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$2,299,000
7 Beds 5 Baths 73556122 MLS NEW Status
Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height throughout. The expanded eat-in kitchen includes granite, SS appliances, island, office area & steps to a custom mudroom. The main level also includes elegant living, dining & family rooms, a butler's pantry, & ½ bath. The 2nd floor showcases a dramatic landing w/ continuously curved railing & has 4 large bedrooms & two full baths, including a spacious primary suite w/ full bathroom and walk-in closet. 3 bedrooms & a full bath complete the 3rd floor. The finished lower level w/ recreation room, mudroom w/ built-in lockers, and full bathroom offers endless possibilities. Recent updates include Pella windows throughout (2020), new & upgraded heating system (2024), and exterior siding, paint & shutters (2020). Set on a flat, oversized lot featuring a bluestone patio w/ seating wall. Located in a highly-coveted neighborhood and less than a mile from the newly built Lynch elementary school, town center & train.This magnificent home pairs timeless character with today’s amenities.

42 Wildwood Street, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,300,000
4 Beds 5 Baths 73541163 MLS ACTIVE Status
Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.

14 Hillside Ave, Winchester

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.

$3,199,000
5 Beds 5 Baths 73535697 MLS ACTIVE Status
Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a beautifully scaled layout offer multiple living spaces, including a 1st floor office. The Chef’s kitchen opens to a dramatic family room with soaring ceilings and French doors leading to outdoor living. The large finished lower level features a spa style bathroom & a beautiful custom wine cellar. An elegant porch & stone paved half moon driveway, enhance the home’s presence, complemented by a 2-car garage and expansive driveway. Moments to Winchester center, Commuter rail, boutiques, dining and Top-rated schools. Private, discreet, an ideal home setting for an exceptional family living!

10 Rangeley Road, Winchester

Listing courtesy of Listing Agent: Karima Alami from Listing Office: Compass.

$2,795,000
4 Beds 5 Baths 73518621 MLS ACTIVE Status
This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate. A lifestyle of luxury/convenience steps away from town, commuter rail, school and walking trails.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Tina Natale from Listing Office: Luxury Living Real Estate.

$1,899,000
6 Beds 5 Baths 73507145 MLS ACTIVE Status
Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district

16 Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,899,000
6 Beds 5 Baths 73507137 MLS ACTIVE Status
Must see! sprawling 2-3 family beautifully renovated & expanded home offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac!

16 & 16A Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

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