The Matthews Team

William Raveis Lifestyles Realty

Sherman CT Luxury Homes for Sale

Find the latest luxury homes for sale in Sherman. Search through a variety of residential listings to find your new property. Save your favorite listings when you register with us, and you can receive email notifications when new properties match your criteria. You may also be interested in viewing luxury real estate listings in Litchfield County.

Luxury Homes in Sherman Connecticut

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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, nestled along the Appalachian Trail, in Sherman Connecticut (Fairfield County). Fully modernized and upgraded Equestrian estate (with paddock, barns and guest cottage) is uniquely located on the border of Dutchess County, New York, and also neighboring Kent, in Litchfield County, Connecticut. Call for more details.

Listed by Lisa Fagan of eXp Realty

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$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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$2,500,000

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: 4.99% last updated on Aug 4, 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

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: 4.99% last updated on Aug 4, 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: 4.99% last updated on Aug 4, 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$1,499,000

Est. Mortgage: $/month

MLS Number 170460439

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 3,850
  • Acreage 3.45

New Construction. Fall Completion. 3.45 Private Acres Hosts 3850 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 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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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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

MLS Number 170512997

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,081
  • Acreage 4.79

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: 4.99% last updated on Aug 4, 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

Under Agreement

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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23A Wagon Wheel Road Sherman CT 06784

Sherman, CT23A Wagon Wheel Road

Price$1,375,000

Est. Mortgage: $/month

MLS Number 170486862

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,462
  • Acreage 3.56

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.

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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: 4.99% last updated on Aug 4, 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: 4.99% last updated on Aug 4, 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

1 Cove Lane Sherman CT 06784

Sherman, CT1 Cove Lane, Holiday Point

Price$1,100,000

Est. Mortgage: $/month

MLS Number 170504507

  • Single Family
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,061
  • Acreage 0.82

DIRECT LEVEL WATERFRONT - CANDLEWOOD LAKE A great get away from the hustle and bustle of your busy daily lives is found here in Holiday Point, a private country lake community at the furthest Northwest tip of the lake. This 2-3 BD versatile home sits on a quiet cul-de-sac in the cove nestled on almost a full LEVEL Acre in enchanted back-to-nature setting w/ lush flowering bushes, Zen gardens & areas of contemplation.Meander down the path to your private DOCK(currently being relocated). Use your imagination to transform the cute shed/cabana on the hill to something private & special just for you! ADORABLE updated year-round Contemporary Lake Bungalow.LR w/builts-ins, frplc open to updated Kitchen & hexagonal Sunroom/DR all lead to Large Wrap Deck. Office/Den & half BA. Spiral staircase to UL Loft Office, primary BDRM w/prvt Deck to water, Full BA & Guest BDRM.Spiral staircase to walk-out Lower Level FR, Summer Kitchen, Laundry & Full BA. Loads of parking. The community offers a private main beach including swim area, picnic area complete w/ charcoal grills, tables, & lots of space for lakeside games. Also direct access to North Beach, a quiet area in the cove. Small Town USA - Sherman has all the beauty of a quaint small New England town w/all of the conveniences of nearby shopping, restaurants. 1M to Town Community Tennis, Pickle Ball, Basket Ball Courts, jogging path & short stroll to pavilion & town beach on the Lake. You'll LOVE our low taxes!45 M White Plains/60 M NYC.

Listed by Kathleen A Harrison of Fazzone & Harrison

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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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14 Route 37 Center Sherman CT 06784

Sherman, CT14 Route 37 Center

Price$1,099,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170486164

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,002
  • Acreage 6.66

This property has been loved by the same family for 152 years - now is your opportunity to make memories in this meticulously maintained home in the historic district of Sherman. A truly wonderful example of a Federal style residence, the house is listed on the National Register of Historic Places and proudly sits on over 6.6 acres in the center of the village, abutting conservation land and bordered by a babbling brook on one side. Antique features abound, including wide plank wood floors, hand hewn beams, wavy glass windows, detailed moldings, 2 wood burning fireplaces and a brick oven. There are several entertaining rooms on the main level with the possibility of a fourth bedroom (which has an en suite bathroom). Two staircases lead to the upper level where you will find the primary bedroom (with en suite), plus two generously proportioned bedrooms and a further bathroom. Modern conveniences such as central air, wifi controlled thermostats, zoned heating, security alarm and a central vacuum system. Recent upgrades include a new driveway, patio fence and painting throughout the house. The large, two level barn has space for several cars and an upper level which could host events such as art exhibitions or functions - a genuine possibility as the property is zoned as commercial & residential. Only 90 mins from NYC and a few mins walk to local shops, Candlewood Lake and Sherman residents town beach...this is the perfect full-time home or weekend getaway.

Listed by Alan O'Doherty and Tyler O'Hazo of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.99% last updated on Aug 4, 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.