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Chester, CT Homes for Sale

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  • 80 W Main St, Chester, CT 06412

    $795,000 Sold Jul 31, 2025

    • 2,389 Sq Ft
    • $333/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1835

    80 W Main St, Chester, CT 06412

    Nestled in the storybook town of Chester, Connecticut-renowned for its vibrant arts scene, scenic countryside, and charming village center-this one-of-a-kind historic home lovingly maintained by its current steward,offers a truly inspiring lifestyle. Set on lush, idyllic grounds framed by mature trees, gardens,&stone walls, the property exudes timeless New England beauty.A collection of

    Mary Jean Agostini RE/MAX Right Choice

    80 W Main St, Chester, CT 06412
  • 79 Cedar Lake Rd, Chester, CT 06412

    $875,000 Sold Jul 25, 2025

    • 3,206 Sq Ft
    • $273/SF
    • 83 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2004

    79 Cedar Lake Rd, Chester, CT 06412

    A perfect opportunity for a 'Gentleman's Farm' in this wonderful 3200 Sq/Ft Farmhouse Colonial on 11.8 Acres of Great Equestrian Lands w/ Beautiful Plantings, Custom Gardens & Direct Access to the Riding Trails of the Cockaponset State Forest & a short walk to Cedar Lake. You cannot beat this location! Check out our Virtual Reality Tour & those Pics! The Open & Contemporary Floor Plan has

    Bill Heenan William Raveis Real Estate

    79 Cedar Lake Rd, Chester, CT 06412
  • 42 W Main St, Chester, CT 06412

    $651,500 Sold May 16, 2025

    • 1,766 Sq Ft
    • $369/SF
    • 35 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1925

    42 W Main St, Chester, CT 06412

    This newly renovated century-old bungalow home offers a harmonious blend of historic charm and modern amenities. The expansive front porch provides an ideal setting for enjoying morning coffee or evening beverages while appreciating the outdoors. The entirely new kitchen features quartz countertops and a marble backsplash, with ample natural light illuminating the space. An adjacent pantry

    Pardi & Zucco Team William Pitt Sotheby's Int'l

    42 W Main St, Chester, CT 06412
  • 35 -16 Castle View Dr, Chester, CT 06412

    $1,325,000 Sold Sep 06, 2024

    • 2,006 Sq Ft
    • $661/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1996

    35 -16 Castle View Dr, Chester, CT 06412

    WATERFRONT-NEW PRICE-Directly situated on the CT River, this 1.04 acre, 3 bedroom home with private dock and private viewing/seating area offers tranquility and stunning views. Updated/remodeled in 2017, this home offers an open floor plan with exquisite architectural details. Craftsmanship abounds showcasing custom millwork, wide plank wood flooring, wood beams and crown molding throughout.

    Sandra Manafort Silver and Oak Realty

    35 -16 Castle View Dr, Chester, CT 06412
  • 28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    28 S Wig Hill Rd, Chester, CT 06412
    /40

    $645,000

    • 2 Beds
    • 3 Baths
    • 3,091 Sq Ft

    28 S Wig Hill Rd, Chester, CT 06412

    Step into history with this 1770 Cape, part of "Old Homes of Chester." Nestled on beautiful grounds featuring rolling hills, gardens, and stunning stone walls, the property abuts 8 acres of serene land trust, offering unparalleled privacy and a park-like setting. The main house spans 1303 square feet and includes 2 bedrooms and 2 full baths. Recent upgrades include a new furnace (2023), electric

    Andrew O'Reilly Seaport Real Estate Services

    28 S Wig Hill Rd, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412
    25 Spring St, Chester, CT 06412
    25 Spring St, Chester, CT 06412
    /37

    $895,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    25 Spring St, Chester, CT 06412

    Tucked away on Spring Street in the heart of Chester village, this stately two-story residence gracefully combines classic farmhouse tradition with all the amenities of modern living. As you enter the home through the foyer, sunlight pours through generous windows, illuminating the living room anchored by an elegant fireplace. Recessed lighting and gleaming wide-plank wood floors lend an

    Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412
    28 Hoop Pole Hill Rd, Chester, CT 06412
    28 Hoop Pole Hill Rd, Chester, CT 06412
    /39

    $774,000

    • 4 Beds
    • 3.5 Baths
    • 3,396 Sq Ft

    28 Hoop Pole Hill Rd, Chester, CT 06412

    Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm,

    Teri Strain-Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, Chester, CT 06412
  • 95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    95 Cedar Swamp Rd, Chester, CT 06412
    /40

    $1,017,000

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Cedar Swamp Rd, Chester, CT 06412

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester. Bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning views over Shailer Pond, this home brings the outdoors in from every angle.

    Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
  • 43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    43 N Main St, Chester, CT 06412
    /40

    $749,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 1,538 Sq Ft

    43 N Main St, Chester, CT 06412

    Fantastic home in wonderful private setting with views of Chester Creek and sounds of the waterfall across the street. Calling all artists, authors, creatives. This is the perfect space to create, dream, let your imagination bloom. Beautiful farm porch, detached two car garage, the "glass house" at the edge of Chester Creek to relax and watch nature. 3 bedrooms, 1 1/2 baths, beautiful propane

    Susan Malan William Pitt Sotheby's Int'l

    43 N Main St, Chester, CT 06412
  • 137 Main St, Chester, CT 06412

    $610,000 Sold Aug 01, 2025

    • 1,570 Sq Ft
    • $389/SF
    • 15 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1915

    137 Main St, Chester, CT 06412

    VILLAGE OF CHESTER- Embrace the perfect blend of modern comfort and serene living in this beautifully upgraded home, nestled just moments from Chester's enchanting village center. With a newer roof and fresh paint both inside and out, this property offers a seamless move-in experience for the discerning buyer. The home's unique position, secluded without immediate neighbors and bordered by a park

    Teri Strain-Lewis William Pitt Sotheby's Int'l

    137 Main St, Chester, CT 06412
  • 67 Maple St, Chester, CT 06412

    $575,000 Sold May 29, 2025

    • 1,803 Sq Ft
    • $319/SF
    • 44 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    67 Maple St, Chester, CT 06412

    Welcome to this delightful meticulous Cape Cod home, featuring 3 spacious bedrooms, 2.5 baths and a home office. The primary bedroom suite is generous in size with his and her closets, a jacuzzi tub in the primary bathroom and is conveniently located on the first floor. The main level also includes a dedicated home office that has access to the beautiful, huge trex deck. The kitchen has been

    Laura Cariati Coldwell Banker Realty

    67 Maple St, Chester, CT 06412
  • 108 Middlesex Ave, Chester, CT 06412

    $675,000 Sold May 01, 2025

    • 4,056 Sq Ft
    • $166/SF
    • 65 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2002

    108 Middlesex Ave, Chester, CT 06412

    Welcome to 108 Middlesex Ave. A multi family Colonial income producing property in the heart of Chester! The home was built in 2002, and in 2006 an attached accessory dwelling unit / inlaw apartment was added and is now occupied at $2,000 a month. The main house features a bright and inviting layout with hardwood floors, a cozy fireplace in the living room and sliders from the dining room out to

    Trever Smith Chiarito Real Estate LLC

    108 Middlesex Ave, Chester, CT 06412
  • 67 W Main St, Chester, CT 06412

    $637,500 Sold Jan 31, 2025

    • 1,916 Sq Ft
    • $333/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    67 W Main St, Chester, CT 06412

    Chester Village...a home you will love! Designed with natural grace and style, the timeless simplicity of this Quintessential New England Arts & Crafts style home offers the perfect blend of traditional architectural features with modern home design. Lovingly restored by the current owners, a welcoming front porch leads to a gracious entryway and elegant well-proportioned rooms that blend

    Kyle Hinding Coldwell Banker Realty

    67 W Main St, Chester, CT 06412
  • 28 Goose Hill Rd, Chester, CT 06412

    $582,000 Sold Nov 21, 2024

    • 2,398 Sq Ft
    • $243/SF
    • 5 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1870

    28 Goose Hill Rd, Chester, CT 06412

    Step into history with this 1870 colonial home on over 1.5 acres. Featuring three bedrooms and two fully finished bathrooms, plus a third en suite awaiting your touch, this property is a canvas for your creativity. Enjoy high ceilings on the first floor, bathed in natural light from large windows that create a warm and inviting atmosphere. Relax on the front porch or in the screened-in back

    Cheryl Bergeron-Lucca LPT Realty - IConn Team

    28 Goose Hill Rd, Chester, CT 06412
  • 95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    95 Shailer Pond Rd, Deep River, CT 06417
    /40

    $1,017,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    95 Shailer Pond Rd, Deep River, CT 06417

    Modern Contemporary Cape with Panoramic Water Views in Deep River and Chester, bordering Connecticut's second-largest forest and surrounded by hundreds of acres of protected land, this striking modern Cape offers the perfect blend of privacy, natural beauty, and upscale living. Perched to take full advantage of stunning panoramic views over Shailer Pond, this home brings the outdoors in from

    Rachel Welch William Raveis Real Estate

    95 Shailer Pond Rd, Deep River, CT 06417
  • 18 Saddlebrook Dr, Killingworth, CT 06419

    $625,000 Sold Sep 12, 2024

    • 2,658 Sq Ft
    • $235/SF
    • 83 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1989

    18 Saddlebrook Dr, Killingworth, CT 06419

    Nestled on a quaint and serene street, stands a breathtaking Saltbox Colonial, elegantly poised on 2.2 acres of verdant, level land. This stately home, surrounded by mature trees and the sprawling Cockaponset State Forest, offers a retreat into tranquility away from the hustle of everyday life. The saltbox colonial's timeless facade, with its steeply pitched roof and symmetrical windows, exudes

    Lisa Daniele William Raveis Real Estate

    18 Saddlebrook Dr, Killingworth, CT 06419
  • 6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    6 Spring St, Chester, CT 06412
    /40

    $790,000

    • 2 Beds
    • 3 Baths
    • 1,598 Sq Ft

    6 Spring St, Chester, CT 06412

    Welcome to 6 Spring Street, a residence that transcends the ordinary. Known affectionately as "The Recycle House," this home is a testament to over a decade of meticulous craftsmanship, with the majority of its structure composed of upcycled materials. Its acclaim extends beyond its eco-friendly design, having been rated as one of the top 70 Airbnbs near NYC by the online magazine "Curbed" and

    Amy Graham William Pitt Sotheby's Int'l

    6 Spring St, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /4

    $985,000

    • 2 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    88 Winthrop Rd, Chester, CT 06412

    The charming 3 bedroom colonial with a large attached garage and 2 outbuildings overlooks a lovely 5 acre pond. The home features a large kitchen and 2 1/2 baths with laundry on the second floor. Highlighting the living room is a 30 ft. Cathedral ceiling. Master bedroom includes an interior balcony, overlooking the living area. Generous windows and sliders afford beautiful open views of the

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • 7 Old Depot Rd, Chester, CT 06412
    7 Old Depot Rd, Chester, CT 06412
    7 Old Depot Rd, Chester, CT 06412
    /40

    $1,150,000

    • 4 Beds
    • 2.5 Baths
    • 3,149 Sq Ft

    7 Old Depot Rd, Chester, CT 06412

    Bella Vista: A Timeless Italianate Treasure on 6 Acres. Step into a piece of history, a magnificent Italianate country villa that has graced the landscape since 1908. First time on the market, this storied estate has been lovingly preserved by the same family for generations, a testament to its enduring allure. Listed on the National Registry of Historic Places, Bella Vista is an architectural

    Colette Harron William Pitt Sotheby's Int'l

    7 Old Depot Rd, Chester, CT 06412
  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    /10

    $232,500

    • Land
    • 1.50 Acres
    • $155,000 per Acre

    11 Kings Hwy, Chester, CT 06412

    1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

    Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
  • 88 Winthrop Rd, Chester, CT 06412
    88 Winthrop Rd, Chester, CT 06412
    /2

    $985,000

    • Land
    • 34 Acres
    • $28,996 per Acre

    88 Winthrop Rd, Chester, CT 06412

    The wooded 33.97 acre site has extensive open water views with frontage on Winthrop Road (Rt 145) and Butter Jones Road. The property abuts Deep River and Killingworth with convenient access to charming shopping areas. Also, the Chester Airport is within walking distance. A long driveway winds through the spacious, park-like setting, ideal for a planned unit development.

    Peter Walsh Re/Max Valley Shore

    88 Winthrop Rd, Chester, CT 06412
  • 14 Ferry Rd, Chester, CT 06412
    14 Ferry Rd, Chester, CT 06412
    14 Ferry Rd, Chester, CT 06412
    /25

    $399,000 Under Contract

    • 4 Beds
    • 1.5 Baths
    • 2,025 Sq Ft

    14 Ferry Rd, Chester, CT 06412

    Located by the Chester-Hadlyme Ferry, this 4 bedroom, 1.5 bath home is waiting your customization. Built in 1950, this home has original wainscoting in the living room, hardwood floors and built-in cabinets throughout. A large family room with fireplace is the perfect location to enjoy a cold winter night. There are three bedrooms on the main floor and a fourth on the second floor, which is

    Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, Chester, CT 06412
  • 4 Sypher Rd, Chester, CT 06412

    $525,000 Sold Jul 25, 2025

    • 2,272 Sq Ft
    • $231/SF
    • 29 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1969

    4 Sypher Rd, Chester, CT 06412

    Discover a rare gem in the picturesque town of Chester, Connecticut, with this charming 3-bedroom, 2.5-bath colonial home. Nestled on a private 2-acre lot, this property is a dream come true for horse lovers, featuring a barn that offers ample space for your equestrian needs and a chicken coop. Enjoy direct access to nearby state forest trails for riding or exploring. As you step inside, you will

    Kelly Puorro Puorro Realty Group

    4 Sypher Rd, Chester, CT 06412
  • 69 Spring St, Chester, CT 06412

    $715,000 Sold Jul 25, 2025

    • 1,702 Sq Ft
    • $420/SF
    • 30 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1883

    69 Spring St, Chester, CT 06412

    *Multiple offers received - offer deadline for 6/9 by noon* Quintessential Modernized Antique in Chester ~ Step into timeless charm with this beautifully updated antique colonial nestled near the heart of Chester. This visually stunning home seamlessly blends classic character with thoughtful modern updates. Offering 3 light and bright bedrooms, beautifully refinished original 1880 pine floors,

    Rachel Welch William Raveis Real Estate

    69 Spring St, Chester, CT 06412
  • 32 Gilbert Hill Rd, Chester, CT 06412

    $952,397 Sold Jul 10, 2025

    • 3,788 Sq Ft
    • $251/SF
    • 70 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1986

    32 Gilbert Hill Rd, Chester, CT 06412

    Welcome to a one-of-a-kind estate where history meets modern comfort - located within walking distance to Chester's charming downtown area. Built in 1986, this home was crafted using materials from a 1740 barn that were relocated to the stunning 5.31-acre rocky hillside it occupies today. The original timbers frame a breathtaking residence, blending rustic character with a contemporary and

    Steve Q Exclusive Properties

    32 Gilbert Hill Rd, Chester, CT 06412
  • 96 Goose Hill Rd, Chester, CT 06412

    $370,000 Sold Jul 09, 2025

    • 642 Sq Ft
    • $576/SF
    • 3 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2017

    96 Goose Hill Rd, Chester, CT 06412

    A thoughtfully designed home set on four acres in the heart of Chester. With a mix of open land and lightly wooded areas, the property offers both privacy and usable space in a peaceful, natural setting. Inside, the home features a bedroom on the main level, a full bathroom, and a full eat-in kitchen equipped with a stove, refrigerator, microwave, and ample cabinet space. The open living area is

    Jason Archer PMI East Lyme

    96 Goose Hill Rd, Chester, CT 06412
  • 25 Gilbert Hill Rd, Chester, CT 06412

    $1,135,000 Sold Jun 30, 2025

    • 3,351 Sq Ft
    • $339/SF
    • 16 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1987

    25 Gilbert Hill Rd, Chester, CT 06412

    Experience the stunning views of the Connecticut River, Lyme's hills, and the expansive valley from your heated Gunite in-ground swimming pool. The beautifully manicured grounds reflect years of dedicated care. This home showcases exceptional quality, featuring customized designs and meticulous details throughout, including custom moldings and cabinetry in the kitchen, bathrooms, and closets.

    Robin Linares William Pitt Sotheby's Int'l

    25 Gilbert Hill Rd, Chester, CT 06412
  • 15 Gilbert Hill Rd, Chester, CT 06412

    $1,000,050 Sold Jun 25, 2025

    • 3,054 Sq Ft
    • $327/SF
    • 18 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1950

    15 Gilbert Hill Rd, Chester, CT 06412

    Mid-Century Modern Private Compound Overlooking the CT River Valley. Discover this exceptional mid-century modern retreat, a private compound set in a park-like setting with distant water views of the Connecticut River Valley. This expanded Cape blends timeless design with modern updates, featuring an open floor plan flooded with natural light from skylights, two fireplaces, and hand-laid terra

    Angela Ruel Berkshire Hathaway NE Prop.

    15 Gilbert Hill Rd, Chester, CT 06412
  • 31 Parkers Point Rd, Chester, CT 06412

    $3,100,000 Sold Jun 10, 2025

    • 4,727 Sq Ft
    • $656/SF
    • 27 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2010

    31 Parkers Point Rd, Chester, CT 06412

    Nestled near the heart of the quaint Chester Village, this exquisite Nantucket-style home offers a serene retreat on the banks of the CT River. Spanning an impressive 4,727sqft, this architectural gem is all enveloped in traditional shingle elegance. As you step inside, you're welcomed by a two-story, paneled living room that exudes drama and sophistication. The space is adorned with beautiful

    Colette Harron William Pitt Sotheby's Int'l

    31 Parkers Point Rd, Chester, CT 06412
  • 24 E Liberty St, Chester, CT 06412

    $450,000 Sold May 14, 2025

    • 1,926 Sq Ft
    • $234/SF
    • 13 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1790

    24 E Liberty St, Chester, CT 06412

    Step back into Chester history! This home sits on over an acre within the town limits of Chester. It's sits on a quiet street with an expansive back yard. Much of structure has the historical details that antique home enthusiasts look for: wide plank chestnut floors, hand forged hardware, exposed beams, stone fireplaces, etc. Practicality also exists with the main house having higher ceilings

    Bonnie Fillion Berkshire Hathaway NE Prop.

    24 E Liberty St, Chester, CT 06412
  • 93 W Main St, Chester, CT 06412

    $180,000 Sold May 09, 2025

    • 752 Sq Ft
    • $239/SF
    • 32 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1955

    93 W Main St, Chester, CT 06412

    Charming One-Bedroom Ranch in Chester Village - A Hidden Gem! Discover the perfect investment opportunity with this delightful one-bedroom ranch located within walking distance to the picturesque downtown Chester Village. Known for its charming ambiance, this quaint town serves as a backdrop for Hallmark movies, offering a delightful mix of fantastic restaurants, unique galleries, and boutique

    Kelly Puorro Puorro Realty Group

    93 W Main St, Chester, CT 06412
  • 16 Waterhouse Ln, Chester, CT 06412

    $1,250,000 Sold May 02, 2025

    • 4,661 Sq Ft
    • $268/SF
    • 24 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1988

    16 Waterhouse Ln, Chester, CT 06412

    Discover the essence of elegance and tranquility in this exquisite Chester estate, boasting a host of 2024 upgrades including a new roof, furnace, and a tastefully renovated half bath. This property also comes with an approved separate building lot, enhancing your privacy and offering potential investment opportunities. The home is perfectly oriented to capture the morning sunrises, providing

    Teri Strain-Lewis William Pitt Sotheby's Int'l

    16 Waterhouse Ln, Chester, CT 06412
  • 6 Old County Rd, Chester, CT 06412

    $975,000 Sold Apr 30, 2025

    • 2,680 Sq Ft
    • $364/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2002

    6 Old County Rd, Chester, CT 06412

    Private, pristine, and with proximity to the Connecticut River, many wonderful restaurants, and boutiques. This meticulously maintained four bedroom 2 1/2 bath home is less than 2 miles from fabulous Chester Village. Set on over 2 acres this beautiful home has been carefully updated and enhanced. The meandering driveway takes you to a perfectly sited home with an amazing heated barn which also

    Susan Malan William Pitt Sotheby's Int'l

    6 Old County Rd, Chester, CT 06412
  • 19 W Main St, Chester, CT 06412

    $1,363,500 Sold Apr 15, 2025

    • 4,205 Sq Ft
    • $324/SF
    • 136 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    19 W Main St, Chester, CT 06412

    Welcome to the Waterfall House, an iconic custom home perched above the scenic Pattaconk Brook in the heart of historic Chester Village. Overlooking a picturesque 15-foot waterfall and offering sweeping views of the serene Jennings Pond from every room, this home is a masterpiece. Meticulously renovated in 2021, it blends modern luxury with timeless historic charm. Just a 5-minute stroll from

    Michael Marsden Compass Connecticut, LLC

    19 W Main St, Chester, CT 06412
  • 14 Straits Rd, Chester, CT 06412

    $285,000 Sold Apr 09, 2025

    • 1,519 Sq Ft
    • $188/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1702

    14 Straits Rd, Chester, CT 06412

    **Incredible Opportunity Awaits!** Discover the potential of this charming three-bedroom colonial, ideally situated in the heart of Chester Village. With a new septic system, roof, and windows already installed, the groundwork is laid for your dream home. The interior is completely gutted down to the studs, offering a blank canvas for a full rehab or the perfect opportunity to build your own

    Kelly Puorro Puorro Realty Group

    14 Straits Rd, Chester, CT 06412
  • 11 Bishop Rd, Chester, CT 06412

    $350,000 Sold Apr 07, 2025

    • 1,188 Sq Ft
    • $295/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    11 Bishop Rd, Chester, CT 06412

    Enjoy one-level living with protected year -round views of Cedar Lake in this 2-3 bedroom ranch. The smaller bedroom features convenient laundry access. A spacious living room with a fireplace and bay window offers a perfect spot to take in the scenic view. The home boasts hardwood floors throughout. The full basement is partially finished and offers plenty of potential. Located next to

    Craig Milton Re/Max Valley Shore

    11 Bishop Rd, Chester, CT 06412
  • 10 Old County Rd, Chester, CT 06412

    $900,000 Sold Mar 24, 2025

    • 2,755 Sq Ft
    • $327/SF
    • 26 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    10 Old County Rd, Chester, CT 06412

    Private and peaceful with seasonal views of the Connecticut River yet less than two miles to fabulous Chester Village with shops, restaurants, art galleries, spectacular (in season) farmers market and more. This 4-bedroom custom built home has a wonderful floor plan consisting of 4 bedrooms, 3 1/2 baths, 9' ceilings, huge primary bedroom with cathedral ceilings, oversized ensuite full bath and

    Susan Malan William Pitt Sotheby's Int'l

    10 Old County Rd, Chester, CT 06412
  • 71 Maple St, Chester, CT 06412

    $540,000 Sold Mar 20, 2025

    • 2,144 Sq Ft
    • $252/SF
    • 172 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1980

    71 Maple St, Chester, CT 06412

    Close to the town center, yet on a two acre tree shaded lot set back from the street. Gambrel colonial with a two car attached garage and three car detached garage. Garden area with in-ground pool feature. Possible in-law apartment on first floor. Furnace is oil with optional wood burning capability. Living room fireplace has a wood burning stove. New washer and dryer. Newer septic tank. Wide

    Louisa Ketron Berkshire Hathaway NE Prop.

    71 Maple St, Chester, CT 06412
  • 15 Kirtland Terrace, Chester, CT 06412

    $280,000 Sold Mar 07, 2025

    • 1,170 Sq Ft
    • $239/SF
    • 3 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1951

    15 Kirtland Terrace, Chester, CT 06412

    Nestled at the end of a quiet street, this 3-bedroom, 1.5-bath ranch offers a rare chance to create your dream home in historic Chester. Overlooking the serene Chester Fairgrounds fields, this property features stunning views and a spacious lot, making it ideal for renovation or a fresh new build. With easy one-floor living and central air, this home offers comfort and convenience. Whether you

    Kristina Quinones William Pitt Sotheby's Int'l

    15 Kirtland Terrace, Chester, CT 06412
  • 261 Middlesex Ave, Chester, CT 06412

    $360,000 Sold Feb 25, 2025

    • 1,248 Sq Ft
    • $288/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1935

    261 Middlesex Ave, Chester, CT 06412

    Come & enjoy all that Chester has to offer! Chester is one of the most sought after Connecticut village towns! This sweet Colonial built in 1935 is set back from the road on 2 picturesque acres of land offering plenty of expansion possibilities! Family owned since 1935. First floor offers a living room with stone fireplace, a dining room, a kitchen & mud room. All original hardwood floors

    Theresa Bitondo Berkshire Hathaway NE Prop.

    261 Middlesex Ave, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 2

Connecticut Middlesex County Chester

Real Estate & Homes for Sale in Chester, CT

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 102 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, CT over the last 12 months is $540,000.

Housing Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$540,000
Average Price Per Sq Ft
$440
Number of Homes for Sale
0
Last 12 months Home Sales
13
Months of Supply
0.00
Median List Price
$599,000
Median Change From 1st List Price
10%
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