2 Longwood Drive
Redding, CT, 06896 $ 1,849,000
Bedrooms4 Baths4.1 Sq 6,259 Monthly Estimate*
$ 11,535
for $1,849,000 with 4 bedrooms and 4 full baths, 1 half bath. This 6,259 square foot home was built in 1998 on a lot size of 2.72.
Attractive Price Adjustment on this Quintessential New England Retreat in Redding, CT* Welcome to 2 Longwood Drive, an exquisite property providing an idyllic lifestyle amidst natural beauty. This custom-built colonial residence has been meticulously cared for by its sole owner and features 6,259 sq. ft. of open concept living on 2.72 private, landscaped acres, offering the perfect blend of timeless charm and modern luxury. A dramatic entryway with a stunning covered stone patio and central foyer welcomes you into the expansive first-level with 9-foot ceilings, hardwood floors throughout, and light-filled living spaces designed for both relaxation and entertaining. The heart of the home is the updated gourmet kitchen, featuring a Sub-Zero oversized refrigerator/freezer, Thermidor double ovens, a 6-burner Wolf gas cooktop, custom cabinetry, a large center island, and a butler's pantry. A wet bar with a wine refrigerator, ice maker, and sink complements the space, while a cozy sunlit breakfast nook overlooks the serene backyard. The kitchen flows seamlessly into a spacious family room with a gas fireplace. A formal dining room, private office with custom built-ins, and a large mudroom with 3 entrances from the garage, front stone walkway, and rear patio complete the first-level. The second-level primary suite offers the rare luxury of two full bathrooms, joined by three additional bedrooms, a large recreation room, and laundry room with a sink. The residence was thoughtfully constructed with a 5-bedroom septic system, allowing the dramatic third-level bonus room to be used as a 5th bedroom/in-law suite, with two large closets, multiple cozy window alcoves, and a private bathroom featuring a steam shower - ideal for quiet relaxation. This stately home includes a 2,298 sq. ft. unfinished lower-level, providing abundant storage or the opportunity to create customized living, fitness, or entertainment spaces. Outdoor living is equally impressive, with two stone patios surrounded by mature flowering trees, lush plantings, and classic New England stone walls. The expansive yard provides plenty of room to add a pool, enhancing the property's resort-like appeal. A three-car garage, whole-home generator, and refined attention to detail elevate this residence into a true Redding sanctuary. Enjoy golf, tennis, paddle, pickle-ball, swimming and fine dining at the nearby Redding Country Club (membership required), or walk to the nearby Redding Elementary School and Community Center for free pickleball, tennis, and summer concerts at the Town Green.
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FeaturesGeneralZoning R-2
Neighborhood Gallows Hill
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.72
Directions Gallows Hill Road to Longwood Drive. Drive around cul-de-sac to enter private drive. 2nd home on right. Park in driveway by garage. There is no "for sale" sign on property.
High School Per Board of Ed
City Redding
Elementary School Per Board of Ed
Sq Ft Total 6259
DOM 108
Year Built 1998
Style Colonial
Year Built Source Public Records
Energy Features Generator Thermopane Windows
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InteriorCooling System Ceiling Fans Central Air Zoned
Total Rooms 16
Basement Description Full Unfinished Storage Interior Access Concrete Floor
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ExteriorWater Source Private Well
Lot Description Secluded Lightly Wooded Dry Sloping Lot On Cul-De-Sac Professionally Landscaped
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* Excluded FeaturesList ByJeffrey KaplanListing Agent
William Raveis Real EstateBroker
Jeff.Kaplan@raveis.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $11,535
- Monthly Property Taxes
- $2,552
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Redding, CT
Average List Price $1,399,075
Percent of Sale Price 24%
About Redding, CT 9,350 Population
13% Since 2002
$ 138,936 Median Income
50.56 Median Age
33% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 11/13/2025 | $1,849,000 | | Listed Price |