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3 Days on market
253 Pond St Winchester — Photo 1 of 40

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.

View Standard Listing

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

Original Price$1,299,000
Annual Taxes$12,026

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms10
Fireplaces2
FlooringVinyl, Laminate, Hardwood, Flooring - Vinyl
BasementFull, Partially Finished, Walk-Out Access, Garage Access

Climate & Utilities

HeatingBaseboard, Electric Baseboard, Oil
CoolingWindow Unit(s)
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDB

Property & Lot

Acres0.49
SqFt Lot21,288
Lot FeaturesLevel

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

Second
Bedroom 4
First
Bathroom 1
Basement
Family RoomBathroom 2
Main,First
Living RoomDining RoomKitchenMaster BedroomBedroom 2Bedroom 3
Living Room
Lvl Main,First

14 x 22

Flooring - Hardwood, Recessed Lighting

Dining Room
Lvl Main,First

11 x 13

Flooring - Hardwood, Lighting - Overhead, Crown Molding, Pocket Door

Kitchen
Lvl Main,First

9 x 11

Closet, Flooring - Vinyl, Window(s) - Picture, Dining Area, Countertops - Stone/Granite/Solid, Exterior Access, Recessed Lighting, Stainless Steel Appliances

Family Room
Lvl Basement

13 x 21

Flooring - Wall to Wall Carpet, Recessed Lighting

Master Bedroom
Lvl Main,First

12 x 19

Closet, Flooring - Hardwood, Recessed Lighting

Bedroom 2
Lvl Main,First

10 x 14

Bedroom 3
Lvl Main,First

12 x 12

Closet, Flooring - Hardwood, Recessed Lighting

Bedroom 4
Lvl Second

19 x 32

Vaulted Ceiling(s), Closet, Flooring - Hardwood, Recessed Lighting

Bathroom 1
Lvl First

7 x 8

Bathroom - Full, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub

Bathroom 2
Lvl Basement

4 x 6

Bathroom - Half

Property History

Listed
$1,299,000

Sep 9, 2026

MLS® 73574477

Sold
$1,075,000

Sep 26, 2024

MLS® 73260439

Listed
$1,125,000

Jul 5, 2024

MLS® 73260439

Listing Provided By

Listing Agent: Pirani & Wile Group

Listing Office: Advisors Living - Winchester

MLS® Number: 73574477