Sherman, CT Homes

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  $1,250,000

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft

  2 Coburn Road W, She Coburn Rd W, Sherman, NY 06784

  Discover the rare opportunity to build your custom modern ranch in the tranquil countryside of Sherman, Connecticut, just minutes from the New York line. Nestled on a private, wooded 1.02-acre lot in the exclusive Timber Trails area, this to-be-built contemporary home blends sleek design with serene living. Built by renowned SHERMAN BUILDING DESIGNS, every element will reflect the latest in

  Chelsea Stinson Coldwell Banker Realty

  2 Coburn Road W, She Coburn Rd W, Sherman, NY 06784
• Explore Sherman

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  /15

  $2,000 total monthly price

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

  17 Curtis Dr, Sherman, CT 06784

  Welcome to 17 Curtis Drive, a private and charming 1-bedroom, 1-bath studio apartment, nestled on a quiet cul-de-sac in the picturesque town of Sherman, CT. Perfectly blending rustic charm with modern comfort, this recently renovated home offers a warm and inviting escape surrounded by nature. Set on a beautifully wooded 2.03-acre lot, this apartment sits above the garage with its own private

  

  Shaylene Neumann

  Houlihan Lawrence

  (860) 606-4367

  17 Curtis Dr, Sherman, CT 06784
• 

  $560,000 Sold Oct 30, 2025

  • 3,100 Sq Ft
  • $181/SF
  • 13 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1967

  15 Wagon Wheel Rd, Sherman, CT 06784

  Fixer upper on waterfront lot with approximately 100 feet on Squantz Pond! Gorgeous location on beautiful Wagon Wheel Road with views and level access to lake. A diamond in the rough. Large open two-story floor plan on main level with extra loft space on second level. Oversized windows offer beautiful views. A level walk into the water, great for fishing, kayaking, canoeing and just enjoying the

  Katherine Bennett William Pitt Sotheby's Int'l

  15 Wagon Wheel Rd, Sherman, CT 06784
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  Est $832,262 Not Listed For Sale

  23 Wagon Wheel Rd, Sherman, CT 06784

  23 Wagon Wheel Rd, Sherman, CT 06784
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  /38

  $1,595,000

  • 3 Beds
  • 2.5 Baths
  • 3,020 Sq Ft

  35 Skyline Dr, Sherman, CT 06784

  It's All About the Views! Surrounded by lake views, 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 bedroom,2.5 bath custom designed home with multilevel wrap decks & balconies and an oversized bonus room for great family fun center or studio for the

  Barbara Sivba Coldwell Banker Realty

  35 Skyline Dr, Sherman, CT 06784
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  $4,600 total monthly price

  • 4 Beds
  • 3 Baths
  • 2,252 Sq Ft
  • House for Rent

  58 Big Trail, Sherman, CT 06784

  Built in 2022, this ulta chic Colonial lies just 90 minutes from Manhattan and zoned to recently constructed New Fairfield High School. Don't overthink this one - Our home's measure in efficiency, curb appeal, location and value is unparalleled. Delicately customized and designed from the foundation up, each inch oozes 'Home' with purpose. Selective finishes throughout, Discover details in the

  Kyle Neumann Houlihan Lawrence

  58 Big Trail, Sherman, CT 06784
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  $175,000 Sold Oct 27, 2025

  • Land
  • 0.5 Acre
  • $350,000 per Acre

  • 26 Days On Market

  18 Candlewood Lake Dr, Sherman, CT 06784

  Exclusive Opportunity in Sherman, CT: Build Your Dream Home on Candlewood Lake Estates Prime Building Lot with Partial Candlewood Lake Views - Just Steps from Beach and Docks Discover the ultimate lakeside lifestyle in the prestigious, gated community of Candlewood Lake Estates. This rare 4-bedroom home site is fully approved and ready for your floorplans, offering unparalleled convenience and

  Melissa Gordon Coldwell Banker Realty

  18 Candlewood Lake Dr, Sherman, CT 06784
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  Est $99,622 Not Listed For Sale

  1 Lakeview Dr, New Fairfield, CT 06812

  1 Lakeview Dr, New Fairfield, CT 06812
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  /40

  $1,600,000

  • 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
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  /13

  $3,600 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,186 Sq Ft
  • House for Rent

  17 Pinewood Shores, Sherman, CT 06784

  Enjoy the lake life all year long! Sit on your private dock and swim, fish, kayak, paddleboard- ice skate in the winter. Watch the seasons unfold before your eyes. 3 bedrooms plus an office 2 full baths and fully equipped home with western exposure for long days and a firepit for cozy nights. Big deck, sandy beach and level yard for fun and games. This is a perfect yearly rental to make special

  Cory Neumann Houlihan Lawrence

  17 Pinewood Shores, Sherman, CT 06784
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  $205,000 Sold Oct 09, 2025

  • Land
  • 4.07 Acres
  • $50,369 per Acre

  • 175 Days On Market

  3-20 Wagon Wheel Rd, Sherman, CT 06784

  Discover the tranquil allure of Southern Sherman on this 4 acre property, just a serene 69-mile drive from NYC. Enveloped in the soothing sounds of Glen Brook as it gracefully flows into the picturesque expanse of Squantz Pond, this offering comprises two distinct parcels melded into one idyllic retreat. 20 Wagon Wheel (2.04 acres) and 3 Wagon Wheel (2.03 acres) totaling 4.07 acres. # 20 is an

  Donna Kennedy Keller Williams Realty

  3-20 Wagon Wheel Rd, Sherman, CT 06784
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  Not Listed For Sale

  5 Crooked Furrows Ln, Sherman, CT 06784

  5 Crooked Furrows Ln, Sherman, CT 06784
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  /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
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  $4,000 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,247 Sq Ft
  • House for Rent

  18 Pinewood Shores, Sherman, CT 06784

  Pull into the end of the cul-de-sac and enjoy your just under half acre of privacy with 100' DIRECT LEVEL WATERFRONT on Squantz Pond in the private lake community of Pinewood Shores. Pinewood Shores has a community beach to socialize or embrace the privacy and exclusivity of lakefront living w/your own large private sandy beach with large dock for multiple water toys. Easy living in this

  Courtney Smith Houlihan Lawrence

  18 Pinewood Shores, Sherman, CT 06784
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  $640,000 Sold Oct 01, 2025

  • 1,896 Sq Ft
  • $338/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  4 Wanzer Hill Rd, Sherman, CT 06784

  Near the natural beauty of Candlewood Lake, Squantz Pond, and a nearby state park, this 1,896 sq ft 3-bedroom, 2.5-bath home offers an open layout featuring a stunning kitchen with a large center island and brand-new stainless steel appliances, dining room with sliding doors for additional outdoor seating and entertaining. The spacious living room is warm and welcoming with a cozy wood stove. The

  Rosalia Casorla Premier Re Group LLC

  4 Wanzer Hill Rd, Sherman, CT 06784
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  Est $182,759 Not Listed For Sale

  • 4 Beds

  7 River Bend Ln, Sherman, CT 06784

  7 River Bend Ln, Sherman, CT 06784
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  /29

  $1,049,000

  • 4 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  42 Long River Rd, Sherman, CT 06784

  Spend your summer in this beautiful, gated community playing golf on the signature 18-hole course, enjoying a game of tennis or swimming in the heated in ground pool. There is full-service club house complete with a pro shop, pub and restaurant. You can enjoy dining on the patio that overlooks the greens. Inquire about membership details. The home is ready for immediate occupancy, so come up and

  Cynthia Szentkuti Ridgefield Homes Realty

  42 Long River Rd, Sherman, CT 06784
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  /16

  $2,100 total monthly price

  • 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
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  $630,000 Sold Sep 29, 2025

  • 3,608 Sq Ft
  • $175/SF
  • 61 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1975

  2 Bridgeworth Ln, Sherman, CT 06784

  A fabulous investment! An elegant, well appointed colonial offering endless possibilities in the heart of Sherman's desirable 06784 area code. Features include a 20x40 Gunite pool, three room finished basement, a primary suit with three walk in closets, whole house generator, partial AC, attached two car garage and separate storage shed, spacious entry mud room with washer/dryer and high ceilings

  Rebecca Ward William Pitt Sotheby's Int'l

  2 Bridgeworth Ln, Sherman, CT 06784
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  Est $1,111,580 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  32 Big Trail, Sherman, CT 06784

  32 Big Trail, Sherman, CT 06784
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  /38

  $1,225,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 4,509 Sq Ft

  2 Autumn Dr, Sherman, CT 06784

  Tucked away on a private enclave of homes in desirable Southern Sherman, just minutes from the NY line, this stunning residence offers the perfect blend of seclusion, luxury and convenience for year-round living, weekend and summer escapes from the city. A very special property interior designed and decorated by AlvinYorkDesign of NYC, this is nothing short of exceptional, blending comfort with

  Angelina Valentini Coldwell Banker Realty

  2 Autumn Dr, Sherman, CT 06784
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  $761,500 Sold Sep 23, 2025

  • 3,144 Sq Ft
  • $242/SF
  • 491 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  79 Route 39 N, Sherman, CT 06784

  Open and airy 4 bedroom contemporay home sitting pretty with privacy and views on 3.3 acres. Open layout features soaring ceilings and plenty of windows. Sunken 2 story family room with stone fireplace. Large eat in kitchen. Main level office. 2 car attached garage with easy access through mudroom. Hardwood floors. Newer minisplits for efficient heat and air conditioning. 4 bedrooms all with

  Joe Chemero Coldwell Banker Realty

  79 Route 39 N, Sherman, CT 06784
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  Est $865,016 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  27 Skyline Dr, Sherman, CT 06784

  27 Skyline Dr, Sherman, CT 06784
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  /40

  $670,000

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

  7 Ridge Rd, Sherman, CT 06784

  Don't be fooled by first glances, When you pull into the driveway you will see a sweet log home in a peaceful and private landscape, what you don't see is the large newer thoughtful Architect designed addition on the north side of the house. This is the heart of Sherman, a short walk to the store, school, park and library. Charm and character through out ! There is a country kitchen with lots of

  Beth Simon William Raveis Real Estate

  7 Ridge Rd, Sherman, CT 06784
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  $2,225,000 Sold Sep 16, 2025

  • 5,990 Sq Ft
  • $371/SF
  • 185 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 2021

  Unlisted Address

  This pristine, like new estate home sits majestically on 10+ acres on the historic Atchison Farm homestead in rural Sherman CT. Sited for picture perfect panoramic views of the surrounding hills, the main house, built in 2021, has been very lightly used so is in mint condition! With a seven bedroom septic, the rooms laid out off of a beautiful wide central upstairs hall can have multiple uses

  Richard Pomerantz William Pitt Sotheby's Int'l

  Unlisted Address
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  Est $1,203,152 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,561 Sq Ft

  7 Cozier Hill Rd, Sherman, CT 06784

  7 Cozier Hill Rd, Sherman, CT 06784
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  /40

  $1,849,000

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

  0 Brinsmade Ln, Sherman, CT 06784

  Discover this wonderful estate, formerly Brinsmade Farm, in Sherman, Connecticut, offered for the first time in 60 years. Set on approximately 10 scenic acres in the heart of charming Sherman, this exceptional country home combines timeless New England charm with modern living. Originally a working dairy farm, the property was transformed in 1945 when the barn became a private residence. The

  Ginny Gordon-O’Neill William Raveis Real Estate

  0 Brinsmade Ln, Sherman, CT 06784
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  $800,000 Sold Sep 15, 2025

  • 3,973 Sq Ft
  • $201/SF
  • 106 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  70 Wakeman Hill Rd, Sherman, CT 06784

  Location Location Location! 5.6+ Flat Private Sherman Acres on the New York Border with low Taxes. This Spacious 4 Bedroom 4135 sq ft Colonial has Plenty to Offer. Large Living Area Perfect for Entertaining with Custom Kitchen, Piped Propane for Outside Grill, 2 Story Foyer, Primary Bedroom with Sitting Room and New Jet Soaker Tub. Home Conveniently Offers an Automatic Standby Generator. Tons of

  Joseph Perun Perun Properties

  70 Wakeman Hill Rd, Sherman, CT 06784
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  Est $1,198,852 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,035 Sq Ft

  4 Wakeman Hill Rd, Sherman, CT 06784

  4 Wakeman Hill Rd, Sherman, CT 06784
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  /5

  $631,750

  • 4 Beds
  • 5 Baths
  • 5,342 Sq Ft

  7 Glenview Dr, Sherman, CT 06784

  Contemporary home located on a cul de sac. Property is currently occupied and the occupants are not to be disturbed. Property will be sold as is on a reserve auction site. Review all terms on the auction site. Cash only or a hard money loan. This property is now under auction terms. All Bids must be submitted during the auction via the property's listing page at www.servicelinkauction.com. This

  Leslie Brent Coldwell Banker Realty

  7 Glenview Dr, Sherman, CT 06784
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  $475,000 Sold Sep 15, 2025

  • 1,860 Sq Ft
  • $255/SF
  • 134 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  10 Meadow Ln, Sherman, CT 06784

  Cape on level lot in great location on the New York border. So much potential. 2 car attached garage. Main level primary bedroom. Sunroom. Fireplace with wood stove. Walkout basement. 4 bedrooms and 2.5 baths. Lots of character and storage galore. Sale is subject to probate approval and being sold as is.

  Joe Chemero Coldwell Banker Realty

  10 Meadow Ln, Sherman, CT 06784
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  Est $698,034 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,648 Sq Ft

  19 Wakeman Hill Rd, Sherman, CT 06784

  19 Wakeman Hill Rd, Sherman, CT 06784
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  /16

  $250,000

  • Land
  • 1.02 Acres
  • $245,098 per Acre

  2 Coburn Rd W, Sherman, CT 06784

  Absolute Privacy Tucked Away on 1+ Acre in true nature setting- abuts open space. POTENTIAL FOR VIEWS EAST TOWARD TIMBER LAKE. This approved building lot offers an acceptional opportunity awaits a savvy buyer to create their own personal retreat in the small Town of Sherman. Test work completed with approved 4 BDRM Septic Plan. Driveway is 1600 ft long, passiing through a majestic pond at the

  Kathleen Harrison Coldwell Banker Realty

  2 Coburn Rd W, Sherman, CT 06784
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  $550,000 Sold Sep 05, 2025

  • 2,239 Sq Ft
  • $246/SF
  • 175 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1950

  2 Oak Dr, Sherman, CT 06784

  Seller is motivated to sell! Welcome to 2 Oak Drive in Sherman, a charming 4-bedroom, 2-bathroom with your own private dock! Don't worry about finding a marina or using the town launch, you have a private dock slip steps away. This home is nestled in the coveted Holiday Point Association. This inviting residence features newly remodeled bathrooms with both modern elegance and comfort. The

  Gary Crawford RE/MAX RISE

  2 Oak Dr, Sherman, CT 06784
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  Est $714,456 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  4 Bridgeworth Ln, Sherman, CT 06784

  4 Bridgeworth Ln, Sherman, CT 06784
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  /40

  $3,795,000

  • 4 Beds
  • 6 Baths
  • 6,704 Sq Ft

  5 Sail Harbour Dr, Sherman, CT 06784

  Grand FULLY FURNISHED 6,700 SF Mediterranean, direct waterfront on two seriously private acres in Sail Harbor Club. Entertainer's paradise offers unlimited possibilities. Dramatic NEW 26x13 Sun Room displays exciting wall of glass that overlooks NEW 36x14 porcelain tiled deck above sprawling NEW 39x21 covered porcelain tiled patio. NEW 90' deck surrounds 45' saltwater gunite pool having its own

  Paul Valeri Paul Valeri, Realtors

  5 Sail Harbour Dr, Sherman, CT 06784
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  $675,000 Sold Aug 15, 2025

  • 2,500 Sq Ft
  • $270/SF
  • 42 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  1 Quaker Ridge Rd, Sherman, CT 06784

  Nestled just minutes fm New York border, this beautiful home offers serene retreat surrounded by rolling farmland & verdant hills. Set on lush, level landscaped acreage, the property is bordered by mature flowering trees providing exceptional privacy & peaceful natural views. Sun-filled Classic Colonial-style home offers a welcoming layout. Main lvl features frml living & dining rms, spacious

  Shalini Madaras Silver Pine Real Estate

  1 Quaker Ridge Rd, Sherman, CT 06784
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  Est $646,923 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  9 Meadow Ln, Sherman, CT 06784

  9 Meadow Ln, Sherman, CT 06784
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  /40

  $869,900

  • 4 Beds
  • 2.5 Baths
  • 2,613 Sq Ft

  5 Bridgeworth Ln, Sherman, CT 06784

  Welcome to this striking Cape/Colonial nestled on a picture-perfect, dead-level parcel in one of Sherman's most desirable locations. With timeless curb appeal featuring classic wood clapboard siding and a charming cedar shingle roof, this home effortlessly blends character, comfort, and functionality. Step inside to discover a warm and inviting interior. The spacious family room is a true

  Cory Neumann Houlihan Lawrence

  5 Bridgeworth Ln, Sherman, CT 06784
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  $540,000 Sold Jul 31, 2025

  • 1,560 Sq Ft
  • $346/SF
  • 22 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  135 Green Pond Rd, Sherman, CT 06784

  You Can Have It All - Lake Living at Its Finest! Don't miss this incredible opportunity in Candlewood Lake Estates, a gated water community in scenic Sherman, CT. This 3-bedroom, 3-bath ranch offers over 1,500 sq ft of finished living space, with an additional 450 sq ft ready to be transformed into whatever you imagine-home gym, office, or guest suite! The real draw? Access to four private

  Todd Sargent Coldwell Banker Realty

  135 Green Pond Rd, Sherman, CT 06784

Showing Results 1 - 40, Page 1 of 18