Open House 7/19 11am - 1pm
2 Longwood Drive
Redding, CT, 06896 $ 1,745,000
Bedrooms4 Baths4.1 Sq 6,259 Monthly Estimate*
$ 11,018
for $1,745,000 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.
***Rare turn-key opportunity at an unbeatable price point*** For buyers seeking exceptional craftmanship, serenity, a strong sense of community, award winning schools and uncompromised value. 2 Longwood Drive is a rare opportunity to purchase a 6,200+ square foot luxury home in southern Redding below recent comparable sales. Experience the exceptional lifestyle that has made Redding one of Fairfield County's most desirable towns for discerning buyers. Known for its scenic landscapes, extensive open space, award-winning parks, the Redding Country Club, and highly regarded public schools, Redding offers an unmatched quality of life just over an hour from Manhattan. With convenient access to Metro-North stations in Westport, Wilton, and West Redding, commuting and weekend travel are effortless. This 6,259 square foot custom built and meticulously maintained colonial is a must see, perfectly positioned on 2.72 professionally landscaped acres in one of Redding's most sought-after neighborhoods. Surrounded by mature trees, rolling lawns, and classic New England charm, the property provides a peaceful retreat while remaining just minutes from Redding schools, hiking trails, top-rated restaurants, shopping, cultural attractions, and the neighboring towns of Ridgefield, Westport, and Wilton. Families will appreciate Redding's highly acclaimed public schools, consistently recognized for small class sizes, dedicated educators, and strong academic achievement. The town's commitment to education, combined with its welcoming community and abundant recreational opportunities, makes it one of the area's most desirable places to call home. This exceptional residence was designed for today's lifestyle, the home features an open, light-filled floor plan with soaring nine foot ceilings, rich hardwood floors, generously proportioned rooms, and seamless spaces for both everyday living and elegant entertaining. The beautifully updated chef's kitchen showcases premium Sub-Zero refrigeration, Thermador double ovens, a six-burner Wolf gas cooktop, an oversized center island, butler's pantry, and wet bar. It flows effortlessly into the spacious family room with a gas fireplace, while formal living and dining rooms provide sophisticated settings for holidays and special occasions. Whether working remotely, hosting extended family, or simply enjoying the luxury of extra space, the home's thoughtful design offers exceptional flexibility and comfort. Step outside to your own private sanctuary where expansive lawns, mature landscaping, and peaceful outdoor living spaces capture the beauty and tranquility that define Redding. For added confidence, the home includes a brand new HVAC unit and a comprehensive full home warranty, providing valuable coverage for many major home systems and appliances during your first year of ownership. Offering over 6,200 square feet of exceptional craftsmanship, a premier Redding location, access to outstanding schools, and compelling value compared with recent luxury home sales, 2 Longwood Drive presents a rare opportunity to enjoy the very best of Connecticut country living, whether as a full-time residence or an elegant weekend retreat.
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Open House
7/19/2026 11:00 AM - 1:00 PM
12:00 PM - 2:00 PM
2 Longwood Drive Redding, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
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 55
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 9
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
- $11,018
- Monthly Property Taxes
- $2,552
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% 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 $1,514,794
Percent of Sale Price 13%
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 |
|---|
| 6/26/2026 | $1,745,000 | -2.79% | Price Down |
| 5/22/2026 | $1,795,000 | | Listed Price |