# 40 Oleson Drive, Southbury, CT 06488 > **TL;DR:** 5bd/2ba single family, $499,900 ($245/sqft), built 1963, 2,040 sqft. > Fireplace, 2-car garage. Est. $2,674/mo. Listed 47 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $499,900 | | Price/sqft | $245 | | Bedrooms | 5 | | Bathrooms | 1 full, 1 half | | Square Feet | 2,040 | | Year Built | 1963 | | Lot Size | 126,324 sqft (2.90 acres) | | Garage | 2-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 47 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,528 | | Estimated Insurance | $146 | | **Total** | **$2,674** | ## Nearby Schools - **Elementary:** Per Board of Ed - **High:** Pomperaug ## Key Amenities - Fireplace - 2-car garage ## Property Highlights - Built in 1963 - 2.90 acre lot - 4 parking spaces - Fireplace ## Description ### Agent Description Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from NYC, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living rm features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the 3BRs on the main level, including the primary bedroom, offering flexibility for single-level living, guests, a home office, or multigenerational needs. The main level also includes an eat-in kitchen with a large pantry, a dining rm, a full bath, & a bright four-season rm w/large sliders overlooking the wooded landscape. Upstairs are two additional BRs and a half bath with potential for future expansion. The unfinished basement offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, & access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, stone walls, multiple outbuildings & woodsheds. The property is being sold in its present, "as-is" condition. Significant improvements already done. New roof (2023), furnace (2023), septic tank (2026). New well pump/tank/cap (2024). New pool liner (2024). A whole-house Generac generator provides peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own. ## Location - **Address:** 40 Oleson Drive, Southbury, CT 06488 - **County:** New Haven - **Coordinates:** 41.475578, -73.184507 - **Google Maps:** https://www.google.com/maps?q=41.475578,-73.184507 ## Listing Agent - **Name:** Liz Newnham - **Brokerage:** William Pitt Sotheby's International Realty - **Broker Phone:** 2037967700 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/40-Oleson-Dr_Southbury_CT_06488_M35651-69267?f=listhub&s=CTMLS&m=24207493&c=propsimple) ## Photos ![40 Oleson Drive - Photo 1](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4065272409r.jpg) ![40 Oleson Drive - Photo 2](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3697689967r.jpg) ![40 Oleson Drive - Photo 3](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3581243787r.jpg) ![40 Oleson Drive - Photo 4](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f2288066630r.jpg) ![40 Oleson Drive - Photo 5](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3399860157r.jpg) ![40 Oleson Drive - Photo 6](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f1358051891r.jpg) ![40 Oleson Drive - Photo 7](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f2745109317r.jpg) ![40 Oleson Drive - Photo 8](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f2758731570r.jpg) ![40 Oleson Drive - Photo 9](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3771648897r.jpg) ![40 Oleson Drive - Photo 10](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f38675507r.jpg) ![40 Oleson Drive - Photo 11](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f598412468r.jpg) ![40 Oleson Drive - Photo 12](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3220100297r.jpg) ![40 Oleson Drive - Photo 13](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4190846621r.jpg) ![40 Oleson Drive - Photo 14](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3525884664r.jpg) ![40 Oleson Drive - Photo 15](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f669562908r.jpg) ![40 Oleson Drive - Photo 16](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f354709566r.jpg) ![40 Oleson Drive - Photo 17](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4151237796r.jpg) ![40 Oleson Drive - Photo 18](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f2461330112r.jpg) ![40 Oleson Drive - Photo 19](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f866083064r.jpg) ![40 Oleson Drive - Photo 20](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f851285532r.jpg) ![40 Oleson Drive - Photo 21](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f448796270r.jpg) ![40 Oleson Drive - Photo 22](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4024833704r.jpg) ![40 Oleson Drive - Photo 23](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4064305573r.jpg) ![40 Oleson Drive - Photo 24](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3419952736r.jpg) ![40 Oleson Drive - Photo 25](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f1870115234r.jpg) ![40 Oleson Drive - Photo 26](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f2902568005r.jpg) ![40 Oleson Drive - Photo 27](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3852271096r.jpg) ![40 Oleson Drive - Photo 28](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3641327925r.jpg) ![40 Oleson Drive - Photo 29](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f4152620089r.jpg) ![40 Oleson Drive - Photo 30](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f942027202r.jpg) ![40 Oleson Drive - Photo 31](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f58333301r.jpg) ![40 Oleson Drive - Photo 32](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f775340125r.jpg) ![40 Oleson Drive - Photo 33](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f854066672r.jpg) ![40 Oleson Drive - Photo 34](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3959231598r.jpg) ![40 Oleson Drive - Photo 35](http://lh.rdcpix.com/4b1c4888521e2717d898381b131dd0eel-f3907770801r.jpg) --- **MLS#:** 24207493 | **Updated:** 2026-10-28 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/40-oleson-drive-southbury-ct-06488-edcb97a21ef04b5385db000f7f005319) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/40-oleson-drive-southbury-ct-06488-edcb97a21ef04b5385db000f7f005319#listing", "url": "https://staging.propertysimple.ai/listing/40-oleson-drive-southbury-ct-06488-edcb97a21ef04b5385db000f7f005319", "name": "40 Oleson Drive, Southbury, CT 06488", "description": "Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from NYC, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living rm features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the 3BRs on the main level, including the primary bedroom, offering flexibility for single-level living, guests, a home office, or multigenerational needs. The main level also includes an eat-in kitchen with a large pantry, a dining rm, a full bath, & a bright four-season rm w/large sliders overlooking the wooded landscape. Upstairs are two additional BRs and a half bath with potential for future expansion. The unfinished basement offers workshop space, laundry & mechanical areas, a storage rm suitable for a wine or root cellar, & access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open areas for recreation, stone walls, multiple outbuildings & woodsheds. The property is being sold in its present, \"as-is\" condition. Significant improvements already done. New roof (2023), furnace (2023), septic tank (2026). New well pump/tank/cap (2024). New pool liner (2024). A whole-house Generac generator provides peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. 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