Searching ...

39862 Big Pine Trl , Leonardtown, MD 20650

$420,000

4
beds
2 full · 1 half
baths
1,656
sqft
2002
year built

Discover the serene charm of this Cape Cod-style home nestled in the coveted Woods at Bayside, where water-oriented living meets modern comfort. This delightful 4-bedroom, 2.5-bathroom residence offers a perfect blend of tranquility and convenience, ideal for those seeking a peaceful retreat. Imagine waking up to the gentle sounds of nature, with the beautiful Bay just a stone's throw away. Enjoy easy access to the water, perfect for kayaking, paddleboarding, or simply soaking in the stunning views. The 0.21-acre lot provides ample space for outdoor gatherings, while the detached garage offers practical storage solutions. Step inside to find a thoughtfully designed layout that maximizes space and light. The Cape Cod architecture exudes timeless elegance, while the durable vinyl siding ensures low maintenance for years to come. With four spacious bedrooms, there's plenty of room for relaxation and personalization. The heart of this home is its inviting atmosphere, where you can create lasting memories with loved ones. Whether you're hosting summer barbecues or enjoying quiet evenings on the porch, the outdoor lifestyle here is truly enchanting. This property is not just a home; it's a lifestyle. Embrace the joys of waterfront living in a community that values nature and leisure. Don't miss your chance to own this slice of paradise-schedule your private tour today and envision your future in this idyllic setting!

  • Bedrooms
    4
  • Bathrooms
    2 full · 1 half
  • Year Built
    2002
  • Architectural Style
    Cape Cod
  • Construction Materials
    Frame, Vinyl Siding, Batts Insulation
  • Garage Spaces
    1.0
  • Parking Features
    Garage, Detached
  • Living Area
    1656.0
  • Appliances
    Electric Water Heater
  • Pool Features
    None
  • Cooling
    Ceiling Fan(s), Electric
  • Heating
    Electric, Heat Pump
  • Basement
    Crawl Space

  • Acres
    0.21
  • Water
    Well


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 39862 Big Pine Trl?

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 39862 Big Pine Trl.

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 39862 Big Pine Trl?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 2 bath, listed for $420,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Leonardtown, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 39862 Big Pine Trl?

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 39862 Big Pine Trl at around $2,646. 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 39862 Big Pine Trl?

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 Saint Marys 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 39862 Big Pine Trl?

In most cases, yes. Whether 39862 Big Pine Trl is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Leonardtown'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 39862 Big Pine Trl?

We can handle that for you. Our preferred local agent specializes in residentials in Leonardtown 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 $420,000 with 1,656 sqft of space—that comes out to approximately $254 per square foot.

How long has this property been on the market?

39862 Big Pine Trl was listed on November 06, 2026, which means it's been on the market for 5 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 2002, making it approximately 24 years old.

What is the lot size of this property?

39862 Big Pine Trl sits on a 0.21-acre lot, which is 9,148 square feet.

What are the property taxes for 39862 Big Pine Trl?

The most recent public record shows annual property taxes for 39862 Big Pine Trl were approximately $3,074. 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 39862 Big Pine Trl still available for sale?

Source: ez Home Search, MLS Data

Popular Home Searches in Leonardtown, MD


Search Nearby Cities


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 04:41AM | Source: Bright | MLS#: MDSM2034592