1,680

Chester, CT Homes

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  • 131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    131 Middlesex Ave, Chester, CT 06412
    /27

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    131 Middlesex Ave, Chester, CT 06412

    Discover this waterfront delight in charming Chester, sure to reward with year-round views! Completely and thoughtfully renovated in 2012 from the ground up (including brand new septic system), this pristine Colonial offers 3 floors of living space and a smart L-shape open floor plan ensuring that you always have a gorgeous view. In addition to some hardworking 1st floor spaces (roomy mudroom,

    Agent Photo

    Claudia O'Connell

    William Raveis Real Estate

    (860) 590-3562

    131 Middlesex Ave, Chester, CT 06412
  • 55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    /27

    $2,500 per month

    • 2 Beds
    • 2.5 Baths
    • 1,328 Sq Ft
    • House for Rent

    55 Liberty St, Chester, CT 06412

    Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its delicious restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

    Agent Photo

    Janet Cronin-Rumanoff

    William Pitt Sotheby's Int'l

    (860) 730-1941

    55 Liberty St, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412

    $860,000 Sold Sep 17, 2025

    • 2,344 Sq Ft
    • $367/SF
    • 38 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1860

    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
  • 0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
    /18

    $249,497

    • Land
    • 25.53 Acres
    • $9,773 per Acre

    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412

    Residential - 25.53 ac Lot in Chester, CTPricing Details:Seller Financing: $54,889.34 Down | $4,167.84 per monthHere’s your chance to own a remarkable 25.53-acre property in the heart of Chester, CT, Middlesex County. While the parcel is landlocked with no legal access, it can be reached via the Deep River through state-owned land, and Pine Ledge Road comes close to the

    Timothy Ebie

    0 Hoop Pole Hill Rd Unit 24625958, Chester, CT 06412
  • 42 Bokum Rd Unit In-Law Apartment, Chester, CT 06412
    42 Bokum Rd Unit In-Law Apartment, Chester, CT 06412
    42 Bokum Rd Unit In-Law Apartment, Chester, CT 06412
    /6

    $1,500 per month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    42 Bokum Rd Unit In-Law Apartment, Chester, CT 06412

    2 bedroom 1 bath private entrance with small deck overlooking yard with koi pond

    42 Bokum Rd Unit In-Law Apartment, Chester, CT 06412
  • 6 Ridge Rd, Chester, CT 06412

    $345,000 Sold Aug 20, 2025

    • 1,472 Sq Ft
    • $234/SF
    • 31 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    6 Ridge Rd, Chester, CT 06412

    Beautifully maintained split-level home just a short walk to town and the elementary school. Featuring 3 bedrooms and 2 full baths, this home offers updated bathrooms, newer siding, and windows throughout. The main level includes an eat-in kitchen and a bright living area, while the lower level boasts a cozy family room with a fireplace and slider leading to a patio. Enjoy outdoor living with a

    Craig Milton Re/Max Valley Shore

    6 Ridge Rd, Chester, CT 06412
  • 16 Hickory Hill Dr, Chester, CT 06412
    16 Hickory Hill Dr, Chester, CT 06412
    16 Hickory Hill Dr, Chester, CT 06412
    /40

    $785,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    16 Hickory Hill Dr, Chester, CT 06412

    Welcome to this well maintained 3 Bedroom Cape in the charming town of Chester, just a short distance from downtown. The first floor of this home has an upscaled eat-in kitchen with newer appliances, breakfast bar and granite countertops, a Living/Dining room running front to back, an Office with built-in custom bookshelves and file drawers and a large (17 X 14), inviting Family Room with Propane

    Suzanne McConville William Raveis Real Estate

    16 Hickory Hill Dr, Chester, CT 06412
  • 159 W Main St Unit E, Chester, CT 06412
    159 W Main St Unit E, Chester, CT 06412
    159 W Main St Unit E, Chester, CT 06412
    /15

    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft
    • Apartment for Rent

    159 W Main St Unit E, Chester, CT 06412

    SPACIOUS 2 BEDROOM RANCH APARTMENT WITH NEWLY RENOVATED KITCHEN / LOCATED IN PICTURESQUE MIXED USE BUILDING / FRESHLY PAINTED WITH NEW APPLIANCES, HARDWOOD FLOORS & 9 FOOT CEILINGS / MAIN BEDROOM HAS WALKIN CLOSET / ENJOY HIKING & LIVING NEXT TO "NORTH QUARTER PARK" AND THE CONVENIENCE OF BEAUTIFUL DOWNTOWN CHESTER

    Tom Clancy William Pitt Sotheby's Int'l

    159 W Main St Unit E, 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
  • 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
  • 15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    /39

    $7,500 per month

    • 4 Beds
    • 4.5 Baths
    • 4,708 Sq Ft
    • House for Rent

    15 Liberty St, Chester, CT 06412

    Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an

    Lynn Lehrman Re/Max Valley Shore

    15 Liberty St, Chester, CT 06412
  • 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
  • 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
  • 68 Middlesex Ave, Chester, CT 06412
    68 Middlesex Ave, Chester, CT 06412
    68 Middlesex Ave, Chester, CT 06412
    /8

    $1,650 per month

    • 1 Bed
    • 1 Bath
    • 630 Sq Ft
    • House for Rent

    68 Middlesex Ave, Chester, CT 06412

    Comfortable Chester 1 bedroom first floor apartment. Privately set on 3/4 acre level parcel close to Chester center, marinas and the surrounding shoreline towns. Convenient access to Route 9. The multi-family property consists of a single family house and two 1 bedroom side-by-side units with ample parking.

    Pat Callahan Coldwell Banker Realty

    68 Middlesex Ave, 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
  • 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
  • 27 Spring St, Chester, CT 06412
    27 Spring St, Chester, CT 06412
    27 Spring St, Chester, CT 06412
    /18

    $3,400 per month

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft
    • House for Rent

    27 Spring St, Chester, CT 06412

    Beautiful Chester home directly across from Jenkins pond and waterfall views. Recently renovated kitchen, charming beds and bath, large yard for sports, two car attached garage. This owner is flexible with lease term length but would like a minimum of 6 months. A pet will be considered.

    Bonnie Fillion Berkshire Hathaway NE Prop.

    27 Spring St, 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
  • 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 Pending

    • 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
  • 19 Denlar Dr Unit C, Chester, CT 06412
    19 Denlar Dr Unit C, Chester, CT 06412
    19 Denlar Dr Unit C, Chester, CT 06412
    /14

    $1,750 per month

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Townhouse for Rent

    19 Denlar Dr Unit C, Chester, CT 06412

    Discover this spacious 2-bedroom, 2-bath townhouse-style apartment in the picturesque town of Chester, available from October 1st. Enjoy your private balcony accessible from the main floor living room that is equipped with a wall air conditioning unit. The main floor features an eat-in kitchen with access to the lower-level. Upstairs, you'll find two generously sized bedrooms with ample closet

    Carol Parda-Ziolko Carl Guild & Associates

    19 Denlar Dr Unit C, 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
  • 14 Maple St, Chester, CT 06412
    14 Maple St, Chester, CT 06412
    14 Maple St, Chester, CT 06412
    /9

    $799,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,322 Sq Ft

    14 Maple St, Chester, CT 06412

    Quintessential Chester! This Federal Greek Revival Post and Beam Antique Colonial has been lovingly restored and updated. Mere steps to the Town Center! Taste the true flavor of New England by enjoying this characteristically charming Connecticut Village, well known for its resturants, art galleries, and seasonal events, along with boat marinas and yacht clubs for summer fun. Special features of

    Deborah Rowe William Raveis Real Estate

    14 Maple 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
  • 60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    60 Goose Hill Rd, Chester, CT 06412
    /36

    $865,000

    • 7 Beds
    • 2 Baths
    • 2,947 Sq Ft

    60 Goose Hill Rd, Chester, CT 06412

    Spectacular 2 Family home newly renovated. Separate entrances and separate driveways. One unit has 4 bedrooms and a bonus room and the other has 3 bedrooms. New septic system. Central air and washer/dryer hookups in each unit. Huge open kitchen/dining/living room area in both units. All wood and tile floors. Even the basement looks new with all new mechanicals. Stone wall along the driveway

    Alexis Devlin Coldwell Banker Realty

    60 Goose 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
  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /40

    $3,375,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    East View is a long-admired Connecticut Riverfront property, a rare offering that perfectly marries historic provenance with elevated modern living. The circa 1800 home was masterfully renovated and expanded in 2010 with an architect's eye and a reverence for its storied past. Meticulous attention to detail is found in the extensive millwork, custom built-ins and hand-hewn beams lending warmth

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, 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
  • 50 Bokum Rd, Chester, CT 06412
    50 Bokum Rd, Chester, CT 06412
    50 Bokum Rd, Chester, CT 06412
    /31

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 807 Sq Ft

    50 Bokum Rd, Chester, CT 06412

    Welcome to this delightful 2-bedroom, 1.5 bath home tucked in the heart of historic Chester, CT. Brimming with character, this cozy home blends modern updates with small-town New England charm. Step inside to find a bright and inviting living space, an updated kitchen, and thoughtful touches throughout. Perfectly sized for easy living, the property offers a low-maintenance yard ideal for

    Cynthia Sigurdson William Pitt Sotheby's Int'l

    50 Bokum 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

Showing Results 1 - 40, Page 1 of 18

Connecticut Middlesex County Chester

Real Estate & Homes

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 48 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, CT over the last 12 months is $538,500, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$538,500
Median Single Family Sale Price
$596,000
Average Price Per Sq Ft
$324
Number of Homes for Sale
11
Last 12 months Home Sales
42
Months of Supply
3.10
Median List Price
$645,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
19%
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