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

Contact The Matthews Group for more information and to schedule a showing.

1 Glen Brook Farm Sherman CT 06784

MLS Number 170353820

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 7
  • Acreage 73.77

Just 90 minutes from NYC and minutes to both Kent and Sherman Connecticut this completely custom-built stone and timber Contemporary home offers modern country living on one of the rare acreages found in Sherman, CT. Situated on 75 acres, the substantial acreage is the perfect blend of open views, hilltop pastures, and mature forestland. Completed in 2018, featuring soaring cathedral ceilings, floor-to-ceiling walls of glass, lustrous walnut millwork, wide white oak floors, and rich tones of marble and granite. The heart-of-the-house bespoke kitchen is ready for entertaining with Miele appliances, a light-flooded breakfast area, and a spacious center island. Opening to the family room with a dramatic fireplace, soaring walls of glass invite you out to the broad entertaining terrace to enjoy breathtaking views. The second-floor master suite features a marble-appointed bath with a soaking tub and a glass-enclosed shower and two large walk-in closets. An additional ensuite bedroom has a custom-fitted dressing area. For work-at-home privacy, there's a coveted studio/office with a full bath. The walk-out garden level adds an additional private bedroom with an ensuite bath, media room, gym/recreation room, and laundry all with radiant heat floors. Across the sweeping lawn, there's a fully-equipped 11-stall barn with a caretaker's house, and a large working studio is ready for the hobby/sports enthusiast. Surrounded by Land Trust ensures forever protection and privacy.

Listing Courtesy of Houlihan Lawrence

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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22 & 27 Cedar Sherman CT 06784

Sherman, CT22 & 27 Cedar Lane

Price$2,795,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170321384

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 5
  • Acreage 2.73

The answer to your waterfront dream! Escape to the shores of CT's Pristine Lake Candlewood. Intriguing new construction opportunity. Build form the ground up. Still time to customize the design. Proposing a 4100 SF , 4 Br, 4.5 Bath organic modern design, on 2 separate panels with an amazing 2.73 acres, Waterfront property with dynamic views from nearly every room, in the quiet lakeside town of Sherman, CT. Just a short jaunt form New York city, in 1 hour, you can enjoy swimming, boating, fishing or just relaxing on your multi-level decks and stone terraces. Sunbathe on your private dock with amazing views and serene surroundings. Enjoy lake and mountain views. morning sunrises and evening sunsets on this lightly treed site. Property is large enough to accommodate a pool complex with cabana , tennis courts or a barn at the top of the larger parcel plus lakeside patios, gazebo or cabana lakeside. Don't miss this rare and exciting opportunity. Two parcels have been joined to create this lakeside setting. One of the last great waterfront parcels offered with a premier waterfront builder!

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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21 Deer Run Sherman CT 06784
Pending Continue to Show

MLS Number 170393582

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.43

Direct LEVEL WATERFRONT w/130+ frontage on CANDLEWOOD LAKE. Southern Sherman in DEER RUN SHORES, a private lake community with clubhouse, beach & pool. Situated in privacy on a quiet cul-de-sac w/lush, professionally landscaped front & back yards. Open floorplan contemporary with a wall of windows overlooking the lake. Oversized Two-level deck for entertaining. 2 Car Detached Garage. Transaction to include Cobalt ski boat and boat lift. 20 M to Metro North Train Station. 45M to White Plains/60M to Manhattan.

Listing Courtesy of Fazzone & Harrison

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%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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43 Route 37 Sherman CT 06784

Sherman, CT43 Route 37 South

Price$1,499,000

Est. Mortgage: $/month

MLS Number 170381377

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 7
  • Acreage 5.42

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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6 Oriole Sherman CT 06784

Sherman, CT6 Oriole Drive

Price$1,400,000

Est. Mortgage: $/month

MLS Number 170383492

  • Single Family
  • Property Style Cape Cod, Other
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.97

Discover breathtaking Sherman CT & endless lake views on this Squantz Pond waterfront property! Perched on 1.3 acres of land, facing unbuildable Pootatuck State Forest, this contemporary cape offers spectacular western exposure views of Squantz Pond. Boasting 220' of direct water frontage and direct access to the pond via a private dock, complete w/ newly renovated sailboat shed nearby. This 2010 built home exemplifies elegant lake living, giving you the privacy, luxury detail, & craftsmanship you have always dreamed of. Exterior features include two 66' long cedar decks adorned w/ beautiful columns, architectural shingles, oversized Anderson windows & Hardy Board siding. Walk in through the formal entry to see a spacious living room greeting you, complete with 9' ceilings, surround sound speakers, & access to the first level deck via french doors. Dining room/ Kitchen nearby makes entertaining friends & family a breeze, complete with beautiful tile floors, center island w/ additional sink, breakfast bar, french doors, and ample cabinet space. Finish off the first floor with 2 bedrooms, each with ample closet space and attached private baths. the LL has in-law suite capabilities w/ kitchen, radiant floor heat, large BR, full bath & access to LL deck. The upper level is yet to be completed and is ready for your creativity. With close proximity to the center of town, 25 min from MetroNorth and one hour, fifteen minutes to Midtown. Come see why this property is perfect for you!

Listing Courtesy of Compass Connecticut, LLC

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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6 Hardscrabble Sherman CT 06784

Sherman, CT6 Hardscrabble Road

Price$1,400,000

Est. Mortgage: $/month

MLS Number 170379992

  • Single Family
  • Property Style Other
  • Bedrooms 4
  • Bathroom 6
  • Acreage 12.39

Tired of The Hustle and Bustle of City Living?? This Custom Designed and Built Home Surrounded By Mother Nature Is Awaiting Your Personal Touches. As You Enter The Front Entry You Will Be Greeted By a Sun-filled Open Floor Plan Perfect for Entertaining Family and Friends. Great Room with Stone Fireplace Built In's. - Hardwood Floors a Hearth Room ,Floor to Ceiling Windows and Sliders to a Screened In Porch Where You Enjoy Majestic Views. A Chef's Delight Kitchen with Top of The Line Appliances - Granite Counters - Wall Ovens - Warming Oven - A Beverage Cooler and Built Ins Plus A Floor To Ceiling Pantry. There Is A Formal Dining Room with Crown Molding and Hardwood Floors to Serve your Guests In. The Main Floor Master Suite is Filled with Sunshine and Boasts a Huge Walk In Closet a Luxurious Bath With Double Sinks - A Make Up Area A Beautiful Tiled Shower and Large Tub. There are 3 Additional Bedrooms With Their Own Full Baths . A Family Room for Family Fun and Sliders Leads To a Patio for Outdoor Entertaining. Work from Home In Your Own Private Office . There Is Crown Molding Throughout and Special Baseboard Molding, A Two Car Attic Garage and for all Your Toy A Four Car Garage Under Plus A Workshop. This is a Very Unique Custom Floor Design and Must Be Seen To Be Appreciated. All this on over 12 Acres of Beautiful Wooded Land. MINUTES TO NEW YORK BORDER AND TRAIN STATION FOR EASY COMMUTING !! THE PERFECT HOME FOR YOU !

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 Sherman CT 06784

Sherman, CT30 Long River Road

Price$1,395,000

Est. Mortgage: $/month

MLS Number 170369891

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 5
  • 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.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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5 Autumn Sherman CT 06784

Sherman, CT5 Autumn Drive

Price$1,295,000

Est. Mortgage: $/month

MLS Number 170398701

  • Single Family
  • Property Style Contemporary
  • Bedrooms 5
  • Bathroom 5
  • Acreage 3.79

When you walk into this home, you will immediately take in the attention to detail of this one-of-a-kind, dramatic, contemporary home. Perfect for entertaining or peaceful sanctuary, the sprawling layout offers warm living space and open-concept, customized style. Surrounded by a private 3+acres, enjoy the peace of the country with the convenience of nearby NYC trains and resident beach rights. The new subzero fridge and Bosch induction stove are the perfect complement to the abundant space of the kitchen, down to the sunlit breakfast nook and butler's pantry. The list of updates is extensive, with no attention to detail spared. Each room is the epitome of warmth and private serenity - from the family room that overlooks the trees, to the impressive Living Room with floor to ceiling windows, to the 800 sq ft Primary Suite complete with fireplace and private balcony. With over 4900 square feet of living space, there are so many flexible options for use of the various rooms. The library has a closet for optional main floor guest room, across the home in the north wing (beyond the kitchen) is a flexible space currently used for office, guestroom with another bedroom/bath combo adjacent. As you complete your tour, as you walk outside the lower level, you will see the possibilities for creating your outdoor retreat are endless.

Listed by William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 Sherman CT 06784

Sherman, CT32 Long River Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170372914

  • Single Family
  • Property Style Ranch
  • Bedrooms 4
  • Bathroom 4
  • 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.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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10 Old Greenwoods Sherman CT 06784

Sherman, CT10 Old Greenwoods Road

Price$1,250,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170382264

  • Single Family
  • Property Style Colonial, Barn
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.52

Circa 1840-The Ebenezer Sherwood House,a Greek Revival Farmhouse-never before on market.Sitting pretty at the edge of Town w/the babbling brook that abuts Naromi Land Trust,this residence has lovingly been restored & transformed into OLD GREENWOODS HILL,an Arts & Crafts private compound.In addition to Main House there is a GUEST HOUSE 1 BD/1.5 BA(add 1036 sq ft) & Detached Party BARN/GARAGE.A perfect balance between Business & Pleasure includes flexible work space. Private Pool Area w/inground htd Gunite POOL surrounded by whimsical naturalized gardens & open meadow area.Enjoy flexible space for multi-generational uses.Master Craftsmanship/Fine Woodworking.All roofs-yellow Alaskan Cedar. Reproduction period 1830's lighting/Reclaimed Oak & Chestnut Flrs.Enter a unique foyer w/heated stone floor, loft w/ladder to book nook,laundry room & Full BA.Magnificent Eat-In Kitchen,Frpl w/original hearth,Vermont soap stone counters,subzero/6 burner stove w/grill,nooks & crannies plus walk in old fashioned pantry.Formal DR, Music Room & LR,a romantic ML Vltd BDRM Suite boats Frplc & sumptuous BA.A Cozy covered Porch is a natural extension off both the kitchen and the ML bedroom & over looks garden & an outdoor firepit or cozy up w/a book & enjoy private relaxation.UL w/front & back staircase -charming 3 BD/Full BA.Basement has room perfect for wine cellar/rec room.Take a short stroll in to Town,ride your bike to Park/Community Tennis//Pavilion/Beach/Boat Slips on Candlewood Lake.

Listing Courtesy of Fazzone & Harrison

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 Route 37 Sherman CT 06784

Sherman, CT30 Route 37 East

Price$1,250,000

Est. Mortgage: $/month

MLS Number 170398719

  • Single Family
  • Property Style Farm House, Log
  • Bedrooms 4
  • Bathroom 3
  • Acreage 10.47

Welcome to Blue Bell Farm. Located 90 minutes from Manhattan, this meticulously maintained equestrian property sits on 10+ acres of land. The 9 stall barn has a 12X20 heated tack room, bathroom with laundry, wash stall with hot and cold water, hayloft with room for 3,000 +/- bales and is roughed with plumbing and electric for option to be turned into additional living space. Additional 3 stalls located outside of the barn. The riding ring is 100X200 with mirrors and Travel Right footing which is every horses dream! 12 expansive paddocks, 6 frost free hydrants for easy watering and 4 run in sheds. The picturesque log cabin has white walls with dark beams, dark hardwood floors, double sided fireplace and a white marble kitchen. The first floor features a master bedroom, full bathroom, double sided fireplace between the kitchen and living room and laundry. The second floor has a bedroom with ample storage, a full bathroom and loft that serves as a great office space or additional living space. The lower level features an additional two bedrooms, full bathroom, laundry and full kitchen which could be a great option for in-law, au pair or barn staff. The property boarders 200 acres of conservation land providing additional privacy and serene atmosphere. Also, conveniently located next to White Silo Winery. Located 15 minutes from Candlewood Lake public boat launch and 30 minutes from Lake Lillinonah.

Listing Courtesy of Brown Harris Stevens

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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25 Cedar Sherman CT 06784

Sherman, CT25 Cedar Lane

Price$1,200,000

Est. Mortgage: $/month

Open House

MLS Number 170391001

  • Single Family
  • Next Open House: Sun 05/16 12:00 pm. to 3:00 pm.
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3

Breathtaking views of Candlewood Lake from the top of the world! Sunrises and sunsets unobscured year-round. This spacious and natural light-filled home sits on almost 2 acres of land just minutes from the center of town. Offering a sanctuary for a relaxing escape and the convenience of four seasons of enjoyment. With 3/4 bedrooms and 3 baths, it comfortably accommodates active lifestyles. With over 200 feet of direct frontage, this property boasts private lake access for boating, swimming, sailing and fishing. There are docks for 2 boats (with professional whips for one) in a no-wake zone. Dockside boathouse feature a practical incinerating toilet. Central air and heat with propane furnace added to previously existing electric heat. Kitchen upgrades include granite counters, gas cooktop, French-door refrigerator and pot rack. Generac whole house generator. Soapstone wood stove in Great Room. Mature landscaping which will delight year-round. Direct propane line for deck BBQ. 90 minute drive to midtown NYC and easy access to Metro North from Harlem Valley Wingdale, Pawling and Southeast Train Stations.

Listing Courtesy of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2021 Smart MLS, Inc. All rights reserved.