Rarely available, this 3-bedroom, 2-bathroom upper-duplex condominium spans the top two floors of a charming boutique building on a quiet, residential Brookline street. Flooded with natural light from Pella windows on three exposures, the home features warm hardwood floors and a flexible, airy layout perfect for daily living, remote work, and entertaining.The main level opens to an oversized, sun-filled living and dining room highlighted by a ceiling fan, mini-split A/C, and a stunning wall of custom floor-to-ceiling built-ins. Ideal for home chefs, the eat-in kitchen pairs abundant wood cabinetry and granite countertops with a generous breakfast peninsula. Premium stainless steel appliances include a gas range with an externally vented hood, a dishwasher, and a full-size French-door refrigerator. A concealed, stacked laundry setup adds everyday convenience nearby. This floor also hosts a versatile bedroom, perfectly sized for a queen bed and a desk, and a stylish full bath with a glass-enclosed tiled rainfall shower and a smart toilet seat. Upstairs, two spacious bedrooms easily accommodate king-sized beds and feature individual mini-split AC, ceiling fans, and excellent storage, including a large walk-in closet in the primary bedroom. A second renovated full bath has a glass-enclosed tiled shower and smart toilet. Outside, residents enjoy a fully fenced backyard shared with only one neighbor, offering a peaceful retreat for grilling and outdoor dining. High-efficiency gas heat, secure keypad entry, and one assigned parking space at 275 Cypress St. complete this exceptional offering. Perfectly situated, the home offers effortless access to the Lincoln School, Brookline High School, the Emerald Necklace, Jamaica Pond, and Brookline Village. Commuting is seamless with the #60 bus right on the street and the Green Line "D" branch just a 10-minute walk away, providing direct connections to Longwood Medical Area, Chestnut Hill, and Downtown Boston. One cat and one small dog are welcome with vaccination records. Parking is for rent at $225/month.