House Prices

East Side Winchester, MA House Prices & Home Values 2026


Average Data

average house price$941,815
average size per house1950 ft²
average price per ft²511 $ / ft²

04/19/2026 - The value range (VR) for house prices in East Side Winchester, MA is $485.45/ sqft to $536.55/ sqft. An average home with 1950 sqft costs approximately $1,000,586 to $1,105,911. Winchester, MA includes 1 ZIP codes and it is located in Middlesex county. The lowest prices are found in ZIP 01890, while the highest are in ZIP 01890. The average price per sqare feet is $511. Our analysis is based on 19 property listings.

Avergage prices by ZIP codes East Side Winchester

01890588 $ / ft²




Historical development of home values in East Side Winchester

Year Estimated value (USD) Change vs. 2025
2010 $437,396 -53.6%
2011 $420,482 -55.4%
2012 $419,350 -55.5%
2013 $435,024 -53.8%
2014 $456,655 -51.5%
2015 $480,092 -49.0%
2016 $505,147 -46.4%
2017 $532,412 -43.5%
2018 $561,846 -40.3%
2019 $587,898 -37.6%
2020 $618,290 -34.4%
2021 $703,238 -25.3%
2022 $819,817 -13.0%
2023 $864,536 -8.2%
2024 $914,550 -2.9%
2025 $941,815 0.0%

Graph: estimated home values in East Side Winchester over time (USD)



Example: 100% financing house in East Side Winchester

Loan amount: $941,815

Interest rate: 6.34%

Fixed monthly payment: $5,855.39

Breakdown in the 1st month:
Interest portion: $4,977.49  –  Principal portion: $877.90

Yearly breakdown (100% financing)

Year Interest per year ($) Principal per year ($) Remaining balance at year-end ($)
1 $59,418.23 $10,846.42 $930,968.58
2 $58,710.00 $11,554.65 $919,413.92
3 $57,955.52 $12,309.13 $907,104.79
4 $57,151.78 $13,112.87 $893,991.92
5 $56,295.56 $13,969.09 $880,022.83
6 $55,383.43 $14,881.22 $865,141.60
7 $54,411.74 $15,852.91 $849,288.69
8 $53,376.60 $16,888.05 $832,400.64
9 $52,273.87 $17,990.78 $814,409.86
10 $51,099.14 $19,165.51 $795,244.35
11 $49,847.70 $20,416.95 $774,827.40
12 $48,514.55 $21,750.10 $753,077.30
13 $47,094.35 $23,170.30 $729,907.00
14 $45,581.42 $24,683.24 $705,223.76
15 $43,969.69 $26,294.96 $678,928.80
16 $42,252.73 $28,011.93 $650,916.87
17 $40,423.65 $29,841.00 $621,075.87
18 $38,475.14 $31,789.51 $589,286.36
19 $36,399.40 $33,865.25 $555,421.11
20 $34,188.13 $36,076.52 $519,344.59
21 $31,832.46 $38,432.19 $480,912.40
22 $29,322.98 $40,941.67 $439,970.73
23 $26,649.64 $43,615.01 $396,355.72
24 $23,801.74 $46,462.91 $349,892.81
25 $20,767.89 $49,496.77 $300,396.04
26 $17,535.93 $52,728.72 $247,667.32
27 $14,092.94 $56,171.72 $191,495.60
28 $10,425.13 $59,839.52 $131,656.08
29 $6,517.83 $63,746.82 $67,909.26
30 $2,355.40 $67,909.26 $0.00

Note: The calculation is based on a standard annuity mortgage with a fixed monthly payment over the entire term. Extra payments, interest rate changes, and additional purchase costs (e.g. taxes, notary fees) are not included.


How to sell in East Side Winchester, MA


1500 sqft3900 sqft
Ø selling price$980,331$2,085,431
Ø fast selling$891,210$1,876,888
Ø high price sale$1,069,452$2,293,974

In 2026, houses in East Side Winchester, MA will be offered at an average price of $511 per square foot. A 1,500 sqft home priced at $980,331 is 24.31% more expensive per square foot than a 3,900 sqft home priced at $2,085,431. Home prices in East Side Winchester, MA vary significantly depending on the property’s condition and exact location. For a quick sale, a 2,700 sqft home should be listed at around $1,443,760. Sellers who can wait longer may achieve a higher price of up to $1,764,595.


Discover the East Side of Winchester, MA

The East Side of Winchester, MA is a serene residential neighborhood known for tree-lined streets, classic New England charm, and proximity to nature. Located east of Winchester Center, it offers a balanced lifestyle with small-town character and convenient access to greater Boston.

Homes and Neighborhood Character

Housing on the East Side Winchester MA ranges from well-kept Capes and Colonials to thoughtfully updated contemporaries on generous lots. Quiet side streets, sidewalks, and mature shade trees create a walkable, family-friendly feel.

Parks and Outdoor Access

Residents enjoy immediate access to the Middlesex Fells Reservation for hiking, biking, and year-round outdoor recreation. Nearby green spaces and ponds provide scenic escapes and weekend adventures close to home.

Schools and Community

The neighborhood is served by Winchester Public Schools, including the Lynch Elementary attendance area and convenient links to McCall Middle School and Winchester High. Strong community programming, youth sports, and library events foster a welcoming, connected atmosphere.

Commute and Everyday Convenience

Commuters appreciate quick connections to Winchester Center, the MBTA Commuter Rail (Lowell Line), and I-93 for routes into Boston and Cambridge. Local dining, boutiques, and essential services in Winchester Center and nearby towns round out daily convenience and livability.



FAQ – Home Values in East Side Winchester

What is the median home value in East Side Winchester in 2026?

In 2026, the typical home value in East Side Winchester is about $941,815 for an average home size of 1950 square feet. This corresponds to an average price of roughly $511 per square foot.

What is the average cost per square foot in East Side Winchester?

In 2026, homes in East Side Winchester sell for an average of around $511 per square foot, with a typical range between $485.45 and $536.55 per square foot, depending on the property’s location, condition, and lot size.

What is the average home size in East Side?

The average home size in East Side Winchester is about 1950 square feet, with an estimated 2026 value around $941,815.



Neighborhoods close to East Side Winchester, MA

Cliftondale Saugus, MA316 $ / ft²
Beach Bluff Swampscott, MA336 $ / ft²
Little Nahant Nahant, MA328 $ / ft²
Silver Lake Wilmington, MA324 $ / ft²
Forge Village Westford, MA222 $ / ft²
Greenwood Wakefield, MA315 $ / ft²
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