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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Coming Soon8 Hickory Hill Chester CT 06412
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Price$525,000

Est. Mortgage: $/month

MLS Number170572693

  • Single Family
  • Square Feet 1,740
  • Property Style Cape Cod
  • Bedrooms 3
  • Year Built 1984

THIS IS THE ONE YOU HAVE BEEN WAITING FOR! This adorable, very well maintained cape is located in a cul de sac neighborhood JUST STEPS AWAY FROM CHESTER VILLAGE, where you will find wonderful restaurants, charming shops and one of the best farmers markets on the shoreline! Three bedrooms, 2 updated full baths, beautiful hardwood throughout and a walk-out basement, are just some of what this home has to offer. Situated on a beautiful private level lot and a 2-car oversized attached garage make this a wonderful place to call home. The first floor with large living room, dining room, eat-in kitchen, family room with a wood burning fireplace and sliders to the deck overlooking the beautiful backyard. There is also a full bath on the first floor offering the possibility of one floor living. The second floor has 3 bedrooms and an updated full bath. The lower level is a walk-out with beautiful natural light and sliders to a bluestone patio. Don't miss this rare opportunity to have it all, a lovely home, a great lot and truly a short stroll to town! This home has been very well maintained by its current owner as well as the previous owner. All appliances stay and occupancy can be immediate.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Laurie Mazzeo of William Pitt Sotheby's Int'l

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24 Deep Hollow Chester CT 06412
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Price$475,000

Est. Mortgage: $/month

MLS Number170573818

  • Single Family
  • Square Feet 1,927
  • Property Style Cape Cod
  • Bathroom 2
  • Year Built 1929

Minutes from Historic Chester Village!! Come preview this Quintessential Cape with so much to offer! The home boasts a Large Living room with an impressive granite fireplace with wood stove insert for cozy New England winter nights, built in bookcases and eat in Dining area. Charming Kitchen features stainless steel appliances, and Corian counters. Newly refinished wood floors throughout. A Bright airy Sunroom/family room is complimented with an abundance of windows, slate floor, waxy pine pickwick walls and exposed stone creating a quaint space. The Home's sleeping quarters consist of 4 bedrooms. Two bedrooms located on first floor, one of which is being utilized as a spacious laundry room. Upstairs leads to two Bedrooms freshly painted and a Remodeled modern Primary ensuite with walk in closet. The scenic sprawling 1.15-acre lot is landscaped with apple trees, raspberry bushes, mature plantings and further allowing space for gardening and outdoor entertainment on back patio. An adorable "She Shed" is a bonus which can have many uses for outdoor private office, meditation or children's special playroom. Home is in close proximity to Beaches, CT River access, Ferry and local restaurants and boutiques. Generator hook up, Buderus boiler and Hardy board Siding are a plus. Come preview this Charming One of Kind Home as it won't last long!

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 T. Golebiewski of Coldwell Banker Realty

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Active With Contract7 Pine Chester CT 06412
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Price$525,000

Est. Mortgage: $/month

MLS Number170571105

  • Single Family
  • Square Feet 2,607
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3

Welcome to your Dream home situated on a quiet cul-de-sac. Your going to fall in love with your 3/4 bedroom, 2.5 bath Colonial that has been completely remodeled & freshly painted throughout! You will love the newly updated eat in kitchen with island, Quartz countertops, plenty of counter/cabinet space, stainless steel appliances, Fisher & Paykel gas range as well as tile backsplash. This open floor plan makes entertaining a dream with a spacious family room, living room with Cathedral ceilings and dining area with access to your outdoor patio. Your first floor features an additional bonus room for an office, playroom, study or bedroom. A mud room on the main level with washer/dryer/sink opens to a large two car garage. The upper level features a large primary en-suite bedroom with ample space, two Large walk in closets and full bathroom with double sinks. You have 2 additional bedrooms that share second full bath and walk in attic for additional storage space. The beauty of this home isn't limited to the inside, enjoy the great outdoors in your private 2+ acre private setting. Three zone heat/central air make for convenient temperature control. In addition your huge basement offers many options from additional living space, storage and so much more. Unpack your bags and get ready to enjoy your new home located in walking distance to popular Chester Village, Cedar Lake Beach and less than 2 miles from Route 9 with easy access to Middletown, Hartford, Rte 95 & train stations!

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Jamie Franco of Coldwell Banker Realty

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Active With Contract3 Meadow Chester CT 06412
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Price$249,900

Est. Mortgage: $/month

MLS Number170571195

  • Single Family
  • Square Feet 1,032
  • Year Built 1956
  • Bedrooms 2
  • Property Style Ranch

Welcome home to this meticulously well maintained 2 bedroom 1 bath Ranch home, located close to downtown Chester, Goodspeed Opera House, and a short walk to the Connecticut River as well as the Chester Fair grounds. The home offers a Eat in-kitchen, large living room for more entertaining, newer Split a/c systems, new metal roof, newer windows and so much more. walk out to your private backyard with garden area, one car detached garage.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Cheryl Cook of REMAX Valley Shore

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7 Johnson Chester CT 06412
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Price$599,900

Est. Mortgage: $/month

MLS Number170570457

  • Single Family
  • Square Feet 2,584
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1956

Location, location: Nestled on the hillside on a quiet cul de sac side street with only four homes. Stroll to Chester Village known for its art galleries, well-known restaurants, boutiques and quaint ambience, with nearby award-winning theaters and other cultural assets. Gem of the Connecticut River Valley, minutes from the Connecticut River, yacht clubs and marinas, as well as Chester's Cedar Lake for swimming and picnicking. The home has both cozy and large spaces: first floor, handsome library/den, gracious dining room, dramatic step-down large living room with fireplace; updated efficient kitchen with pantry, adjacent large space with private entrance for in-home business and/or live work studio/exercise room; primary bedroom with full bathroom with tub and separate walk-in shower. Light-filled, large south-facing windows, floor-to-ceiling window in living room and bay windows in dining and bedroom, all facing impressive grounds, expansive back lawn with full garden of new and mature plantings, flowers, evergreens, no-mow grasses; front-and back patios perfect for enjoying nature, relaxing or entertaining, large private back brick patio and intimate crushed stone sunken garden. Second floor, two bedrooms and a full bathroom; basement with partially finished room for more space, separate room with W/D and ample storage space. Separate parcel across the road with two-car garage. Chester is approximately 2 hours from Boston and NYC.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Susan A. Malan of William Pitt Sotheby's Int'l

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Pending Continue to Show26 Middlesex Chester CT 06412
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Price$399,900

Est. Mortgage: $/month

MLS Number170567862

  • Single Family
  • Square Feet 1,496
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1920

Walk to Chester Village from this charming Colonial. Open floor plan. Remodeled Eat-in Kitchen with Island. The living areas are open and bright. Winter water views from the large deck. Upstairs is the 11x21 Master bedroom, 2 additional bedrooms and a full bath. Split systems are being added for central air. New septic system in 2012. Full walkout basement. Solar Panels keep electric bills very affordable.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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

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Active With Contract8 School Chester CT 06412
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Price$449,000

Est. Mortgage: $/month

MLS Number170568899

  • Single Family
  • Square Feet 1,512
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1986

Walk to downtown Chester!!! You will be hard pressed to find a better location to enjoy all Chester has to offer. This 3 bedroom, 2 bath Cape is located on a small dead-end street walking distance to downtown Chester. The large back yard with deck abuts the town of Chester's North Quarter Park where there are hiking trails, a basketball court, a playground for the kids and just added...disc golf. The home has many new updates including a new roof, outside paint, hardwood floors, new appliances and hot water heater. This home has a highly sought after first floor bedroom and full bath. The open eat-in kitchen has a large pantry. There is also convenient first floor laundry. The second floor has two large bedrooms and a full bath. Enjoy the large back deck, one car garage and separate storage shed on the property. This home is a must see and in the perfect location.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Ian M. Sacks of Coldwell Banker Realty

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Pending Continue to Show75 Cedar Lake Chester CT 06412
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Price$1,199,900

Est. Mortgage: $/month

MLS Number170560400

  • Single Family
  • Square Feet 3,690
  • Bedrooms 4
  • Bathroom 4
  • Year Built 2016

Remarkable Horse Property Resort in the Cedar Lake Area of Chester. 'One of Kind' is not an exaggeration. Check out those Pics & our Virtual Reality Tour. Set on over 7 Acres and ideally utilizing every inch. Six Stall Horse Barn w/ Feed & Tack Room, 7 Run Dog Kennel, Multiple Grass Paddocks, 2 Dirt Paddocks, Outdoor Arena, Run-In Shed, Heated In-Ground Pool & a Spectacular 3600 Sq/Ft Home w/ a Full In-Law set up. Re-engineered in 2016 this Fabulous Contemporary Colonial leaves no stone unturned! Beautiful First Floor Master Suite w/ Vaulted Ceilings, Fireplace & Custom Shower, Gleaming Wide Board Hardwoods, Radiant Floor Heat, Whole House & Barn Generator, Three Car Garage, 1st Floor Laundry, Custom Moldings, Coffer Ceilings, Luxurious Double Box Kitchen w/ Granite, Sub Zero Refrigerator & Wolf 6 Burner Gas Cooktop & Wall Ovens, Additional Second Floor FR, In Law Suite w/ Kitchenette & Separate Entrance, Tremendous Exterior Upper & Lower Decking w/ Retractable Awnings that take full advantage of the Unique Equestrian Views over the Beautiful Rear Yard & Heated In-Ground Pool. Convenient Waterfront Community w/ Easy access to the Cockaponset State Park Trails. It is a great time to purchase a Horse Resort! We are always here to help!

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Bill Heenan of William Raveis Real Estate

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65 Bokum Chester CT 06412
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Price$1,050,000

Est. Mortgage: $/month

MLS Number170556884

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

Make your dreams come true on this gorgeous 24 acre Ivory Pond Estate! Privately situated off a country road, yet only minutes to the quaint Connecticut River Valley Village of Chester with it's numerous shops & restaurants. This wonderful 4 BR, 4 bath home is hidden away on a private drive beyond the Ivory Pond. The home was built to take full advantage of beautiful Pond views and has had many renovations by the current owners! The main level of the home has a spacious living room with fireplace, hardwood floors & glass doors to the expansive deck. A formal dining area is adjacent to a lovely Sunroom Solarium, and the renovated kitchen with Island & stainless appliances. 1st floor BR is currently used as an office. The second level has a massive Primary Bedroom with fireplace & full bath. There is also a 2nd BR & full bath. Lower level has a large Family Room with fp & 4th bedroom, bath & laundry plus garage. In addition to the home there is an unbelievable Carriage House garage with a private main level office, a very spacious second floor studio with bath and an area for your gym. This building has also been recently renovated. The heated garage is extra deep (29') and 3 -11" oversized garage doors to accommodate RV's, boats, trucks and other vehicles This property must be seen to be appreciated. You will love it! Though extremely private this property is ideally located near major highways & centrally located between Boston & New York. Live the good life in Chester!

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Philip Warner of William Pitt Sotheby's Int'l

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43 Straits Road Chester CT 06412
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Price$375,000

Est. Mortgage: $/month

MLS Number170560694

  • Single Family
  • Square Feet 1,536
  • Year Built 1860
  • Property Style Antique, Farm House
  • Bedrooms 3

In the lovely town of Chester, this house was built in 1860 along with many other antique homes throughout the once shipbuilding city. This home has 3 bedrooms,1 baths, a large kitchen, LR, DR and 2 porches. There is a separate building with a bedroom, kitchen, LR and bath that has been used as a rental. The property is fairly private on 2.35 acres overlooking a pretty pond. It does need some TLC and is being "SOLD AS IS". There is a right of way to a driveway going to two newer homes up the hill. Most of the architecturally built houses in Chester are located on the banks of the Ct River so there are many marinas and lakes, the most famous being Deer Lake. The picturesque downtown has many great shops, restaurants and art museums. There is also the Chester Airport, the famous Goodspeed Opera House, the Essex Steam Train near by, and a large State Forest with many hiking trails. New York City and Boston are only two hours away.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Turton of William Pitt Sotheby's Int'l

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Pending Continue to Show16 Ridge Chester CT 06412
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Price$550,000

Est. Mortgage: $/month

MLS Number170559880

  • Single Family
  • Square Feet 2,722
  • Bathroom 3
  • Year Built 1928
  • Bedrooms 4

This stunning Colonial has been stylishly remodeled with many updates. You'll love the open floor plan & flow as you walk through. The remodeled kitchen has tons of cabinetry, Quartz counter tops, SS appliances & a breakfast nook. It opens to the Great Rm with cathedral ceilings, sky lights & wall to wall windows letting in the natural sunlight. The formal dining rm/living rm with built ins & French doors gives a grand feeling blending both modernized & time period charm. There's an office for those working from home. Head upstairs to the 4 bdrms. 2 1/2 baths total thru out. The walk-up attic is perfect for storage or convert into add'l living space. The basement features new mechanicals & laundry. For the wine enthusiast, you'll appreciate the large wine cellar! There's more! The 4 car garage/party room is an entertainers dream for outdoor parties! The wrap around porch is perfect for relaxing with your morning coffee while listening to the sounds of the river. Enjoy the oversized trex deck for afternoon cocktails. Projects completed in the last 2 years include new furnace, C-Air, on demand hot water, interior paint, refinished hard wood floors, new architectural roof w/plywood, windows, gutters, siding, trex deck, vinyl fence, new chimney (roof line up), electrical, 500 gallon propane tank, & a new septic system. All within walking distance of Chester Village where you will find amazing restaurants overlooking the CT River & shops. What isn't there to love?

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 J. Conchado of KW Legacy Partners

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Active With Contract21 Baker Chester CT 06412
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Price$525,000

Est. Mortgage: $/month

MLS Number170557433

  • Single Family
  • Square Feet 3,178
  • Property Style Colonial
  • Bedrooms 3
  • Year Built 1991

Wonderful and unique design that creates a home to be proud of in secluded setting but close to all things wonderful in Chester and commuting routes. The living room is large and sports hardwood flors, a cathedral ceiling and two French doors that flank the floor to ceiling fireplace providing access to the verdant outdoors and the 1,000 sf deck. The efficient u-shaped Kitchen has easy to care for tile floors and is replete with quartz countertops and stainless steel appliances. It further offers an often forgotten pantry and adjoins the light and bright dining room with hardwood floors. A sought after main level primary bedroom suite gives you the convenience and privacy of an en suite full bathroom with double sinks, and an ample walk-in closet. Aloft one will be be delighted with a sun lit loft that overlooks the living room which can be purposed to many uses. The two amble guest bedrooms are served by a large full bathroom that offers a private tub shower unit and sink in a private lavatory leaving the vanity sink and mirror right outside to be used by others. Other features include central air conditioning to keep you cool and dry, central vacuum for fast and convenient cleaning, screened porch to keep you from being mosquito food, and a generator hook up for those times the power is out and you want to still run your home and not lose your valuable food. Lastly...for the gentleman farmer there is a 30 chicken coop and run for fresh eggs.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Michael Marsden of Page Taft - Compass

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2 Inspiration Chester CT 06412
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Price$199,000

Est. Mortgage: $/month

MLS Number170529007

  • Land
  • Acreage 3
  • MLS Status Active
  • Other Amenities Waterfront
  • Zoning CDD

Opportunity to build office/warehouse/storage in Chester's Research Park. Large parcel - great signage opportunities. Just off Exit 6 of Route 9. Frontage on Inspiration Lane and West Main Street. See attachments for zoning regs, deed, perc test info.

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Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Susan A. Malan of William Pitt Sotheby's Int'l

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11 Kings Chester CT 06412
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Price$199,000

Est. Mortgage: $/month

MLS Number170533629

  • Land
  • Acreage 2
  • MLS Status Active
  • Zoning R-1

Extraordinary views down and across the Connecticut River Valley from this 1.5+ acre building lot located in Chester less than a mile from the village. Current owner has completed much of the hard work to make this one-of-a-kind site build ready: Septic tested and approved for 3-bedroom house, public water hookup at the street, clear cut, and a well-engineered driveway to reach the house site at the top. From there, four-mile, all-season views to Lyme and Deep River, and a limited view of Gillette Castle create an ever-changing, real-life tableau. The lot is high, dry, ideal for active and passive solar, think GREEN efficient home. The driveway may be challenging for some, but for those who choose to follow it to the house site at the top, well worth effort for these stunning views. Build your nest home in Chester and enjoy all the village has to offer with views to impress!Drone footage available https://youtu.be/Ks6ut-XOkng

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Jun 1, 2023
* 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 Rachel Welch 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 2023 SmartMLS, Inc.