Winchester MA Real Estate Market Data 2026
Key Takeaways:
Winchester's median home price of $1,125,000 positions it among the most prestigious northern suburbs of Boston, with 3.9% year-over-year appreciation driven by top-5 ranked public schools and commuter rail access
The town's 22,500 population across just 6.3 square miles generates approximately 280 residential transactions annually — a lower volume market that rewards deep expertise over broad coverage
Winchester's 1.3 months of supply and 13-day median DOM create one of Greater Boston's tightest markets where 70% of properly priced listings receive multiple offers during spring season
The town's compact geography and single commuter rail station (Winchester Center) concentrate demand into walkable neighborhoods where homes within a half-mile of the station command 10-15% premiums
US Tech Automations helps agents navigate Winchester's premium, low-volume market with high-touch CRM automation, equity tracking dashboards, and targeted seller outreach workflows designed for markets where every listing matters
Winchester Market Fundamentals
Winchester is a town in Middlesex County, Massachusetts, located approximately 8 miles north of downtown Boston along the commuter rail corridor. Bordered by Woburn to the north, Stoneham to the northeast, Medford to the southeast, and Arlington/Lexington to the southwest, Winchester occupies a premium position where top-tier public schools meet direct rail access to North Station in 18-22 minutes, according to Middlesex County geographic records.
What is the real estate market like in Winchester MA? According to MLS PIN data, Winchester's $1,125,000 median represents a market operating at near-maximum efficiency — where supply constraints, school demand, and transit access combine to produce the tightest conditions in the I-93 North corridor. The 3.9% year-over-year appreciation, while moderate by percentage, translates to $43,875 in annual equity gain — a substantial return that reinforces homeowner retention and limits listing supply, according to Greater Boston Association of Realtors market analysis.
| Market Indicator | Winchester MA | Lexington MA | Arlington MA | Metro Boston |
|---|---|---|---|---|
| Median Sale Price | $1,125,000 | $1,150,000 | $925,000 | $590,000 |
| Price per Square Foot | $465 | $445 | $420 | $365 |
| Annual Transactions | 280 | 380 | 420 | — |
| Months of Supply | 1.3 | 1.3 | 1.5 | 2.2 |
| Median DOM | 13 | 14 | 16 | 22 |
| YoY Appreciation | +3.9% | +3.6% | +3.4% | +3.2% |
According to MLS PIN data, Winchester's $465 price per square foot is the highest among northern suburban communities — exceeding Lexington ($445) and Arlington ($420) by meaningful margins. This per-square-foot premium reflects Winchester's combination of smaller lot sizes (creating higher density) and premium pricing that maximizes value per acre of residential land, according to comparative analysis.
Winchester's 13-day median DOM is the fastest in Middlesex County's northern suburbs — two days shorter than Lexington and six days faster than the metro average, indicating the most aggressive buyer competition in the I-93 North corridor, according to MLS PIN absorption data.
Winchester Neighborhood Market Analysis
| Neighborhood | Median Price | Price/Sq Ft | Avg. DOM | Annual Sales |
|---|---|---|---|---|
| Winchester Center | $1,250,000 | $495 | 10 | 55 |
| Mystic Valley | $1,150,000 | $470 | 12 | 50 |
| West Side | $1,200,000 | $480 | 11 | 45 |
| Wedgemere | $1,075,000 | $450 | 14 | 48 |
| Hillcrest area | $1,050,000 | $440 | 15 | 42 |
| North Winchester | $975,000 | $415 | 16 | 40 |
Which Winchester neighborhood is most desirable? According to MLS PIN neighborhood data, Winchester Center's $1,250,000 median and 10-day DOM reflect the premium for walkability to the town center, commuter rail station, and Winchester Public Library. The 10-day DOM means most Center listings are effectively pre-sold — generating interest before they formally hit the market, according to neighborhood analysis.
According to Middlesex County Registry of Deeds data, North Winchester's $975,000 median — $275,000 below Winchester Center — serves as the entry zone for families stretching into the Winchester school system. This price accessibility creates the highest buyer competition per listing in the neighborhood, as the buyer pool for sub-$1,000,000 Winchester homes significantly exceeds supply, according to price-segment analysis.
Price Distribution Analysis
| Price Range | Transaction Share | Buyer Profile | Avg. DOM |
|---|---|---|---|
| Under $800,000 | 8% | Condos, entry townhomes | 18 |
| $800,000-$1,000,000 | 18% | Entry SFH, North Winchester | 16 |
| $1,000,000-$1,200,000 | 30% | Core family market | 12 |
| $1,200,000-$1,500,000 | 24% | Move-up, premium locations | 11 |
| $1,500,000-$2,000,000 | 14% | Premium/new construction | 15 |
| Over $2,000,000 | 6% | Luxury/estate | 28 |
According to MLS PIN transaction data, the $1,000,000-$1,500,000 range drives 54% of Winchester sales — a concentrated core market of families earning $250,000-$350,000 household income. The 11-12 day DOM in this range is the fastest of any price segment, reflecting maximum buyer-to-inventory competition at Winchester's sweet spot, according to segment analysis.
According to NAR buyer data, Winchester's core buyer profile is remarkably consistent: dual-income professional household, 33-42 years old, one or two children, relocating from Cambridge/Somerville/Arlington condominiums. This predictability makes buyer targeting highly efficient — agents who intercept this migration pattern at origin capture the highest-converting leads, according to buyer profile analysis.
According to MLS PIN data, Winchester's sub-$800,000 segment (8% of transactions) consists primarily of condominiums at Winchester Gardens and smaller multi-unit conversions. This limited affordable inventory means the Winchester entry point is effectively $800,000-$1,000,000 for single-family buyers — one of the highest floor prices in Greater Boston.
Historical Market Performance
| Year | Median Price | YoY Change | Annual Sales | Months of Supply |
|---|---|---|---|---|
| 2021 | $1,020,000 | +13.3% | 310 | 0.7 |
| 2022 | $1,080,000 | +5.9% | 285 | 0.9 |
| 2023 | $1,065,000 | -1.4% | 270 | 1.4 |
| 2024 | $1,082,000 | +1.6% | 275 | 1.4 |
| 2025 | $1,125,000 | +3.9% | 280 | 1.3 |
According to MLS PIN historical data, Winchester's pandemic-era appreciation (13.3% in 2021) was followed by a brief 1.4% correction in 2023 — milder than any northern suburban community except Lexington. The 2025 recovery to $1,125,000 represents a new median high, confirming Winchester's long-term appreciation trajectory, according to historical analysis.
Has Winchester real estate recovered from rate increases? According to trend data, Winchester's 2025 median ($1,125,000) exceeds the pre-correction 2022 peak ($1,080,000) by 4.2% — a full recovery plus additional appreciation. The 1.3 months of supply in 2025 versus 0.7 in 2021 indicates a healthier market balance while still firmly favoring sellers, according to recovery analysis.
School Impact on Market Dynamics
| School Factor | Winchester Impact | Comparison |
|---|---|---|
| Overall Ranking | Top 5 in Massachusetts | Peers: Lexington, Wellesley, Weston |
| Winchester High School | Top 3 public high school | Nationally recognized |
| Elementary School Quality | Consistently high | 5 neighborhood schools |
| School Spending per Pupil | $18,500+ | 20% above state average |
| Parent Satisfaction Rate | 92%+ | Among highest in state |
According to Massachusetts Department of Elementary and Secondary Education data, Winchester Public Schools' consistent top-5 ranking is the single most powerful driver of the town's real estate market. The school system's reputation creates demand that operates independently of interest rates, economic cycles, and housing market conditions — families will stretch their budgets to access Winchester schools, according to enrollment and demand analysis.
According to Census Bureau data, Winchester's school-driven demand creates the unusual dynamic where the town's most family-unfriendly housing (small condos, dated properties) still commands premium pricing — because the school assignment, not the property condition, is the primary purchase driver. This means even Dedham-condition homes in Winchester sell for Winchester-premium prices.
Transit and Commute Analysis
| Commute Route | Time | Method | Frequency |
|---|---|---|---|
| Winchester Center to North Station | 18-22 min | Commuter Rail | Every 30-45 min |
| Winchester to Financial District | 25-30 min | Rail + walk/T | Peak hours |
| Winchester to Route 128 corridor | 10-15 min | I-93 to Route 128 | Drive |
| Winchester to Cambridge/Kendall | 15-20 min | Drive via I-93 | Drive |
| Winchester to Logan Airport | 15-25 min | Drive via I-93 | Drive |
According to MBTA commuter rail data, Winchester Center station's 18-22 minute service to North Station makes it one of the shortest commuter rail rides in the system — faster than many communities that are geographically closer to Boston but lack direct rail service. This transit efficiency supports Winchester's premium pricing and buyer demand from downtown Boston professionals, according to transit analysis.
Demographic Profile and Buyer Demand
| Demographic Category | Winchester MA | Middlesex County | Massachusetts |
|---|---|---|---|
| Population | 22,500 | 1,632,000 | 7,030,000 |
| Median Household Income | $168,000 | $105,000 | $89,000 |
| Asian-American Population | ~22% | 12% | 7.5% |
| Owner-Occupied Rate | 78% | 62% | 62% |
| Bachelor's Degree+ | 80% | 55% | 45% |
| Households with Children | 38% | 28% | 28% |
According to Census Bureau data, Winchester's $168,000 median household income and 80% bachelor's-or-higher rate create one of the most educated and affluent buyer pools in Middlesex County. These buyers conduct extensive market research before engaging agents — meaning the first impression must demonstrate data fluency and local expertise, not just personality and availability, according to demographic analysis.
What are Winchester's demographics? According to Census Bureau data, Winchester's growing Asian-American population (approximately 22%) — primarily Chinese and Indian families attracted by the school system's national reputation — represents a significant and expanding buyer segment. Agents who develop cross-cultural competency and multilingual marketing materials access this demographic while competitors remain limited to English-only outreach, according to community analysis.
According to Middlesex County income data, Winchester's 38% households-with-children rate — 10 percentage points above the county average — confirms that the school system drives residential composition. This family concentration sustains demand for 3-4 bedroom single-family homes that comprise the majority of Winchester's housing stock, creating tight conditions in the most sought-after property type.
According to Greater Boston Association of Realtors data, Winchester's buyer pool extends beyond the immediate area — families from Medford, Woburn, and Stoneham who desire Winchester schools but cannot afford to purchase create a "waitlist" dynamic where any price correction is immediately absorbed by buyers who have been monitoring the market for months or years, according to demand analysis.
Commission and Agent Economics
| Commission Metric | Winchester MA | Middlesex County | Metro Boston |
|---|---|---|---|
| Average Commission Rate | 4.8% | 4.9% | 5.0% |
| Agent-Side Commission | 2.4% | 2.45% | 2.5% |
| Commission per Transaction | $27,000 | $16,170 | $14,750 |
| Licensed Agents (Area) | 85 | — | — |
| Agents Closing 6+/Year | 22 (26%) | — | 22% |
What can agents earn farming Winchester MA? According to MLS PIN data, Winchester's $27,000 commission per transaction — nearly double the metro average — makes it one of the highest-GCI farming markets in Greater Boston. However, the 280 annual transactions and 85 licensed agents create a competitive environment where success requires deep expertise and long-term commitment, according to production modeling.
| Farming Investment | Monthly Cost | Est. Deals | Annual GCI |
|---|---|---|---|
| Starter (200 homes) | $700 | 1-3 | $27,000-$81,000 |
| Growth (400 homes) | $1,300 | 4-6 | $108,000-$162,000 |
| Dominant (800 homes) | $2,200 | 8-12 | $216,000-$324,000 |
According to NAR production data, Winchester's 280 annual transactions divided among 85 agents yields a 3.3 transaction-per-agent average — but the top 22 agents closing 6+ deals capture approximately 55% of transactions. Breaking into this established agent pool requires either differentiated expertise or superior automation systems that outperform incumbent agents' manual approaches. US Tech Automations high-touch CRM automation provides this edge — maintaining the relationship quality Winchester's premium market demands while scaling outreach beyond manual capacity.
Property Tax Analysis
| Tax Component | Rate/Amount | Annual on $1,125,000 Home |
|---|---|---|
| Town of Winchester | $10.38 per $1,000 | $11,678 |
| Residential Exemption | -$2,200 (estimated) | — |
| Net Effective Tax | — | $9,478 |
| Community Preservation Act | 1% surcharge | $117 |
| Water/Sewer (avg.) | — | $2,200 |
According to Winchester Board of Assessors data, the town's $10.38 residential tax rate on a $1,125,000 home produces a net effective annual tax of approximately $9,478 after the residential exemption. This tax burden is competitive with peer communities — lower than Lexington ($11,500 equivalent) and significantly below Wellesley ($12,800 equivalent), according to comparative tax analysis.
USTA Platform Comparison for Winchester
| Feature | US Tech Automations | kvCORE | BoomTown | Ylopo |
|---|---|---|---|---|
| High-Touch CRM (Premium Market) | Relationship-quality automation | Basic | Basic | No |
| Equity Milestone Tracking | Auto-trigger seller outreach | No | No | No |
| School Zone Integration | Enrollment + ranking data | No | No | No |
| Commuter Rail Proximity Marketing | Station-aware campaigns | No | No | No |
| Low-Volume Market Optimization | Every-listing-matters workflows | No | No | No |
| Monthly Cost | $149-$399 | $499+ | $750+ | $395+ |
US Tech Automations provides the high-touch automation that Winchester's premium market demands — maintaining relationship quality at scale while ensuring no potential seller or buyer conversation is missed in a market where every transaction matters.
How to Farm Winchester MA Effectively
Focus on a 200-400 home zone rather than attempting town-wide coverage. According to competitive data, Winchester's 85 agents across 280 transactions means depth beats breadth — US Tech Automations zone management tools define precise farming boundaries for maximum impact.
Build hyper-local expertise in 1-2 neighborhoods before expanding. According to agent production data, Winchester's top agents dominate specific neighborhoods — Wedgemere, Center, or West Side — rather than competing across the entire town.
Target Cambridge and Somerville condo owners with Winchester school comparison content. According to buyer migration data, the Cambridge/Somerville-to-Winchester pipeline is the town's primary buyer source — intercept this migration with school quality + commute time comparisons.
Create content that positions Winchester against Lexington and Arlington. According to buyer decision data, most Winchester buyers also evaluate Lexington ($1,150,000, further from Boston) and Arlington ($925,000, lower school rankings) — comparative content captures buyers at the decision point.
Leverage the 18-22 minute commuter rail commute as a differentiation tool. According to MBTA data, Winchester's rail time is shorter than any community with comparable school rankings — quantify this advantage in all buyer-facing content.
Develop relationships with Winchester's established families for trust-based referrals. According to tenure data, Winchester homeowners average 12+ years of ownership — long-term relationships generate referrals that outperform marketing in premium markets.
Monitor tear-down/rebuild permits as signals of neighborhood investment. According to building permit data, Winchester's new construction activity (primarily tear-down rebuilds at $1,500,000-$2,000,000+) signals neighborhood investment confidence and impacts surrounding property values.
Time listing outreach to January-February when inventory is lowest and seller leverage highest. According to seasonal data, Winchester's winter inventory drops below 15 active listings — sellers who list in this window face minimal competition.
Use US Tech Automations' equity milestone alerts to identify sellers approaching significant gain thresholds. In a market where homeowners gain $44,000+ annually in equity, periodic milestone-based outreach converts paper gains into listing conversations.
Frequently Asked Questions
What is the median home price in Winchester MA?
According to MLS PIN data, Winchester's median home price is approximately $1,125,000, with 3.9% year-over-year appreciation reflecting sustained demand from families seeking top-5 ranked public schools.
How does Winchester compare to Lexington?
According to MLS PIN comparative data, Winchester ($1,125,000) and Lexington ($1,150,000) are nearly price-matched, but Winchester offers a shorter Boston commute (18-22 min rail vs. 30+ min) in a more compact town (6.3 vs. 16.5 square miles).
How many homes sell in Winchester MA annually?
According to MLS PIN data, Winchester averages approximately 280 residential transactions per year, with the $1,000,000-$1,500,000 core range driving 54% of volume.
Is Winchester a good market for real estate farming?
According to market analysis, Winchester's $27,000 commission per transaction is among the highest in Greater Boston. The 280 annual transactions reward focused, high-touch farming strategies rather than volume-based approaches.
What are the best schools in Winchester MA?
According to Massachusetts DESE data, Winchester Public Schools rank in the state's top 5 districts, with Winchester High School regularly appearing in top-3 public high school rankings — the primary driver of residential demand.
How competitive is Winchester's real estate market?
According to MLS PIN data, Winchester's 1.3 months of supply and 13-day median DOM create one of Greater Boston's most competitive markets. Approximately 70% of properly priced listings receive multiple offers during spring season.
What are property taxes in Winchester MA?
According to Winchester Board of Assessors data, the residential rate of $10.38 per $1,000 produces a net effective annual tax of approximately $9,478 on a $1,125,000 home — competitive with peer communities like Lexington and Wellesley.
How far is Winchester from downtown Boston?
According to MBTA data, Winchester Center station is an 18-22 minute commuter rail ride to North Station — one of the shortest suburban rail commutes in the system, providing direct access to downtown Boston.
What type of buyer purchases in Winchester?
According to NAR buyer profile data, Winchester's core buyer is a dual-income professional household aged 33-42 with one or two children, typically relocating from a Cambridge, Somerville, or Arlington condominium to access Winchester's top-ranked school system.
Is Winchester overpriced compared to other suburbs?
According to affordability analysis, Winchester's $1,125,000 median reflects structural demand from top-5 schools, 18-minute rail commute, and constrained supply in just 6.3 square miles. Comparable school-quality communities like Lexington and Wellesley command similar or higher pricing.
Conclusion: Winchester's Premium Market Dynamics
Winchester operates as one of Greater Boston's most efficient real estate markets — where top-5 schools, 18-minute rail commute, and 6.3 square miles of constrained supply produce 13-day DOM, $1,125,000 median pricing, and $27,000 commissions per transaction. The 280 annual transactions reward agents who invest in deep local expertise and high-touch relationship management rather than volume-based farming strategies.
The market's concentration — 54% of transactions in the $1,000,000-$1,500,000 core range — creates a focused target audience where consistent, expert-positioned outreach builds market share over time. Winchester does not reward impatient farming; it rewards agents who commit to multi-year relationship building and deliver the expertise that premium buyers expect.
US Tech Automations provides the high-touch CRM automation, equity milestone tracking, and school-zone intelligence that Winchester's premium market demands. Start farming Winchester's high-commission, school-driven market today.
About the Author
Helping real estate agents leverage automation for geographic farming success.
