Edgartown, Massachusetts

Market Quick Stats

About Edgartown

Edgartown is a Dukes County village on Martha's Vineyard, one of New England's most exclusive communities. The town is known for pristine waterfront, maritime heritage, and upscale residential character. Properties range from historic sea captains' homes to modern estates.

Edgartown appeals to affluent families and professionals seeking island prestige and waterfront living. The town maintains strict character standards and limited development. Seasonal tourism and year-round residents create a sophisticated community atmosphere.

Winslow Homes serves Edgartown buyers and sellers across FL, MA, CT, and RI. Ryan and Megan Winslow provide both brokerage and mortgage services (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.

Housing Market Overview

Current Market Conditions & Trends

Edgartown's real estate market is ultra-premium. Median price exceeds $1.2M reflecting island scarcity and prestige. Properties sell to affluent buyers seeking luxury island living. Inventory is extremely limited.

📊 📊 Median Home Price

Median home price: $1,200,000+. Range: $800K-$3M+. Expect $400-$800+/sqft depending on waterfront location.

📈 📈 Market Trends

Strong demand from affluent families and investors. Waterfront properties command significant premiums. Island supply constraints drive values.

🏗️ 🏗 New Construction

New construction is minimal due to lot constraints and conservation focus. Most activity centers on renovation.

💰 💰 Price Per Square Foot

$400-$600 per square foot for established homes. Waterfront and new construction $600-$1,000+/sqft.

Notable Communities & Developments

Where to Live in Edgartown

🏘️ 🏘 Edgartown Village - historic waterfront center with shops and harbor

Notable Community

Edgartown Village - historic waterfront center with shops and harbor is a notable community in the area.

Demographics:Diverse mix of residents.

🏘️ 🏘 Waterfront neighborhoods - prestigious coastal areas

Notable Community

Waterfront neighborhoods - prestigious coastal areas is a notable community in the area.

Demographics:Diverse mix of residents.

🏘️ 🏘 Inland residential - upscale estates

Notable Community

Inland residential - upscale estates is a notable community in the area.

Demographics:Diverse mix of residents.

Neighborhood Breakdown

Explore Edgartown Neighborhoods

🏘️ 🏠 Edgartown Harbor area

Edgartown Harbor area

🏘️ 🏠 North Water Street historic

North Water Street historic

🏘️ 🏠 Summer Street estates

Summer Street estates

🏘️ 🏠 Cooke Street residential

Cooke Street residential

🏘️ 🏠 Cloudlandway area

Cloudlandway area

🏘️ 🏠 South Summer Street

South Summer Street

Specialty Housing

Unique Property Types in Edgartown

🌊 🌊 Edgartown Harbor and coves

Edgartown Harbor and coves

🌊 🌊 Atlantic Ocean waterfront

Atlantic Ocean waterfront

🌊 🌊 Protected anchorages and beaches

Protected anchorages and beaches

HOA & CDD Breakdown

Understanding Your True Monthly Costs

CDD vs. HOA:HOA fees cover community amenities and maintenance. CDD assessments are a separate tax-like charge that pays for infrastructure built by the developer. CDDs appear on your property tax bill and are not optional.

Pro Tip:When comparing homes, calculate total monthly cost including HOA + CDD + property taxes + insurance. A lower-priced home with high fees costs more monthly than a pricier home with no HOA.

Flood Zones & Insurance Impact

What Every Buyer Must Know

🔴 🔴 Zone AE (High Risk)

Coastal flood zones and FEMA-mapped areas throughout waterfront.

🟡 🟡 Zone X-Shaded (Moderate Risk)

Significant shaded flood zones in waterfront areas.

🟢 🟢 Zone X (Minimal Risk)

Inland areas mostly Zone X.

Insurance Tip:Homeowners insurance $2,000-$4,000+ annually. Flood insurance required for waterfront, $800-$3,000+ annually.

Investment & Rental Potential

Real Estate Investment in Edgartown

📈 💰 Waterfront property investment for prestige and long-term appreciation

Waterfront property investment for prestige and long-term appreciation

🏖️ 💰 Historic home restoration for upscale market

Historic home restoration for upscale market

🏖️ 💰 Island scarcity creates strong hold values

Island scarcity creates strong hold values

🏖️ ⚠️ Investment Risks

Island isolation, ferry dependence, hurricane exposure, high insurance costs, limited buyer pool, market sensitivity to economy

New Construction

Where New Homes Are Being Built

🏗️ 🏗 Limited to protected areas with special permits

Limited to protected areas with special permits

🏗️ 🏗 Island development constraints very restrictive

Island development constraints very restrictive

Buyer Tips for New Construction:Always hire your own inspector for new builds. Review CDD obligations carefully. Negotiate upgrades, not price. A buyer's agent costs you nothing with new construction and provides critical representation.

Commute Pockets

Drive Times & Work-From-Anywhere

🚗 🚗 Ferry to Woods Hole (45 min from West Tisbury)

Ferry to Woods Hole (45 min from West Tisbury)

🚗 🚗 Boston (3+ hours with ferry)

Boston (3+ hours with ferry)

🚗 🚗 New York (4+ hours)

New York (4+ hours)

💻 💻 Remote Work Lifestyle

Broadband adequate. Island infrastructure improves broadband consistently.

Schools & Education

Dukes County School District

🎒 🎒 Elementary Schools

Edgartown Elementary School (K-6)

📚 📚 Middle & High Schools

Martha's Vineyard Public Schools (7-12) regional

🏛️ 🎓 Private & Higher Education

Limited private schools on island

School Zone Impact:Schools adequate but less driver of values than proximity to water and island prestige.

Taxes & Cost of Living

Your Dollar in Edgartown

🏛️ 🏦 Property Taxes

Effective tax rate: 1.0% - 1.2% of assessed value. $12,000-$14,400 annually on $1.2M property.

💵 💵 Massachusetts Tax Considerations

Massachusetts has a flat 5% income tax rate plus a 4% surtax on income over $1M (effective 2023). Property tax rates vary by municipality. The residential exemption in some communities reduces the assessed value of owner-occupied homes. No sales tax on clothing under $175.

🛒 🛒 Cost of Living

Very high. Island living premium reflects scarcity and services costs.

📋 🏥 Insurance Costs

Homeowners: $2,000-$4,000/year. Auto: $1,400-$1,800/year.

Lifestyle & Community

Living the Edgartown Life

🏄 🎨 Island prestige and waterfront lifestyle dominate. Boating, fishing, and beach culture define living. Yacht clubs and marine activities central.

Island prestige and waterfront lifestyle dominate. Boating, fishing, and beach culture define living. Yacht clubs and marine activities central.

🏨 🎨 Artistic and cultural community strong. Galleries, theatrical productions, and musical performances throughout year. Seasonal tourism drives cultural activity.

Artistic and cultural community strong. Galleries, theatrical productions, and musical performances throughout year. Seasonal tourism drives cultural activity.

🎣 🎨 Outdoor recreation includes beaches, water sports, biking, and nature walks. Island offers peaceful alternatives to mainland rush.

Outdoor recreation includes beaches, water sports, biking, and nature walks. Island offers peaceful alternatives to mainland rush.

Local Hot Spots

Where the Locals Go

🔥 ⭐ Edgartown Harbor - iconic waterfront with village atmosphere

Edgartown Harbor - iconic waterfront with village atmosphere

🔥 ⭐ Edgartown Lighthouse - scenic landmark and tourist attraction

Edgartown Lighthouse - scenic landmark and tourist attraction

🔥 ⭐ Martha's Vineyard Film Festival area - cultural events and prestige

Martha's Vineyard Film Festival area - cultural events and prestige

Hidden Gems

The Insider's Edgartown

💎 💎 Historic sea captain homes - architectural gems and stories

Historic sea captain homes - architectural gems and stories

💎 💎 Katama Beach - pristine barrier beach

Katama Beach - pristine barrier beach

💎 💎 Local nature preserves - hiking and wildlife viewing

Local nature preserves - hiking and wildlife viewing

Jobs & Economy

Employment & Economic Drivers

🏨 🏥 Tourism and hospitality

Tourism and hospitality

🎣 🏥 Seasonal recreation services

Seasonal recreation services

💼 🏥 Arts and culture

Arts and culture

💻 💼 Remote Work & Entrepreneurship

Appeal for established professionals valuing island prestige. High broadband now supports remote work.

Transportation & Commuting

Getting Around Edgartown

🏘️ 🛣 Major Roads

North Water Street (Main Street), South Water Street, limited road infrastructure

🏘️ 🚲 Biking & Walking

Highly walkable village center. Island biking culture strong. Mixed infrastructure.

🏘️ ✈️ Airport Access

Martha's Vineyard Airport (10 min), Boston Logan (1.5 hrs with ferry)

New Development & Growth

What's Coming to Edgartown

🏝️ 🏗 Limited development potential due to island conservation

Limited development potential due to island conservation

🏘️ 🏗 Town preserves character over growth

Town preserves character over growth

🏘️ 📈 Market Outlook

Strong long-term appreciation expected. Island scarcity and prestige sustain values.

Investment Insights

Real Estate Investment in Edgartown

📈 💰 Waterfront properties offer premium appreciation and prestige value.

Waterfront properties offer premium appreciation and prestige value.

💰 💰 Island scarcity creates strong hold values for patient investors.

Island scarcity creates strong hold values for patient investors.

DISCUSS INVESTMENT STRATEGY

Common Buyer Mistakes

Avoid These Costly Errors

⚽ ⚠️ ❌ Underestimating ferry dependence and transportation costs

Underestimating ferry dependence and transportation costs

🏘️ ⚠️ ❌ Assuming year-round island living without seasonal experience

Assuming year-round island living without seasonal experience

📋 ❌ Overlooking hurricane exposure and insurance costs

Overlooking hurricane exposure and insurance costs

🏘️ ⚠️ ❌ Skipping a Local Agent

A local Edgartown agent knows which streets flood, which buildings have pending special assessments, and which neighborhoods are appreciating fastest. Buyer agent services are free to the buyer in most transactions.

Who Should Live Here

Is Edgartown Right for You?

👥 ✅ You'll Love It If...

Island prestige, waterfront living, artistic community, summer season culture, privacy, exclusive character

👥 ✅ Perfect For...

Affluent families seeking island prestige, creative professionals, retirees on substantial means, vacation home investors

👥 🤔 Consider Carefully If...

Ferry dependence, high insurance costs, hurricane exposure, isolation, seasonal population swings, very high costs

👥 ⚠️ Think Twice If...

You need urban proximity, want affordability, dislike isolation, prefer established infrastructure, sensitive to weather risk

Why People Leave

The Honest Downsides

🏝️ 🔄 Island isolation becomes challenging

Island isolation becomes challenging

🏘️ 🔄 Hurricane and weather concerns

Hurricane and weather concerns

🏘️ 🔄 Ferry commuting becomes burdensome

Ferry commuting becomes burdensome

Local Market Strategy

How to Win in the Edgartown Market

🏘️ 🎯 For Buyers

Work with island real estate specialists. Understand seasonal living. Budget for island costs and insurance.

🏘️ 📋 For Sellers

Emphasize island prestige and waterfront access. Market to qualified affluent buyers. Price at premium levels.

🏘️ 💡 For Investors

Waterfront for appreciation and prestige. Vacation rental potential. Patient long-term hold.

🏘️ 🔑 Insider Tips

Rent first to experience island living. Visit in off-season to understand year-round reality. Tour in multiple seasons.

Living in Edgartown: Honest Pros & Cons

The Balanced View

Buying & Selling in Edgartown

Your Next Steps

🏘️ 🏠 Buying Tips

Get comprehensive flood insurance estimate. Understand seasonal living impacts. Budget for all island costs. Call 386-690-5858 or visitwww.winslowloan.com.

🏘️ 💰 Selling Tips

Showcase waterfront and island prestige. Highlight artistic community. Market to qualified affluent buyers globally.

Mortgage & Financing

Your Path to Homeownership

Mortgage Services — Ryan & Megan Winslow

As both your real estate broker and loan officer, Ryan Winslow offers a streamlined experience from home search through closing. Ryan and Megan Winslow provide competitive rates on all major loan types:

Conventional Loans:As low as 3% down for qualified buyers. Ideal for borrowers with strong credit.

FHA Loans:3.5% down with flexible credit requirements. Perfect for first-time buyers entering the Edgartown market.

VA Loans:Zero down payment for eligible veterans and active-duty military. No PMI requirement.

USDA Loans:Zero down for qualifying rural properties. Income limits apply.

Down Payment Assistance:Multiple DPA programs available for qualifying buyers in Dukes County.

APPLY NOW — 386-690-5858

Local Insight from Winslow Homes

"Edgartown is where island prestige meets artistic soul. It's a place people dream of, even if briefly."

— Ryan & Megan Winslow, Winslow Homes

Browse Active Edgartown Listings

See every home for sale in Edgartown — from Historic sea captain and Federal homes - $900K-$2M+ to Waterfront estates and modern luxury homes - $1.5M-$3M+. Updated daily from the MLS.

About Winslow Homes LLC

Winslow Homes LLC is a full-service real estate brokerage licensed in Florida, Massachusetts, Connecticut, and Rhode Island. Ryan and Megan Winslow combine experience with commitment to client success and market expertise.

🏘️ Brokerage Services

Buyer representation guides clients through property selection, negotiation, and closing. Seller marketing strategies position properties competitively. Investment advisory services assist buyers seeking income-producing properties. Relocation assistance helps families moving to new communities.

📊 Market Expertise

The Winslow Homes team brings specialized knowledge of Edgartown neighborhoods, property values, market trends, and investment opportunities. Regular market analysis keeps agents informed on current conditions.

📞 Contact Information

Winslow Homes LLC
Email: Broker@WinslowHomesLLC.com
Phone: 386-690-5858

MLS Disclaimer & Legal Information

All real estate information provided by Winslow Homes LLC is derived from the Multiple Listing Service (MLS) and public sources. Information is deemed accurate but not guaranteed. Buyers should verify all information independently before making purchase decisions.

This website and all information provided does not constitute legal, financial, or tax advice. Buyers should consult qualified professionals including real estate attorneys, tax advisors, and financial planners before making property decisions.

Equal Housing Opportunity: Winslow Homes LLC operates under fair housing principles. Discrimination based on race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity is prohibited.