The Matthews TeamWilliam Raveis

The Matthews Team

Sherman CT Real Estate

Sherman Old Store in Connecticut View in Sherman CTThe scenic town of Sherman is located in the Housatonic Valley at the northern end of Candlewood Lake, north of Danbury on the border of New York. Named the “best small town in Connecticut” 3 times by Connecticut Magazine, Sherman is a rural community of 23.4 square miles with a historic downtown listed on the National Register of Historic Places. With a population of 4,106, it is the least populous and northern-most town in Fairfield County, with access to the Appalachian Trail that goes through the Northern end of Sherman. The town is accessed by state routes 39, 37, and 55, and is approximately 70 miles from New York City.

>> Learn more about the town of Sherman, CT

Properties in Sherman

Contact The Matthews Team at 860-868-0511 with any questions or to schedule a private tour.

Time Saving Tip: Sign up for a free account to save your favorite listings and get notified when new properties match your criteria.

Narrow Your Search: Luxury Homes | Homes with Land | Single Family Homes | Land

6 Hoyt Road Sherman CT 06784

Sherman, CT6 Hoyt Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 170448888

  • Single Family
  • Square Feet 1,933
  • Bedrooms 3
  • Year Built 1803
  • Bathroom 2

Welcome to Black Dog Farm, the entrancing treasure of artist Elaine Voghelle. One-of-a-kind, exquisite rebuilt and curated storybook estate. "Beyond renovated” 1803 Antique Eyebrow Colonial Farmhouse. 4.6ac (on Appalachian Trail) NY border of Dutchess County, neighboring Kent. Sprawling multi buildings, 3-lev cottage, garage, sauna/spa & enormous paddock with water/elec. Brought to life by Elaine's remarkable talent, a museum quality home. White Oak HW flrs batched from the MOMA, with almost no grain, ultra-clean palette and rare, as are most materials and the execution of appointments thru out home. Custom handmade Mahogany windows w/mouth blown imported wavy German glass w/state of the art Argon gas. Bronze Metal roofs, snow guards, copulas protect & adorn all structures (new windows,hw flrs,stairs,doors). Chefs' kitchen w/gnarled brass pulls, leather limestone marble & gold counters. Perrin & Rowe faucets. Basement jacked, repointed, trenched. Massive French drain runs length of farm. Meticulous boxwoods line stone walls, walkways, private garden & sauna. Eloquent, pristine, polished retreat designed by the artist in Blackwood Forest, Gustavian style. More uses for buildings w/cathedral ceilings (hobby, working farm) Architecturally alluring, MUST see! A chance to live in perfection. Indescribable true artistic masterpiece & retreat. More pics/videos avail. Extensive upgrade sheet. Crafted with materials intended to outlast another 200 yrs. Located in Fairfield County.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

138 Route 39 North Sherman CT 06784

MLS Number 170456108

  • Land
  • MLS Status Active
  • Acreage 116.37
  • Zoning Zone A

Ultra private parcel abutting Naromi Land Trust. Truly a rare opportunity to own one of the six largest land parcels in Sherman, CT. Gated access off route 39 N leads to 118 private acres with beautiful hilltop views. Long roughed in driveway to two beautiful meadows and the perfect building sites. The perfect mix of majestic estates, open farmland, and acres of land trust surrounding the property. Sub-division potential. Many possibilities. Must see. Located just 90 minutes from NYC and minutes to Kent, Sherman, and Candlewood lake.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Anderson Road Sherman CT 06784

Sherman, CTAnderson Road, Quaker Ridge

Price$1,695,000

Est. Mortgage: $/month

MLS Number 170462429

  • Land
  • MLS Status Active
  • Acreage 110
  • Other Amenities Waterfront
  • Zoning subvision

110-acre property with an approved 18 lot subdivision. Complete privacy and beautiful hilltop view just minutes from Sherman and Kent. A great opportunity for builders and developers. Amazing building opportunity just 90 minutes from NYC. A rare acreage opportunity in Sherman, CT.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Chapel Hill Road Sherman CT 06784

Sherman, CTChapel Hill Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 170456872

  • Land
  • MLS Status Active
  • Subdivision Chapel Hill Estates
  • Acreage 66.37
  • Other Amenities Golf, Waterfront

A rare opportunity has come to market to acquire a hilltop home site on 66 pristine acres bordered by 24 acres of conserved land in historic Sherman, CT. Build your dream escape-from-it-all at over 1,000 feet above sea level. Enjoy commanding views of the countryside & Berkshires from your home, while surrounded by a private forest with babbling brooks. In an already quiet neighborhood, the forest keeps out the sounds of civilization, the sounds of nature are all that remain. Along the hillside several small wetlands feed tumbling rivulets that flow to Glen Brook. The property is a mature hardwood forest that shades an open understory. A substantial capital improvement on the land completed in December 2021: a bridge over Glen Brook with curb cut on Chapel Hill Road & a stone drive over the bridge. The D-shaped property is partially buffered along the perimeter by Glen Brook flowing through the Northwest CT Land Conservancy holdings along the road. Criss-crossed by stone walls & game trails the land is easily walked in any direction. Not developed since the farming days of the 19th century, the natural beauty of the parcel is breathtaking. A previously executed 14 lot subdivision provides strategic options to donate or conserve lots for flexible tax benefits into the future. The surrounding community is sparsely developed with a country estate vibe. Near shopping in New Milford & Danbury. Sherman is a quaint village & is a quick drive to Pawling, NY & its Metro North Station.

Listing Courtesy of McGrath Realty Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

43 Route 37 South Sherman CT 06784

Sherman, CT43 Route 37 South

Price$1,399,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170381377

  • Single Family
  • Square Feet 3,250
  • Bedrooms 4
  • Year Built 1940
  • Bathroom 7

Rare opportunity to own one of the most special and unique properties available on the market anywhere! Secluded yet convenient, this gated 5.42 acre property boasts a historic main residence, guest house and detached, heated 6 car garage with guest quarters/office space. You'll find secret gardens, stone path to a guest house with brook fed swimming hole, mesmerizing brook with water falls, renovated Gunite pool, horseshoe pits and stonewalls, Over $500k of improvements include chef kitchen, bathrooms, windows, doors, blinds, electrical, floors, decks, patio, chimney, metal roofing, siding, fencing, HVAC, electric entry gate, stone walls, walks, bridge, and pool. Main House: 2 en-suite bedrooms, family/media room, 2 half baths. chef kitchen with fireplace, massive living room with vaulted ceilings, unique fireplace finished with Moravian tile and stone, wide plank wood floors, working elevator and wet bar. Hand carved spiral staircase leads to loft and third bedroom. Guest House: Peaceful retreat with bedroom, kitchen, living room and full bath with deck overlooking Glen Brook with swimming hole and water fall. Detached, heated garage: Room for 6+ cars, upstairs guest or caretakers quarters/office/hobby rooms. Perfect for car enthusiast. 90 minutes from Manhattan, low Sherman taxes

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

23 Wagon Wheel Road Sherman CT 06784

Sherman, CT23 Wagon Wheel Road

Price$1,375,000

Est. Mortgage: $/month

MLS Number 170456949

  • Single Family
  • Square Feet 2,462
  • Year Built 2022
  • Bedrooms 4
  • Bathroom 3

Premier local builder. Five hundred feet of direct waterfront on Squantz Pond with 3.55 acres of land at the end of a quiet country road. "To be built" gorgeous contemporary farmhouse design with lake views. Open floor plan concept includes kitchen with center island and pantry, large great room with fireplace and generous dining area, leading to rear covered porch. The mud room and laundry area are located at garage entry. The master suite is located on the main level and there is an additional bedroom that can be used as either a bedroom or an office on the main floor. The upper level features two more bedrooms w/jack & jill bath. Optional bonus room that can be used as an additional bedroom, recreation room or simple storage. Main floor offers 12 foot ceilings. At the waterfront, there is an existing structure that can be grandfathered in as a small waterfront shed w/dock. House plans can be modified to your specifications! Generous allowance for kitchen cabinets, appliances, lighting fixtures and landscaping.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

32 Long River Road Sherman CT 06784

Sherman, CT32 Long River Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170372914

  • Single Family
  • Square Feet 3,200
  • Property Style Ranch
  • Bedrooms 4
  • Bathroom 4

Nestled in the rolling hills of Connecticut along the Housatonic River, you will find the area's premier Golf Course Community. River Oaks is a quiet gated community with magnificent homes and properties situated around an 18 hole golf course with captivating views year-round. Just 65 miles north of NYC, River Oaks offers the relaxed experience of a country neighborhood combined with all amenities of a luxury lifestyle close by. Leave the stress behind you as you pass through the gates of this desirable, private residential community. The Prescott is a custom 3200 sf Ranch Style home that features 4 bedrooms, 3.5 baths, Gourmet Kitchen, 3 car attached garage, and sprawling backyard. This new home will allow you to indulge in all that country living has to offer with views overlooking the mountains and 7th fairway of an amazing championship golf course. The Club at River Oaks offers golf memberships for a signature 18-hole private course and social memberships providing tennis, gym, pool, restaurant and so much more. Just one of the many conveniences of the community is the short scenic walk down the road to the luxurious clubhouse full of amenities for all ages. Venture outside of the neighborhood and visit nearby Candlewood Lake, Sherman Town Beach, Bull's Bridge, Kent Falls, Mohawk Ski Mountain, Appalachian Trail, Restaurants and Shopping. Easy 90-minute commute to NYC or minutes to nearby Metro-North train.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

73 Long River Road Sherman CT 06784

Sherman, CT73 Long River Road

Price$1,225,000

Est. Mortgage: $/month

MLS Number 170335863

  • Single Family
  • Square Feet 6,600
  • Property Style Ranch
  • Bedrooms 4
  • Year Built 2021

READY FOR IMMEDIATE OCCUPANCY!! Spend you holidays with views of the Litchfield Hills. Home is located in the the Club at River Oaks, a full service golf community, the only of its kind,. Total 4500 square feet above grade. 3300 heated, 300 unfinished roughed for bath above garage. 900 sq feet of covered porches. Come to the Club at River Oaks in beautiful Sherman, Connecticut. Social membership entitles use of all the amenities you can wish for nestled in the picturesque Litchfield Hills. This home is very private and the back patio has seasonal views of the river. There is room for your own pool or use the one at the club house. Spend your days playing tennis or golf or visit the nearby quaint town of Kent. Beautiful club house with full service bar and restaurant. Outdoor dining on the patio overlooking the golf course. Use of golf course for an additional membership fee. World Class Fly fishing on the Housatonic River is just steps away. Boating, water skiing and swimming on Lake Candlewood just minutes away. Truly living in a vacation area year round. Easy commute to NYC. Agent related to builder.

Listing Courtesy of Ridgefield Homes Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3 Pond View Lane Sherman CT 06784

Sherman, CT3 Pond View Lane

Price$1,199,000

Est. Mortgage: $/month

MLS Number 170336044

  • Single Family
  • Square Feet 3,650
  • Year Built 2021
  • Property Style Colonial
  • Bathroom 4

Welcome to The Club at River Oaks in beautiful Sherman Connecticut. Wonderful golf course lot. Beautiful 5 bedroom custom home. Hardwood floors through out. Gourmet kitchen with granite counter tops. Deck overlooking the golf course. Social membership entitles you to all the amenities you could hope for. Nestled in the picturesque Litchfield Hills. Spend your days playing tennis and then take a dip in the pool Beautiful club house with full service bar and gourmet restaurant. Outdoor dining on the patio overlooking the signature 18 hole golf course. Use of golf course to additional membership fee. World class fly fishing in the Housatonic River just steps away. Enjoy boating water-skiing and swimming on nearby Lake Candlewood. Live in a vacation area year round, easy commute to NYC. Agent related to builder.

Listing Courtesy of Ridgefield Homes Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

201 Route 37 South Sherman CT 06784

MLS Number 170459832

  • Single Family
  • Square Feet 4,258
  • Bathroom 5
  • Property Style Colonial, Antique
  • Bedrooms 6

Formerly The Old Timber Trails Inn, this splendid residence is an absolute dream for the ardent devotee of historically significant antique homes. Situated harmoniously on 1.4 perfectly level private acres, minutes to routes down county or NYC, with wide board chestnut & white pine floors, 2 staircases, a walk-up attic for the writer, artist, au pair and the pool ... oh yes the salt water, Gunite, heated, inground pool includes an outdoor shower and auto cover. The main level floor plan is generous but not overwhelming & perfectly designed for your family needs, entertaining or working from home - don't forget the additional space in the walk-up attic! The HVP kitchen is tastefully updated reflecting today's demands while retaining all the charm of yesterday - soapstone counters, upgraded appliances, stained cabinetry, original fireplace, walk-in pantry/laundry room w wine cellar. Some original light fixtures are included. Combination steam/hot air heat Weil McLean & generator hookup. Oodles of nooks and crannies, built-ins, terrific attic space, lovely grounds, view of the valley lake/pond, ideal location for the commuter and plenty of space for those working from home. Very low Sherman taxes, too!

Listing Courtesy of Luks Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

26 Long River Road Sherman CT 06784

Sherman, CT26 Long River Road

Price$1,184,999

Est. Mortgage: $/month

MLS Number 170336075

  • Single Family
  • Square Feet 3,350
  • Property Style Farm House
  • Bedrooms 4
  • Year Built 2021

READY FOR IMMEDIATE OCCUPANCY!! Spend the holdidays in Connecticut with views of the Litchfield Hills. Contemporary farm house on beautiful lot located in the Club at River Oaks in Sherman, Connecticut. Located in the rolling hills of Litchfield County, the Club at River Oaks has a signature 18 hole golf course, beautiful club house with a full service bar, gourmet restaurant. tennis courts and a pool. A socail membership entitles you to all the amenities you could hope for, an additional fee allows golf course membership as well. The contemporary farm house has an open floor plan, 9+ ceilings on the first floor, hardwood floors throughout and a gourmet kitchen. Buy now while there is still time to customize and make it your own. Gated community call for access.

Listing Courtesy of Ridgefield Homes Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Wagon Wheel Road Sherman CT 06784

MLS Number 170396879

  • Land
  • MLS Status Active
  • Acreage 55.85
  • Waterfront
  • Zoning RA5

55 Wooded Acres along beautiful Wagon Wheel Rd. with 300' +/- Squantz Pond Waterfrontage.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2022 SmartMLS, Inc.