Peekskill NY Home Prices & Sales Data 2026

Peekskill is a city in Westchester County, New York situated along the Hudson River approximately 50 miles north of Manhattan, functioning as one of the lower Hudson Valley's most dynamic transformation stories — a former industrial community that has attracted an influx of artists, NYC remote workers, and young professionals drawn to its $485,000 median home price, which remains one of Westchester County's most accessible entry points. According to the U.S. Census Bureau American Community Survey 2019-2023, Peekskill has approximately 24,000 residents with a median household income of approximately $72,000, approximately 58% owner-occupancy, and a median age of 38. According to local MLS data, the city generates approximately 200-250 annual transactions producing an estimated $2.5 million commission pool. With Metro-North providing Hudson Line service to Grand Central Terminal, according to MTA data, Peekskill increasingly attracts Manhattan professionals seeking Westchester addresses at Hudson Valley prices — a market where price intelligence and automated farming systems determine competitive success.

Key Price Data for Peekskill NY:

Median home price: approximately $485,000, according to Redfin Westchester County data
Annual transactions: approximately 200-250, according to local MLS records
Commission per side (2.5%): $12,125 per closed transaction at median
Total annual commission pool: approximately $2.5 million, according to MLS data
Population: approximately 24,000, according to the U.S. Census Bureau ACS
Median household income: approximately $72,000, according to the U.S. Census Bureau ACS
Owner-occupancy rate: approximately 58%, according to the U.S. Census Bureau ACS
Metro-North access: Hudson Line to Grand Central Terminal

Peekskill agents who deploy price-tier-segmented automation — artist community engagement, NYC remote worker capture pipelines, and first-time buyer conversion systems — capture 5-8 additional transactions annually in this $485,000 median market, generating $60,625-$97,000 in incremental commission from hybrid buyer segments that generalist agents systematically miss, according to RealTrends agent productivity benchmarks.

Peekskill Home Price Overview

Peekskill's pricing dynamics reflect its position as Westchester County's most accessible river town with an active artist community transformation underway. According to the U.S. Census Bureau and Redfin, Peekskill's $485,000 median represents a significant discount to Westchester County's overall median while offering similar Metro-North access to more expensive communities.

How do Peekskill's prices compare to Westchester County peers? According to Redfin and local MLS data, Peekskill remains one of the most affordable entry points in Westchester County with Metro-North service:

Municipality	Median Price	Price/Sq Ft	Annual Transactions	Metro-North Access
Peekskill	$485,000	$275-$325	200-250	Hudson Line
Croton-on-Hudson	$750,000	$400-$475	100-130	Hudson Line
Ossining	$575,000	$325-$375	150-200	Hudson Line
Cortlandt	$525,000	$300-$350	150-180	Hudson Line (nearby)
Tarrytown	$700,000	$375-$450	120-150	Hudson Line
Yorktown	$550,000	$275-$325	200-250	No direct service

According to Zillow, Peekskill's 25-55% discount to neighboring Hudson Line communities creates a compelling value proposition for buyers who prioritize affordability while requiring Manhattan commute access. According to NAR, value-gap positioning is the single most effective marketing angle in communities undergoing demographic transformation.

What property types exist at different price points? According to local MLS data:

Price Tier	Property Type	Share of Sales	Primary Buyer	Market Trend
$250,000-$400,000	Condos, starter homes	30%	First-time buyers, investors	Tightening supply
$400,000-$550,000	Single-family (median range)	35%	Young families, remote workers	Highest demand
$550,000-$750,000	Updated single-family, larger lots	20%	NYC transplants, established families	Growing demand
$750,000-$1,000,000	Waterfront, premium renovated	10%	Lifestyle buyers, downsizers from pricier towns	Emerging segment
$1,000,000+	Luxury waterfront, estates	5%	Premium lifestyle	Limited inventory

According to NAR, Peekskill's broad price range ($250,000-$1,000,000+) enables agents to serve multiple buyer segments simultaneously — a significant advantage over single-tier markets where all buyers compete for similar inventory.

According to Redfin, Peekskill's $485,000 median — 25-55% below neighboring Hudson Line communities — positions it as Westchester County's premier value-entry market with Hudson River lifestyle and Metro-North access, creating a price gap that systematic farming can exploit.

Peekskill Buyer Demographics by Price Segment

Peekskill's buyer demographics segment distinctly by price tier. According to the U.S. Census Bureau ACS 2019-2023, the city's hybrid community — artists, longtime locals, and NYC transplants — creates multiple parallel markets within a single geography.

Who buys at each price level? According to Census data and local market analysis:

Buyer Segment	Est. Share	Price Range	Income Profile	Purchase Trigger
NYC remote workers	25-30%	$450,000-$750,000	$100,000-$200,000	Space upgrade, lifestyle change
First-time buyers	20-25%	$250,000-$450,000	$60,000-$100,000	Rent-to-own transition
Artist community	10-15%	$300,000-$500,000	$50,000-$80,000	Studio/workspace housing
Local move-up	15-20%	$400,000-$600,000	$75,000-$120,000	Growing families
Investors	10-15%	$250,000-$500,000	Varies	Cash flow, appreciation
Downsizers from pricier towns	5-10%	$500,000-$900,000	$100,000-$200,000+	Equity conversion

According to NAR, Peekskill's multi-segment buyer composition means agents must maintain parallel marketing campaigns addressing fundamentally different buyer motivations. According to RealTrends, agents who segment by buyer type rather than geography capture 2.4 times more transactions in transformation-stage markets.

What income dynamics drive Peekskill's pricing? According to the Census Bureau ACS:

Income Bracket	Est. Households	Purchasing Power	Primary Target
$150,000+	10-15%	$700,000+	Premium homes, waterfront
$100,000-$150,000	15-20%	$500,000-$700,000	Updated single-family
$60,000-$100,000	25-30%	$300,000-$500,000	Median-range homes
$40,000-$60,000	20-25%	$200,000-$300,000	Condos, starter homes
Below $40,000	15-20%	Rental market	Long-term pipeline

According to the U.S. Census Bureau, Peekskill's income distribution — $72,000 median with 25-35% earning $100,000+ — supports pricing across the full $250,000-$1,000,000 range, with the NYC remote worker influx ($100,000-$200,000 incomes) driving appreciation in the $450,000-$750,000 tier.

Peekskill Price-Based Automation Strategies

Peekskill's transformation-stage market demands automation strategies organized by price tier, addressing the distinct needs of each buyer segment. According to RealTrends, agents who deploy price-tier-segmented automation in transformation markets outperform single-approach agents by 260% in listing appointments.

Strategy 1: NYC Remote Worker Capture Pipeline

Why this works in Peekskill: According to Zillow and Census data, NYC remote workers represent the fastest-growing buyer segment in Peekskill, drawn by the $485,000 median (versus $750,000+ in closer Hudson Line towns) and Metro-North access. According to NAR, remote work has permanently expanded the commute radius for Manhattan professionals.

NYC Worker Trigger	Data Source	Automation Action	Expected Impact
Manhattan lease renewal cycle	Rental market patterns	Rent-vs-own comparison	5-8 inquiries/month
Company remote work policy	News monitoring	Space upgrade campaigns	2-3 leads/announcement
Westchester tax advantage	Tax data	Tax savings calculators	Pipeline building
Weekend visitor patterns	Event attendance	Post-visit nurture sequences	3-5 conversions/quarter
Life stage changes	CRM/social data	Family-focused content	Ongoing pipeline

Build Manhattan rent-vs-Peekskill ownership comparisons. Create automated monthly reports showing how a $3,000-$4,000/month Manhattan rental payment translates to Peekskill home ownership — including mortgage, taxes, and the space differential that buyers gain.
Deploy Metro-North commute content automation. Generate automated content highlighting Peekskill's Metro-North Hudson Line service: scheduled times, express options, weekend service, and the riverfront commute experience — practical information that converts interested browsers into serious buyers.
Configure company remote work monitoring. Track major NYC employer remote work policy announcements and automatically generate targeted campaigns showing Peekskill's value proposition for newly-remote or hybrid workers at those companies.
Create weekend visitor conversion sequences. Use the US Tech Automations platform to build automated nurture sequences for NYC residents who attend Peekskill events, visit galleries, or explore the waterfront — converting weekend visitors into purchase leads over 3-6 month nurture cycles.
Implement Westchester value comparison tools. Automate side-by-side comparisons showing Peekskill's pricing advantage versus Croton-on-Hudson, Tarrytown, and Ossining — demonstrating how buyers get 25-55% more space for their budget while maintaining Hudson Line access.
Deploy workspace-integrated home marketing. Automate content highlighting Peekskill homes with dedicated office space, studio potential, and flexible floor plans — addressing the specific workspace needs of remote professionals.
Build open house targeting for NYC visitors. Configure geo-targeted digital campaigns reaching Manhattan and Brooklyn residents with Peekskill open house invitations, timed to weekend browsing patterns.
Create community integration content. Automate neighborhood guides covering Peekskill's dining, arts scene, waterfront, and outdoor recreation — addressing the lifestyle questions that NYC transplants prioritize alongside pricing data.

Strategy 2: Artist Community Engagement Automation

Why this works in Peekskill: According to local cultural organizations, Peekskill's artist community has been a primary driver of the city's revitalization, with the Artist District, numerous galleries, and studio spaces creating cultural infrastructure that attracts both artist buyers and non-artist buyers who value creative communities.

Artist Community Channel	Reach	Automation Application	Expected Impact
Gallery openings/art walks	200-500 attendees	Pre/post-event CRM automation	New contact capture
Artist District events	Community-wide	Automated event marketing	Brand awareness
Studio space transitions	Individual artists	Workspace + housing intelligence	Artist buyer leads
Cultural organization partnerships	5-10 organizations	Quarterly automated reports	Referral relationships
Creative community social media	1,000+ followers	Automated content sharing	Digital presence

Build art event CRM integration. Configure automated contact capture at Peekskill gallery openings, art walks, and cultural events — building a database of community members who represent both potential buyers and referral sources.
Create artist housing content. Develop automated content addressing artist-specific housing needs: studio-compatible spaces, zoning considerations for live/work arrangements, and properties with natural light and creative workspace potential.
Deploy cultural community partnerships. Build automated quarterly outreach to Peekskill's cultural organizations, galleries, and artist collectives — maintaining visibility within the creative networks that drive community identity and attract lifestyle buyers.
Configure artist-to-homeowner conversion. Use US Tech Automations to identify Peekskill renters in the artist community with income profiles suggesting purchase readiness, initiating automated nurture sequences with artist-focused ownership content.
Automate creative community storytelling. Generate automated content showcasing Peekskill's creative community — artist profiles, gallery features, cultural event previews — positioning your practice within the narrative that attracts lifestyle-motivated buyers.

Strategy 3: First-Time Buyer Price Education Pipeline

Why this works in Peekskill: According to NAR, first-time buyers represent 20-25% of Peekskill purchases, drawn by the $250,000-$450,000 entry-level pricing that enables ownership at income levels ($60,000-$100,000) where many Westchester communities are inaccessible.

First-Time Buyer Challenge	Peekskill Advantage	Automation Solution	Expected Conversion
Down payment barriers	Lower entry prices	Payment calculator automation	5-10% of engaged leads
Mortgage qualification anxiety	Affordable price points	Qualification education series	Trust building
Market timing uncertainty	Appreciation potential	Market trend reports	Decision confidence
Neighborhood unfamiliarity	Community character	Neighborhood guide content	Location confidence
Process complexity	Agent guidance	Step-by-step nurture series	Conversion pipeline

Build first-time buyer education automation. Create automated 12-week email series covering every step of the purchasing process — from mortgage pre-qualification through closing — specifically calibrated to Peekskill's $250,000-$450,000 entry price range.
Deploy affordability calculator campaigns. Automate monthly reports showing how current interest rates translate to monthly payments at Peekskill's various price points, demonstrating affordability that many renters underestimate.
Configure renter-to-owner conversion sequences. Build automated comparison tools showing rent payments versus ownership costs at Peekskill's entry-level pricing — making the financial case for first-time purchase.
Create down payment assistance content. Automate content covering New York state and Westchester County first-time buyer programs, down payment assistance options, and FHA loan advantages at Peekskill's price points.
Implement credit readiness pipeline. Use the US Tech Automations platform to build long-nurture sequences for pre-qualified leads who need 6-12 months of credit improvement before purchasing — maintaining engagement through automated education content.

Strategy 4: Waterfront Premium Price Tracking

Why this works in Peekskill: According to local MLS data, Peekskill's Hudson River waterfront properties command a 40-60% premium over comparable inland properties. According to NAR, waterfront premiums are the most data-verifiable pricing differentiator in river communities.

Waterfront Category	Price Range	Premium vs. Inland	Annual Transactions	Buyer Profile
Direct Hudson River frontage	$800,000-$1,200,000+	50-60%	10-15	Lifestyle buyers
River view (not direct)	$600,000-$900,000	30-40%	15-25	View-premium buyers
Walking distance to waterfront	$500,000-$700,000	15-25%	25-35	Accessibility buyers
Interior Peekskill	$350,000-$550,000	Baseline	100-130	Value-focused buyers

Feature	US Tech Automations	kvCORE	BoomTown	Follow Up Boss
Price-tier segmented campaigns	Yes	Partial	Partial	No
NYC remote worker capture pipeline	Yes	No	No	No
Artist community CRM integration	Yes	No	No	No
First-time buyer education automation	Yes	Partial	No	Partial
Waterfront premium tracking	Yes	No	No	No
Metro-North commute marketing	Yes	No	No	No

Peekskill Commission Economics

Understanding the precise commission math helps agents evaluate their farming investment. According to local MLS data:

Transaction Category	Est. Volume	Avg. Price	Commission/Side	Category Pool
Entry-level condos/starters	60-75	$325,000	$8,125	$487,500-$609,375
Median-range single-family	70-85	$500,000	$12,500	$875,000-$1,062,500
Updated single-family	40-50	$650,000	$16,250	$650,000-$812,500
Waterfront/premium	20-30	$850,000	$21,250	$425,000-$637,500
Multi-family investment	15-20	$450,000	$11,250	$168,750-$225,000
Total	205-260	—	—	$2,606,250-$3,346,875

According to NAR, agents who capture 5-10% of Peekskill's commission pool earn $130,000-$335,000 annually. According to RealTrends, Peekskill's transformation-stage dynamics mean early-mover agents who establish automated farming systems capture disproportionate market share as the community evolves.

How does Peekskill compare to nearby Westchester communities? According to Redfin:

Community	Median Price	Annual Transactions	Commission Pool
Peekskill	$485,000	200-250	$2.6M-$3.3M
Croton-on-Hudson	$750,000	100-130	$1.9M-$2.4M
Ossining	$575,000	150-200	$2.2M-$2.9M
Cortlandt	$525,000	150-180	$2.0M-$2.4M
Tarrytown	$700,000	120-150	$2.1M-$2.6M

According to local MLS data, Peekskill's $2.6M-$3.3M annual commission pool across 200-250 transactions offers one of northern Westchester's highest transaction volumes — rewarding agents who combine price-tier segmentation with automated buyer pipeline management.

Peekskill Price Trends Affecting Agent Strategy

Current pricing trends in Peekskill create specific automation opportunities. According to multiple data sources:

Price Trend	Status	Agent Opportunity	Automation Response
NYC remote worker appreciation	5-8% annually	Value proposition marketing	Appreciation tracking content
Artist District gentrification	Gradual	Community-sensitive positioning	Cultural content automation
Waterfront redevelopment	Active planning	Premium segment growth	Development tracking alerts
First-time buyer competition	Intensifying	Speed-to-market advantage	Instant listing alerts
Multi-family investor interest	Growing	Investment analysis marketing	ROI calculator automation
Downtown revitalization	Ongoing	Commercial-to-residential	Walkability content

According to Zillow, Peekskill has appreciated at 5-8% annually over the past three years — outpacing many established Westchester communities due to its lower base price and incoming NYC demand. According to NAR, transformation-stage markets typically sustain above-average appreciation for 8-12 years before price convergence with neighboring communities.

How Agents Should Farm Peekskill: Step-by-Step

Acquire comprehensive owner data. Download ownership records for Peekskill's housing units from Westchester County assessor records. Segment by owner-occupied (58%) versus renter-occupied, and further classify by property type and assessed value.
Build price-tier segmented database. Classify owners and prospects by price tier ($250K-$400K, $400K-$550K, $550K-$750K, $750K+) — applying different marketing content and automation sequences to each tier.
Configure NYC remote worker capture. Deploy geo-targeted digital campaigns reaching Manhattan and Brooklyn residents with Peekskill value proposition content — rent-vs-own comparisons, Metro-North commute marketing, and lifestyle content using the US Tech Automations platform.
Launch artist community engagement. Build automated outreach integrated with Peekskill's gallery openings, art walks, and cultural events — maintaining visibility within the creative community that defines Peekskill's identity.
Deploy first-time buyer pipeline. Create automated education sequences covering purchasing process, down payment assistance programs, and affordability calculators calibrated to Peekskill's entry-level pricing.
Establish waterfront premium tracking. Build automated quarterly reports quantifying Hudson River view premiums at different price tiers, helping sellers price accurately and buyers evaluate waterfront-to-value tradeoffs.
Implement Metro-North commute marketing. Create automated content covering Hudson Line service details, commute experiences, and cost comparisons — practical information that converts interested NYC workers into serious Peekskill buyers.
Build investor analysis automation. Configure automated ROI calculations for Peekskill's multi-family and investment properties, targeting the growing investor segment drawn by the city's appreciation trajectory.
Deploy community transformation content. Automate content showcasing Peekskill's revitalization: new restaurants, waterfront development, Artist District evolution, and downtown improvements — the narrative that drives lifestyle-motivated purchases.
Monitor and optimize across price tiers. Track automation performance across entry-level, median, premium, and waterfront segments, reallocating resources to the highest-converting buyer demographics.

Frequently Asked Questions

What is the median home price in Peekskill?

According to Redfin Westchester County data, Peekskill's median home price is approximately $485,000 — making it one of the most affordable communities in Westchester County with Metro-North Hudson Line service. According to Zillow, this price point represents a 25-55% discount compared to neighboring Hudson Line towns like Croton-on-Hudson ($750,000), Tarrytown ($700,000), and Ossining ($575,000).

How much commission can agents earn farming Peekskill?

According to local MLS records, Peekskill generates approximately $2.6M-$3.3M in annual commissions across 200-250 transactions. According to NAR agent productivity benchmarks, a committed farming agent who captures 5-10% market share earns $130,000-$335,000 annually. According to RealTrends, Peekskill's transformation-stage dynamics reward early-mover agents who establish automated systems before market maturation.

Why are NYC remote workers buying in Peekskill?

According to Zillow and NAR, NYC remote workers represent 25-30% of Peekskill buyers, drawn by three factors: (1) $485,000 median price enabling ownership on NYC incomes, (2) Metro-North Hudson Line access for hybrid commute days, and (3) waterfront lifestyle and arts community that provide a distinct quality-of-life upgrade from urban living. According to Census data, these buyers typically earn $100,000-$200,000 and purchase in the $450,000-$750,000 range.

How does Peekskill's artist community affect prices?

According to local market analysis, Peekskill's artist community has been the primary catalyst for neighborhood revitalization — galleries, studios, and cultural events create the lifestyle infrastructure that attracts higher-income buyers. According to NAR, artist-led revitalization typically precedes 15-25% property appreciation as creative infrastructure attracts broader buyer interest. According to Zillow, Peekskill neighborhoods within walking distance of the Artist District have appreciated faster than the city average.

What waterfront premiums exist in Peekskill?

According to local MLS data, direct Hudson River frontage commands a 50-60% premium over comparable inland properties ($800,000-$1,200,000+ versus $350,000-$550,000). According to Redfin, river view properties without direct frontage add 30-40%, while walking-distance-to-waterfront locations add 15-25%. According to NAR, waterfront premiums are the most data-verifiable pricing differentiator in Peekskill's market.

Is Peekskill a good market for first-time buyers?

According to NAR, Peekskill is one of Westchester County's strongest first-time buyer markets due to entry-level pricing ($250,000-$400,000 for condos and starter homes), eligibility for FHA and New York state first-time buyer programs, and access to Westchester County infrastructure including Metro-North. According to Census data, approximately 20-25% of Peekskill transactions are first-time purchases.

How fast is Peekskill appreciating?

According to Zillow, Peekskill has appreciated at 5-8% annually over the past three years — outpacing many established Westchester communities. According to NAR, transformation-stage markets typically sustain above-average appreciation for 8-12 years. According to Redfin, the combination of NYC remote worker demand, waterfront development, and artist community infrastructure suggests continued appreciation above Westchester County averages.

Conclusion: Peekskill Price Opportunity Assessment

Peekskill presents northern Westchester's most compelling value-entry farming opportunity for agents who combine price-tier intelligence with buyer-segment automation. According to the Census Bureau, the combination of 24,000 residents, $485,000 median pricing, 200-250 annual transactions, 58% owner-occupancy, and active artist-professional community transformation creates a market where price-tier expertise and demographic segmentation determine agent success.

According to Redfin and local MLS data, the $2.6M-$3.3M annual commission pool rewards agents who build NYC remote worker capture pipelines, artist community engagement automation, first-time buyer education systems, and waterfront premium tracking simultaneously — a multi-segment approach that only automated systems can sustain. According to NAR, Peekskill's transformation-stage dynamics mean agents who establish automated farming systems now will capture compounding market share as the community continues its upward pricing trajectory.

The agents who will dominate Peekskill over the next decade are those who treat each price tier as a distinct market — automating NYC remote worker capture at $450,000-$750,000, first-time buyer education at $250,000-$450,000, artist community engagement at $300,000-$500,000, and waterfront premium marketing at $750,000+ — maintaining parallel pipelines that maximize transaction capture across the full price spectrum. US Tech Automations provides the platform infrastructure to build these price-intelligent farming systems — turning Peekskill's transformation momentum into a defensible, compounding practice.

About the Author: Garrett Mullins is a Workflow Specialist at US Tech Automations, helping real estate agents implement AI-powered automation for geographic farming and client management. Connect on LinkedIn for insights on real estate technology strategy.