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$2,150,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,641 Sq. Ft.
  • 3 Car Garage
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Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath, including a sought-after first-floor primary bedroom suite that provides convenience and flexibility. The impressive great room serves as a standout feature, complete with a mahogany bar, stone fireplace, mounted TV area, and ample room for billiards and table games-creating an ideal setting for relaxing or hosting guests year-round. Designed for both everyday living and entertaining, the home showcases expansive gathering spaces filled with natural light. The screened-in porch extends the living space outdoors and provides a comfortable place to enjoy the surrounding private yard in multiple seasons. Outside, the in-ground pool and landscaped grounds create a peaceful retreat with space for entertaining, recreation, and outdoor dining. **962 sqft is the finished walk out lower level and included in total sqft.**

Full Property Details for 161 Sherwood Dr

General

  • Sold For: $2,150,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24178764
  • Added to Site: 93 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Mud Room
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom, Main
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom - Full Bath, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Main
  • Great Room: Great Room - Fireplace, Upper
  • Family Room: Family Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Laundry: Main Level
  • Other Room 1: Other - Full Bath, Lower

Additional Information

  • Pool: Yes
  • Pool Description: Fiberglass, In Ground Pool

Exterior

  • Exterior Features: Grill, Shed, Garden Area, Patio
  • Color: Gray

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 4
  • Parking: Attached Garage, Paved, Driveway

Location

  • County: Fairfield
  • Neighborhood: Southport
  • Driving Directions: Warner Hill to Sherwood Drive

School Information

  • Elementary School: Mill Hill
  • Middle School: Roger Ludlowe
  • High School: Fairfield Ludlowe

Community

  • Community Name: Southport

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Partial
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,641
  • Above Ground: 4,641 Sq. Ft.
  • Year Built: 1957

Lot Features

  • Lot Size (Acres): 1.52
  • Driveway/Sidewalk: Private
  • Zoning: AA
  • Lot Description: Sloping Lot

Water Features

  • Water Front Desc.: Beach Rights, Water Community

Financial Considerations

  • Assessment Amount: $836,080
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: See attached inclusion/Exclusion Agreement
  • Property ID: 133325

Meet the selling agent

Meet the selling agent
— 161 Sherwood Dr —

Get Pre-Approved Today

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 161 Sherwood Dr

School District:Fairfield School District
NameGradesDistance
Mill Hill School
635 Mill Hill Terrace, Fairfield, CT 06890
K-50.8 mi
Roger Ludlowe Middle School
689 Unquowa Road, Fairfield, CT 06824
6-81.3 mi
Fairfield Ludlowe High School
785 Unquowa Road, Fairfield, CT 06824
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 161 Sherwood Dr

Date
Details
Price
Change
Source
7/20/2026
Sold
$2,150,000
-5.49%
MLS
5/27/2026
Listed
$2,275,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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161 Sherwood Drive, Fairfield, CT 06890 (MLS# 24178764) is a Single Family property that was sold at $2,150,000 on July 20, 2026. This property was sold by Cindy Raney & Team from our Westport Office.Want to learn more about 161 Sherwood Drive? Do you have questions about finding other Single Family real estate for sale in Southport? You can browse all Southport real estate or contact a Coldwell Banker agent to request more information.