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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65 Bokum Road Chester CT 06412
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Price$1,300,000

Est. Mortgage: $/month

MLS Number170521627

  • Single Family
  • Square Feet 3,926
  • Year Built 1979
  • Bedrooms 4
  • Bathroom 4

WELCOME TO IVORY POND ESTATE! A beautiful custom Chalet and separate Carriage House located on 24 acres of property. This estate is perfect for the large family, perhaps a multi-generational family, rental income, or business enterprise. The possibilities are endless. Walk up to the main home with wrap around deck to sit and enjoy your very own Ivory Pond and the lovely nature that surrounds it. Glass French doors to large family room with wood burning stove and large windows; kitchen with beamed ceiling is updated with stainless appliances, granite counters, new cabinets; dining room and sunny solarium are part of this open floor plan. Rounding out the first floor is an office and a full bath. The primary bedroom suite is located upstairs and includes a lovely stone fireplace, cathedral beamed ceiling, multiple closets and full bath with jacuzzi tub. A second bedroom and new updated full bath with skylight finish up the second floor. Onto the lower level, this well-done finished space can be an In-Law or Guest suite, with private bedroom, hardwood floors, a brand-new full bath with tiled shower and cozy living room with fireplace equipped with wood burning stove. Your guests will love the light that comes in from sliders that lead to paved patio space where they can enjoy the pond view. A separate laundry room and garage round out this floor. The outdoor gazebo and inviting space in the backyard is tranquil and pool ready. CLICK ADDITIONAL REMARKS ARROW

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Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Margaret Curry of William Raveis Real Estate

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81 Turkey Hill Road Chester CT 06412
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Price$1,224,000

Est. Mortgage: $/month

MLS Number170480783

  • Single Family
  • Square Feet 3,687
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1996

PRIVACY and NATURE abound on this 48.6 acre property. Enjoy the RESORT like lifestyle in this spectacular cedar clapboard colonial with a salt water pool, pool house with covered patio, stone pizza oven, 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 & bedroom. 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, 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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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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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14 & 16 Waterhouse Lane Chester CT 06412
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Price$1,125,000

Est. Mortgage: $/month

MLS Number170490501

  • Single Family
  • Square Feet 4,661
  • Bedrooms 4
  • Year Built 1988
  • Bathroom 5

Welcome to the unprecedented Estate with its unmatched quality, meant to be appreciated by the most discerning buyer. A true masterpiece that reminds me of homes in Nantucket which stands out among all others. The gorgeous professional landscaped yard can easily entertain any gala. The private drive to your 4.86 acre estate is secluded & can only be viewed by you and your guest. Expertly crafted structured home will not disappoint. The 9 Ft ceilings, open 2 story areas, walls of glass-spill natural light through out. The summer fun can be found as you enter the back yard oasis which boast of stone patios, an in-ground heated pool over looking the luxurious sprawling gardens. The expansive 5000-square-foot living space exudes unrestrained beauty and superior craftsmanship. Voluminous rooms fashioned with rich woods, this impeccable estate boast a fireplaced Master Bedroom wing, three guest suites and a private office, cozy den, 3 car detached garage & Building Lot! The Ct River is around the bend offering multiple marina's, and the quint Chester Village is with-in walking distance!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Linda B O'Hara of William Raveis Real Estate

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16 Waterhouse Lane Chester CT 06412
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Price$1,000,000

Est. Mortgage: $/month

MLS Number170494322

  • Single Family
  • Square Feet 4,661
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1988

Welcome to the unprecedented Estate with its unmatched quality, meant to be appreciated by the most discerning buyer. A true masterpiece that reminds me of homes in Nantucket which stands out among all others. The gorgeous professional landscaped yard can easily entertain any gala. The private drive to your 4.86 acre estate is secluded & can only be viewed by you and your guest. Expertly crafted structured home will not disappoint. The 9 Ft ceilings, open 2 story areas, walls of glass-spill natural light through out. The summer fun can be found as you enter the back yard oasis which boast of stone patios, an in-ground heated pool over looking the luxurious sprawling gardens. The expansive 5000-square-foot living space exudes unrestrained beauty and superior craftsmanship. Voluminous rooms fashioned with rich woods, this impeccable estate boast a fireplaced Master Bedroom wing, three guest suites and a private office, cozy den, 3 car detached garage & Building Lot! The Ct River is around the bend offering multiple marina's, and the quint Chester Village is with-in walking distance!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Linda B O'Hara of William Raveis Real Estate

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28 South Wig Hill Road Chester CT 06412
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Price$779,000

Est. Mortgage: $/month

MLS Number170525004

  • Single Family
  • Square Feet 1,303
  • Bathroom 2
  • Year Built 1770
  • Bedrooms 2

Included in "Old Homes of Chester" this 1770 Cape with magnificent grounds of lawns, rolling hills, gardens and stone walls abuts 8 acres of peaceful land trust. Off the back of the home is a charming patio, a place to sit with a glass of wine and observe the beauty of this property which also includes a separate 1020 square foot "artist studio' with its own kitchen and bath. There is also a separate garage with its own driveway as well as a storage shed. The property is private and serene yet close to the center of Chester with its fine restaurants and boutiques as well as to Cedar Lake which has two public beaches. Please do not walk or park at property without an appointment

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Lucy Elias of Berkshire Hathaway NE Prop.

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Pending Continue to Show17 Wig Hill Road Chester CT 06412
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Price$689,000

Est. Mortgage: $/month

MLS Number170512031

  • Single Family
  • Square Feet 2,343
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1993

Welcome to 17 Wig Hill! Looking for privacy? This is the property for you! This Turnkey Custom Cape located on 8+ acres features post and beam, hard wood floors, open floor concepts and natural light throughout. The first floor features a beautifully remodeled eat-in Kitchen with sand stone backsplash, Granite countertops, island and pantry, Large Family room with a stone fireplace complete with wood stove, a full bath and an Office perfect for remote work options. As you ascend to the second floor, you will appreciate the open concept. This floor features two generously sized bedrooms, and the Primary bedroom all with cathedral ceilings. The remodeled main bathroom doesn't spare any attention to detail! Step outside to peace and quiet on the large deck overseeing the backyard. This property also has a two car heated garage ready for any project. Just unpack and start living! Schedule your showing today before its gone!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Century 21 AllPoints Realty

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9 Prospect Street Chester CT 06412
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Price$598,000

Est. Mortgage: $/month

MLS Number170505000

  • Single Family
  • Square Feet 3,483
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1994

VILLAGE LOCATION, LOCATION, LOCATION - 4 Bedroom Colonial with covered front porch close to the quaint village of Chester. Walk to town, Jennings Pond, the park, shops, restaurants, and the seasonal farmers market to name a few. In addition to the comfortable living interior there are also great outdoor spaces to enjoy with this home. Enjoy your morning coffee or an evening beverage on your covered front porch. The large rear deck, 12'x16' screened Gazebo, outdoor fire pit, patio, & large open yard make for some great entertainment opportunities. Home consists of garage mud room entry with benches & cubbies, 1/2 bath, warm, comfortable Family Room with wood stove next to the eat-in Kitchen with breakfast bar. The Kitchen is connected to all the action and boasts of stainless appliances, maple cabinets, granite, bay windows, and newer tile floors. There is also the formal side with Dining Room trimmed with wainscoting & chair rail which opens to the spacious Living Room. Upstairs are the bedrooms, laundry, & baths. The primary Bedroom has plenty of windows for natural light, walk-in closet with organizer system, bath with walk-in tile shower. The 3 other Bedrooms, the Family Bath, & Laundry finish out the upper floor space. This home has served the original owners well for close to 30 years. You can move right in or give it a quick refresh & enjoy all this home and location have to offer. 2 hours from New York or Boston make this a great permanent or spectacular weekend home.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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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Pending Continue to Show123 Goose Hill Road Chester CT 06412
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Price$499,000

Est. Mortgage: $/month

MLS Number170504516

  • Single Family
  • Square Feet 3,422
  • Property Style Colonial
  • Bathroom 4
  • Bedrooms 3

Beautiful 2000 built colonial style home set off the road on a pastoral 4.07 acre lot with distance views of CT River. Nice open flow on first floor with a stone fireplace in great room and hardwood floors. Open kitchen to dining room with French doors to deck. A chefs kitchen with stainless steel appliances, an island and Corian countertops. A large first floor office could be used as a den. The upper level has the 3 large bedrooms plus a bonus room that could be a 4th bedroom. A total of 2 full bathrooms, 2 half bathrooms and Central Air conditioning. The lower level is finish is fabulous! It has a 1/2 bath and is day lite with a walkout to a patio area with a hot tub. Surround by nature and beautiful country views. A garden lovers delight !!! *** Note: new hardwood floors just added - all older carpet removed! Move in ready!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Joel Lucas of Coldwell Banker Realty

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9 Brooks Lane Chester CT 06412
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Price$409,900

Est. Mortgage: $/month

MLS Number170524187

  • Single Family
  • Square Feet 1,344
  • Property Style Cape Cod
  • Year Built 1992
  • Bathroom 2

Welcome to 9 Brooks Lane in picturesque Chester, CT. This three-bedroom, two-bathroom home sits at the end of a private cul-de-sac. As you turn onto Brooks Lane, the charm of small-town New England surrounds you. This fully updated Cape Cod house sits on 2 acres of your own private yard. As you enter this home, you're greeted by stunning hardwood floors throughout the first floor and the warmth of the living room's wood burning fireplace. The updated kitchen includes quartz countertops, and the dining room steps out into the updated deck and private back yard. The first floor has one bedroom and one full bath, with the additional two large bedrooms and second full bathroom on the second level. The basement already has a workshop just ready for someone else to call their own. Major updates in 2020 include replacement of the hot water heater and all windows and doors from Renewal by Anderson. This beautiful property is just down the road from Chester Elementary School and less than 1 mile to center of town. This home won't last!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Robert Squeglia of William Raveis Real Estate

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Pending Continue to Show56 Goose Hill Road Chester CT 06412
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Price$399,900

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. Brand new septic tank, now serves a 4 bedroom house. the grading and seeding will be finished soon. Brand new Efficient heating system and new vertical oil tank, to see garage, door is not locked, carefully turn handle and lift door. do not lock when you leave.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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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134 Middlesex Avenue Chester CT 06412
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Price$395,000

Est. Mortgage: $/month

MLS Number170515544

  • Multi Family Multi-Family For Sale
  • Square Feet 1,601
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1934

Two family income opportunity in this VERY well cared for two family home a short walk to Chester and Hayes Haven marinas, bountiful restaurants, CT River Ferry, Chester Fairgrounds and of course, quaint Chester Village. Each apartment has two bedrooms, one full bath and a family room area. First floor apartment has access to an incredible deck overlooking Chester Creek and adjacent land trust property. Second floor apartment has access to the unheated front porch. There is a full walk out basement where shared washer and dryer are found. You'll find a manicured yard, storage shed and ample parking. This is a great opportunity to live in one and rent the other unit. Both units are currently rented. Just perfect!

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Nancy Mesham of Coldwell Banker Realty

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Active With Contract66 Cedar Lake Road Chester CT 06412
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Price$370,000

Est. Mortgage: $/month

MLS Number170515011

  • Single Family
  • Square Feet 1,312
  • Property Style Cape Cod
  • Year Built 1950
  • Bathroom 1

Turn key, 3 bedroom Cape. Outbuildings for storage. Water access to kayak from your back yard into Cedar Lake. New well in 2021. New roof to be installed on back of house before closing.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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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47 Winthrop Road Chester CT 06412
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Price$284,700

Est. Mortgage: $/month

MLS Number170522280

  • Single Family
  • Square Feet 1,408
  • Year Built 1986
  • Bedrooms 3
  • Property Style Cape Cod

Built in 1986, this 2 story home, offers 3 bedrooms, 2 full baths with ~1,408 sq ft of living space on +/- .65 acre lot. Seller WILL NOT ACTIVATE UTILITIES. Buyer to view home, inspect and confirm all listing information prior to making offer. Water CANNOT be turned on for inspections. Property sold “AS-IS” without contingencies.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Deb Woodard of Realhome Services & Solutions

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2 Inspiration Lane Chester CT 06412
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Price$239,000

Est. Mortgage: $/month

MLS Number170490794

  • Land
  • MLS Status Active
  • Acreage 3.45
  • Other Amenities Waterfront
  • Zoning CDD

Great Commercial lot, located directly off of the Highway. When coming up route 9 N, take exit 6 and Inspiration lane is directly across from the exit ramp. making this an exceptional location for many different types of business. This lot is located on an industrial park road with other business's, but has 893' of West Main St frontage. The lot itself does have some sloping but levels out quite nicely making this property easier to build your dream building.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Angela M Ferguson of Tier 1 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: 6.29% last updated on Sep 22, 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 ShowProspect Street Chester CT 06412
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Price$125,000

Est. Mortgage: $/month

MLS Number170505524

  • Land
  • Acreage 0.4
  • Other Amenities Waterfront
  • Zoning R-1

Elevated corner lot just steps from Chester Village Center and the historic Jennings pond. Quiet residential neighborhood accented with historic Victorian homes. This is a rare opportunity to build your perfect home in a perfect location. The property has been recently surveyed and ready for your development ideas.

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Patrick D Kilty of William Raveis Real Estate

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14 Waterhouse Lane Chester CT 06412
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Price$125,000

Est. Mortgage: $/month

MLS Number170494327

  • Land
  • MLS Status Active
  • Acreage 2.08
  • Other Amenities Golf, Waterfront
  • Zoning R-1

Hard to find Building Lot in Chester * Underground utilities * Walking distance to Chester Village * Shared Driveway * Cul-de-Sac location * 2 Acre Lot * This Lot is also listed as a package with 16 Waterhouse Lane for $1,125,000 MLS #170490501 which is a 4661 Sq.Ft. gorgeous home

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$/month over payments
Federal 30-year interest rate: 6.29% last updated on Sep 22, 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 Linda B O'Hara of William Raveis Real Estate

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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.