Introducing 227 Gay Street, a timeless gem in the coveted Thompson Park neighborhood in Old Town Longmont. Situated on a generous 1/3 acre lot, this centrally located property includes a spacious 3 bedroom/3 bath main house (with multiple flex spaces), and a beautifully updated, energy-efficient, 2 bedroom/1 bath carriage house tucked toward the back of the oversized lot. This unique setup provides ample space for family, friends, creative endeavors, work-from-home comfort, and easy host space for tenants or guests. Step in from the welcoming front porch to a lovely flowing layout, with comfortable dining and living spaces - plus a wood-burning fireplace that beckons you to come and settle in for a while. Complete with a modern main-floor full bath, a light-filled office, and a kitchen designed for the aspiring chef (with double ovens and custom butcher block & poured concrete countertops), this house will make you feel right at home. Upstairs you'll find three bedrooms, an updated ensuite bath, and a bonus flex space for overflow. The carriage house serves as a versatile ADU with modern touches: Brazilian Cherry floors, a chef's range, two bedrooms and a full bath upstairs with deep soaking tub, making it ideal for guests, or as a rental opportunity. Venture outside to discover a generous lot with mountain views and fruit trees - perfect for gardening, playing hide and seek, or cultivating your own hobby farm oasis. Just blocks from Central Elementary, Juniper Goods and the West side Tavern, this home's location could not be better! Zoned Duplex/Triplex, there is plenty of opportunity to expand. Recent updates include: New roof/siding, refreshed landscaping, and nicely finished paint and floors that offer a contemporary touch to this historic residence. Come experience the unique charm and character of 227 Gay Street, where historic elegance meets modern living. Call to schedule a private tour of this turn of the century Victorian and ADU/carriage house today!