27

Sherman, CT Homes for Sale

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  • /40

    $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
  • /36

    $899,777

    • 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

    Agent Photo

    Gary Crawford

    RE/MAX RISE

    (860) 735-1471

    25 Hillside Dr, Sherman, CT 06784
  • /40

    $1,489,000

    • 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. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A welcoming columned entry opens to bright, versatile living spaces designed for today's lifestyle, anchored by an oversized

    Ginny Gordon-O’Neill William Raveis Real Estate

    27 Smoke Ridge Dr, Sherman, CT 06784
  • /39

    $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
  • /18

    $1,495,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,770 Sq Ft

    4 Pond View Ln, Sherman, CT 06784

    New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft

    Joe Chemero Coldwell Banker Realty

    4 Pond View Ln, 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
  • /36

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    35 Skyline Dr, Sherman, CT 06784

    It's All About the Views!Fabulous Price Reduction on this one of a kind, custom built contemporary with extraordinary 50 mile views in all directions. Set in the Lake community of Candlewood Lake Estates, this stately Contemporary, set on a private acre plus an additional lot (.82 acs), at the end of a cul-de-sac, is just waiting for your customization. This incredible setting hosts this 3

    Barbara Sivba Coldwell Banker Realty

    35 Skyline Dr, Sherman, CT 06784
  • /22

    $1,999,000

    • 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

    $1,599,500 Open Sun 12PM - 1:30PM

    • 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
  • /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

    $565,000

    • 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
  • /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
  • /10

    $850,000

    • Land
    • 24 Acres
    • $35,417 per Acre

    0 Rte 39 South State Route, Sherman, CT 06784

    Discover an exceptional opportunity to own a substantial 24+ acre parcel that presents a multitude of possibilities. This expansive open lot boasts superb road frontage (approx 1,650 ft) and western, sunset views. It offers a welcoming gateway to potential development and the chance to craft a legacy property or a community of homes, subject to subdivision approvals. Situated in a prime location,

    Alan O'Doherty William Pitt Sotheby's Int'l

    0 Rte 39 South State Route, Sherman, CT 06784
  • /35

    $2,490,000

    • 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

    $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

    $799,500

    • 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
  • /10

    $369,000

    • Land
    • 7.4 Acres
    • $49,865 per Acre

    8A Taber Rd, Sherman, CT 06784

    TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 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

    Kathleen Harrison Coldwell Banker Realty

    8A Taber Rd, 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
  • /5

    $1,350,000

    • Land
    • 110 Acres
    • $12,273 per Acre

    00 Anderson Rd, Sherman, CT 06784

    A rare 110-acre offering in Sherman, CT, where open skies and eastern-facing views create a truly peaceful setting. Whether you're envisioning a private estate, family compound, or future development, this property offers endless potential. Ideally located close to town and just a short drive to NYC, it strikes the perfect balance between seclusion and accessibility. With subdivision potential

    Carolyn Morrison William Pitt Sotheby's Int'l

    00 Anderson Rd, Sherman, CT 06784
  • /4

    $825,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 4,089 Sq Ft

    12 Mauweehoo Hill, Sherman, CT 06784

    This 4-Bedroom/3-Bath Contemporary Ranch is privately set in desirable southern Sherman, bordering six acres of protected open space and offering a blend of comfort, style, and the convenience of single-level living. Surrounded by nature on a fully usable 2-acre property, the home's inviting L-shaped design fills the interior with natural light while seamlessly connecting indoor living spaces to

    Irit Granger William Pitt Sotheby's Int'l

    12 Mauweehoo Hill, Sherman, CT 06784
  • /24

    $499,000

    • Land
    • 14.3 Acres
    • $34,895 per Acre

    5 Brinsmade Ln, Sherman, CT 06784

    FOUNDATION READY BUILD SITE! Down a quiet stretch of road in the quaint town of Sherman a hidden drive leads you away from the world into 14 acres of absolute tranquility. As you walk the land you'll find the remnants of historic stone walls intertwining through the woods. The air is still, save for the rustle of native trees and the quiet life surrounding a private vernal pond. While the land

    Donna Kennedy Compass Connecticut, LLC

    5 Brinsmade Ln, Sherman, CT 06784
  • /25

    $279,000

    • Land
    • 5.46 Acres
    • $51,099 per Acre

    41 Long River Rd, Sherman, CT 06784

    This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

    Donna Kennedy Compass Connecticut, LLC

    41 Long River Rd, Sherman, CT 06784
  • /39

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 4,599 Sq Ft

    17 Curtis Dr, Sherman, CT 06784

    Welcome to 17 Curtis Drive, a serene and private retreat tucked away on a quiet cul-de-sac in the picturesque town of Sherman, CT. Set on a beautifully wooded 2.03-acre lot just minutes from Candlewood Lake and the New York border, this unique property offers both a charming 3-bedroom, 3-bath main residence and a separate 1-bedroom, 1-bath studio apartment-perfect for flexible living

    Shaylene Neumann Houlihan Lawrence

    17 Curtis Dr, Sherman, CT 06784
  • /47

    $949,000

    • 33 Beds
    • 2.5 Baths
    • 2,314 Sq Ft

    29 Farm Rd, Sherman, CT 06784

    Nestled on a quiet cul-de-sac in the highly desirable Sherman subdivision, this beautifully remodeled country contemporary offers over 2,700 square feet of inviting living space. Designed to capture natural light, the home features an open floor plan with dramatic floor-to-ceiling windows and stunning views of Happy Acres Farm, delivering breathtaking sunsets every evening. At the heart of the

    Angelina Valentini Coldwell Banker Realty

    29 Farm Rd, Sherman, CT 06784
  • /33

    $689,900

    • 4 Beds
    • 2 Baths
    • 2,838 Sq Ft

    363 Connecticut 37, New Fairfield, CT 06812

    Some homes are built. This one was crafted. Hand-laid fieldstone construction, old-world masonry, and timeless character define this casual, livable Post-War/Mid-Century Traditional - a home the land itself seems to have produced. Straddling New Fairfield and Sherman, this 4-bedroom, 2-bath retreat sits on 2.24 private acres with over 2,800 square feet of comfortable living space. Two fieldstone

    Todd Sargent Coldwell Banker Realty

    363 Connecticut 37, New Fairfield, CT 06812
  • /4

    $130,000

    • Land
    • 4,356 Sq Ft
    • $1,300,000 per Acre

    54 Lavelle Ave, New Fairfield, CT 06812

    Fantastic opportunity to build your dream getaway just steps from the water! This .10-acre lot is ideally located directly across from Squantz Pond and just minutes to Candlewood Lake, offering the perfect setting for year-round living or a weekend retreat in a desirable lake community. The property currently includes a fire-damaged structure that must not be entered. Buyers are responsible for

    Brian Christy William Raveis Real Estate

    54 Lavelle Ave, 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.

Frequently Asked Questions

What is the average home price in Sherman, CT?
Homes for sale in Sherman, CT have an average home price of $1,069,067.
How many homes have sold over the last 12 months in Sherman, CT?
49 homes have sold in Sherman, CT over the last 12 months.
What are the most popular zip codes in Sherman, CT?
The most popular zip codes in Sherman, CT include 06784, 06776, 12564, 06755 and 12594.
How much do you need to make to afford a house in Sherman?
The median home price in Sherman is $837,450. If you put a 20% down payment of $167,500 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $4,180 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $179K a year to afford the median home price in Sherman. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Sherman, CT?
Sherman, CT has highly rated public and private schools. Some of the best schools in Sherman based on Niche Grades are South Kent School, Pawling High School and Shepaug Valley School. Browse all the schools in Sherman, CT to learn more.

Home Trends in Sherman, CT

Housing Trends

Median Sale Price
$695,000
Median Single Family Sale Price
$768,250
Average Price Per Sq Ft
$370
Number of Homes for Sale
19
Last 12 months Home Sales
49
Months of Supply
4.70
Median List Price
$837,450
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
18%
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