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 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: 5.81% last updated on Jun 23, 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
  • Year Built 1988
  • Bedrooms 4
  • 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: 5.81% last updated on Jun 23, 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
  • Year Built 1988
  • Bedrooms 4
  • 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!

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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33 Liberty Street Chester CT 06412
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Price$799,000

Est. Mortgage: $/month

MLS Number170492565

  • Single Family
  • Square Feet 21,433
  • Property Style Other
  • Year Built 1848
  • Bathroom 1

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 just outside of the quaint and historic Chester village. M.S. Brooks & Sons built this property in the 1800's and utilized it until the 1980's. Descendants of the Brooks have been slowly restoring the property, much more need to be done. Perfect for a retreat/compound. Many possibilities await you with this unique property.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Patterson of KW Legacy Partners

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Under Agreement15 South Wig Hill Road Chester CT 06412
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Price$549,000

Est. Mortgage: $/month

MLS Number170482143

  • Single Family
  • Square Feet 2,429
  • Bathroom 3
  • Property Style Colonial, Antique
  • Year Built 1820

This amazing South Wig Hill Landmark can be yours! Located in the lovely Countryside of the Historic Connecticut River town of Chester. Ely Dickinson built his Homestead here in 1820. Classic chestnut frame and exposed beams on the main level. The current owners have made many upgrades & improvements. The main level consists of a beautiful Living Room with bay window, fireplace and built-ins. The charming Dining Room has built-in display shelves & is the perfect place to entertain your friends and family. The cork floored kitchen has a wonderful breakfast bar and opens to the light and bright Sunroom complete with a gas stove fireplace. From the Sunroom you enter onto a very spacious deck overlooking nature and your expansive yard. The Primary Bedroom Suite is on the second floor and consists of an office, dressing room, walk-in closet and bath. The second Bedroom has an original fireplace and wideboard floors. Two additional Bedrooms, a full bath & pretty landing complete this level. There is also a walkup attic for storage. The property has two driveways, one leads to a barn/garage and the other is on the opposite side of the house where you can access the front porch or the Sunroom. This Historic Homestead is only minutes from town, the Connecticut River, Cedar Lake and Main Street. You will enjoy all the quaint Village Shops and Restaurants that are located here. Midway between Boston and New York, come to Chester and make this your home. You will love it!

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Kathleen W Schellens of William Pitt Sotheby's Int'l

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Under Agreement7 Pattaconk Drive Chester CT 06412
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Price$545,000

Est. Mortgage: $/month

MLS Number170483632

  • Single Family
  • Square Feet 4,250
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1998

This is a like new, well maintained 3 plus bedroom home on 2.24 acres with bright and sunny open views! The gourmet kitchen boasts high end appliances with wall oven, warming draw, a microwave, granite island with grill and retractable exhaust system. The living room has bright, wall to wall windows looking out onto a wooded area. Upstairs there is a large separate laundry room with large primary bedroom. The primary bath is brand new with a lovely jacuzzi tub, separate shower, towel warming rack and two separate sinks for busy mornings. There is an additional room which can be a wonderful option for an office. A full attic with walk up stairs allows for plenty of storage. Yes you can hear birds singing, it is that quiet! See you there...

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Lynn Rist of Coldwell Banker Realty

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7 Pine Knoll Drive Chester CT 06412
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Price$529,000

Est. Mortgage: $/month

MLS Number170493803

  • Single Family
  • Square Feet 2,607
  • Year Built 2002
  • Bedrooms 3
  • Property Style Colonial

Walking distance to Cedar Lake and 5 min to Chester Village sited privately on a short cul-de-sac. This 3 bedroom, 2.5 bath Colonial features a bright open floor plan with hardwood floors, has a kitchen with new tile backsplash, new quartz countertops, stainless steel appliances and a Fisher & Paykel gas range. The kitchen nook opens to the rear patio and adjacent family room with built-ins. The living room with a cathedral ceiling, ceiling fan and fireplace flows into the formal dining room with French doors opening to the back patio. An additional room on the first floor is great for a den or office. A mud room with washer and dryer opens to a large two car garage. Upstairs, the Primary en-suite bedroom has ample space, a full bathroom with soaking tub, tiled shower and two walk-in closets. Two additional bedrooms share the second full bath. 3 zone heat/central air make efficient temperature control. Easy access to Route 9, I-95, and train stations. Professionally landscaped and well maintained, This is a must see. Shown by appointment only. Masks mandatory.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Carol O'hare and Irene Keene of Coldwell Banker Realty

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Pending Continue to Show107 West Main Street Chester CT 06412
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Price$525,000

Est. Mortgage: $/month

MLS Number170439447

  • Single Family
  • Square Feet 3,617
  • Property Style Colonial
  • Bathroom 3
  • Bedrooms 4

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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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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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Pending Continue to Show8 Turkey Hill Road Chester CT 06412
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Price$499,000

Est. Mortgage: $/month

MLS Number170494237

  • Single Family
  • Square Feet 2,070
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1985

Make this contemporary Cape in historic Chester your own with plenty of space including three bedrooms, two baths, and a three-car garage. Watch movies, set up a game room, or just relax with friends in the large bonus/rec-room above the garage. Enjoy open spaces both indoors and out with two partially-wooded acres, two large decks, and a pergola-covered patio to barbecue, entertain, or take in the abundant wildlife visiting the property. Meet great neighbors in this friendly and quiet neighborhood, enjoy art galleries, shopping and restaurants in the village center, ride the Chester/Hadlyme ferry across the scenic Connecticut River, visit the historic Gillette Castle, bike through the Cockaponsett State Forest, or swim at nearby Cedar Lake.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Jason Saphire of www.HomeZu.com

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56 Goose Hill Road Chester CT 06412
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Price$465,000

Est. Mortgage: $/month

MLS Number170428494

  • Single Family
  • Square Feet 1,964
  • Bathroom 3
  • Bedrooms 4
  • 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: 5.81% last updated on Jun 23, 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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Under Agreement6 Prospect Street Chester CT 06412
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Price$339,900

Est. Mortgage: $/month

MLS Number170475537

  • Single Family
  • Square Feet 1,320
  • Bedrooms 3
  • Bathroom 1
  • Year Built 1910

Highest and best offers by Wednesday 5/11 at 12 noon. Walk to Chester Village from this charming Victorian style home. Private setting. Open, wrap around front porch. This home is in good condition, but could use some updating. It retains the charm of its era with original trim, doors and hardware.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Craig Milton of REMAX Valley Shore

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96 Goose Hill Road Chester CT 06412
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Price$319,000

Est. Mortgage: $/month

MLS Number170498818

  • Single Family
  • Square Feet 676
  • Bedrooms 1
  • Property Style Bungalow
  • Bathroom 1

Tiny home living at its finest! Enjoy 4 private acres conveniently located in Chester CT with views of Gillette Castle in the distance. Wood paneling throughout gives the feel of log-cabin living and the open concept design makes “tiny living” feel spacious. There's no compromise in downsizing when you have a full eat-in kitchen, living room, private bedroom, and full bath with laundry! The large loft gives an option for a second bedroom or additional space. The possibilities are endless! Enjoy your morning coffee on the covered porch and warm weather dinners on the stone patio with views of your secluded property surrounding you. This home is in an R-2 zone which gives you the option to split and sell the acres in the future. Enjoy the beautiful town of Chester and its fabulous dining and shopping just minutes away! Don't miss out on a chance to own a tiny slice of heaven in the much-desired Chester, CT!

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Andrew O'Reilly of Seaport Real Estate Services

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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: 5.81% last updated on Jun 23, 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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234 Middlesex Avenue Chester CT 06412
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Price$219,900

Est. Mortgage: $/month

MLS Number170474407

  • Single Family
  • Square Feet 1,632
  • Bedrooms 1
  • Bathroom 2
  • Year Built 1820

Single Family or Multi Family fix up opportunity just outside of Chester Center. Opened up and ready for your finishing. Currently a weather tight shell w/ 15 year old roof, newer thermal windows. There is an exsisting 3-4 BDR septci system in place. Newer outbuilding. Level lot. Used to have an addition of the back of the house, but can be replaced.

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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 Craig Milton of REMAX Valley Shore

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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: 5.81% last updated on Jun 23, 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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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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$
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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 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.