253 Pond St Winchester, MA $ 1,299,000
253 Pond St
$ 1,299,000
Recently Listed
Open House 9/11 11am - 12pm
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253 Pond St

Winchester, MA, 01890
$ 1,299,000
Bedrooms4 Baths1.1 Sq 3,307

Monthly Estimate*

$ 8,202

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Single Family Home for sale in Winchester, MA

for $1,299,000 with 4 bedrooms and 1 full bath, 1 half bath. This 3,307 square foot home was built in 1952 on a lot size of 0.49.

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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Open House

9/11/2026 11:00 AM - 12:00 PM
9/12/2026 12:00 PM - 1:30 PM
9/13/2026 12:00 PM - 1:30 PM
253 Pond St Winchester, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 1,299,000

Bedrooms

4

Full Bath

1

Half Bath

1

Property Type

Single Family

Taxes

$ 12,026

Style

Cape

Lot Size

0.49

Year Built

1952

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73574477

List By
Pirani & Wile Group

Listing Agent

Gibson Sotheby's International Realty

Broker

Affordability Calculator

$9,204
Per Month
89%
11%
0%
Monthly Principal & Interest
$8,202
Monthly Property Taxes
$1,002
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
9/9/2026$1,299,000 Listed Price

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253 Pond St, Winchester, MA, 01890 is a Single Family Home for sale at $1,299,000 with 3,307 sqft and a lot size of 0.49. 253 Pond St has 4 bedrooms, 1.1 baths, and was built in 1952. The property's zip code is 01890 which is in Winchester, MA