
253 Pond St Winchester — Photo 1 of 39
$1,299,000
253 Pond St, Winchester, MA 01890
Winchester, MA 01890
Beds
4
Baths
1.5
SqFt
3,307
Style
Single Family
Built
1952
Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.
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Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Range • Dishwasher • Refrigerator • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Medical Facility
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First14 x 22
Flooring - Hardwood, Recessed Lighting
Dining Room
Lvl Main,First11 x 13
Flooring - Hardwood, Lighting - Overhead, Crown Molding, Pocket Door
Kitchen
Lvl Main,First9 x 11
Closet, Flooring - Vinyl, Window(s) - Picture, Dining Area, Countertops - Stone/Granite/Solid, Exterior Access, Recessed Lighting, Stainless Steel Appliances
Family Room
Lvl Basement13 x 21
Flooring - Wall to Wall Carpet, Recessed Lighting
Master Bedroom
Lvl Main,First12 x 19
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 2
Lvl Main,First10 x 14
Bedroom 3
Lvl Main,First12 x 12
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 4
Lvl Second19 x 32
Vaulted Ceiling(s), Closet, Flooring - Hardwood, Recessed Lighting
Bathroom 1
Lvl First7 x 8
Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub
Bathroom 2
Lvl Basement4 x 6
Bathroom - Half
Property History
$1,299,000
Sep 9, 2026
MLS® 73574477
$1,075,000
Sep 26, 2024
MLS® 73260439
$1,125,000
Jul 5, 2024
MLS® 73260439
Population
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Middlesex County
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,307 sq ft principal dwelling). Lot size: 21,288 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Pirani & Wile Group
Listing Office: Advisors Living - Winchester
MLS® Number: 73574477
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