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Sherman, CT Homes for Sale with Pool

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  • 25 Hillside Dr, Sherman, CT 06784
    25 Hillside Dr, Sherman, CT 06784
    /2

    $899,777 Coming Soon

    • 4 Beds
    • 4 Baths
    • 3,303 Sq Ft

    25 Hillside Dr, Sherman, CT 06784

    A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a

    Agent Photo

    Gary Crawford

    RE/MAX RISE

    (860) 735-1471

    25 Hillside Dr, Sherman, CT 06784
  • 201 Route 37 S, Sherman, CT 06784
    201 Route 37 S, Sherman, CT 06784
    201 Route 37 S, Sherman, CT 06784
    /40

    $1,599,500 Open Sun 12PM - 2PM

    • 6 Beds
    • 4 Baths
    • 4,258 Sq Ft

    201 Route 37 S, Sherman, CT 06784

    Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and

    Cory Neumann Houlihan Lawrence

    201 Route 37 S, Sherman, CT 06784
  • 2 Sail Harbour Dr, Sherman, CT 06784
    2 Sail Harbour Dr, Sherman, CT 06784
    2 Sail Harbour Dr, Sherman, CT 06784
    /40

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 5,041 Sq Ft

    2 Sail Harbour Dr, Sherman, CT 06784

    Majestic Sail Harbour Home, in this premier Candlewood Lake community, on 2 sprawling, level acres has it all! Elegant 2 story marble foyer w/circular stair welcomes you, flanked by a formal living & dining room in this classic plan. An expansive kitchen w/bay dining area, offers open views of the family room, tiled 4 season sunroom, in ground pool & masterfully created gardens. A grand primary

    Barbara Sivba Coldwell Banker Realty

    2 Sail Harbour Dr, Sherman, CT 06784
  • 27 Osborn Rd, Sherman, CT 06784
    27 Osborn Rd, Sherman, CT 06784
    27 Osborn Rd, Sherman, CT 06784
    /30

    $1,595,000

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    27 Osborn Rd, Sherman, CT 06784

    Sited on 7.7 private acres on a quiet country lane, this impeccable 4 bedroom home has a sought after open floor plan on the first level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an

    Sally Slater Douglas Elliman of Connecticut

    27 Osborn Rd, Sherman, CT 06784
  • 11 Chestnut Hill Rd, Sherman, CT 06784
    11 Chestnut Hill Rd, Sherman, CT 06784
    11 Chestnut Hill Rd, Sherman, CT 06784
    /40

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    11 Chestnut Hill Rd, Sherman, CT 06784

    Sprawling 3-bedroom, 2 full and 1 half bath home, in-ground swimming pool set on 2 beautiful acres with access to a community beach and boat dock with designated slip on Candlewood Lake in the Orchard Rest Candlewood Lake community. This sunny and spacious home features soaring ceilings, hardwood floors, wood burning fireplace, sunroom, large living room and eat in kitchen on the main level and

    Liz Pepin Luks Realty

    11 Chestnut Hill Rd, Sherman, CT 06784
  • 41 Long River Rd, Sherman, CT 06784
    41 Long River Rd, Sherman, CT 06784
    41 Long River Rd, Sherman, CT 06784
    /25

    $279,000

    • Land
    • 5.46 Acres
    • $51,099 per Acre

    41 Long River Rd, Sherman, CT 06784

    This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

    Donna Kennedy Compass Connecticut, LLC

    41 Long River Rd, Sherman, CT 06784
  • 6 Brinsmade Ln, Sherman, CT 06784
    6 Brinsmade Ln, Sherman, CT 06784
    6 Brinsmade Ln, Sherman, CT 06784
    /39

    $1,849,000

    • 6 Beds
    • 5 Baths
    • 5,500 Sq Ft

    6 Brinsmade Ln, Sherman, CT 06784

    Discover a private country retreat just 90 minutes from New York City in Sherman, CT, set on approximately 10 acres near Candlewood Lake with beach and boat rights. This exceptional estate blends historic New England charm with modern luxury and low taxes. Three residences-the Main House, Carriage House, and Pool House-offer 5,200 sq ft with six bedrooms and five full baths, ideal for

    Ginny Gordon-O’Neill William Raveis Real Estate

    6 Brinsmade Ln, Sherman, CT 06784
  • 7 Anderson Rd E, Sherman, CT 06784
    7 Anderson Rd E, Sherman, CT 06784
    7 Anderson Rd E, Sherman, CT 06784
    /40

    $900,000 Open Mon 11AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 3,419 Sq Ft

    7 Anderson Rd E, Sherman, CT 06784

    Welcome to 7 Anderson Hill Rd - a serene retreat set on over 7 acres of beautifully landscaped grounds, featuring specimen trees and vibrant perennial gardens that create a true sense of peace and privacy. A charming stone gravel driveway leads you to this stunning contemporary home offering 3 bedrooms, 2.5 baths, and a detached, heated 2-car garage. Inside, the dramatic two-story living room

    Regan Andrews Coldwell Banker Realty

    7 Anderson Rd E, Sherman, CT 06784
Connecticut Fairfield County Sherman

Homes for Sale with Pool in Sherman, CT

Home Trends in Sherman, CT

On average, homes in Sherman, CT sell after 98 days on the market compared to the national average of 56 days. The median sale price for homes in Sherman, CT over the last 12 months is $697,500, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$697,500
Median Single Family Sale Price
$740,000
Average Price Per Sq Ft
$358
Number of Homes for Sale
16
Last 12 months Home Sales
50
Months of Supply
3.80
Median List Price
$849,900
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
18%
How to Buy a Home How to Finance a Home How to Sell a Home

In Sherman, there are currently 8 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Sherman, CT and discover your ideal residence.

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