28

Sherman, CT Houses for Sale

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  • /34

    $3,900,000

    • 3 Beds
    • 2 Baths
    • 1,933 Sq Ft

    6 Hoyt Rd, Sherman, CT 06784

    Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a

    Agent Photo

    Eric Bergers

    William Raveis Real Estate

    (860) 936-9247

    6 Hoyt Rd, Sherman, CT 06784
  • /37

    $1,100,000

    • 4 Beds
    • 2.5 Baths
    • 3,232 Sq Ft

    3 Partridge Trail, Sherman, CT 06784

    Set back on a tranquil cul-de-sac enclave of prestigious Hubbell Mountain Farm North this 4 bedroom, 2.5 bath Custom Colonial offers the ultimate carefree lifestyle, blending modern elegance with vintage character. Situated on 9.24 level acres, the property boasts mature, colorful trees, sprawling stone walls, and an expansive composite deck with serene country views. Inside, an open floor plan

    Agent Photo

    Lorraine Amaral

    William Pitt Sotheby's Int'l

    (860) 734-4964

    3 Partridge Trail, Sherman, CT 06784
  • /40

    $1,489,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 3.5 Baths
    • 4,884 Sq Ft

    27 Smoke Ridge Dr, Sherman, CT 06784

    A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, offering you seclusion. The stand out one-of-a-kind oversized six car garage easily adapts for, car collections, workspace, or recreational needs. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A

    Ginny Gordon-O’Neill William Raveis Real Estate

    27 Smoke Ridge Dr, Sherman, CT 06784
  • /34

    $850,000

    • 3 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    1 Eagles Nest Dr, Sherman, CT 06784

    Experience the perfect blend of architectural character, thoughtful updates, and peaceful surroundings in this beautifully refreshed mid-century modern home. Soaring ceilings, an open floor plan, and 12 skylights fill the interior with natural light, creating a bright and inviting atmosphere throughout the day. The remodeled kitchen offers updated style and functionality, while the loft provides

    Karen Gilmore Redfin Corporation

    1 Eagles Nest Dr, Sherman, CT 06784
  • /39

    $565,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    38 Cedar Lane Extension, Sherman, CT 06784

    Unique and open mid century modern at end of cul de sac. Great curb appeal. Updated Kitchen with stainless appliances. 3/4 bedrooms and 2 full baths. Primary with 2 closets and private bathroom. Mini split for AC. Crown moldings. 2 car heated attached garage plus 1 car detached. Hardwood floors. Front and rear decks for relaxing and entertaining. Added potential in the unfinished basement.

    Joe Chemero Coldwell Banker Realty

    38 Cedar Lane Extension, Sherman, CT 06784
  • /34

    $1,595,000

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    27 Osborn Rd, Sherman, CT 06784

    This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room

    Sally Slater Douglas Elliman of Connecticut

    27 Osborn Rd, Sherman, CT 06784
  • /39

    $899,000

    Open Sun 1PM - 4PM
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    3 Ledgewood Dr, Sherman, CT 06784

    Turnkey Candlewood Lake Luxury in Deer Run Shores! Experience the perfect blend of modern luxury and lakeside living in this 2900 sq ft contemporary situated on a rare, private 1 acre lot. Extensively expanded and completely renovated in 2022. This 3/4 bedroom 3.5 bath home offers flawless, move in ready sanctuary just a short, flat few minute walk to the community clubhouse, beach, and your own

    Joe Chemero Coldwell Banker Realty

    3 Ledgewood Dr, Sherman, CT 06784
  • /40

    $390,000

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft

    2 Sawmill Rd, Sherman, CT 06784

    Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the

    Lori Campbell Coldwell Banker Realty

    2 Sawmill Rd, Sherman, CT 06784
  • /2

    $1,195,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,675 Sq Ft

    60 Long River Rd, Sherman, CT 06784

    River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

    Joe Chemero Coldwell Banker Realty

    60 Long River Rd, Sherman, CT 06784
  • /40

    $1,100,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 4,854 Sq Ft

    21 Holiday Point Rd, Sherman, CT 06784

    Contemporary home in Atchison Cove lake community w/ clubhouse & deeded beach rights perfect for family living and entertaining. This unique residence offers the perfect mix of social hub and private sanctuary for year-round living or weekend escapes, located in Southern Sherman just 60 miles from NYC. The home is anchored by a large kitchen equipped w/ granite countertops, all new appliances,

    Donna Kennedy Compass Connecticut, LLC

    21 Holiday Point Rd, Sherman, CT 06784
  • /32

    $2,449,000

    Open Sat 11AM - 1PM $41K PRICE DROP
    • 10 Beds
    • 7.5 Baths
    • 5,856 Sq Ft

    29 Route 37 E, Sherman, CT 06784

    Exceptional Renovated Farmhouse with Expansive Living & Unforgettable Views Bordering the 70 Acre Naromi Land Trust. Welcome to this Stunning, Fully Renovated Farmhouse with In-law Apartment, where Timeless Character meets Modern Comfort on a Grand Scale. Offering 10 spacious Bedrooms and 8 Beautifully Updated Bathrooms, this One-of-a-Kind Property is Perfectly Suited for Extended Living, Guest

    Joseph Perun Perun Properties

    29 Route 37 E, Sherman, CT 06784
  • /40

    $2,495,000

    • 5 Beds
    • 4.5 Baths
    • 6,368 Sq Ft

    2 Pond View Ln, Sherman, CT 06784

    Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning newer-construction residence offers spacious open living, abundant natural light and thoughtfully designed details throughout. From the moment you enter you'll notice the airy layout, oversized windows, 10ft ceilings and seamless flow. The heart of the home

    Joe Chemero Coldwell Banker Realty

    2 Pond View Ln, Sherman, CT 06784
  • /22

    $1,999,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,500 Sq Ft

    8 Taber Lot 1 Rd, Sherman, CT 06784

    Taber Acres 3 lot subdivision is offering the last lot available, and this is the building lot you've been waiting for to build your dream home upon! The 7+ acre lot is mostly flat with a gentle rise, has sandy soil, 400 AMP service installed and is ready to build. With the 400 AMP service this means the lot can accommodate a pool, a 2-bedroom guest house, sport court, and more. The private

    Claudia Jiskra McGrath Realty Inc

    8 Taber Lot 1 Rd, Sherman, CT 06784
  • /40

    $999,000

    • 3 Beds
    • 3.5 Baths
    • 3,258 Sq Ft

    6 River Bend Ln, Sherman, CT 06784

    A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached

    Tyler O'Hazo William Pitt Sotheby's Int'l

    6 River Bend Ln, Sherman, CT 06784
  • /40

    $775,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,488 Sq Ft

    34 Hardscrabble Rd, Sherman, CT 06784

    Perched on 4.52 private acres with complete seclusion, 34 Hardscrabble Rd offers the perfect blend of space, comfort, and peaceful country living in beautiful Sherman. An expansive front porch provides plenty of room to entertain, relax, and take in the scenic surroundings. Inside, the main level features a renovated eat-in kitchen with island seating and a slider leading to the backyard,

    Cory Neumann Houlihan Lawrence

    34 Hardscrabble Rd, Sherman, CT 06784
  • /25

    $2,250,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 4,900 Sq Ft

    8 Taber Rd, Sherman, CT 06784

    TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation,

    Kathleen Harrison Coldwell Banker Realty

    8 Taber Rd, Sherman, CT 06784
  • /36

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    2 Laurel Hill Rd S, Sherman, CT 06784

    Incredibly charming Ranch set on a peaceful and private .53-acre lot in quaint Sherman, offering the perfect blend of small-town charm, natural beauty, and incredibly low taxes. Tucked away in a serene setting, this well-maintained home provides both privacy and convenience, just minutes from marinas, Candlewood Lake, and Squantz Pond for year-round recreation and enjoyment. The main level

    Cory Neumann Houlihan Lawrence

    2 Laurel Hill Rd S, Sherman, CT 06784
  • /40

    $1,599,500

    • 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
  • /38

    $1,699,000

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

    6 Brinsmade Ln, Sherman, CT 06784

    Exceptional private country estate set on approximately 10 acres in Sherman, just 90 minutes from New York City and moments from Candlewood Lake with beach and boat rights. Formerly the historic Brinsmade Dairy Farm, this remarkable property blends timeless New England charm with modern comfort and exceptional versatility. Comprising three residences on two lots-the Main House, Carriage House,

    Ginny Gordon-O’Neill William Raveis Real Estate

    6 Brinsmade Ln, Sherman, CT 06784
  • /40

    $550,000

    • 4 Beds
    • 2 Baths
    • 1,804 Sq Ft

    5 Laurel Hill Rd N, Sherman, CT 06784

    Tucked away at the private end of a cul-de-sac in desirable Sherman and just minutes from Candlewood Lake, this charming Cape offers great space, and a peaceful setting on .92 acres. The home features 3-4 bedrooms and 2 full baths with an inviting open floor plan designed for easy everyday living and entertaining. A spacious living room with fireplace creates a warm gathering space, while the

    Lori Campbell Coldwell Banker Realty

    5 Laurel Hill Rd N, Sherman, CT 06784
  • /31

    $899,000

    Open Sat 2PM - 3PM
    • 4 Beds
    • 3 Baths
    • 5,342 Sq Ft

    7 Glenview Dr, Sherman, CT 06784

    Welcome to this Contemporary masterpiece nestled in the serene town of Sherman, CT. The home boasts incredible curb appeal with crisp white architectural siding, bold dark-trimmed windows, a grand stone-accented entryway, and a spacious attached 2-car garage. Step inside to discover a bright, beautifully updated interior anchored by a massive, sun-drenched living area. the fluid, open-concept

    Wilmer Duran Marinablue Realty

    7 Glenview Dr, Sherman, CT 06784
  • /34

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    4 Pepper Pond Rd, Sherman, CT 06784

    Welcome to rustic Timber Trails and Pepper Pond Road, located in southern Sherman, CT, near the New Fairfield and New York state border, offering a peaceful back-to-nature setting. Techbuilt home, part of the iconic mid-century modern prefabricated designs by architect Carl Koch, blends timeless character with warmth and functionality. Hardwood floors throughout, while the living room is flooded

    Liz Pepin Luks Realty

    4 Pepper Pond Rd, Sherman, CT 06784
  • /36

    $874,999

    $25K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,303 Sq Ft

    25 Hillside Dr, Sherman, CT 06784

    A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a

    Gary Crawford RE/MAX RISE

    25 Hillside Dr, Sherman, CT 06784
  • /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
  • /39

    $1,195,000

    • 2 Beds
    • 1.5 Baths
    • 1,150 Sq Ft

    131 Route 39 N, Sherman, CT 06784

    Instantly inviting this pristine circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with

    Karen Casey William Pitt Sotheby's Int'l

    131 Route 39 N, Sherman, CT 06784
  • /39

    $865,000

    • 2 Beds
    • 2 Baths
    • 2,996 Sq Ft

    3 Old Forest Rd, Sherman, CT 06784

    The Lake Experience! Candlewood Lake Estates, a private gated community on Lake Candlewood hosts this 1998 built, 3 bedroom, 2 bath contemporary with 2 dramatic stone, floor to ceiling fireplaces, gleaming hardwood floors, new 2 car garage with loft and fabulous wrap deck to enjoy the private yard & seasonal views! An idyllic weekend.summer retreat or full time residence, this home exudes a

    Barbara Sivba Coldwell Banker Realty

    3 Old Forest Rd, Sherman, CT 06784
  • /24

    $1,999,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 5,900 Sq Ft

    40 Long River Rd, Sherman, CT 06784

    Craft your dream home from the ground up with this luxury built-to-suit offering set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated community in Sherman, CT. This 4 bd / 3.5 bath / 3500 SF open-concept residence with main level primary suite seamlessly connects a chef's kitchen (w/ pantry) to an elegant dining area and a living room w/ cozy fireplace.

    Donna Kennedy Compass Connecticut, LLC

    40 Long River Rd, Sherman, CT 06784
  • /40

    $499,000

    • 3 Beds
    • 3 Baths
    • 1,930 Sq Ft

    19 Hilldale Rd, New Fairfield, CT 06812

    Beautifully updated 3-bedroom, 3 bath energy efficient home with year-round mountain views and seasonal lake vistas. Designed for sustainable living, this property features a 5.4KW owned net metered solar array offsetting over $1,600/year in electricity costs, a heat pump hot water heater, heat pump dryer, Level 2 EV charger, and the attic with double insulation, a radiant barrier, and solar

    Lisa Weisenberger Luks Realty

    19 Hilldale Rd, New Fairfield, CT 06812

Why Live in Sherman

Sherman, CT, is a tranquil lakeside community located in the foothills of Connecticut wine country, offering a small-town atmosphere with proximity to Candlewood Lake. This man-made lake is a major attraction, featuring over 60 miles of shoreline where residents enjoy boating, hiking, ice skating, and skiing. Sherman is just an hour from New York City's theater district, making it a popular choice for second homes among Manhattan residents. The area boasts a variety of home styles, including Modern-influenced split levels, Modern Traditional homes, and lakeside lodges, often situated on multi-acre woodland lots. Education is a highlight, with The Sherman School serving kindergarten through eighth grade and Shepaug Valley Regional High offering a highly rated agriscience academy and a planetarium. Sherman is part of Connecticut wine country, hosting events like the rhubarb festival at White Silo Farm and community theater performances at Sherman Playhouse. For necessities, locals shop at Sherman IGA or drive 6 miles to New Milford for additional options like Big Y and Starbucks. New Milford also features Housatonic Brewing and Johana’s diner. Transportation is convenient with Route 7 leading to Danbury and I-84 connecting to Brewster's Southeast Station for trains to Grand Central Station. Sherman’s small-town charm is evident during national holiday celebrations, with fireworks on the Fourth of July and streets lined with American flags for Memorial Day.

Single Family Home Prices in Sherman, CT

Single Family Home Price Trends

Median Home Price
$865,000
Median 3-Bedroom Home Price
$640,000
Median 4-Bedroom Home Price
$982,500
Median 5-Bedroom Home Price
$1,592,500
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