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Experience the best of Eastern Shore living at 419 Osprey Circle, a spacious and beautifully appointed home offering over 3,400 square feet of thoughtfully designed living space in one of Cambridge's most desirable neighborhoods. Combining generous room sizes, flexible living areas, and an exceptional location just minutes from the waterfront, this home delivers the perfect blend of comfort, convenience, and lifestyle. Step inside to discover a dramatic two-story family room filled with natural light that serves as the heart of the home. The open and inviting floor plan offers plenty of space for both everyday living and entertaining, while a dedicated main-level office or den provides the perfect setting for remote work, studying, or a private retreat. The upper level is highlighted by an impressive luxury primary suite designed to be your own private sanctuary. This expansive retreat features a large bedroom, a separate sitting area, a stunning fully renovated spa-inspired bathroom, and a custom walk-in closet that offers both beauty and exceptional storage. Also located upstairs is a spacious loft or den overlooking the two-story family room below, creating additional living space that could easily be converted into a fourth bedroom if desired. Outside, the property offers a generous yard with plenty of room to relax, entertain, garden, or simply enjoy the peaceful surroundings. Located just minutes from historic downtown Cambridge and the scenic shores of the Choptank River, residents enjoy easy access to waterfront dining, marinas, parks, shopping, and year-round outdoor recreation. Cambridge has become one of Maryland's most sought-after waterfront communities, known for its vibrant downtown, rich maritime heritage, boating, fishing, kayaking, paddleboarding, and proximity to the renowned Blackwater National Wildlife Refuge. The area is also home to the internationally recognized IRONMAN Maryland and Eagleman 70.3 triathlons, which attract athletes and visitors from around the world each year. These iconic events showcase Cambridge's stunning waterfront setting, scenic country roads, and active outdoor lifestyle, adding to the energy and appeal of this unique community. Whether you're enjoying a day on the water, exploring local restaurants and shops, or simply relaxing in your spacious home, 419 Osprey Circle offers an opportunity to embrace the lifestyle that makes Maryland's Eastern Shore such a special place to live. Conveniently located within easy reach of Annapolis, the Delaware and Maryland beaches, and the Washington-Baltimore metropolitan area, this exceptional property is ready to welcome you home.

Highlights

  • Residential
  • Single Family Residence
  • Built in 2006
  • 0.31 Acre Lot
  • $56/mo HOA
  • 2 Car Garage
  • 156 days on Market

  • Bedrooms
    4
  • Bathrooms
    2 full · 1 half
  • Year Built
    2006
  • Architectural Style
    Colonial
  • Construction Materials
    Vinyl Siding
  • Foundation
    Block
  • Garage Spaces
    2.0
  • Parking Features
    Attached, Garage
  • Living Area
    3486.0
  • Appliances
    Dishwasher, Disposal, Gas Water Heater
  • Flooring
    Wood
  • Pool Features
    None
  • Cooling
    Central Air, Electric
  • Heating
    Forced Air, Natural Gas
  • Basement
    Crawl Space

  • Acres
    0.31
  • Water
    Public


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Frequently Asked Questions

How do I schedule a tour of 419 Osprey Cir?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 419 Osprey Cir.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 419 Osprey Cir?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 2 bath, listed for $424,900. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Cambridge, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 419 Osprey Cir?

With a 20% down payment and a 30-year fixed loan at an illustrative 6.75% rate, the ez Mortgage Calculator estimates the monthly payment for 419 Osprey Cir at around $2,869. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 419 Osprey Cir?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Dorchester County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 419 Osprey Cir?

In most cases, yes. Whether 419 Osprey Cir is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Cambridge's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 419 Osprey Cir?

We can handle that for you. Our preferred local agent specializes in residentials in Cambridge and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $424,900 with 3,486 sqft of space—that comes out to approximately $122 per square foot.

How long has this property been on the market?

419 Osprey Cir was listed on June 04, 2026, which means it's been on the market for 156 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 2006, making it approximately 20 years old.

What is the lot size of this property?

419 Osprey Cir sits on a 0.31-acre lot, which is 13,504 square feet.

What are the property taxes for 419 Osprey Cir?

The most recent public record shows annual property taxes for 419 Osprey Cir were approximately $6,784. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $56 paid monthly.

Is 419 Osprey Cir still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Bright. All rights reserved.

Last Updated: November 07, 2026 at 07:46PM | Source: Bright | MLS#: MDDO2012428