The Matthews Team

William Raveis Lifestyles Realty

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 William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

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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 170465045

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,933
  • Acreage 4.6

Black Dog Farm is nestled along the Appalachian Trail in the beautiful town of Sherman Connecticut (in Fairfield County). Fully modernized and upgraded Equestrian estate (with paddock, barns and guest cottage). Uniquely located on the border of Dutchess County, New York, and also neighboring Kent, in Scenic Litchfield County, Connecticut. So much to tell about this property. Artist owned and exquisitely designed. Call for more details.

Listed by Lisa Fagan of eXp Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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105 Route 39 North Sherman CT 06784

Sherman, CT105 Route 39 North

Price$2,250,000

Est. Mortgage: $/month

MLS Number 170498499

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,765
  • Acreage 5.22

Panoramic, pastoral views overlooking the silos and farm. Eco and energy efficient home with hydro solar panels for heating and hot water. Sleek and polished concrete floors are stunning. A gracious foyer greets you with an open floor plan for modern living. A row of windows to the expansive views, the living room has high ceilings and a bio ethanol fireplace. Top kitchen appliances include Bosch, Kitchen Aid and Wolf with walk-in pantry. Primary suite on the main floor with marble shower, double sink and walk-in closet. 2 additional en-suite bedrooms are nicely privatized on the other end of the house share a den. Office/4th bedroom with laundry on the main floor and powder room. Walk-up attic can be finished and a massive, 3 car, radiant heated garage with 1/2 bath. Bask in the views from the 8 person hot tub, outdoor fireplace with travertine stone patios and your own golf tee! Super efficient home with 12" foam insulated walls provides very low energy costs. Turn-key and move in ready and a quick trip to NYC or to the train. Perfection!

Listed by Joseph Lorino of Klemm Real Estate Inc

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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138 Route 39 North Sherman CT 06784

MLS Number 170499484

  • Land
  • 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.

Listed by Cagney Morrison of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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2 Hubbell Ridge Road Sherman CT 06784

Sherman, CT2 Hubbell Ridge Road

Price$1,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170479565

  • Single Family
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 6,594
  • Acreage 5

Exquisite and spacious country home in the beautiful gated Mill Pond Farms lake community in Sherman. Privately set on 5 acres, the property offers far reaching western view of hilltops, level yard with possible pool location and professional landscaping with an abundance of flowering mountain laurel. The main level consists of cozy living room with fireplace, formal dining room, chef's kitchen, breakfast room, sitting room with window seats, office with half bath, powder room, mudroom and great room. The two-story great room is the highlight of the first floor with two sets of French doors; one opening to spacious bluestone patio and the others feature the amazing view. Just off this room is the den/library with the second fireplace. Upstairs the primary suite is all commanding with two walk-in closets, full bath with two vanities, shower, soaking tub and separate water closet and a charming sitting room in the turret. The south wing of the second floor has three bedrooms all with full baths and its own sitting room. A curved stairwell leads up to the third floor of the turret perfect for an artist's studio, reading room or office has window seats and 180 degree view. In the lower level is the rec room and exercise room. There is central vac, audio system and security system. The association includes beach, dock, tennis and hiking trails. Just 90 minutes from NYC.

Listed by Maria Taylor and Claudine McHugh of Klemm Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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14A Jericho Road North Sherman CT 06784

Sherman, CT14A Jericho Road North

Price$1,650,000

Est. Mortgage: $/month

MLS Number 170460439

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,100
  • Acreage 3.45

New Construction. Fall Completion. 3.45 Private Acres Hosts over 4000 Square Feet of Modern yet Rustic design. Jericho Road North is a Quiet, Scenic Country Lane with Substantial Homes and Estates. Drive down Your Private, Winding Drive to a Beautiful Property with Views and Seclusion. The Home Features Custom Designed Woodwork, Trim and Built ins, High End Appliances, Marvin Elevate Windows, Doors and Sliders, Exterior Barnwood Details, Metal Roofing, Wrap Around Covered Deck. Open Concept Kitchen/Dining/Great Room has Character Grade Wide Oak Flooring, Soap Stone Fireplace. Main Floor Master Suite Features 500 Square Feet with Vaulted Ceilings, Free Standing Tub, Walk-in Shower and Custom-Built Vanities. Upper Level has a 200 Square Foot Loft, an En-suite Bedroom and a Two more Bedrooms Sharing a Jack and Jill Bath. The Lower Level has a Full Bath and is Finished for use as a Rec/Playroom or could be a Fifth Bedroom. Heated 3 Car Garage with finished, heated, Bonus Room above. Sherman Schools, Close to Town Center, Candlewood Lake. 90 Minutes from Manhattan, Convenient to Trains

Listed by Bill Hunniford of Coldwell Banker Realty

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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3 Pond View Lane Sherman CT 06784

Sherman, CT3 Pond View Lane

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170336044

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,650
  • Acreage 1.93

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.

Listed by Cynthia Szentkuti of Ridgefield Homes Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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2 Wagon Wheel Road Sherman CT 06784

Sherman, CT2 Wagon Wheel Road

Price$1,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170512997

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,081
  • Acreage 5.6

Gracious antique colonial, C. 1830, beautifully sited on 5.6 picturesque country acres just off a designated scenic road in Sherman, CT. Stylishly renovated with two fireplaces, a beautiful butternut wood library, updated kitchen and baths, large screened porch with built-ins, and a stone terrace leading to elegant gardens and a freeform gunite pool. Striking architectural details can be seen throughout the home, from Juliet balconies off each of the three bedrooms, to a decorative portico flanking the handsome front door, a main level office with built-in shelving, desks and file drawers and multiple French doors leading out into the truly spectacular gardens. A partially finished lower level with wet bar offers another great place to entertain and from which to enjoy easy access to and from the pool. Stone steps connect the south facing stone patio to a gently sloping lawn above where there is a private hilltop overlook over scenic Glen Brook. There is a detached two car garage, an additional parking area for oversized vehicles and a separate .80-acre parcel on the opposite side of the road. A true New England beauty: elegant and country comfortable, warm and inviting, and presenting an atmosphere that inspires and welcomes! Includes beach rights to Candlewood Lake, and located just 90 minutes from Manhattan and 15 minutes to Metro North trains.

Listed by Irit R Granger and Matt McElhone of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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30 Long River Road Sherman CT 06784

Sherman, CT30 Long River Road

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 170369891

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,752
  • Acreage 1.84

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. “The Roger Sherman”, is a custom two story Colonial featuring four bedrooms, 4.5 baths, Bonus room and three car garage. Spacious first floor Master Suite, Gourmet Kitchen with panoramic views of the mountains and 7th fairway all throughout. Enjoy the serene outdoors from your covered porch and awake to stunning sunrise views. 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.

Listed by Kelly Ann Predham and Joe Chemero of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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32 Long River Road Sherman CT 06784

Sherman, CT32 Long River Road

Price$1,349,000

Est. Mortgage: $/month

MLS Number 170372914

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,200
  • Acreage 1.85

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.

Listed by Kelly Ann Predham and Joe Chemero of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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42 Long River Road Sherman CT 06784

Sherman, CT42 Long River Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 170336075

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,350
  • Acreage 1.84

READY FOR IMMEDIATE OCCUPANCY!! Look forward to spring 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. Gated community call for access.

Listed by Cynthia Szentkuti of Ridgefield Homes Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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7 Shelter Cove Road Sherman CT 06784

Sherman, CT7 Shelter Cove Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170527388

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 6,200
  • Acreage 2.42

This spectacular Georgian style Colonial with exceptional curb appeal is located in the prestigious Sail Harbour Club. Warm and inviting Family Room with a see through fireplace and beams. The awesome Living Room offers a floor to ceiling stone fireplace. Beautiful Kitchen / Breakfast Room leads to the Sun Room. Formal Dining Room.Main level Office with a see through fireplace. Three car attached Garage. The primary Bedroom features a fireplace, access to a primary Bedroom Suite with a vaulted ceiling a luxurious renovated Bath with a stream shower and large soaking tub. The upper levels also consists of four additional Bedrooms, two baths and a Recreation Room with a back staircase to the main level. The lower level offers three additional Rooms plus a full Bath. The front of the home features a flagstone Patio. The back of the home is ideal for entertaining. It features a large patio, extensive stonework and a seasonal Lake view.This amazing home is located in The Sail Harbour Club, a report style Candlewood Lake community offering a beautiful clubhouse, sandy beach, tennis/pickleball courts and a private marina. Very special!

Listed by Jeff Neumann and Cory Neumann of Houlihan Lawrence

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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Wagon Wheel Road Sherman CT 06784

MLS Number 170486854

  • Land
  • Acreage 55.85
  • Zoning RA5

55 Wooded Acres along the western side of beautiful Wagon Wheel Rd. with 300' +/- Squantz Pond Water frontage.Have your own private nature preserve/compound or potentially build your dream home; 300 '+/- On Squantz Pond. Property sold As Is. No permits, percs or applications available. Untouched, undeveloped land. Sloped terrain. Deed restrictions- Conservation easement. Land trust gifting opportunity. There is a new access road to hike the land.

Listed by Katherine M Bennett of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 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.

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