2,802

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
  • 29 Lavelle Ave, New Fairfield, CT 06812
    29 Lavelle Ave, New Fairfield, CT 06812
    29 Lavelle Ave, New Fairfield, CT 06812
    /19

    $2,250 per month

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

    29 Lavelle Ave, New Fairfield, CT 06812

    DIRECT WATERFRONT! A real CREAM PUFF. Apartment on serene Squantz Pond. Bring your canoe/kayak/boat & guitar. Shared Dock on Property for your use. Huge Water's Edge Patio and lovely rolling lawn. Consider this your New York Chic renovated apartment in the Country! Light & Airy - 1 Bedroom plus Den/Office. Separate Entrance from Main House with private porch/terrace directly overlooking the lake.

    Kathleen Harrison Coldwell Banker Realty

    29 Lavelle Ave, New Fairfield, CT 06812
  • 3B Flak Ln, New Fairfield, CT 06812

    $585,000 Sold Aug 04, 2025

    • 2,532 Sq Ft
    • $231/SF
    • 52 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1990

    3B Flak Ln, New Fairfield, CT 06812

    Welcome to a spacious colonial house featuring four bedrooms and 2.5 bathrooms on a private 1.2-acre lot within walking distance to Candlewood Lake. This home offers a perfect blend of comfort and convenience. Enjoy the high ceiling in the family room, creating an open and airy atmosphere. A lovely deck is ideal for BBQs and outdoor gatherings. The second floor boasts a spacious main bedroom with

    Niurka Rodriguez Coldwell Banker Realty

    3B Flak Ln, New Fairfield, CT 06812
  • 2 Autumn Dr, Sherman, CT 06784
    2 Autumn Dr, Sherman, CT 06784
    2 Autumn Dr, Sherman, CT 06784
    /38

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 4,509 Sq Ft

    2 Autumn Dr, Sherman, CT 06784

    Tucked away on a private enclave of homes in desirable Southern Sherman, just minutes from the NY line, this stunning residence offers the perfect blend of seclusion, luxury and convenience for year-round living, weekend and summer escapes from the city. A very special property interior designed and decorated by AlvinYorkDesign of NYC, this is nothing short of exceptional, blending comfort with

    Angelina Valentini Coldwell Banker Realty

    2 Autumn 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
  • 135 Green Pond Rd, Sherman, CT 06784

    $540,000 Sold Jul 31, 2025

    • 1,560 Sq Ft
    • $346/SF
    • 22 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1978

    135 Green Pond Rd, Sherman, CT 06784

    You Can Have It All - Lake Living at Its Finest! Don't miss this incredible opportunity in Candlewood Lake Estates, a gated water community in scenic Sherman, CT. This 3-bedroom, 3-bath ranch offers over 1,500 sq ft of finished living space, with an additional 450 sq ft ready to be transformed into whatever you imagine-home gym, office, or guest suite! The real draw? Access to four private

    Todd Sargent Coldwell Banker Realty

    135 Green Pond Rd, Sherman, CT 06784
  • 15 Osborn Rd, Sherman, CT 06784
    15 Osborn Rd, Sherman, CT 06784
    15 Osborn Rd, Sherman, CT 06784
    /40

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,989 Sq Ft

    15 Osborn Rd, Sherman, CT 06784

    Set along a scenic country road with sweeping views of the western hills, this beautifully renovated ranch offers the rare ease of single-level living and is situated on nearly 4 acres of perfectly level, park-like grounds. Move-in ready and thoughtfully updated, the home spans 2,400 square feet and includes three bedrooms, two and a half baths, and an expansive open-concept great room. Anchoring

    Irit Granger William Pitt Sotheby's Int'l

    15 Osborn Rd, 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
  • 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

    • 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
  • 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
  • 28 Lavelle Ave, New Fairfield, CT 06812

    $690,000 Sold Jul 23, 2025

    • 2,005 Sq Ft
    • $344/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2012

    28 Lavelle Ave, New Fairfield, CT 06812

    Welcome to your ultimate water-view home oasis overlooking Squantz Pond and minutes from Candlewood Lake! With unobscured views of the wooded hills sloping down to the cool blue water, this retreat-like home boasts ready access to the state park and recreation area with year-round recreation opportunities including hiking, boating, fishing and much more. The three-bedroom, two full bath Cape was

    Gregor Vidmar Patriot Realty Group

    28 Lavelle Ave, New Fairfield, CT 06812
  • 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
  • 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 Fair Ln, New Fairfield, CT 06812

    $309,900 Sold Jul 18, 2025

    • 1,120 Sq Ft
    • $277/SF
    • 16 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    16 Fair Ln, New Fairfield, CT 06812

    Cozy home in the desirable Candlewood Hills Community. The home was completely renovated in 2016; including kitchen with granite counters and newer appliances, updated bathroom, new windows and new hot water heater and gas range (2024). Mechanical systems were new in 2016 and feature a highly efficient, gas-fired central heating and air conditioning system, plumbing, electrical system, and even

    Jason Saphire www.HomeZu.com

    16 Fair Ln, New Fairfield, CT 06812
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

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

    Jorge Zea Blue Lighthouse Realty, Inc

    21 Holiday Point Rd, 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
  • 70 Wakeman Hill Rd, Sherman, CT 06784
    70 Wakeman Hill Rd, Sherman, CT 06784
    70 Wakeman Hill Rd, Sherman, CT 06784
    /37

    $899,900

    • 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
  • 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
  • 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
  • 10 Misty Brook Ln, New Fairfield, CT 06812

    $1,595,000 Sold Jun 30, 2025

    • 3,854 Sq Ft
    • $414/SF
    • 18 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1998

    10 Misty Brook Ln, New Fairfield, CT 06812

    This exceptional custom built home features unparalleled craftsmanship and special attention to detail throughout. Grand two-story Foyer. Amazing Kitchen with Kingswood cabinetry, large island, granite counters and premium appliances. The Media Room has a see-thru fireplace. Soaring two-story Family Room boasts a floor-to-ceiling stone fireplace and an abundance of windows for natural light.

    Jeff Neumann Houlihan Lawrence

    10 Misty Brook Ln, New Fairfield, CT 06812
  • 79 Route 39 N, Sherman, CT 06784
    79 Route 39 N, Sherman, CT 06784
    79 Route 39 N, Sherman, CT 06784
    /28

    $735,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,144 Sq Ft

    79 Route 39 N, Sherman, CT 06784

    Open and airy 4 bedroom contemporay home sitting pretty with privacy and views on 3.3 acres. Open layout features soaring ceilings and plenty of windows. Sunken 2 story family room with stone fireplace. Large eat in kitchen. Main level office. 2 car attached garage with easy access through mudroom. Hardwood floors. Newer minisplits for efficient heat and air conditioning. 4 bedrooms all with

    Joe Chemero Coldwell Banker Realty

    79 Route 39 N, 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
  • 19 Candle Hill Rd, New Fairfield, CT 06812
    19 Candle Hill Rd, New Fairfield, CT 06812
    19 Candle Hill Rd, New Fairfield, CT 06812
    /12

    $150,000

    • 1 Bed
    • 1.5 Baths
    • 690 Sq Ft

    19 Candle Hill Rd, New Fairfield, CT 06812

    CASH ONLY .... This is a tear down ... DO NOT ENTER THE BUILDING IT IS UNSAFE. Buyers to conduct your own due diligence on this property and improvements. Nice .25 acre lot.

    Office Fidelity Real Est Fidelity Real Estate

    19 Candle Hill Rd, New Fairfield, CT 06812

Showing Results 1 - 40, Page 1 of 18

Connecticut Fairfield County New Fairfield Sherman

Real Estate & Homes

Learn more about living in Sherman

Home Trends in Sherman, CT

On average, homes in Sherman, New Fairfield sell after 104 days on the market compared to the national average of 70 days. The median sale price for homes in Sherman, New Fairfield over the last 12 months is $355,585, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$355,585
Median Single Family Sale Price
$418,302
Median Townhouse Sale Price
$293,000
Median 2 Bedroom Sale Price
$275,500
Average Price Per Sq Ft
$203
Number of Homes for Sale
6
Last 12 months Home Sales
98
Months of Supply
0.70
Median List Price
$359,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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