Searching ...

Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

  • Bedrooms
    4
  • Bathrooms
    3 full · 1 half
  • Year Built
    1981
  • Architectural Style
    Ranch/Rambler
  • Construction Materials
    Vinyl Siding
  • Garage Spaces
    2.0
  • Parking Features
    Oversized, Asphalt, Garage, Detached, Inside Entrance
  • Living Area
    2052.0
  • Interior Features
    Ceiling Fan(s), Eat-in Kitchen
  • Appliances
    Dryer, Dishwasher, Electric Range, Electric Water Heater, Microwave, Refrigerator, Washer, Electric Oven, Stainless Steel Appliance(s), Ice Maker
  • Flooring
    Vinyl
  • Furnished
    Partially
  • Pool Features
    None
  • Cooling
    Ceiling Fan(s), Central Air, Electric
  • Heating
    Electric, Heat Pump
  • Basement
    Crawl Space

  • Acres
    0.44
  • Lot Features
    Corner Lot
  • Water Front Features
    Lake
  • Water
    Public

  • County
    Queen Annes
  • City
    Stevensville
  • Neighborhood
    BAY CITY
  • Zip Code
    21666
  • High School
    KENT ISLAND
  • Middle School
    MATAPEAKE
  • Elementary School
    MATAPEAKE

Ask a Question

What's your home worth?

Calculate your current home value within seconds.

Frequently Asked Questions

How do I schedule a tour of 709 Chesapeake Dr?

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 709 Chesapeake Dr.

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 709 Chesapeake Dr?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $550,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Stevensville, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 709 Chesapeake Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 709 Chesapeake Dr at around $3,380. 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 709 Chesapeake Dr?

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 Queen Annes 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 709 Chesapeake Dr?

In most cases, yes. Whether 709 Chesapeake Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Stevensville'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 709 Chesapeake Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Stevensville 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 $550,000 with 2,052 sqft of space—that comes out to approximately $268 per square foot.

How long has this property been on the market?

709 Chesapeake Dr was listed on November 01, 2026, which means it's been on the market for 10 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 1981, making it approximately 45 years old.

What is the lot size of this property?

709 Chesapeake Dr sits on a 0.44-acre lot, which is 19,166 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: MATAPEAKE
  • Middle: MATAPEAKE
  • High: KENT ISLAND

Want to see how these schools compare? Check out our Queen Annes County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 709 Chesapeake Dr?

The most recent public record shows annual property taxes for 709 Chesapeake Dr were approximately $2,998. 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 $150 paid annually.

This covers access to community features including: Picnic Area, Playground, Boat Dock, Beach Access, Jogging Path, Boating.

Is 709 Chesapeake Dr still available for sale?

Source: ez Home Search, MLS Data

Popular Home Searches in Stevensville, MD


Search Nearby Cities


Search Nearby Counties


Search Nearby Postal Codes

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 11, 2026 at 03:00AM | Source: Bright | MLS#: MDQA2019190