2,140

Sherman, CT Homes

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  • 2 Oak Dr, Sherman, CT 06784
    2 Oak Dr, Sherman, CT 06784
    2 Oak Dr, Sherman, CT 06784
    /38

    $619,999 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,239 Sq Ft

    2 Oak Dr, Sherman, CT 06784

    Seller is motivated to sell! Welcome to 2 Oak Drive in Sherman, a charming 4-bedroom, 2-bathroom with your own private dock! Don't worry about finding a marina or using the town launch, you have a private dock slip steps away. This home is nestled in the coveted Holiday Point Association. This inviting residence features newly remodeled bathrooms with both modern elegance and comfort. The

    Agent Photo

    Gary Crawford

    RE/MAX RISE

    (860) 909-8341

    2 Oak Dr, Sherman, CT 06784
  • 8 River Bend Ln, Sherman, CT 06784
    8 River Bend Ln, Sherman, CT 06784
    8 River Bend Ln, Sherman, CT 06784
    /25

    $6,500 per month

    • 4 Beds
    • 2.5 Baths
    • 3,791 Sq Ft
    • House for Rent

    8 River Bend Ln, Sherman, CT 06784

    A contemporary home with heated infinity swimming pool perfect for relaxing or entertaining, whilst enjoying sunshine views over the golf course. Located within the River Oaks Country Club with resort quality amenities, this large and tastefully furnished 4 bedroom, 2 & 1/2 bath home is offered fully furnished and in mint condition. This well equipped home includes central air-conditioning and a

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

    8 River Bend Ln, Sherman, CT 06784
  • 15 Sunset Terrace, Sherman, CT 06784

    $887,500 Sold Jun 11, 2025

    • 2,822 Sq Ft
    • $314/SF
    • 82 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1975

    15 Sunset Terrace, Sherman, CT 06784

    Welcome home! This brightly lit contemporary home with open panoramic views looks out to the western hills over protected land trust property. The wall of west facing windows showcases the natural beauty of this location. This custom contemporary features vaulted ceilings, a custom kitchen with granite, a beautiful stone fireplace and hearth, along with a unique catwalk connecting the main living

    Kurt Stoffel Howard Hanna Rand Realty

    15 Sunset Terrace, Sherman, CT 06784
  • 21 Holiday Point Rd, Sherman, CT 06784
    21 Holiday Point Rd, Sherman, CT 06784
    21 Holiday Point Rd, Sherman, CT 06784
    /25

    $1,199,000

    • 4 Beds
    • 3.5 Baths
    • 4,854 Sq Ft

    21 Holiday Point Rd, Sherman, CT 06784

    Stunning Home in Atchison Cove Lake Community - A Family Paradise! Nestled in the desirable Atchison Cove community on Candlewood Lake, this spacious home offers everything you need for a peaceful and luxurious lifestyle. With 4 bedrooms, 3 baths, and almost 5,000 sq. ft., it's perfect for growing families. The large backyard is a true oasis, complete with a gunite in-ground pool, slide, and

    Jorge Zea Blue Lighthouse Realty, Inc

    21 Holiday Point Rd, Sherman, CT 06784
  • 18 Pinewood Shores, Sherman, CT 06784
    18 Pinewood Shores, Sherman, CT 06784
    18 Pinewood Shores, Sherman, CT 06784
    /40

    $4,500 per month

    • 3 Beds
    • 3 Baths
    • 2,247 Sq Ft
    • House for Rent

    18 Pinewood Shores, Sherman, CT 06784

    Pull into the end of the cul-de-sac and enjoy your just under half acre of privacy with 100' DIRECT LEVEL WATERFRONT on Squantz Pond in the private lake community of Pinewood Shores. Pinewood Shores has a community beach to socialize or embrace the privacy and exclusivity of lakefront living w/your own large private sandy beach with large dock for multiple water toys. Easy living in this

    Courtney Smith Houlihan Lawrence

    18 Pinewood Shores, Sherman, CT 06784
  • 10 Laurel Dr S, Sherman, CT 06784

    $1,015,000 Sold Jun 06, 2025

    • 2,000 Sq Ft
    • $508/SF
    • 12 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    10 Laurel Dr S, Sherman, CT 06784

    First time on the market, "The Fischer House" is a lakefront property of unobtrusive brilliance. It was designed by renowned architect, Norman Jaffe to be a weekend retreat immersed in natural beauty with a sense of life among the treetops. Tucked into a wooded hillside and overlooking Green Pond, this enchanting home blends rustic warmth with contemporary style. Entry to the residence via a

    Kellie Martone William Pitt Sotheby's Int'l

    10 Laurel Dr S, Sherman, CT 06784
  • 70 Wakeman Hill Rd, Sherman, CT 06784
    70 Wakeman Hill Rd, Sherman, CT 06784
    70 Wakeman Hill Rd, Sherman, CT 06784
    /37

    $924,900 Open Sun 11:30AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 3,973 Sq Ft

    70 Wakeman Hill Rd, Sherman, CT 06784

    Location Location Location! 5.6+ Flat Private Sherman Acres on the New York Border with low Taxes. This Spacious 4 Bedroom 4135 sq ft Colonial has Plenty to Offer. Large Living Area Perfect for Entertaining with Custom Kitchen, Piped Propane for Outside Grill, 2 Story Foyer, Primary Bedroom with Sitting Room and New Jet Soaker Tub. Home Conveniently Offers an Automatic Standby Generator. Tons of

    Joseph Perun Perun Properties

    70 Wakeman Hill Rd, Sherman, CT 06784
  • 36 Connecticut 39, Sherman, CT 06784
    36 Connecticut 39, Sherman, CT 06784
    36 Connecticut 39, Sherman, CT 06784
    /40

    $10,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    36 Connecticut 39, Sherman, CT 06784

    Summer Rental in Sherman, CT. Escape to tranquility this summer in this stunning Contemporary-style 4-bedroom, 3.5-bathroom home, perfectly nestled in a secluded, resort-like setting in beautiful Sherman, CT. Fully furnished and thoughtfully designed for luxurious living, this exceptional property is just minutes from Candlewood Lake, Squantz Pond, local dining, and nearby New Milford, CT. Step

    Yasmina Rink Coldwell Banker Realty

    36 Connecticut 39, Sherman, CT 06784
  • 13A Osborn Rd, Sherman, CT 06784

    $225,000 Sold Jun 05, 2025

    • Land
    • 2.41 Acres
    • $93,361 per Acre
    • 15 Days On Market

    13A Osborn Rd, Sherman, CT 06784

    Your perfect build site awaits you. With amazing hillside and sunset views just waiting for your new home to be built. Need a builder? No problem, we can recommend one to fit your needs. Grandfathered by the town as an approved building lot, This lot has it all from the level approach to the build site to the sunset views!

    Kurt Stoffel Howard Hanna Rand Realty

    13A Osborn Rd, Sherman, CT 06784
  • 42 Long River Rd, Sherman, CT 06784
    42 Long River Rd, Sherman, CT 06784
    42 Long River Rd, Sherman, CT 06784
    /19

    $1,300,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    42 Long River Rd, Sherman, CT 06784

    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

    Cynthia Szentkuti Ridgefield Homes Realty

    42 Long River Rd, Sherman, CT 06784
  • 8 Glenview Dr, Sherman, CT 06784
    8 Glenview Dr, Sherman, CT 06784
    8 Glenview Dr, Sherman, CT 06784
    /25

    $11,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,350 Sq Ft
    • House for Rent

    8 Glenview Dr, Sherman, CT 06784

    Furnished Summer Rental | July 1 - Aug 31 Enjoy the ultimate summer escape in this 4BR, 2.5BA Colonial set on nearly 2 private acres in a quiet Sherman cul-de-sac. The backyard feels like your own private resort, featuring a beautiful in-ground pool heated by propane, with varying depths reaching over 7 feet-perfect for both relaxing floats and refreshing swims. Unwind in the separate hot tub

    Melissa Franco William Raveis Real Estate

    8 Glenview Dr, Sherman, CT 06784
  • 3 Mauweehoo Hill, Sherman, CT 06784

    $700,000 Sold Jun 02, 2025

    • 2,641 Sq Ft
    • $265/SF
    • 38 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1968

    3 Mauweehoo Hill, Sherman, CT 06784

    Nestled in the picturesque town of Sherman, this extraordinary property seamlessly blends southwestern-inspired rustic charm with modern luxury. Situated along a designated Scenic Road, the nearly 8-acre property is comprised of two adjoining parcels & features rolling terrain, historic stone walls & lush native landscaping creating a private and serene retreat. Taxes on both=$6,422. Enjoy

    Lisa Briscoe William Raveis Real Estate

    3 Mauweehoo Hill, Sherman, CT 06784
  • 21 Holiday Point Rd, Sherman, CT 06784
    21 Holiday Point Rd, Sherman, CT 06784
    21 Holiday Point Rd, Sherman, CT 06784
    /23

    $1,250,000

    • 4 Beds
    • 3.5 Baths
    • 4,854 Sq Ft

    21 Holiday Point Rd, Sherman, CT 06784

    [ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake community the house sits atop a hill, safely tucked away from the road and features everything a family may desire: boat dock, large inground gunite pool with a slide, kids' playground, volleyball, supersized deck, magnificent library, 2 floor game room, 3 fireplaces, giant kitchen, separate dining room, 4

    Jorge Zea Blue Lighthouse Realty, Inc

    21 Holiday Point Rd, Sherman, CT 06784
  • 21 Route 39 S Unit A, Sherman, CT 06784
    21 Route 39 S Unit A, Sherman, CT 06784
    21 Route 39 S Unit A, Sherman, CT 06784
    /16

    $2,200 per month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • House for Rent

    21 Route 39 S Unit A, Sherman, CT 06784

    One of a kind rental opportunity. Set on 10 magical acres with pond and brook. Private 1 bedroom above garage rental. Open concept with hardwood floors throughout. Center island kitchen opens to living room. Bedroom with built ins, walk in closet and small storage area. Laundry room (washer/dryer not included-front loader needed). Private entrance and mudroom/foyer. Beautiful tiles bathroom.

    Joe Chemero Coldwell Banker Realty

    21 Route 39 S Unit A, Sherman, CT 06784
  • 15 Skyline Dr, Sherman, CT 06784

    $1,350,000 Sold May 28, 2025

    • 3,068 Sq Ft
    • $440/SF
    • 84 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2003

    15 Skyline Dr, Sherman, CT 06784

    This beautiful Craftsman-style home offers an exceptional blend of charm, elegance and luxury, along with breathtaking lake views over Candlewood. Located in the gated community of Candlewood Lake Estates, the home is set in a private, tranquil setting and welcomes you with impressive landscaping and a Belgian block and gravel driveway that set the stage for the thoughtful design and premium

    Irit Granger William Pitt Sotheby's Int'l

    15 Skyline Dr, Sherman, CT 06784
  • 41 Long River Rd, Sherman, CT 06784
    41 Long River Rd, Sherman, CT 06784
    41 Long River Rd, Sherman, CT 06784
    /38

    $938,500 New Construction

    • 3 Beds
    • 3 Baths
    • 3,500 Sq Ft

    41 Long River Rd, Sherman, CT 06784

    Fully customizable Scandinavian modern home with walkout finished lower level set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated golf course community in Sherman, CT. You select exterior & interior colors, finishes, tile/stone, appliances, etc. 3 bd / 3 bath / 3,500 SF open-concept residence with main level primary, seamlessly connects kitchen (w/

    Donna Kennedy Keller Williams Realty

    41 Long River Rd, Sherman, CT 06784
  • 1 Pine Hill Trail, Sherman, CT 06784
    1 Pine Hill Trail, Sherman, CT 06784
    1 Pine Hill Trail, Sherman, CT 06784
    /36

    $12,500 per month

    • 4 Beds
    • 3 Baths
    • 2,763 Sq Ft
    • House for Rent

    1 Pine Hill Trail, Sherman, CT 06784

    TIMBER TRAILS charmer - Delightful country home on a beautiful 3.47-acre property, featuring an inground pool, and captivating interiors that offer a mixture of mid century elements with many tasteful updates. The living room features an original stone fireplace and is open to the dining room and kitchen and connects with a screened porch that leads to the pool. The pool and its stone surround,

    Irit Granger William Pitt Sotheby's Int'l

    1 Pine Hill Trail, Sherman, CT 06784
  • 40 Wagon Wheel Rd, Sherman, CT 06784

    $69,000 Sold May 23, 2025

    • Land
    • 1.44 Acres
    • $47,917 per Acre
    • 6 Days On Market

    40 Wagon Wheel Rd, Sherman, CT 06784

    Welcome to 40 Wagon Wheel Rd., Sherman! Imagine the possibilities for your dream home on this approved 1.44-acre non-conforming building lot. Nestled in a quiet, secluded setting, this unique property is just a short drive from the Great Hollow Nature Preserve, Pootatuck State Forest, and the New York State border- all while being only 1.5 hours from NYC! Well and septic installation required. A

    Besart Dani William Raveis Real Estate

    40 Wagon Wheel Rd, Sherman, CT 06784
  • 60 Long River Rd, Sherman, CT 06784
    60 Long River 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
  • 6 Irene Ln, Sherman, CT 06784
    6 Irene Ln, Sherman, CT 06784
    6 Irene Ln, Sherman, CT 06784
    /37

    $6,500 per month

    • 5 Beds
    • 6 Baths
    • 4,022 Sq Ft
    • House for Rent

    6 Irene Ln, Sherman, CT 06784

    Private Home with Beautiful Pool and Plenty of Space In & Out! Enjoy Peace and Tranquility on 4+ Private Acres Bordering Land Trust at end of Long Level Driveway. Great for Entertaining! Colonial with Contemporary Flair Boasts Designer Chef's Kitchen, 2 Story Foyer, Main Level Office with French doors, 2 Story Great Room with Arched Picture Windows to bring in Wonderful Sunsets. This Amazing 5

    Joseph Perun Perun Properties

    6 Irene Ln, Sherman, CT 06784
  • 17 Curtis Dr, Sherman, CT 06784

    $695,000 Sold May 23, 2025

    • 4,599 Sq Ft
    • $151/SF
    • 45 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1987

    17 Curtis Dr, Sherman, CT 06784

    Are you looking to escape? This home should be your final destination. You could be living the dream in this modern colonial which has amazing space inside & out. Come enjoy this home & everything Sherman has to offer- it is a short walk to beautiful Happy Acres farm. Sitting at the end of a cul de sac, set back on 2 beautiful, lightly wooded acres. This modern colonial boasts flexibility in how

    Ginny Gordon-O’Neill William Raveis Real Estate

    17 Curtis Dr, Sherman, CT 06784
  • 65 Church Rd, Sherman, CT 06784
    65 Church Rd, Sherman, CT 06784
    65 Church Rd, Sherman, CT 06784
    /32

    $1,100,000 Pending

    • 4 Beds
    • 3 Baths
    • 3,230 Sq Ft

    65 Church Rd, Sherman, CT 06784

    Castle in the Sky-First time on the market! Experience breathtaking views and complete privacy in this one-of-a-kind 4-bedroom, 3 bath contemporary in the heart of charming Sherman. Set high above the road on a private, winding driveway, this 2003-built home offers over 3200 sq ft of sun-filled living space plus an additional 1,000+sq ft walk-out basement with endless potential. Soaring ceilings

    Donna Garr William Raveis Real Estate

    65 Church Rd, Sherman, CT 06784
  • 32 Leach Hollow Rd, Sherman, CT 06784
    32 Leach Hollow Rd, Sherman, CT 06784
    32 Leach Hollow Rd, Sherman, CT 06784
    /40

    $18,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • House for Rent

    32 Leach Hollow Rd, Sherman, CT 06784

    Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for the 2025 summer season or by summer month. Scenic distant views frame this private 15-acre compound. Elegantly presented interiors, with extensive renovations supervised by an AIA architect specializing in historic preservation. Attention to detail and quality

    Irit Granger William Pitt Sotheby's Int'l

    32 Leach Hollow Rd, Sherman, CT 06784
  • 5 Short Ln, Sherman, CT 06784

    $570,000 Sold May 21, 2025

    • 1,592 Sq Ft
    • $358/SF
    • 29 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    5 Short Ln, Sherman, CT 06784

    Lakeside Living at Its Best in Holiday Point! Tucked away at the end of a quiet dead-end street, this charming Contemporary Colonial 3-bedroom home offers the perfect lake retreat in the desirable Holiday Point water community. With a 3-bedroom septic system installed in 2020 (and rarely used), this home is move-in ready and full of thoughtful upgrades. The beautifully renovated kitchen features

    Toni Riordan Berkshire Hathaway NE Prop.

    5 Short Ln, Sherman, CT 06784
  • 4 Wanzer Hill Rd, Sherman, CT 06784
    4 Wanzer Hill Rd, Sherman, CT 06784
    4 Wanzer Hill Rd, Sherman, CT 06784
    /36

    $665,000

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    4 Wanzer Hill Rd, Sherman, CT 06784

    Near the natural beauty of Candlewood Lake, Squantz Pond, and a nearby state park, this 1,896 sq ft 3-bedroom, 2.5-bath home offers an open layout featuring a stunning kitchen with a large center island and brand-new stainless steel appliances, dining room with sliding doors for additional outdoor seating and entertaining. The spacious living room is warm and welcoming with a cozy wood stove. The

    Rosalia Casorla Premier Re Group LLC

    4 Wanzer Hill Rd, Sherman, CT 06784
  • 60 Leach Hollow Rd, Sherman, CT 06784
    60 Leach Hollow Rd, Sherman, CT 06784
    60 Leach Hollow Rd, Sherman, CT 06784
    /24

    $6,000 per month

    • 2 Beds
    • 1 Bath
    • 1,666 Sq Ft
    • House for Rent

    60 Leach Hollow Rd, Sherman, CT 06784

    Located on a hill overlooking the main house of this 14 acre compound on a designated "Scenic Road," this 2BR/1B 1929 solid stone cottage is just 60 M from NYC!Guests have access to the entire cottage full wooded property,water views of private lake are just past the driveway.Screened Porch & Extended Dining.This cottage was originally built by Helen Graham,assistant to Norman Vincent Peale.Stone

    Kathleen Harrison Coldwell Banker Realty

    60 Leach Hollow Rd, Sherman, CT 06784
  • 1 Mary Bee Ln, Sherman, CT 06784

    $637,000 Sold May 19, 2025

    • 3,002 Sq Ft
    • $212/SF
    • 196 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1974

    1 Mary Bee Ln, Sherman, CT 06784

    Deer Run Shores 4 bedroom 3.5 bath home sitting pretty with winter lake views! Large rooms and open concept. Center island granite eat in kitchen. Vaulted living room and dining room with hardwood floors. Family room with brick foireplace. Upper level has 4 bedrooms and 3 baths including spacious primary suite with walk in closet and awesome bath. Oil heat and central air. Lots of storage. Large

    Joe Chemero Coldwell Banker Realty

    1 Mary Bee Ln, Sherman, CT 06784
  • 2 Pleasant View Rd, New Fairfield, CT 06812
    2 Pleasant View Rd, New Fairfield, CT 06812
    2 Pleasant View Rd, New Fairfield, CT 06812
    /20

    $594,900

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    2 Pleasant View Rd, New Fairfield, CT 06812

    Welcome to this Move in Ready Home! Live Like You are on Vacation Everyday! Nestled in the Serene Squantz Pond Community of New Fairfield, CT. w/ Deeded Access & Walking Distance to Lake. This Well Maintained 3 Bedroom, 2 Bath, 1 Car Garage Ranch on a Corner Lot Features Hardwood Floors Throughout, Updated Baths w/ Tile Flooring & Modern Touches, Updated Kitchen w/ Stainless Steel Appliances,

    Debbie Kranidis Preston Gray Real Estate

    2 Pleasant View Rd, New Fairfield, CT 06812
  • 123 Connecticut 39 Unit 2, Sherman, CT 06784
    123 Connecticut 39 Unit 2, Sherman, CT 06784
    123 Connecticut 39 Unit 2, Sherman, CT 06784
    /26

    $2,250 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    123 Connecticut 39 Unit 2, Sherman, CT 06784

    Don't miss this rare rental opportunity in the picturesque town of Sherman! Two bedrooms and two full baths. Sliding glass doors to the patio. This updated unit features modern kitchen, new appliances, and renovated bathrooms. 2 parking spots included. Enjoy a private, wooded backyard and the convenience of being just minutes from the beach, lake, shops, and restaurants. With easy access to

    Ellen Schwartz William Pitt Sotheby's Int'l

    123 Connecticut 39 Unit 2, Sherman, CT 06784
  • 5 Old Hickory Ln, Sherman, CT 06784

    $1,010,000 Sold May 12, 2025

    • 3,940 Sq Ft
    • $256/SF
    • 93 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    5 Old Hickory Ln, Sherman, CT 06784

    Elegant Colonial in the Desirable Timber Trails Community Located in the tranquil and picturesque New Fairfield/Sherman border, this beautifully appointed Colonial has the perfect blend of privacy and convenience-just a short commute to New York City and Metro North. The expansive, professional-grade country kitchen serves as the heart of the home, featuring top-of-the-line Wolf appliances, a

    Eric Bergers William Raveis Real Estate

    5 Old Hickory Ln, Sherman, CT 06784

Showing Results 1 - 40, Page 1 of 18

Connecticut Sherman

Real Estate & Homes

Home Trends in Sherman, CT

On average, homes in Sherman, CT sell after 84 days on the market compared to the national average of 49 days. The median sale price for homes in Sherman, CT over the last 12 months is $649,000, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,000
Median Single Family Sale Price
$699,000
Average Price Per Sq Ft
$379
Number of Homes for Sale
18
Last 12 months Home Sales
51
Months of Supply
4.20
Median List Price
$739,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-4%
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