Sherman, CT Homes

• 

  $475,000

  Sold Jun 26, 2026

  17 Mauweehoo Hill, Sherman, CT 06784

  • 2 Beds
  • 1 Bath
  • 1,393 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Below List Price
  • $341/SF
  • 32 Days On Market

  Current Estimated Value $515,175

  Last Listing Agent Suzann Walsh Walsh Realty Group

  17 Mauweehoo Hill, Sherman, CT 06784
• 

  Est $585,194

  Not Listed For Sale

  126 Green Pond Rd, Sherman, CT 06784

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1981

  126 Green Pond Rd, Sherman, CT 06784

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Diana Newbert William Raveis Real Estate
• 

  

  

  /38

  $599,000

  Open Sun 10AM - 11AM

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  8 Pinewood Shores, Sherman, CT 06784

  Beautifully maintained, move-in ready +1890 sf raised ranch with a deeded boat dock and private sandy beach in desirable Pinewood Shores at Squantz Pond! Enjoy the best of water-community living with a gorgeous, level yard surrounded by perennial plantings & a spacious deck perfect for outdoor entertaining, dining alfresco or simply relaxing after a day on the water. Light and bright throughout,

  Angelina Valentini Coldwell Banker Realty

  8 Pinewood Shores, Sherman, CT 06784
• 

  $205,000

  Sold May 19, 2026

  10 Chimney Hill Rd, Sherman, CT 06784

  • Land
  • 4.91 Acres
  • $41,752 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 11 Days On Market

  Current Estimated Value $205,410

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  10 Chimney Hill Rd, Sherman, CT 06784
• 

  Est $999,657

  Not Listed For Sale

  2 Nutmeg Ln, Sherman, CT 06784

  • 5 Beds
  • 3.5 Baths
  • 3,113 Sq Ft
  • Built 1982

  2 Nutmeg Ln, Sherman, CT 06784

  Last Sold Summary

  • 170 Days On Market

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

  

  /37

  $699,900

  • 3 Beds
  • 2.5 Baths
  • 2,142 Sq Ft

  19 Candleview Dr, Sherman, CT 06784

  Welcome to Deer Run Shores, one of Candlewood Lake's most sought after lake communities! Situated on just under an acre, this beautifully maintained Colonial offers 3 bedrooms plus a private office that can easily serve as a fourth bedroom, 2.5 bathrooms, and a thoughtfully designed floor plan perfect for everyday living and entertaining. The main level features gleaming hardwood floors, a formal

  Matt Rose Keller Williams Realty

  19 Candleview Dr, Sherman, CT 06784
• 

  $560,000

  Sold Oct 30, 2025

  15 Wagon Wheel Rd, Sherman, CT 06784

  • 1 Bed
  • 1.5 Baths
  • 3,100 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $181/SF
  • 13 Days On Market

  Current Estimated Value $603,198

  Last Listing Agent Katherine Bennett William Pitt Sotheby's Int'l

  15 Wagon Wheel Rd, Sherman, CT 06784
• 

  Est $1,050,356

  Not Listed For Sale

  24 Candleview Dr, Sherman, CT 06784

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft
  • Built 1994

  24 Candleview Dr, Sherman, CT 06784

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l
• 

  

  /10

  $369,000

  • Land
  • 7.4 Acres
  • $49,865 per Acre

  8A Taber Rd, Sherman, CT 06784

  TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 7.4 ACRES means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both

  Kathleen Harrison Coldwell Banker Realty

  8A Taber Rd, Sherman, CT 06784
• 

  $761,500

  Sold Sep 23, 2025

  79 Route 39 N, Sherman, CT 06784

  • 4 Beds
  • 2.5 Baths
  • 3,144 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 491 Days On Market

  Current Estimated Value $834,112

  Last Listing Agent Joe Chemero Coldwell Banker Realty

  79 Route 39 N, Sherman, CT 06784
• 

  Est $722,967

  Not Listed For Sale

  1 Mary Bee Ln, Sherman, CT 06784

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

  1 Mary Bee Ln, Sherman, CT 06784

  Last Sold Summary

  • 196 Days On Market

  Last Listing Agent Joe Chemero Coldwell Banker Realty
• 

  

  /38

  $1,399,000

  $300K PRICE DROP

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

  6 Brinsmade Ln, Sherman, CT 06784

  Enjoy the best of country and lake living at this exceptional private estate in Sherman, CT, just 90 minutes from NYC and moments from Candlewood Lake with beach and boat rights. The pool is open and ready for summer fun! Originally the historic Brinsmade Dairy Farm, this remarkable property blends timeless New England charm with modern comfort. Set on two lots with three buildings-the Main

  Ginny Gordon-O’Neill William Raveis Real Estate

  6 Brinsmade Ln, Sherman, CT 06784
• 

  $410,000

  Sold Jul 10, 2026

  4 Pepper Pond Rd, Sherman, CT 06784

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $388/SF
  • 28 Days On Market

  Current Estimated Value $424,313

  Last Listing Agent Liz Pepin Luks Realty

  4 Pepper Pond Rd, Sherman, CT 06784
• 

  Est $626,094

  Not Listed For Sale

  5 Ledgewood Dr, Sherman, CT 06784

  • 4 Beds
  • 3 Baths
  • 1,458 Sq Ft
  • Built 1972

  5 Ledgewood Dr, Sherman, CT 06784

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Liz Pepin Luks Realty
• 

  

  /40

  $1,100,000

  Under Contract

  • 5 Beds
  • 3.5 Baths
  • 3,136 Sq Ft

  2 Hollow Brook Rd, Sherman, CT 06784

  Impeccably maintained home in desirable Southern Sherman on 3.8 private, flat acres, right along the CT/ NY border. Welcome to 2 Hollow Brook Road! A rare find where every major mechanical, structural and cosmetic update has already been expertly handled. Truly turn-key and ready for its next chapter. This meticulously updated home blends smart infrastructure with a resort-style backyard. Inside

  Donna Kennedy Compass Connecticut, LLC

  2 Hollow Brook Rd, Sherman, CT 06784
• 

  $930,000

  Sold Jun 01, 2026

  29 Farm Rd, Sherman, CT 06784

  • 3 Beds
  • 2.5 Baths
  • 2,314 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $402/SF
  • 53 Days On Market

  Current Estimated Value $922,944

  Last Listing Agent Angelina Valentini Coldwell Banker Realty

  29 Farm Rd, Sherman, CT 06784
• 

  Est $730,002

  Not Listed For Sale

  2 Mary Bee Ln, Sherman, CT 06784

  • 3 Beds
  • 4 Baths
  • 2,052 Sq Ft
  • Built 2002

  2 Mary Bee Ln, Sherman, CT 06784

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Joseph Perun Perun Properties
• 

  

  /40

  $900,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft

  15 Brinsmade Ln, Sherman, CT 06784

  Mid-Century Modern Ranch on 4.4 Private Acres in Sherman, CT. Minutes from town center and Candlewood Lake, and just a scenic 90-minute drive from NYC. This one-of-a-kind home delivers style, privacy and serious entertaining space. A newly renovated kitchen (2023) features Bertazzoni appliances, Moroccan terrazzo flooring and leather-finished granite counters. The primary suite offers a fireplace

  Donna Kennedy Compass Connecticut, LLC

  15 Brinsmade Ln, Sherman, CT 06784
• 

  $1,700,000

  Sold May 07, 2026

  2 Sail Harbour Dr, Sherman, CT 06784

  • 4 Beds
  • 4 Baths
  • 5,041 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $337/SF
  • 34 Days On Market

  Current Estimated Value $1,689,835

  Last Listing Agent Barbara Sivba Coldwell Banker Realty

  2 Sail Harbour Dr, Sherman, CT 06784
• 

  Est $3,578,524

  Not Listed For Sale

  9 Orchard Rest Rd, Sherman, CT 06784

  • 4 Beds
  • 5 Baths
  • 4,048 Sq Ft
  • Built 2012

  9 Orchard Rest Rd, Sherman, CT 06784

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Barbara Sivba Coldwell Banker Realty
• 

  

  /34

  $1,880,000

  • 2 Beds
  • 2 Baths
  • 2,235 Sq Ft

  40 Sunset Dr, Sherman, CT 06784

  Rare opportunity to own a unique waterfront home in the desirable Candlewood Lake Estates. Loved by the same family for over 50 years, this 5 bedroom, 3 bath mid-century was designed in the 1960s as a passive solar home and offers amazing lake views from nearly every room. 310 feet of direct shoreline, a private dock and a spacious grassy area...perfect for relaxing, entertaining and enjoying

  Barbara Jacobowitz Luks Realty

  40 Sunset Dr, Sherman, CT 06784
• 

  $847,000

  Sold Jan 30, 2026

  18 Fox Run, Sherman, CT 06784

  • 3 Beds
  • 2.5 Baths
  • 3,474 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 12 Days On Market

  Current Estimated Value $903,024

  Last Listing Agent Judith 'Judy' Albert Berkshire Hathaway NE Prop.

  18 Fox Run, Sherman, CT 06784
• 

  Est $613,441

  Not Listed For Sale

  6 Candleview Dr, Sherman, CT 06784

  • 3 Beds
  • 2.5 Baths
  • 1,344 Sq Ft
  • Built 1967

  6 Candleview Dr, Sherman, CT 06784

  Last Sold Summary

  • 31 Days On Market

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

  

  /27

  $879,000

  New Construction $70K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  86 Route 37 S, Sherman, CT 06784

  COMPLETED New Construction!! Quick closing available. Custom 4 bedroom colonial with lots of upgrades. 9 Ft ceilings on the main level. Propane heat and central air. Fireplace. Center island kitchen. Large dinette/breakfast nook. Hardwood floors throughout. Oversized deck. Primary with awesome bath and walk in closet with custom built ins. Beautiful tile and glass shower doors. Convenient upper

  Joe Chemero Coldwell Banker Realty

  86 Route 37 S, Sherman, CT 06784
• 

  $175,000

  Sold Oct 27, 2025

  18 Candlewood Lake Dr, Sherman, CT 06784

  • Land
  • 21,780 Sq Ft
  • $350,000 per Acre

  Last Sold Summary

  • 26 Days On Market

  Current Estimated Value $198,000

  Last Listing Agent Melissa Gordon Coldwell Banker Realty

  18 Candlewood Lake Dr, Sherman, CT 06784
• 

  Est $696,881

  Not Listed For Sale

  13 Orchard Beach Rd, Sherman, CT 06784

  • 2 Beds
  • 1 Bath
  • 2,190 Sq Ft
  • Built 1960

  13 Orchard Beach Rd, Sherman, CT 06784

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent John Casey Coldwell Banker Realty
• 

  

  /25

  $299,000

  • Land
  • 5.46 Acres
  • $54,762 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
• 

  $2,000,000

  Sold Jun 15, 2026

  5 Upland Pastures Rd, Sherman, CT 06784

  • 5 Beds
  • 4.5 Baths
  • 4,250 Sq Ft
  • Built 2022

  Last Sold Summary

  • $471/SF
  • 32 Days On Market

  Current Estimated Value $1,973,482

  Last Listing Agent Kathleen Harrison Coldwell Banker Realty

  5 Upland Pastures Rd, Sherman, CT 06784
• 

  Est $712,264

  Not Listed For Sale

  5 Orchard Beach Rd, Sherman, CT 06784

  • 2 Beds
  • 1.5 Baths
  • 1,640 Sq Ft
  • Built 1974

  5 Orchard Beach Rd, Sherman, CT 06784

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Barbara Sivba Coldwell Banker Realty
• 

  

  /5

  $1,350,000

  • Land
  • 110 Acres
  • $12,273 per Acre

  00 Anderson Rd, Sherman, CT 06784

  A rare 110-acre offering in Sherman, CT, where open skies and eastern-facing views create a truly peaceful setting. Whether you're envisioning a private estate, family compound, or future development, this property offers endless potential. Ideally located close to town and just a short drive to NYC, it strikes the perfect balance between seclusion and accessibility. With subdivision potential

  Carolyn Morrison William Pitt Sotheby's Int'l

  00 Anderson Rd, Sherman, CT 06784
• 

  $915,000

  Sold May 20, 2026

  45 Big Trail, Sherman, CT 06784

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Above List Price
  • $428/SF
  • 3 Days On Market

  Current Estimated Value $886,303

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

  45 Big Trail, Sherman, CT 06784
• 

  Est $2,786,188

  Not Listed For Sale

  33 Orchard Rest Rd, Sherman, CT 06784

  • 4 Beds
  • 3.5 Baths
  • 4,328 Sq Ft
  • Built 1979

  33 Orchard Rest Rd, Sherman, CT 06784

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Barbara Sivba Coldwell Banker Realty
• 

  

  /27

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 2,562 Sq Ft

  6 Fox Run, Sherman, CT 06784

  Nestled on nearly 5 acres of picturesque countryside, this 3-bedroom, 2.5-bathroom home delivers the rare and coveted balance of dense, private woodlands and big-sky pastoral meadow views. Offering approximately 2,445 square feet of light-filled living space, this sanctuary provides a seamless blend of everyday comfort, natural beauty, and thoughtful accessibility. Step inside to an inviting

  Michelle J. Hansen William Raveis Real Estate

  6 Fox Run, Sherman, CT 06784
• 

  $554,000

  Sold Oct 31, 2025

  4 Mary Bee Ln, Sherman, CT 06784

  • 3 Beds
  • 2 Baths
  • 1,189 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Above List Price
  • $466/SF
  • 6 Days On Market

  Current Estimated Value $587,022

  Last Listing Agent Barbara Jacobowitz Luks Realty

  4 Mary Bee Ln, Sherman, CT 06784
• 

  Est $341,792

  Not Listed For Sale

  129 Route 37 S, Sherman, CT 06784

  • 2 Beds
  • 1 Bath
  • 1,429 Sq Ft
  • Built 1900

  129 Route 37 S, Sherman, CT 06784

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Cory Neumann Houlihan Lawrence
• 

  

  /39

  $689,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  10 Candleview Dr, Sherman, CT 06784

  Welcome to 10 Candleview Drive, a beautifully renovated home in the highly sought-after Deer Run Shores community on Candlewood Lake. Thoughtfully updated from top to bottom, this move-in-ready property offers the perfect blend of modern luxury, lake living, and convenient access to New York City. Step inside to discover a stunning new designer kitchen featuring premium finishes, custom

  Gregory Balek Showcase Realty, Inc.

  10 Candleview Dr, Sherman, CT 06784
• 

  $670,000

  Sold Jan 30, 2026

  7 Ridge Rd, Sherman, CT 06784

  • 3 Beds
  • 4 Baths
  • 2,450 Sq Ft
  • Built 1974

  Last Sold Summary

  • $273/SF
  • 59 Days On Market

  Current Estimated Value $697,774

  Last Listing Agent Beth Simon William Raveis Real Estate

  7 Ridge Rd, Sherman, CT 06784
• 

  Est $377,720

  Not Listed For Sale

  20 Skyline Dr, Sherman, CT 06784

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft
  • Built 1955

  20 Skyline Dr, Sherman, CT 06784

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Bill Hunniford Coldwell Banker Realty
• 

  

  /32

  $339,900

  Open Sat 12PM - 2PM $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,066 Sq Ft

  123 Route 37 S, Sherman, CT 06784

  This 1890 Cape-style residence in Sherman, CT, offers a combination of historic charm and updated features. The interior includes hardwood floors throughout and two fireplaces. The kitchen is equipped with granite countertops, an updated dishwasher, and a modern range. The property features double-insulated windows in both the home and the expansive garage. Climate control is managed by forced

  Carol Riley Berkshire Hathaway NE Prop.

  123 Route 37 S, Sherman, CT 06784
• 

  $180,000

  Sold May 19, 2026

  64 Skyline Dr, Sherman, CT 06784

  • Land
  • 1.96 Acres
  • $91,837 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 33 Days On Market

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  64 Skyline Dr, Sherman, CT 06784

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