40 Oleson Drive, Southbury, CT 06488

• 5 beds |
• 2 baths |
• 2,040 sqft

Property Description

Set at the end of a shared private driveway on 2.9 wooded acres, this 5BR home presents a unique opportunity for those seeking privacy, space, and the chance to create something truly their own. Surrounded by natural beauty, the property offers room to explore, garden, entertain, or simply enjoy a peaceful setting while remaining close to everyday conveniences. A covered porch welcomes you inside where hardwood flooring runs through much of the home. The living room features built in bookshelves, a wood stove, and large windows that bring in natural light. A notable advantage of the home's layout is the presence of three bedrooms on the main level, offering flexibility for single level living, guests, home office space, or multigenerational needs. The main level also includes an eat in kitchen with a large pantry, dining room, full bath, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms and a half bath with space that may accommodate future expansion to a full bath or laundry area. Ample closet space is found throughout. The unfinished lower level provides additional flexibility with workshop space, laundry and mechanical areas, a storage room suitable for a wine or root cellar, and a two car tandem garage. Outside, you'll find an inground pool with a new liner (2024), multiple outbuildings and wood sheds (conveyed as is), and abundant parking.

Listing Status:

Active

Date Added:

May 11, 2026

Data Last Updated:

August 10, 2026 at 8:52PM

Listing Office:

William Pitt Sotheby's Int'l : (203) 796-7700

Listing Agent:

Liz Newnham : (203) 994-4123

MLS ID:

24174641

Interior

• General: Auto Garage Door Opener
• Rooms: FoyerWorkshop
• Appliances: Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer
• Laundry: Lower Level
• Basement: FullUnfinishedStorageGarage AccessInterior Access
• A/C: None
• Heating: Hot AirOil
• Fireplace: Fireplaces: 1

Exterior

• General: ShedPorchGuttersStone Wall
• Style: Cape CodColonial
• Pool: VinylIn Ground Pool
• Parking: Parking spaces: 4

Construction

• Roofing: Asphalt Shingle

Location

• County: New Haven

Lot

• Driveway: PrivateSharedPaved
• Zoning: R-601331688
• Restrictions: Easements

Utilities

• Water: Private Well
• Sewer: Septic

Financial

• Exclusions: As Per Inclusion/Exclusion Rider