Modern Opportunity in the Historic Old Main Street district in South Windsor. Discover this premier compound prospect for a piece of South Windsor's storied history at 90-92 Main St. This special property features two completely independent dwellings on a level 0.56-acre parcel, offering an ideal configuration for owner-occupants and savvy investors alike. The primary residence, with 2 units in the stately 1820 Antique Colonial, boasts 2,094 sq. ft. of timeless character. The 2-bedroom lower part of the home is a dream for those seeking the charm of yesteryear without sacrificing space. The upper unit has a distinctly cozier feel, while giving more separation than an average 1-bedroom. Tucked privately behind the main house is the second dwelling: a versatile 856 sq. ft. cottage-colonial. Whether you utilize this space as a high-performing rental unit to add to a portfolio, or an in-law suite, the flexibility of two separate legal homes on one lot is a true rarity in this market and presents several options. For the Owner-Occupant: Live in the grand main house while the second and third units provide supplemental income. Enjoy the "country feel" of Old Main St, one of the most picturesque and historically significant stretches in Connecticut, with its nearby farm stands and scenic river views, while being only 10 minutes from the high-end shopping and dining at Evergreen Walk. Experience the best of both worlds: a heritage home with a modern financial edge.