Homes in ZIP Code 06412

• 

  

  

  /27

  $549,000 Under Contract

  • 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,

  

  Claudia O'Connell

  William Raveis Real Estate

  (860) 590-3562

  131 Middlesex Ave, Chester, CT 06412
• 

  

  

  /27

  $2,500 total monthly price

  • 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

  

  Janet Cronin-Rumanoff

  William Pitt Sotheby's Int'l

  (860) 730-1941

  55 Liberty St, Chester, CT 06412
• 

  $442,500 Sold Oct 20, 2025

  • 1,198 Sq Ft
  • $369/SF
  • 59 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1930

  30 Bokum Rd, Chester, CT 06412

  Enjoy the perfect blend of small-town charm and everyday comfort in this inviting Cape, ideally located just a few minutes from Chester center. The home features 3 bedrooms upstairs, each with unique charm and natural light, plus 2 full baths-one on the main floor with a sleek walk-in shower and one upstairs with a tub/shower combo. Gleaming hardwood floors run throughout the main living areas,

  Max Gill Puorro Realty Group

  30 Bokum Rd, Chester, CT 06412
• 

  Est $906,631 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,033 Sq Ft

  75 Pinnacle Ln, Chester, CT 06412

  75 Pinnacle Ln, Chester, CT 06412
• 

  

  

  /18

  $189,497

  • Land
  • 25.53 Acres
  • $7,423 per Acre

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

  Residential - 25.53 ac Lot in Chester, CTPricing Details:Seller Financing: $41,689.34 Down | $3,165.54 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 Land Fast Offers, LLC

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

  

  /11

  $1,600 total monthly price

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

  42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412

  2 bedroom 1 bath private entrance with small deck overlooking yard with koi pond, located in a quaint small town with local restaurants, hiking areas, near Rt. 9 for ease of commute, 45 minutes to Hartford, 40 Minutes from New Haven or New London area.

  42 Bokum Rd Unit 2nd Floor Apartment, Chester, CT 06412
• 

  $1,017,000 Sold Oct 20, 2025

  • 4,341 Sq Ft
  • $234/SF
  • 53 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1999

  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
• 

  Est $528,001 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  22 Hickory Hill Dr, Chester, CT 06412

  22 Hickory Hill Dr, Chester, CT 06412
• 

  

  /36

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  8 Butter Jones Rd, Chester, CT 06412

  Enchanting Cape with Artisan Post & Beam Charm - Just Down the Road from Chester Village! Tucked away on 2 acres of picturesque land, this whimsical 3-bedroom, 2.5-bath Cape Cod home invites you to live among nature in style. Only a short distance from Cedar Lake and Chester Village, you'll have easy access to endless outdoor adventures and world-class restaurants and shopping just moments

  Amy Graham William Pitt Sotheby's Int'l

  8 Butter Jones Rd, Chester, CT 06412
• 

  

  /20

  $2,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,366 Sq Ft
  • House for Rent

  15 Laurel St, Chester, CT 06412

  Three-bedroom rental featuring one full bathroom, a private back patio, and an attached one-car garage. The lower level is partially finished, offering additional living or storage space. Located near Cedar Lake, this home includes new double-paned, energy-efficient windows throughout. Credit and background/criminal checks are required with application submission.

  Craig Milton Re/Max Valley Shore

  15 Laurel St, Chester, CT 06412
• 

  $550,000 Sold Oct 15, 2025

  • 1,104 Sq Ft
  • $498/SF
  • 15 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1920

  23 Spring St, Chester, CT 06412

  This precious 1920 bungalow has had only 2 owners! It has been updated and extremely well cared for. Central a/c, 2 bedrooms, 1 1/2 baths, full basement, and the most perfect front porch to sit and watch the world go by. A fabulous two-story barn/garage with a full loft and wonderful lawn and garden area. Peaceful, private and quiet but just a short stroll to Main Street Chester with shops,

  Susan Malan William Pitt Sotheby's Int'l

  23 Spring St, Chester, CT 06412
• 

  Est $422,919 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  8 Winthrop Rd, Chester, CT 06412

  8 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
• 

  /2

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  11 Maple St Unit A, Chester, CT 06412

  2 Bedroom Apartment in the heart of Downtown Chester. Property includes in unit washer/dryer. One bedroom larger than the second. Kitchen includes dishwasher.

  11 Maple St Unit A, Chester, CT 06412
• 

  $420,000 Sold Sep 24, 2025

  • 2,025 Sq Ft
  • $207/SF
  • 35 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1950

  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
• 

  Est $418,224 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,771 Sq Ft

  41 Railroad Ave, Chester, CT 06412

  41 Railroad Ave, Chester, CT 06412
• 

  

  /40

  $785,000 Pending

  • 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
• 

  

  /17

  $2,100 total monthly price

  • 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
• 

  $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
• 

  Est $1,125,064 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,862 Sq Ft

  248 Middlesex Ave, Chester, CT 06412

  248 Middlesex Ave, Chester, CT 06412
• 

  

  /37

  $799,000 Pending

  • 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
• 

  

  /39

  $7,500 total monthly price

  • 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
• 

  $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
• 

  Est $461,529 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  37 Castle View Dr, Chester, CT 06412

  37 Castle View Dr, Chester, CT 06412
• 

  

  /39

  $774,000 Pending

  • 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 Lewis William Pitt Sotheby's Int'l

  28 Hoop Pole Hill Rd, Chester, CT 06412
• 

  

  /8

  $1,450 total monthly price

  • 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
• 

  $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 Lewis William Pitt Sotheby's Int'l

  137 Main St, Chester, CT 06412
• 

  Est $565,742 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  25 Deep Hollow Rd, Chester, CT 06412

  25 Deep Hollow Rd, Chester, CT 06412
• 

  

  /40

  $1,017,000 Pending

  • 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

  $3,000 total monthly price

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

  27 Spring St, Chester, CT 06412

  Beautiful in-town Chester home directly across from Jennings pond with 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
• 

  $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
• 

  Est $637,829 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  16 Ridge Rd, Chester, CT 06412

  16 Ridge Rd, Chester, CT 06412
• 

  

  /40

  $1,095,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft

  47 Ferry Rd, Chester, CT 06412

  A unique offering in Chester on the CT. River in the Pattaconk/Fort Hill area, bordering the Chester ferry. A small historic town known for its Main Street, art galleries, restaurants and hiking in the Cockaponset State Forest. Privately situated, fully remodeled charming colonial home sits above the River overlooking 5+ acres of waterfront meadow landscape. Ferry activity, views of Gillette's

  Mary Poola William Raveis Real Estate

  47 Ferry 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
• 

  Est $529,175 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  4 Turkey Hill Rd, Chester, CT 06412

  4 Turkey Hill Rd, Chester, CT 06412
• 

  

  /40

  $1,150,000 Under Contract

  • 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
• 

  $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
• 

  Est $696,155 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,713 Sq Ft

  12 Liberty St, Chester, CT 06412

  12 Liberty St, Chester, CT 06412
• 

  

  /31

  $499,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 1,470 Sq Ft

  79 Middlesex Ave, Chester, CT 06412

  Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the aspiring chef! The

  Gigi Giordano Taylor Compass Connecticut, LLC

  79 Middlesex Ave, 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

Showing Results 1 - 40, Page 1 of 18