This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while sun-drenched living areas flow seamlessly onto expansive, covered front porches. The first floor features a gas fireplace, and the second is warmed by a wood-burning Yodel stove. Both kitchens are thoughtfully renovated with vintage flair and include butler’s pantries. Thoughtful upgrades to all major systems ensure preserved historic integrity without compromising convenience. Lush landscaping with mature fruit trees, a generous backyard, & a two-car garage enhance the property’s appeal. Just steps from Winchester Center and the commuter rail, this home offers refined living in a prime location.
Listing Courtesy of MLS PIN / Barrett Sotheby's International Realty / Anne Spry
$2,299,900
Winchester Area Multi-Family Home
Active
5 Bacon St Winchester, MA 01890
6 Bed
4 Baths
4385 sqft
MLS# 73411839
This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while sun-drenched living areas flow seamlessly onto expansive, covered front porches. The first floor features a gas fireplace, and the second is warmed by a wood-burning Yodel stove. Both kitchens are thoughtfully renovated with vintage flair and include butler’s pantries. Thoughtful upgrades to all major systems ensure preserved historic integrity without compromising convenience. Lush landscaping w mature fruit trees, a generous backyard, and a two-car garage enhance the property’s appeal. Just steps from Winchester Center and the commuter rail, this home offers refined living in a prime location.
Listing Courtesy of MLS PIN / Barrett Sotheby's International Realty / Anne Spry
$1,999,000
Winchester Area Single Family Home
Contingent
6 Samoset Rd Winchester, MA 01890
4 Bed
3.5 Baths
4731 sqft
MLS# 73416647
Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up private office offers a private & inspiring space for the at-home professional. The separate dining room is ideal for entertaining, while the eat-in kitchen provides a casual space for daily meals. Upstairs, a vaulted-ceilinged primary bath impresses with dramatic windows and a serene ensuite bath. All 4 bedrooms are spacious with plenty of natural light. The finished lower level is a dream—complete with a bonus room, game room, exercise room, and full bath—versatile enough to suit any lifestyle. Outside, the private backyard features a stunning stone patio, professional landscaping, & a hot tub.
Listing Courtesy of MLS PIN / Barrett Sotheby's International Realty / Anne Spry
$6,000 / mo
Winchester Area Rental Home
Active
192 Cross St 192 Winchester, MA 01890
4 Bed
3.5 Baths
3516 sqft
MLS# 73409522
Discover elegant living in this stunning Winchester duplex offering exceptional space and comfort across four thoughtfully designed levels. Ideal for both relaxation and entertaining, the home boasts an expansive kitchen flowing seamlessly into inviting dining and spacious family areas. Retreat upstairs to generously sized bedrooms, each designed for restful privacy, including the ensuite primary bed & bath, complemented by a dedicated home office ideal for remote work. Additional highlights include a finished lower-level room for exercise, hobbies, or to be a playroom. Complete with central air conditioning, garage parking, and ample off-street parking, this residence is the most versatile rental on the market. Renting for September 1st, 2025.
Listing Courtesy of MLS PIN / Barrett Sotheby's International Realty / Anne Spry