Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms, blending timeless architectural details with luxurious modern amenities. Additional highlights include a primary suite with walk-in closet and sitting room, large entertainment room, 3 car garage, and close proximity to downtown and commuter rail. Don’t miss this rare opportunity to own a truly remarkable estate.

Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized shower, soaking tub & double vanity. A second en-suite bedroom, two additional bedrooms & full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court & expansive fenced yard, ideal for recreation & entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation & convenience in a sought-after location.

Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated lighting, SS appliances, & new hardwood flooring. A gorgeous primary suite, inviting screened porch, cozy gas fireplace, & functional mudroom add warmth & everyday convenience. All 3 bathrooms were tastefully refreshed in 2024 w/ new showers, vanities, fixtures, & tile. Additional improvements include a new roof, updated exterior siding, finished basement, refinished hardwood floors, freshly painted interior, custom closet systems, new washer/dryer, updated front entry tile, & extensive landscaping w/a new front walkway. Just steps from award winning VO elementary school and Wright Locke Farm.

Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and powder room complete this level. Upstairs, the generous primary suite includes full bath and convenient laundry and is complemented by four additional bedrooms and a family bath. A walk-up attic provides flexible bonus space and storage, while the finished lower level offers a spacious family room, bonus room, and kitchenette with ADU potential. Enjoy the private backyard retreat complete with a fully fenced yard and pristine in-ground pool, plus two-car attached garage. An extraordinary opportunity to enjoy space, comfort, and refined living in one of Winchester’s most sought-after neighborhoods.

Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open dining area with direct access to the oversized screened porch—perfect for relaxing or entertaining. The eat-in kitchen provides access to the patio and backyard, ideal for summer cookouts. The top floor also features three bedrooms with hardwood floors, a full bath, and a half bath. Conveniently located with easy access to all that Winchester has to offer, this cherished home is not to be missed.

Discover the charm of Cape Cod living at its best, ideally located near Eastham's sought-after beaches. Just about a mile from beautiful bay side Cooks Brook Beach and within close proximity to Nauset Light Beach, this picture-perfect home has been built, cherished, and impeccably maintained by the same owners since 1980. After a day at the beach, rinse off in the outdoor shower and enjoy dining al fresco on the spacious back deck. Inside, the inviting open floor plan is perfect for gathering with family and friends, while a cozy gas fireplace creates a warm setting for cooler evenings. Hardwood floors lie preserved beneath the carpeting throughout much of the home. The first-floor primary bedroom with adjacent 3/4 bath offers convenient one-level living potential. Upstairs features two generously sized bedrooms with ample closet space and a spacious full bath. First-floor laundry adds everyday convenience, while the full unfinished basement with bulkhead access provides exceptional storage and future possibilities. Located near Cape Cod National Seashore beaches, bike trails, restaurants, and all that Eastham has to offer. A classic Cape to make your own!