Set along one of Guilford's most distinguished treelined blocks, 209 E Highfield Road offers the architectural presence and timeless character that define the neighborhood's 1920s residences. Directly across from Sherwood Gardens, this stately home features 5 bedrooms and 5.5 baths across four beautifully scaled levels, beginning with a main floor enhanced by gleaming hardwood floors, custom millwork and a 2024 custom gourmet kitchen by Sunnyfields including quartz countertops including a custom ILVE range and other top-of-the-line appliances. The first upper level hosts 3 bedrooms, including a luxury primary suite with a custom dressing room and an oversized jetted soaking tub. The second upper level adds 2 additional bedrooms and 2 full baths plus laundry room, ideal for guests or flexible living. The finished 2024 lower level, also by Sunnyfields, includes another full bath to support a variety of uses. Other improvements include a 2024 laundry room with. ew appliances, a 2020 Water Heater and 2020 HVAC system with 3 zones and smart thermostats. Framed by mature landscaping and surrounded by Guilford's architectural heritage, this residence blends classic craftsmanship with enduring elegance.