9

Chester, CT Homes for Sale with Acreage

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  • 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
  • 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

    $799,000

    • 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
  • 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
  • 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 Fri 4PM - 6PM

    • 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
  • 8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    8 Route 148, Killingworth, CT 06419
    /40

    $825,000

    • 4 Beds
    • 3 Baths
    • 3,864 Sq Ft

    8 Route 148, Killingworth, CT 06419

    Tucked away in complete privacy, this stunning post and beam home offers a rare opportunity to live in harmony with nature. Situated on 6.4 acres of wooded serenity, the property is a true retreat and offers many outside features including a tranquil pond, ample space for gardens, hobbies, or simply room to roam. The home itself showcases timeless craftsmanship with exposed beams, soaring

    Kara Bell J.M. REALTY

    8 Route 148, Killingworth, CT 06419
Connecticut Chester

Homes for Sale with Acreage in Chester, CT

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 50 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, CT over the last 12 months is $537,000, up 26% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$537,000
Median Single Family Sale Price
$568,500
Average Price Per Sq Ft
$311
Number of Homes for Sale
7
Last 12 months Home Sales
43
Months of Supply
2.00
Median List Price
$615,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
26%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 9 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Chester, CT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Chester and discover the potential and freedom that comes with owning your own piece of property.

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