$4,299,000
About this home
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!
Highlights
Property details
- MLS
- MLS Property Information Network
- MLS #
- 73574948
- Property type
- Single Family Residence
- Subdivision
- N/A
- Status
- Active
- Days on market
- 41
- On market date
- September 10, 2026
- Stories
- N/A
- Total bathrooms
- 5.5
- Garage spaces
- 2
- Parking spaces
- 8
- Lot size
- 0.67 acres
Location
Get directions →Nearby schools
Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.
- Enrollment
- 506
- Student:teacher ratio
- 11.8:1
- District
- Winchester
- Enrollment
- 1,059
- Student:teacher ratio
- 11.8:1
- District
- Winchester
- Enrollment
- 1,349
- Student:teacher ratio
- 13.8:1
- District
- Winchester
Walkability
Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).
Market position
How this listing compares to current activity in Winchester, from live MLS data.
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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 17 days ago.
Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.