS, Inc.