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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81 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
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1996

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: 3.05% last updated on Oct 14, 2021
* 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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36 East Liberty Street Chester CT 06412
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Price$795,000

Est. Mortgage: $/month

MLS Number170436131

  • Single Family
  • Square Feet 3,455
  • Bedrooms 4
  • Year Built 1986
  • Bathroom 4

Stylish Contemporary Cape exceptionally renovated with high quality appointments set privately on a hill on East Liberty Street in Chester. This beautiful home is set up for any scenario with its main level bedroom, full bath, den/office, living room/dining room, fireplace and eat-in kitchen plus three additional bedrooms and two full baths on the upper level. Large windows and skylights allow light to flow throughout the home. The lower level will also impress with its media/game room and wet bar perfect for entertaining. The wrap around deck with access from the kitchen or living room provides wonderful outdoor space with seasonal views of Gilette's Castle and the entire creek. The full house generator will keep everything running in the event of a power loss. And the quaint village of Chester with shops and great restaurants is just four tenths of a mile away. Quick access to Route 9 will easily get you to Hartford, Boston, New Haven or New York.

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Mariette Woolfson of William Pitt Sotheby's Int'l

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107 West Main Street Chester CT 06412
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Price$564,900

Est. Mortgage: $/month

MLS Number170439447

  • Single Family
  • Square Feet 3,617
  • Property Style Colonial
  • Bedrooms 4
  • 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: 3.05% last updated on Oct 14, 2021
* 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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56 Goose Hill Road Chester CT 06412
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Price$499,000

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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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Show3 Story Hill Road Chester CT 06412
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Price$419,000

Est. Mortgage: $/month

MLS Number170441266

  • Single Family
  • Square Feet 1,344
  • Property Style Cape Cod
  • Bathroom 2
  • Bedrooms 2

Charming, updated cape in historic Chester. Enjoy beautiful sunsets from the covered front porch of this home just across from the Chester town green and walking distance to the village. This home has a gorgeous, remodeled kitchen with Granite countertops, white cabinetry and an inviting center island. There are beautiful wide plank pine floors throughout the house and newly added to the second floor. An open floor plan on the main level includes a living room with gas fireplace, a cozy dining room, eat-in kitchen and full remodeled bath. There are 2 nicely sized bedrooms on the second floor that share a full bath. City water, Newer windows, and newly installed Central vac system. A heated and insulated lower level has lots of possibilities for play, office or storage. Come enjoy all that Chester has to offer.

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Kate Jasko of Coldwell Banker Realty

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Pending Continue to Show84 Spring Street Chester CT 06412
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Price$370,000

Est. Mortgage: $/month

MLS Number170423680

  • Multi Family Multi-Family For Sale
  • Square Feet 3,228
  • Bathroom 3
  • Bedrooms 4
  • Year Built 1800

WONDERFUL OPPORTUNITY Awaits!! Two family home offers so much potential .... live in one, rent the other (your tenants help pay for your mortgage); or smaller one-floor unit perfect for extended family members! Larger main house offers 3 bedrooms, 1-1/2 baths, laundry, generous sized kitchen/dining areas, living room plus on the lower level is a large walk-out family room, separate office and half bath. Both floors have split systems for a/c; heating is oil. Second unit offers approx 850 sq ft of lovely renovated space heated by propane and a flexible floor plan; laundry. This charming home has been lovingly updated and maintained by current owners over the past years -- newer windows, siding, roofs, electric, plumbing, on demand hot water. Nothing left to do - just move in or rent out. Beautiful gardens, private lawn areas, outdoor firepit with sounds of the brook across the street. Lots of storage with walk-out basement area plus several storage rooms. WALK TO TOWN - just 8/10 mile to lovely downtown Chester, this charming, quaint town offers some of the best-in-Connecticut restaurants and shops, (even a brew house), and close proximity to theaters, state parks, beaches, major roads and highways!

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Lisa Genovali of REMAX Valley Shore Genovali RE

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105 Middlesex Avenue Chester CT 06412
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Price$354,900

Est. Mortgage: $/month

MLS Number170426760

  • Single Family
  • Square Feet 1,344
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1982

Welcome Home!! Charming Cape Cod located on 1 acre fronting on Chester Cove!! Move right in ..... new kitchen cabinets and quartz counters, new bathrooms, lighting, new flooring including new carpet and new vinyl tiles. Entire house has been repainted, new doors installed too! Gleaming hardwood floors have been redone! A new boiler heating system installed! Bright and cheerful living room with fireplace opens to generous sized dining area, both with beautiful hardwood floors, and slider to large deck perfect for entertaining. The adorable kitchen was just remodeled with new crisp white cabinetry, quartz counter tops, new deep, wide stainless steel sink/faucet and new vinyl floor tiles! There is a first floor separate room perfect for that 3rd bedroom or office space with new carpeting along with a first floor full bath with all new fixtures and tile! The second floor offers two additional bedrooms with new carpeting - the larger of the two (master) has a balcony overlooking rear yard and seasonal views of Chester Cove Waterway. The full bath on this floor has also been updated with new fixtures and tile flooring! With clearing of brush and trees and additional landscaping on the sloped area farthest in the rear, you could take advantage of this perfect waterway location!!

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Lisa Genovali of REMAX Valley Shore Genovali RE

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Pending Continue to Show74 Cedar Lake Road Chester CT 06412
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Price$348,000

Est. Mortgage: $/month

MLS Number170442111

  • Single Family
  • Square Feet 1,966
  • Bathroom 2
  • Bedrooms 3
  • Property Style Ranch

74 Cedar Lake Road, Chester, CT - Highly desirable location only a stone throw to Cedar Lake. This charming house offers convenience of one level living on a private lot, complete with mature planting. Cozy natural sunlight and floor plan with space for entertaining and a growing family. This well maintained 3/4 bedroom, 2 bath has gorgeous hardwood floors throughout. The dry lower level can easily be finished space with high ceilings. The spacious oversized garage is a contractor dream which could easily fit 3 cars. The Sliders off the living room and dining room allows to spend house on the oversized wraparound deck. New Furnace with Central A/C. All of this, and a 2 hour commute to New York or Boston. Easy access to Rt 9, Rt 80 and Rt 95. This shoreline property is close to all the state and local beaches, marina's, golf courses to stores. Easy access to the Amtrack and Metro North commuting trains. The property boarders Cockaponset State Forest where hiking trails are in abundance. Cedar Lake is ideal for swimming and using the boat launch for paddle boards and kayaks. Time to stop looking for a home after visiting this one!

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Jennifer Gurnell of William Raveis Real Estate

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270 Middlesex Avenue Chester CT 06412
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Price$329,900

Est. Mortgage: $/month

MLS Number170422012

  • Single Family
  • Square Feet 2,016
  • Bathroom 2
  • Property Style Colonial
  • Bedrooms 3

Well maintained Saltbox Colonial located just outside of town. A stone gazebo and mature gardens greet you as you arrive. The first floor offers a nice entry with slate floor, spacious Eat-in Kitchen with Granite Counters, Living Room, Family Room, 3/4 bath, and Dining Room that could become a first floor bedroom if desired. The second floor has 3 bedrooms, including the Master Bedroom with access to the full bath which is common to the hall. Newer roof, siding, and windows. Fenced yard. Full basement can be easily finished and has a walk out to the deck overlooking the private backyard.

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Craig Milton of REMAX Valley Shore Genovali RE

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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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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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18 Hoop Pole Hill Road Chester CT 06412
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Price$299,900

Est. Mortgage: $/month

MLS Number170336329

  • Land
  • MLS Status Active
  • Acreage 11.65
  • Other Amenities Waterfront
  • Zoning R-2

18/1 Hoop Pole Hill Rd., Chester, CT! Developers & Builders take note: 11.65 acres, 950+/- frontage nestled on a peaceful country road. Possible 2/3 picturesque lots. Build your dream home and enjoy amazing views, rolling hills, pastures and forests of Hoop Pole Hill. In an area of fine homes of Chester Forest Estates! Enjoy the rich history of Chester and surrounding towns like Deep River, Essex, Haddam and E. Haddam. Amazing views and Summertime enjoyment at Pattakonk Recreational Area and Cedar Lake. Town lake rights to Cedar Lake for residents for swimming, two beaches, life guards on duty, free parking & swimming lesson. Goodspeed Opera House, Gillette Castle, Chester-Hadlyme Ferry, Essex Steam Train, and countless restaurants and shops, are just some of the many reasons you'll want to build your dream home in the quaint rural town of Chester. Close to RT 9 and just a short drive to the shoreline!

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Erik Sousa of William Raveis Real Estate

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52 Main Street Chester CT 06412
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Price$299,900

Est. Mortgage: $/month

MLS Number170440201

  • Single Family
  • Square Feet 918
  • Bedrooms 2
  • Bathroom 2
  • Year Built 1850

Beautiful Downtown Chester Home Available! Charming Antique Cape Cod home in the heart of downtown Chester. Minutes from shops, restaurants, breweries, pizza, etc. Home is zoned for residential and commercial! You can live and have your own business in the same spot. 2 Bedroom, 2 Full bathroom, central air, balcony. Public water and sewer with off street parking. Bus to everywhere. Very unique opportunity to own home filled with artist touch of grace and character and be so close to all downtown Chester has to offer. Don't miss out on this one. It will go fast!!!!

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Anthony Cusano of Berkshire Hathaway NE Prop.

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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

Approved 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: 3.05% last updated on Oct 14, 2021
* 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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278 West Main Street Chester CT 06412
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Price$199,000

Est. Mortgage: $/month

MLS Number170438812

  • Land
  • MLS Status Active
  • 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: 3.05% last updated on Oct 14, 2021
* 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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109 Middlesex Avenue Chester CT 06412
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Price$154,900

Est. Mortgage: $/month

MLS Number170395886

  • Land
  • MLS Status Active
  • Acreage 1.25
  • Other Amenities Waterfront
  • Zoning R-5

Level flat lot available to build potential house. Lot has been surveyed. Excellent location close to town, shopping & highways.

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Liana Grabowski of Huntsman,Meade & Partners Comp

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Bokum Road Chester CT 06412
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Price$110,000

Est. Mortgage: $/month

MLS Number170435801

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

Lightly wooded and gently sloping, fully-approved 2.74 acre Building Lot within walking distance to Chester Village. 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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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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Old County Road Chester CT 06412
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Price$107,500

Est. Mortgage: $/month

MLS Number170430126

  • Land
  • MLS Status Active
  • Acreage 10.11
  • Other Amenities Waterfront
  • Zoning R-2

10.11 Acres on a scenic road Property deed restrictions. Allowed uses conservation and agricultural with accessory buildings, Nonresidential.

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Ron Lyman of Lyman Real Estate

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Pending Continue to Show27 Ridge Road Chester CT 06412
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Price$99,900

Est. Mortgage: $/month

MLS Number170435373

  • Land
  • Acreage 0.49
  • Other Amenities Waterfront
  • Zoning R-1

House destroyed in a fire and will be demolished and yard cleaned up prior to closing. HOUSE IS CONDEMNED... DO NOT ENTER. Level building lot next to the Chester Elementary School and within walking distance to the quintessential New England village of Chester Connecticut. Here's your chance to build your dream home. Subject to probate court approval.

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Travaglino of William Pitt Sotheby's Int'l

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Wig Hill Road Chester CT 06412
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Price$97,000

Est. Mortgage: $/month

MLS Number170424413

  • Land
  • MLS Status Active
  • Acreage 1.89
  • Other Amenities Waterfront
  • Zoning R-2

Beautiful and affordable, lightly wooded, level 1.89 acre lot with old stone walls. Raw land - bring your plans and build your dream home in the lovely town of Chester! Buildable existing non conforming lot (1.89 in a 2 acre zone) for a single or two family home, subject to all approvals, of course. Beautiful quiet lot adjacent to Route 9- look for sign and metal gate. Chester is ideally situated midway between NYC and Boston, making Chester a popular destination for weekend getaways. Stroll the enchanting Village of Chester known for its charming shops, outstanding restaurants and the Norma Terris Theatre. Take a ferry across the Connecticut River to Gillette Castle or drive to the quintessential New England town of Essex, or Mystic Seaport and downtown Mystic. Plenty of places to explore and things to do, so bring your plans and bring your dreams and find yourself HOME SWEET HOME!

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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 Patricia A Cardozo of Coldwell Banker Realty

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