2,148

Sherman, CT Homes

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  • /40

    $3,900,000

    • 3 Beds
    • 2 Baths
    • 1,933 Sq Ft

    6 Hoyt Rd, Sherman, CT 06784

    Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a

    Agent Photo

    Eric Bergers

    William Raveis Real Estate

    (860) 936-9247

    6 Hoyt Rd, Sherman, CT 06784
  • /31

    $2,650 Per Month

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    29 Route 55 W Unit B, Sherman, CT 06784

    Barn-Dominium! Don't miss this stunning, like-new rental in Connecticut's best little town - Sherman. This spacious, open-concept barn-style, one level home delivers over-the-top finishes throughout: rich hardwood floors, professional-grade kitchen appliances, butcher block island, quartz counters, and a high-end Samsung washer/dryer. Central air, an EV charging station, and exceptional energy

    Todd Sargent Coldwell Banker Realty

    29 Route 55 W Unit B, Sherman, CT 06784
  • 1 Cloverleaf Farm S, Sherman, CT 06784

    $1,650,000 Sold Feb 10, 2026

    1 Cloverleaf Farm S, Sherman, CT 06784

    • 4 Beds
    • 4.5 Baths
    • 5,475 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $301/SF
    • 239 Days On Market

    Current Estimated Value $1,370,588

    Last Listing Agent Alan O'Doherty William Pitt Sotheby's Int'l

    1 Cloverleaf Farm S, Sherman, CT 06784
    • 5 Old Hickory Ln, Sherman, CT 06784

      Est $1,007,972 Not Listed For Sale

      5 Old Hickory Ln, Sherman, CT 06784

      • 4 Beds
      • 3.5 Baths
      • 3,940 Sq Ft
      • Built 2005
      5 Old Hickory Ln, Sherman, CT 06784

      Last Sold Summary

      • $256/SF
      • 93 Days On Market
      • Last Sold Price $1,010,000
      • May 12, 2025

      Last Listing Agent Eric Bergers William Raveis Real Estate

  • /36

    $899,777

    • 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
  • /40

    $20,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • House for Rent

    32 Leach Hollow Rd, Sherman, CT 06784

    Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for July and August 2026. Scenic distant views frame this private 15-acre compound. Elegantly presented interiors, with extensive renovations supervised by an AIA architect specializing in historic preservation. Attention to detail and quality is evident throughout

    Irit Granger William Pitt Sotheby's Int'l

    32 Leach Hollow Rd, Sherman, CT 06784
  • 40 Wagon Wheel Rd, Sherman, CT 06784

    $69,000 Sold May 23, 2025

    40 Wagon Wheel Rd, Sherman, CT 06784

    • Land
    • 1.44 Acres
    • $47,917 per Acre

    Last Sold Summary

    • 6% Above List Price
    • 6 Days On Market

    Last Listing Agent Besart Dani William Raveis Real Estate

    40 Wagon Wheel Rd, Sherman, CT 06784
    • 1 Lakeview Dr, New Fairfield, CT 06812

      Est $218,087 Not Listed For Sale

      1 Lakeview Dr, New Fairfield, CT 06812

      1 Lakeview Dr, New Fairfield, CT 06812

      Last Sold Summary

      • 679% Above List Price
      • 226 Days On Market
      • Last Sold Price $28,000
      • Oct 11, 2023

      Last Listing Agent Paul Fadus Paul Fadus Realty,LLC

  • /40

    $1,489,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,884 Sq Ft

    27 Smoke Ridge Dr, Sherman, CT 06784

    A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, offering you seclusion. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A welcoming columned entry opens to bright, versatile living spaces designed for today's lifestyle, anchored by an oversized

    Ginny Gordon-O’Neill William Raveis Real Estate

    27 Smoke Ridge Dr, Sherman, CT 06784
  • /16

    $2,100 Per Month

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

    21 Route 39 S Unit A, Sherman, CT 06784

    One of a kind rental opportunity. Set on 10 magical acres with pond and brook. Private 1 bedroom above garage rental. Open concept with hardwood floors throughout. Center island kitchen opens to living room. Bedroom with built ins, walk in closet and small storage area. Laundry room (washer/dryer not included-front loader needed). Private entrance and mudroom/foyer. Beautiful tiles bathroom.

    Joe Chemero Coldwell Banker Realty

    21 Route 39 S Unit A, Sherman, CT 06784
  • 1 Mary Bee Ln, Sherman, CT 06784

    $637,000 Sold May 19, 2025

    1 Mary Bee Ln, Sherman, CT 06784

    • 4 Beds
    • 3.5 Baths
    • 3,002 Sq Ft
    • Built 1974

    Last Sold Summary

    • 5% Below List Price
    • $212/SF
    • 196 Days On Market

    Current Estimated Value $648,876

    Last Listing Agent Joe Chemero Coldwell Banker Realty

    1 Mary Bee Ln, Sherman, CT 06784
    • 5 Crooked Furrows Ln, Sherman, CT 06784

      Not Listed For Sale

      5 Crooked Furrows Ln, Sherman, CT 06784

      5 Crooked Furrows Ln, Sherman, CT 06784

      Last Sold Summary

      • 482 Days On Market
      • Last Sold Price $375,000
      • Aug 11, 2023

      Last Listing Agent Pat Catchpole William Raveis Real Estate

  • /34

    $1,595,000

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

    27 Osborn Rd, Sherman, CT 06784

    This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st 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

    Sally Slater Douglas Elliman of Connecticut

    27 Osborn Rd, Sherman, CT 06784
  • Unlisted Address

    $1,350,000 Sold Dec 16, 2025

    Unlisted Address

    • 4 Beds
    • 4 Baths
    • 3,994 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Above List Price
    • $338/SF
    • 51 Days On Market

    Current Estimated Value $1,148,263

    Last Listing Agent Chris Garrity Bain Real Estate

    Unlisted Address
    • 7 River Bend Ln, Sherman, CT 06784

      Est $182,395 Not Listed For Sale

      7 River Bend Ln, Sherman, CT 06784

      • 4 Beds
      • Built 2001
      7 River Bend Ln, Sherman, CT 06784

      Last Sold Summary

      • 7% Above List Price
      • $65/SF
      • 38 Days On Market
      • Last Sold Price $170,000
      • May 24, 2024

      Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  • /38

    $1,295,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,121 Sq Ft

    32 Long River Rd, Sherman, CT 06784

    Welcome home to this exceptionally beautiful modern ranch style property, in a gated community and on one of the areas most elite 18 hole Golf Courses. This sprawling 4 bedroom, 3121 sq. ft. floorplan, on one level and located in the Sherman River Oaks Golf Course, is all you will ever need for family, entertainment and quality living. (whether weekend or year round) Enjoy the beautiful scenery

    Joe Chemero Coldwell Banker Realty

    32 Long River Rd, Sherman, CT 06784
  • 12 Sunny Ln, Sherman, CT 06784

    $775,000 Sold Nov 25, 2025

    12 Sunny Ln, Sherman, CT 06784

    • 4 Beds
    • 2.5 Baths
    • 3,214 Sq Ft
    • Built 1995

    Last Sold Summary

    • 9% Below List Price
    • $241/SF
    • 56 Days On Market

    Current Estimated Value $773,643

    Last Listing Agent Heidi Mitchell Luks Realty

    12 Sunny Ln, Sherman, CT 06784
    • 32 Big Trail, Sherman, CT 06784

      Est $1,020,455 Not Listed For Sale

      32 Big Trail, Sherman, CT 06784

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 2019
      32 Big Trail, Sherman, CT 06784

      Last Sold Summary

      • 1% Below List Price
      • $396/SF
      • 44 Days On Market
      • Last Sold Price $1,030,000
      • Mar 28, 2024

      Last Listing Agent Jeff Phillips William Pitt

  • /18

    $1,495,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,770 Sq Ft

    4 Pond View Ln, Sherman, CT 06784

    New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft

    Joe Chemero Coldwell Banker Realty

    4 Pond View Ln, Sherman, CT 06784
  • 172 Route 37 S, Sherman, CT 06784

    $690,000 Sold Nov 13, 2025

    172 Route 37 S, Sherman, CT 06784

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 1800

    Last Sold Summary

    • 5% Below List Price
    • $230/SF
    • 135 Days On Market

    Current Estimated Value $689,951

    Last Listing Agent Joe Chemero Coldwell Banker Realty

    172 Route 37 S, Sherman, CT 06784
    • 27 Skyline Dr, Sherman, CT 06784

      Est $820,551 Not Listed For Sale

      27 Skyline Dr, Sherman, CT 06784

      • 2 Beds
      • 2.5 Baths
      • 1,960 Sq Ft
      • Built 2011
      27 Skyline Dr, Sherman, CT 06784

      Last Sold Summary

      • 3% Below List Price
      • $430/SF
      • 84 Days On Market
      • Last Sold Price $842,000
      • Aug 09, 2024

      Last Listing Agent Diane Stevens William Pitt

  • /2

    $1,195,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 3,675 Sq Ft

    60 Long River Rd, Sherman, CT 06784

    River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

    Joe Chemero Coldwell Banker Realty

    60 Long River Rd, Sherman, CT 06784
  • 24 Quaker Ridge Rd, Sherman, CT 06784

    $715,500 Sold Jun 26, 2025

    24 Quaker Ridge Rd, Sherman, CT 06784

    • 4 Beds
    • 2.5 Baths
    • 2,954 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Above List Price
    • $242/SF
    • 39 Days On Market

    Current Estimated Value $690,045

    Last Listing Agent Irit Granger William Pitt Sotheby's Int'l

    24 Quaker Ridge Rd, Sherman, CT 06784
    • 7 Cozier Hill Rd, Sherman, CT 06784

      Est $1,139,271 Not Listed For Sale

      7 Cozier Hill Rd, Sherman, CT 06784

      • 5 Beds
      • 3.5 Baths
      • 3,561 Sq Ft
      • Built 1939
      7 Cozier Hill Rd, Sherman, CT 06784

      Last Sold Summary

      • 1% Above List Price
      • $316/SF
      • 49 Days On Market
      • Last Sold Price $1,125,000
      • Aug 01, 2023

      Last Listing Agent Irit Granger William Pitt

  • /36

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    35 Skyline Dr, Sherman, CT 06784

    It's All About the Views!Fabulous Price Reduction on this one of a kind, custom built contemporary with extraordinary 50 mile views in all directions. Set in the Lake community of Candlewood Lake Estates, this stately Contemporary, set on a private acre plus an additional lot (.82 acs), at the end of a cul-de-sac, is just waiting for your customization. This incredible setting hosts this 3

    Barbara Sivba Coldwell Banker Realty

    35 Skyline Dr, Sherman, CT 06784
  • 3 Gelston Rd, Sherman, CT 06784

    $336,000 Sold Apr 24, 2026

    3 Gelston Rd, Sherman, CT 06784

    • 1 Bed
    • 1 Bath
    • 536 Sq Ft
    • Built 1800

    Last Sold Summary

    • $627/SF
    • 63 Days On Market

    Current Estimated Value $336,103

    Last Listing Agent Larry Corrow Coldwell Banker Realty

    3 Gelston Rd, Sherman, CT 06784
    • 19 Wakeman Hill Rd, Sherman, CT 06784

      Est $699,602 Not Listed For Sale

      19 Wakeman Hill Rd, Sherman, CT 06784

      • 3 Beds
      • 3 Baths
      • 2,648 Sq Ft
      • Built 1987
      19 Wakeman Hill Rd, Sherman, CT 06784

      Last Sold Summary

      • 18% Above List Price
      • $224/SF
      • 114 Days On Market
      • Last Sold Price $592,000
      • Aug 25, 2023

      Last Listing Agent Irit Granger William Pitt

  • /40

    $999,000

    • 3 Beds
    • 3.5 Baths
    • 3,258 Sq Ft

    6 River Bend Ln, Sherman, CT 06784

    A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached

    Tyler O'Hazo William Pitt Sotheby's Int'l

    6 River Bend Ln, Sherman, CT 06784
  • 70 Wakeman Hill Rd, Sherman, CT 06784

    $800,000 Sold Sep 15, 2025

    70 Wakeman Hill Rd, Sherman, CT 06784

    • 4 Beds
    • 2.5 Baths
    • 3,973 Sq Ft
    • Built 1999

    Last Sold Summary

    • 18% Below List Price
    • $201/SF
    • 106 Days On Market

    Current Estimated Value $824,980

    Last Listing Agent Joseph Perun Perun Properties

    70 Wakeman Hill Rd, Sherman, CT 06784
    • 4 Bridgeworth Ln, Sherman, CT 06784

      Est $660,907 Not Listed For Sale

      4 Bridgeworth Ln, Sherman, CT 06784

      • 3 Beds
      • 3.5 Baths
      • 2,400 Sq Ft
      • Built 1968
      4 Bridgeworth Ln, Sherman, CT 06784

      Last Sold Summary

      • 2% Below List Price
      • $280/SF
      • 47 Days On Market
      • Last Sold Price $672,000
      • Jul 30, 2024

      Last Listing Agent Kimberly Thomson Coldwell Banker Realty

  • /40

    $1,599,500

    • 6 Beds
    • 5.5 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
  • 13 Taber Rd, Sherman, CT 06784

    $740,000 Sold Jun 18, 2025

    13 Taber Rd, Sherman, CT 06784

    • 4 Beds
    • 2.5 Baths
    • 1,828 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $405/SF
    • 56 Days On Market

    Current Estimated Value $717,144

    Last Listing Agent Irit Granger William Pitt Sotheby's Int'l

    13 Taber Rd, Sherman, CT 06784
    • 9 Meadow Ln, Sherman, CT 06784

      Est $580,291 Not Listed For Sale

      9 Meadow Ln, Sherman, CT 06784

      • 4 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 1969
      9 Meadow Ln, Sherman, CT 06784

      Last Sold Summary

      • 14% Above List Price
      • $231/SF
      • 61 Days On Market
      • Last Sold Price $507,750
      • Mar 07, 2024

      Last Listing Agent Arleen Norton Coldwell Banker Realty

  • /39

    $565,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    38 Cedar Lane Extension, Sherman, CT 06784

    Unique and open mid century modern at end of cul de sac. Great curb appeal. Updated Kitchen with stainless appliances. 3/4 bedrooms and 2 full baths. Primary with 2 closets and private bathroom. Mini split for AC. Crown moldings. 2 car heated attached garage plus 1 car detached. Hardwood floors. Front and rear decks for relaxing and entertaining. Added potential in the unfinished basement.

    Joe Chemero Coldwell Banker Realty

    38 Cedar Lane Extension, Sherman, CT 06784
  • 13A Osborn Rd, Sherman, CT 06784

    $225,000 Sold Jun 05, 2025

    13A Osborn Rd, Sherman, CT 06784

    • Land
    • 2.41 Acres
    • $93,361 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 15 Days On Market

    Current Estimated Value $232,397

    Last Listing Agent Kurt Stoffel Coldwell Banker Realty

    13A Osborn Rd, Sherman, CT 06784
    • 7 Hubbell Mountain Rd, Sherman, CT 06784

      Est $557,080 Not Listed For Sale

      7 Hubbell Mountain Rd, Sherman, CT 06784

      • 2 Beds
      • 2 Baths
      • 1,488 Sq Ft
      • Built 1952
      7 Hubbell Mountain Rd, Sherman, CT 06784

      Last Sold Summary

      • 1% Below List Price
      • $378/SF
      • 106 Days On Market
      • Last Sold Price $562,000
      • Jan 09, 2025

      Last Listing Agent Irit Granger William Pitt

  • /40

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft

    2 Sawmill Rd, Sherman, CT 06784

    Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the

    Lori Campbell Coldwell Banker Realty

    2 Sawmill Rd, Sherman, CT 06784
  • 13 Wanzer Hill Rd, Sherman, CT 06784

    $950,000 Sold Jul 28, 2025

    13 Wanzer Hill Rd, Sherman, CT 06784

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft
    • Built 2016

    Last Sold Summary

    • $232/SF
    • 4 Days On Market

    Current Estimated Value $953,943

    Last Listing Agent George Muniz Keller Williams NY Realty

    13 Wanzer Hill Rd, Sherman, CT 06784
    • 9 Hillside Dr, Sherman, CT 06784

      Est $349,865 Not Listed For Sale

      9 Hillside Dr, Sherman, CT 06784

      • 1 Bed
      • 1 Bath
      • 336 Sq Ft
      • Built 1955
      9 Hillside Dr, Sherman, CT 06784

      Last Sold Summary

      • $1,042/SF
      • 113 Days On Market
      • Last Sold Price $350,000
      • Jan 31, 2025

      Last Listing Agent Kathleen Harrison Coldwell Banker Realty

  • /40

    $599,000 Under Contract

    • 3 Beds
    • 4 Baths
    • 2,942 Sq Ft

    47 Rt 39 So, Sherman, CT 06784

    Discover the perfect blend of comfort, convenience, and seasonal beauty in this privately sited ranch home with seasonal views of Candlewood Lake. Nestled within the sought-after Deer Run Shores Lake Club community, this property offers access to fantastic amenities, including a pool, clubhouse, beach area, and guest parking. This home features spray foam insulation for energy efficiency and a

    Patty Wagner Compass Connecticut, LLC

    47 Rt 39 So, Sherman, CT 06784

Showing Results 1 - 40, Page 1 of 18

Home Trends in Sherman, CT

Housing Trends

Median Sale Price
$692,500
Median Single Family Sale Price
$761,500
Average Price Per Sq Ft
$371
Number of Homes for Sale
19
Last 12 months Home Sales
48
Months of Supply
4.80
Median List Price
$825,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
17%
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