A top real estate agent in Osterville, MA is the key to finding luxury waterfront homes and properties on Cape Cod for buyers of all kinds.

Osterville, MA 02655, a village within the town of Barnstable on Cape Cod, consistently ranks among the most coveted waterfront communities in Massachusetts. Whether you're eyeing a Nantucket Sound estate, a Wianno-area cottage, or a tidal river property near Oyster Harbors, the right agent changes everything.

We've been working this coastline long enough to know exactly who those agents are, and why the gap between a good one and a great one tends to show up at the worst possible moment.

Waterfront in Osterville isn't like other Cape Cod real estate

That moment, more often than not, comes down to details most buyers never knew to ask about. And here's the thing: those details are rarely obvious from the listing page.

Waterfront homes in Osterville carry layers of regulatory and financial complexity that quietly cost buyers and sellers tens of thousands of dollars when they go unmanaged.

Factor	What You Need to Know
Flood Zone (FEMA) Designation	Can add $5,000–$30,000+ annually in insurance costs
Dock & Mooring Rights	Not guaranteed with waterfront lots; must be verified before closing
Barnstable Conservation Commission	Controls what can be built, renovated, or expanded near water
Title V Septic Compliance	Cape Cod's strict standards directly affect lot value and buildability
Seasonal Rental Income Potential	Premium Osterville waterfront homes rent for $15,000–$45,000/week
Off-Market Inventory	A significant share of Osterville luxury sales never reach Zillow

When interviewing agents, ask each one how many waterfront closings they've completed in Osterville specifically, not just "Cape Cod." Most answers are shorter than you'd expect.

The agents who come up every time

When you start pressing on that question, a short list of names surfaces. These are the professionals with genuine track records in this specific market.

1. Freitas Monteforte Group

Livia Freitas Monteforte has been working Cape Cod's coastal and waterfront market since 2005. Long enough to know the difference between a property that photographs well and one that actually holds its value. As Broker and Team Principal, she leads a small, focused team with an active presence in Osterville, Wianno, and Falmouth.

2. Robert Kinlin | Robert Paul Properties

Robert Kinlin is a 36-year veteran of the Cape Cod luxury market and one of the most recognized names in waterfront estate sales. His brokerage carries one of the strongest listing portfolios in Barnstable, with excellent reach among Boston-area and national buyers.

3. Chuck Tuttle | William Raveis Real Estate

Chuck Tuttle brings 20+ years of top-producing experience to waterfront and golf properties in Osterville, including homes near the Wianno Club. His local knowledge is a genuine advantage, specifically for buyers pursuing that lifestyle.

4. Linda Whitcomb | William Raveis Real Estate

Linda Whitcomb is ranked in the top 1.5% of realtors nationwide with $100M+ in sales. Her data-driven approach makes her one of the most reliable agents for luxury estate transactions in the area.

5. Kathy Deerman | Robert Paul Properties

Kathy Deerman covers communities from Buzzards Bay to Nantucket Sound, which is useful for buyers still weighing Osterville against Centerville, South Yarmouth, or neighboring Cape villages.

6. Frank Sullivan Real Estate

Frank Sullivan Real Estate is a locally rooted Osterville firm with generational ties to the village, a strong fit for buyers who want hyper-local community knowledge.

Agent	Brokerage	Specialty	Best For
Freitas Monteforte Group	Compass	Coastal, waterfront, luxury, beach	Tech-forward buyers & sellers, all Cape Cod
Robert Kinlin	Robert Paul Properties	Luxury/waterfront estates	Sellers of premium Osterville homes
Chuck Tuttle	William Raveis	Waterfront & golf properties	Wianno lifestyle buyers
Linda Whitcomb	William Raveis	Luxury estate sales	Data-focused buyers & sellers
Kathy Deerman	Robert Paul Properties	Village & waterfront, Bay to Sound	Buyers comparing Cape communities
Frank Sullivan	Frank Sullivan Real Estate	Osterville village history	Hyper-local buyers

Each of these professionals has earned their place here.

The real question is what kind of transaction you're navigating, and which expertise is actually built for it.

What we've been doing here since 2005

That's a question we've been sitting with since 2005, when Livia Freitas Monteforte founded Freitas Realty Group on Cape Cod. Our work evolved (through NextHome Freitas Realty Group, and since 2020 as the Freitas Monteforte Group at Compass), but the focus never changed: coastal and waterfront properties, handled with the kind of detail this market actually requires.

What we bring to Osterville specifically is two decades of Cape Cod coastal experience combined with the marketing infrastructure luxury listings genuinely demand. Compass gives us national and international buyer exposure, premium digital tools, and an off-market network that extends well beyond what traditional brokerages can offer. That matters when you're selling a waterfront estate in the 02655 market and need the right buyer. Not just any buyer.

What the Freitas Monteforte Group offers

Year-round Cape Cod presence. We live and work this market every single month. We maintain active listings and closings in Osterville, Wianno, Falmouth, and throughout Cape Cod. The Compass platform provides national reach, premium digital marketing, and an off-market network. We offer bilingual service in English and Portuguese, valuable for international buyers. We have verified buyer success in Osterville including Wianno-area waterfront homes, and our tech-forward practices are backed by Livia's role as Realtor in Residence for Ylopo/MaverickRE.

We work with a small team by design. In a high-value coastal transaction, you deserve to know exactly who's handling your deal, and that accountability runs all the way from the first showing to the closing table.

What Osterville waterfront gets right, and what catches buyers off guard

That accountability matters most when things get complicated. And in this market, they usually do.

What makes Osterville exceptional

Nantucket Sound frontage is finite and irreplaceable. The Wianno and Oyster Harbors communities offer a lifestyle — beach, bay, boat, and village — that doesn't exist anywhere else on the Cape. Waterfront estates here carry a long track record of appreciation, and strong seasonal rental income can meaningfully offset carrying costs.

What buyers consistently underestimate

Flood insurance on a premium waterfront home can exceed $20,000 annually. Barnstable Conservation Commission requirements can add serious cost and time to renovation plans. Septic upgrades under Title V can run $50,000–$80,000. And without a year-round local agent, off-market listings — which represent a substantial portion of luxury Osterville sales — are simply invisible until it's too late.

Osterville waterfront rewards buyers who go in clear-eyed, and quietly punishes those who don't.

Talk to the Freitas Monteforte Group

Our team at the Freitas Monteforte Group at Compass has spent nearly two decades closing coastal transactions across Cape Cod, learning the details that only come from being here year-round, in every season. We've helped buyers find Osterville waterfront homes before they ever hit the public market. We've helped sellers of luxury estates in the 02655 community close at the top of their range.

If waterfront and coastal real estate on Cape Cod is what you're after, we'd love to be your first call. Whether you're a first-time Cape Cod waterfront buyer, a seller ready to move on a long-held property, or still sorting out which coastal community fits, we work with you directly — not just on your behalf.

Reach Out Today