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2 Longwood DriveRedding, CT 06896

For Sale

$1,745,000

Smart Buyer Rebate $17,450

Rare opportunity to purchase a meticulously maintained, single-owner colonial set amid the rolling lawns and mature trees of southern Redding, offered below recent comparable sales and representing exceptional value for the size, land, and location. Sited on 2.72 secluded, professionally landscaped acres on a private cul-de-sac in the sought-after Gallows Hill neighborhood, this classic New England colonial captures the bucolic charm that has long defined Redding, offering significantly more square footage and acreage per dollar than comparable listings in the area, just over an hour from Manhattan with convenient Metro-North access via Westport, Wilton, and West Redding. The thoughtfully designed floor plan features nine foot ceilings, hardwood floors throughout, and generously proportioned rooms suited to both everyday living and entertaining. The gourmet kitchen showcases Sub-Zero refrigeration, a Wolf six-burner gas cooktop, granite counters, and a large center island, opening to a fireplaced living room with French doors to the patio. Additional highlights include a dedicated office with built-in bookshelves, two versatile upper-level recreation rooms, one with a full bath and steam sauna, and an in-law apartment offering flexibility for extended family or guests. The primary suite includes a walk-in closet and whirlpool tub, and three additional bedrooms complete the upper level. A full unfinished basement provides ample additional storage.

Listed by Jeffrey Kaplan

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William Raveis Real Estate

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(203) 505-3375

Last updated July 31, 2026

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Source: SmartMLS #24177771

Listing Facts

  • TypeSingle-family
  • NeighborhoodRedding
  • Bedrooms4
  • Bathrooms5
  • Days on Prevu72
  • Taxes$31,582/year
  • Size6,259 sqft
  • Price per sqft$279

Location

Mortgage Calculator

Listing History

07/09/2026
Price Decreased
$1,745,000
05/21/2026
Listed by William Raveis Real Estate
$1,795,000

Property Details for 2 Longwood Drive

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1998
  • Year Built Details: Public Records
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Garden Area, Lighting, Covered Deck, Stone Wall, French Doors, Patio

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Secluded, Lightly Wooded, Dry, Sloping Lot, On Cul-De-Sac, Professionally Landscaped
  • Lot Size Acres: 2.72

Financial

Taxes

  • Parcel Number: 269523
  • Tax Annual Amount: $31,582.00
  • Tax Year: 26

Interior

Features

  • Appliances: Gas Cooktop, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Icemaker, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller
  • Fireplaces Total: 1
  • Interior Features: DROPEN, PREWIRED, CENVAC, OPEN, SECURESY

Measurements

  • Living Area: 6,259

Rooms

  • Basement: Full, Unfinished, Storage, Interior Access, Concrete Floor
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 4
  • Rooms Total: 9

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 3

Schools

Elementary School

  • Elementary School: Per Board Of Ed

High School

  • High School: Per Board Of Ed

Middle or Junior School

  • Middle Or Junior School: Per Board Of Ed

Utilities

Equipment

  • Cooling: Ceiling Fans, Central Air, Zoned
  • Heating: Hot Air
  • Laundry Features: Upper Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 5 bathrooms in this single-family home at 2 Longwood Drive.

What schools are nearby to 2 Longwood Drive?

Nearby schools include the Per Board Of Ed Elementary School, Per Board Of Ed Middle School, and Per Board Of Ed High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 2 Longwood Drive.

What are the annual taxes for 2 Longwood Drive?

Annual taxes for this single-family home are estimated at $31,582.

How does 2 Longwood Drive compare to other single-family homes in Redding?

This single-family home is listed 10% below the average price for single-family homes in Redding and has been on the market for 7 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 6,259 sqft.

2 Longwood Drive is a 4-bedroom, 5-bath single-family home for sale in Redding CT 06896. Listed on Prevu for 72 days at $1,745,000. This includes a recent price decrease of $50,000. This residence features 6,259 square feet of living space, located in Redding. The median listing price for single-family homes in this area is $1,245,000. Nearby schools include Per Board Of Ed Elementary School, Per Board Of Ed Middle School, and Per Board Of Ed High School. Explore more single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.