Sherman, CT Homes

• 

  Est $951,002

  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
• 

  

  

  /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
• 

  $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 $215,600

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  10 Chimney Hill Rd, Sherman, CT 06784
• 

  Est $645,608

  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
• 

  

  

  /40

  $900,000

  Pending

  • 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
• 

  $1,637,500

  Sold Jul 16, 2025

  12 Meadow Ln, Sherman, CT 06784

  • 4 Beds
  • 3.5 Baths
  • 4,486 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Below List Price
  • $365/SF
  • 131 Days On Market

  Current Estimated Value $1,480,053

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC

  12 Meadow Ln, Sherman, CT 06784
• 

  Est $577,280

  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
• 

  

  /38

  $1,499,000

  $200K PRICE DROP

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

  6 Brinsmade Ln, Sherman, CT 06784

  Price has been improved for you to enjoy this exceptional private country 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. Formerly the historic Brinsmade Dairy Farm, this remarkable property blends timeless New England charm with modern comfort and exceptional versatility. Comprising three

  Ginny Gordon-O’Neill William Raveis Real Estate

  6 Brinsmade Ln, 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 $573,839

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

  15 Wagon Wheel Rd, Sherman, CT 06784
• 

  Est $657,250

  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
• 

  

  /40

  $1,100,000

  • 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
• 

  $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 $777,918

  Last Listing Agent Joe Chemero Coldwell Banker Realty

  79 Route 39 N, Sherman, CT 06784
• 

  Est $3,124,348

  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
• 

  

  /34

  $425,000

  Pending

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

  4 Pepper Pond Rd, Sherman, CT 06784

  Welcome to rustic Timber Trails and Pepper Pond Road, located in southern Sherman, CT, near the New Fairfield and New York state border, offering a peaceful back-to-nature setting. Techbuilt home, part of the iconic mid-century modern prefabricated designs by architect Carl Koch, blends timeless character with warmth and functionality. Hardwood floors throughout, while the living room is flooded

  Liz Pepin Luks Realty

  4 Pepper Pond 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 $938,757

  Last Listing Agent Angelina Valentini Coldwell Banker Realty

  29 Farm Rd, Sherman, CT 06784
• 

  Est $555,253

  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
• 

  

  /27

  $949,000

  New Construction

  • 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
• 

  $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 $1,782,460

  Last Listing Agent Barbara Sivba Coldwell Banker Realty

  2 Sail Harbour Dr, Sherman, CT 06784
• 

  Est $621,599

  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
• 

  

  /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
• 

  $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 $839,770

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

  18 Fox Run, Sherman, CT 06784
• 

  Est $640,580

  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
• 

  

  /36

  $873,999

  $26K PRICE DROP

  • 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

  Gary Crawford RE/MAX RISE

  25 Hillside Dr, 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 $189,000

  Last Listing Agent Melissa Gordon Coldwell Banker Realty

  18 Candlewood Lake Dr, Sherman, CT 06784
• 

  Est $2,477,363

  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
• 

  

  /39

  $699,900

  • 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
• 

  $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 $1,985,817

  Last Listing Agent Kathleen Harrison Coldwell Banker Realty

  5 Upland Pastures Rd, Sherman, CT 06784
• 

  Est $350,484

  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
• 

  

  /31

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 3,247 Sq Ft

  73 Long River Rd, Sherman, CT 06784

  This elegant four-bedroom home, built in 2021, is perfectly sited on 1.8 acres of professionally landscaped, private grounds. Designed for effortless single-level living, it features an open-concept layout with a chef's kitchen and center island, a welcoming living room with fireplace, and a sunlit dining area that all flows seamlessly to a covered porch with views toward the Housatonic River.

  Steve Pener William Pitt Sotheby's Int'l

  73 Long River 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 $832,622

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

  45 Big Trail, Sherman, CT 06784
• 

  Est $624,441

  Not Listed For Sale

  8 Glenview Dr, Sherman, CT 06784

  • 4 Beds
  • 2.5 Baths
  • 2,662 Sq Ft
  • Built 1977

  8 Glenview Dr, Sherman, CT 06784

  Last Sold Summary

  • 40 Days On Market
• 

  

  /39

  $1,195,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  131 Route 39 N, Sherman, CT 06784

  Instantly inviting this pristine circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with

  Karen Casey William Pitt Sotheby's Int'l

  131 Route 39 N, 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 $551,271

  Last Listing Agent Barbara Jacobowitz Luks Realty

  4 Mary Bee Ln, Sherman, CT 06784
• 

  Est $313,159

  Not Listed For Sale

  123 Route 37 S, Sherman, CT 06784

  • 2 Beds
  • 1 Bath
  • 1,066 Sq Ft
  • Built 1890

  123 Route 37 S, Sherman, CT 06784

  Last Sold Summary

  • 211 Days On Market
• 

  

  /36

  $1,250,000

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

  35 Skyline Dr, Sherman, CT 06784

  It's All About the Views! REDUCED TO SELL on this one of a kind, custom built contemporary with extraordinary 50 mile views in all directions. Client say make 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 a 3

  Barbara Sivba Coldwell Banker Realty

  35 Skyline 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 $656,760

  Last Listing Agent Beth Simon William Raveis Real Estate

  7 Ridge Rd, Sherman, CT 06784
• 

  Est $318,632

  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
• 

  

  /24

  $499,000

  Under Contract

  • Land
  • 14.3 Acres
  • $34,895 per Acre

  5 Brinsmade Ln, Sherman, CT 06784

  FOUNDATION READY BUILD SITE! Down a quiet stretch of road in the quaint town of Sherman a hidden drive leads you away from the world into 14 acres of absolute tranquility. As you walk the land you'll find the remnants of historic stone walls intertwining through the woods. The air is still, save for the rustle of native trees and the quiet life surrounding a private vernal pond. While the land

  Donna Kennedy Compass Connecticut, LLC

  5 Brinsmade Ln, 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
• 

  Est $1,320,178

  Not Listed For Sale

  15 Skyline Dr, Sherman, CT 06784

  • 3 Beds
  • 4 Baths
  • 3,068 Sq Ft
  • Built 2003

  15 Skyline Dr, Sherman, CT 06784

  Last Sold Summary

  • 84 Days On Market

Showing Results 81 - 120, Page 3 of 18