
253 Pond St Winchester — Photo 1 of 40
$1,299,000
Investment Analysis — 253 Pond St
Winchester, MA 01890
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 1.97% cap rate and $25,548/yr in estimated NOI at the $1,299,000 list price. Adjust every assumption in the calculator below.
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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Open Houses
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
Listing Agent: Pirani & Wile Group
Listing Office: Advisors Living - Winchester
MLS® Number: 73574477
