2,137

Fairfield, 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
  • 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
  • 13 Wanzer Hill Rd, Sherman, CT 06784

    $950,000 Sold Jul 28, 2025

    • 4,092 Sq Ft
    • $232/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2016

    13 Wanzer Hill Rd, Sherman, CT 06784

    Welcome to 13 Wanzer Hill Road, where modern lifestyle meets nature and great outdoor fun. Nestled perfectly between Squantz Pond State Park and Candlewood Lake, you & your family/friends will be sure to enjoy the vast nature trails, picnic areas, soothing kayaking on the pond or motorized boating and water sports on the 8 miles of lake. Then come back home for drinks and snacks on the front

    George Muniz Keller Williams NY Realty

    13 Wanzer Hill Rd, Sherman, CT 06784
  • 2 Bridgeworth Ln, Sherman, CT 06784
    2 Bridgeworth Ln, Sherman, CT 06784
    2 Bridgeworth Ln, Sherman, CT 06784
    /38

    $780,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 3.5 Baths
    • 3,608 Sq Ft

    2 Bridgeworth Ln, Sherman, CT 06784

    Elegant, well appointed colonial with endless possibilites nestled in the heart of Sherman. An exceptionaly thought out floorplan with high ceilings throughout. Features include a kitchen with sliding doors and dining room with French doors both leading to the back porch perfect for outdoor dinning. A large living room with fireplace, spacious bedrooms including a primary suite with full bath and

    Rebecca Ward William Pitt Sotheby's Int'l

    2 Bridgeworth Ln, Sherman, CT 06784
  • 36 Connecticut 39, Sherman, CT 06784
    36 Connecticut 39, Sherman, CT 06784
    36 Connecticut 39, Sherman, CT 06784
    /40

    $15,000 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 available for August 2025. 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

    Yasmina Rink Coldwell Banker Realty

    36 Connecticut 39, Sherman, CT 06784
  • 0 Connecticut 37, Sherman, CT 06784

    $270,000 Sold Jul 18, 2025

    • Land
    • 20 Acres
    • $13,500 per Acre
    • 140 Days On Market

    0 Connecticut 37, Sherman, CT 06784

    Beautiful wooded lot with gentle slopes to two small y

    David Bain Bain Real Estate

    0 Connecticut 37, Sherman, CT 06784
  • 42 Long River Rd, Sherman, CT 06784
    42 Long River Rd, Sherman, CT 06784
    42 Long River Rd, Sherman, CT 06784
    /25

    $1,049,000

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

    42 Long River Rd, Sherman, CT 06784

    Spend your summer in this beautiful, gated community playing golf on the signature 18-hole course, enjoying a game of tennis or swimming in the heated in ground pool. There is full-service club house complete with a pro shop, pub and restaurant. You can enjoy dining on the patio that overlooks the greens. Inquire about membership details. The home is ready for immediate occupancy, so come up and

    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

    $10,500 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
  • 80-82 Connecticut 55, Sherman, CT 06784

    $650,000 Sold Jul 17, 2025

    • 2,000 Sq Ft
    • $325/SF
    • 30 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1820

    80-82 Connecticut 55, Sherman, CT 06784

    Located just steps from the Appalachian Trail and the New York state line, this historic 1820 Colonial and guest cottage offer a unique blend of historic craftsmanship, character, and charm. Set on 8.38 acres in northwest Sherman, the property showcases many period details - from original stone fireplaces and custom built-ins to handsome stone walls, patios, steps, and terracing. The main

    Irit Granger William Pitt Sotheby's Int'l

    80-82 Connecticut 55, 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

    $899,900 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
  • 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
  • 16 Coburn Rd E, Sherman, CT 06784

    $720,000 Sold Jul 17, 2025

    • 3,221 Sq Ft
    • $224/SF
    • 102 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1853

    16 Coburn Rd E, Sherman, CT 06784

    Charming antique property with a guest house set on over 10 acres on a quiet country road, less than two hours from NYC. Upon entering the main home, you're welcomed into a spacious living room, highlighted by a fireplace and uniquely curved vaulted ceiling, which opens to a light-filled sunroom. From there, an incredible great room, anchored by an impressive fieldstone fireplace, features

    Steve Pener William Pitt Sotheby's Int'l

    16 Coburn Rd E, Sherman, CT 06784
  • 86 Connecticut 37, Sherman, CT 06784
    86 Connecticut 37, Sherman, CT 06784
    86 Connecticut 37, Sherman, CT 06784
    /12

    $899,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    86 Connecticut 37, Sherman, CT 06784

    New Construction!! 4 bedroom colonial with lots of upgrades. 9 Ft ceilings on the main level. Propane heat and central air. Fireplace. Center island kitchen. Large dinette/breakfast nook. Hardwood floors throughout. Oversized deck. Primary with awesome bath and walk in closet. Convenient upper level laundry room. 2 car attached garage. Walk out basement. Pond Views!

    Joe Chemero Coldwell Banker Realty

    86 Connecticut 37, 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
  • 12 Meadow Ln, Sherman, CT 06784

    $1,637,500 Sold Jul 16, 2025

    • 4,486 Sq Ft
    • $365/SF
    • 131 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2017

    12 Meadow Ln, Sherman, CT 06784

    Welcome to the epitome of bucolic living in this unparalleled Southern Sherman estate nestled within the Wakeman Farms subdivision of custom-built homes just under a mile from the NY line. Step into luxury with this exquisite residence perfectly positioned on over 9 acres of lush landscape adorned with vibrant hydrangeas and mature trees. Designed for sophisticated yet comfortable living, this

    Donna Kennedy Keller Williams Realty

    12 Meadow Ln, Sherman, CT 06784
  • 172 Route 37 S, Sherman, CT 06784
    172 Route 37 S, Sherman, CT 06784
    172 Route 37 S, Sherman, CT 06784
    /38

    $727,000

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

    172 Route 37 S, Sherman, CT 06784

    Welcome to this sprawling 5 bedroom Antique Colonial in the beautiful town of Sherman. The property invites you with many gardens, flowers and a serene coy pond. Plenty of parking for year round entertainment. Separate heated and cooled detached garage has been converted to a studio or home office. Can also be converted back to garage if that suits your needs. As you enter the large open foyer,

    Joe Chemero Coldwell Banker Realty

    172 Route 37 S, Sherman, CT 06784
  • 65 Church Rd, Sherman, CT 06784

    $1,025,000 Sold Jun 27, 2025

    • 3,230 Sq Ft
    • $317/SF
    • 10 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    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
  • 10 Anderson Rd E, Sherman, CT 06784
    10 Anderson Rd E, Sherman, CT 06784
    10 Anderson Rd E, Sherman, CT 06784
    /38

    $548,000

    • 2 Beds
    • 2 Baths
    • 1,425 Sq Ft

    10 Anderson Rd E, Sherman, CT 06784

    MOVE IN READY! Looking for a country retreat, weekend home, artist escape or a work from home space? This charming, ranch home set in a beautiful serene setting has your name on it. This home has great flow and allows the peaceful outside space in- you can feel this the minute you walk through the front door. The living room has almost a full wall of windows showcasing the private garden with

    Ginny Gordon-O’Neill William Raveis Real Estate

    10 Anderson Rd E, Sherman, CT 06784
  • 24 Quaker Ridge Rd, Sherman, CT 06784

    $715,500 Sold Jun 26, 2025

    • 2,954 Sq Ft
    • $242/SF
    • 39 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1978

    24 Quaker Ridge Rd, Sherman, CT 06784

    Move right into this light-filled, FULLY FURNISHED Colonial, offering scenic views and a desirable location just half a mile from the New York line - perfect for easy commutes. Set on a lush, rolling backyard, this home is designed for outdoor enjoyment with an expansive 41' x 23' inground pool and adjacent patio. Located in a well-established, quiet cul-de-sac subdivision, the property offers a

    Irit Granger William Pitt Sotheby's Int'l

    24 Quaker Ridge Rd, 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
  • 6 Old Greenwoods Rd, Sherman, CT 06784

    $470,000 Sold Jun 18, 2025

    • 1,706 Sq Ft
    • $275/SF
    • 48 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    6 Old Greenwoods Rd, Sherman, CT 06784

    Welcome to your dream retreat! This beautifully maintained 1,706 square foot single-family home features 2 spacious bedrooms and 2 full baths, perfect for both relaxation and entertaining. Step inside to discover an inviting layout, featuring a spacious Kitchen, Dining and Living room. The Family room is amazing with stunning knotty pine walls and soaring vaulted ceilings, creating an airy and

    Cory Neumann Houlihan Lawrence

    6 Old Greenwoods Rd, 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

    $549,550

    • 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
  • 13 Taber Rd, Sherman, CT 06784

    $740,000 Sold Jun 18, 2025

    • 1,828 Sq Ft
    • $405/SF
    • 56 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1973

    13 Taber Rd, Sherman, CT 06784

    Set on an open level lot, this inviting country Cape offers 4 bedrooms, 2.5 baths, and a beautiful 40' refurbished gunite pool with an adjacent bluestone patio - perfect for outdoor enjoyment and entertaining. The expansive, level front and back lawns are adorned with mature specimen and fruit trees, and a picturesque dogwood-lined driveway sets a welcoming tone. Inside, the cozy living room

    Irit Granger William Pitt Sotheby's Int'l

    13 Taber Rd, Sherman, CT 06784
  • 4 Deer Run Trail, Sherman, CT 06784
    4 Deer Run Trail, Sherman, CT 06784
    4 Deer Run Trail, Sherman, CT 06784
    /29

    $632,000

    • 3 Beds
    • 2.5 Baths
    • 1,758 Sq Ft

    4 Deer Run Trail, Sherman, CT 06784

    Deer Run Shores with boat slip!! Totally renovated 3 bedroom 2.5 bath home with open layout. Center island kitchen with new stainless appliances. Hardwood floors. Primary bedroom with full bath and access to the full length deck. Other bedrooms have balcony access. Large lower level family room with brick fireplace. 2 car garage. Winter lake view. Lots of parking. Premier lake community with

    Joe Chemero Coldwell Banker Realty

    4 Deer Run Trail, Sherman, CT 06784
  • 103 Route 39 S, Sherman, CT 06784

    $529,000 Sold Jun 17, 2025

    • 2,068 Sq Ft
    • $256/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2009

    103 Route 39 S, Sherman, CT 06784

    Beautiful 3 Bedroom, 2.5 Bath Colonial home located in the Scenic Town of Sherman CT with hiking trails all around. Close proximity and access to Candlewood Lake and Squantz Pond. This home provides the perfect blend of peaceful country living and modern convenience. Up the private driveway, the house is set on a level lot allowing you to garden, entertain & play in a secluded setting. The home

    Heidi Mitchell Luks Realty

    103 Route 39 S, Sherman, CT 06784
  • 12 Fox Run, Sherman, CT 06784
    12 Fox Run, Sherman, CT 06784
    12 Fox Run, Sherman, CT 06784
    /40

    $1,600,000

    • 6 Beds
    • 7 Baths
    • 6,751 Sq Ft

    12 Fox Run, Sherman, CT 06784

    Soar with the eagles! The climb to the top is never easy, but the prize is worth it! Private Gated Entrance leads up the driveway to this 15 acre sanctuary. Glorious views of hills, valleys, Candlewood Lake and stunning sunsets take your breath away! Architecturally innovative home blends beautifully with the surrounding natural landscape. The interior offers functional, exciting living space

    Dawn Hough Coldwell Banker Realty

    12 Fox Run, 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 Coldwell Banker 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
  • 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

Showing Results 1 - 40, Page 1 of 18

Connecticut Fairfield County Sherman

Real Estate & Homes

Home Trends in Sherman, CT

On average, homes in Sherman, CT sell after 51 days on the market compared to the national average of 70 days. The median sale price for homes in Sherman, CT over the last 12 months is $750,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$750,000
Median Single Family Sale Price
$750,000
Average Price Per Sq Ft
$321
Number of Homes for Sale
0
Last 12 months Home Sales
15
Months of Supply
0.00
Median List Price
$750,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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