Best Real Estate Agents in Vineyard Haven, MA• Updated
Looking for the best real estate agent in Vineyard Haven, MA? This page ranks the top realtors in Vineyard Haven by actual transaction data — not reviews or paid ads. Whether you want to find a top listing agent in Vineyard Haven, MA or buy a home in Vineyard Haven, our 2026 rankings use verified sales records, days on market, and price retention to surface the highest-performing agents.
Market Pulse: Opportunity 📈
The Vineyard Haven, MA real estate market is currently a Buyer's Market. Homes are retaining 97% of their value (Sale Price to List Price Ratio). With 11 active listings and 3 closed sales this month, inventory remains at 6.6 months of supply. Trends over the last half-year show median values moving up by 2%, while Average Days on Market has increased by 29%. Transaction speed in Vineyard Haven is currently 23 days slower than the broader Dukes benchmark.
Top Listing & Buyer's Agents in Vineyard Haven, MA
Detached Homes
Entry Level Detached Home Market Trends Median Price Market Trend The average price in the Entry Level Detached Home segment has softened by 22% over the last 3 months. Days On Market Avg. Market Trend Lower is better Days on market for Entry Level Detached Home is increasing, with homes now staying on market for 113 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the Entry Level Detached Home market is strengthening, with the Sale Price to List Price Ratio now at 100%.
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Mid-Market Detached Home Market Trends Median Price Market Trend The Mid-Market Detached Home tier commands a price of $1.2M. Days On Market Avg. Market Trend Lower is better Detached Home homes in the Mid-Market range average 122 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Mid-Market Detached Home assets receive 94% of list price.
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High-End Detached Home Market Trends Median Price Market Trend The average price in the High-End Detached Home segment has softened by 10% over the last 2 months. Days On Market Avg. Market Trend Lower is better Days on market for High-End Detached Home is decreasing, with homes now staying on market for 54 days on average. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Seller leverage in the High-End Detached Home market is strengthening, with the Sale Price to List Price Ratio now at 100%.
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Ultra-Luxury Detached Home Market Trends Median Price Market Trend The Ultra-Luxury Detached Home tier commands a price of $3.9M. Days On Market Avg. Market Trend Lower is better Detached Home homes in the Ultra-Luxury range average 104 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Ultra-Luxury Detached Home assets receive 99% of list price.
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Condo/Co-op
Entry Level Condo/Co-op Market Trends Median Price Market Trend The Entry Level Condo/Co-op tier commands a price of $550K. Days On Market Avg. Market Trend Lower is better Condo/Co-op homes in the Entry Level range average 37 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Entry Level Condo/Co-op assets receive 92% of list price.
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Townhomes
Mid-Market Townhome Market Trends Median Price Market Trend The Mid-Market Townhome tier commands a price of $1.5M. Days On Market Avg. Market Trend Lower is better Townhome homes in the Mid-Market range average 170 days on market. Sale Price to List Price Ratio Market Trend Higher is better Lower is better Sellers of Mid-Market Townhome assets receive 92% of list price.
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Vineyard Haven Real Estate Market Trends September 2026
Inventory Breakdown by Segment
| Property Type | Entry Level | High-End | Mid-Market | Ultra-Luxury | Total |
|---|---|---|---|---|---|
| Condo/Co-op | 1 | — | — | — | 1 |
| Detached Home | — | 2 | 6 | 1 | 9 |
| Multi-Family (2-4 Unit) | — | — | 1 | — | 1 |
Market Insights & FAQ
How is the real estate market in Vineyard Haven, MA performing right now?
The data indicates a stable environment in Vineyard Haven, MA. Inventory is at 6.6 months, meaning a balanced environment with steady turnover. Inventory levels provide a healthy range of options for prospective buyers.
What are the current pricing trends for Vineyard Haven, MA real estate?
Currently, $1,480,000 represents the median entry point in Vineyard Haven, MA. Over the past half-year, home values in Vineyard Haven have moved upward by approximately 2% based on regional transaction data.
Are sellers in Vineyard Haven, MA getting their full asking price?
Buyers have room for negotiation in Vineyard Haven, MA, with a Sale Price to List Price Ratio of 97.3%. On average, properties in Vineyard Haven are transitioning from active to sold status in 112 days.
Who is the best agent to sell my home in Vineyard Haven?
Based on closed transaction data, Idalyn Macchia Gilstad ranks at the top of our Vineyard Haven leaderboard earning an algorithm performance score of -50. Agent Algo's rankings are built entirely from real deal outcomes — not reviews or paid placements — so this reflects actual results in the local market.
How does the Vineyard Haven, MA market compare to Dukes trends?
Vineyard Haven, MA maintains a distinct profile within the broader Dukes region. Median home values are currently 33% lower than the regional average, reflecting the unique demand and inventory dynamics of Vineyard Haven.
Which agent is best for buying a Entry Level Detached Home in Vineyard Haven, MA?
Buyers targeting Entry Level Detached Home homes in Vineyard Haven, MA may want to work with Alisan Lohan Conway. Their buyer transactions in this segment close faster than the local norm and at sale-to-list ratios that are more favorable than typical — meaning they move quickly and negotiate effectively for the buyers they represent.
Which agent is best for buying a Mid-Market Detached Home in Vineyard Haven, MA?
Our data flags Kathleen Kendrick as a top buyer's advocate for Mid-Market Detached Home properties in Vineyard Haven, MA. The data shows a consistent pattern across their deals here: shorter time to close than the segment average, and acquisition terms that tend to land below-average relative to list price. Two things buyers care about most.
Who is a top listing agent for Entry Level Detached Home homes in Vineyard Haven, MA?
Among agents with recent closings in the Entry Level Detached Home space, Idalyn Macchia Gilstad has the strongest performance metrics in Vineyard Haven, MA. In a category where leaving money on the table is easy, their sale-to-list performance in this segment stands above the local benchmark — reflecting an ability to negotiate and price effectively.
Who is a top listing agent for Mid-Market Detached Home homes in Vineyard Haven, MA?
Stephanie Roache has been particularly active in Vineyard Haven's Mid-Market Detached Home segment, and the numbers back it up. Their listings in this segment have consistently closed faster than the local average while achieving above-average sale-to-list ratios — a rare combination that directly benefits sellers on both time and final price.