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39862 BIG PINE TRL, LEONARDTOWN, MD, 20650
$420,000
- 4 beds
- 2 full baths
- 1 half baths
- 1,656 sq. ft
39862 BIG PINE TRL, LEONARDTOWN, MD, 20650
$420,000
Coming Soon
- Beds 4
- Baths 2.5
- Sq. ft 1,656
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!
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Year Built:
2002
Days on Market:
1
Listing ID:
MDSM2034592
Bathrooms:
2 full , 1 half
List Date:
November 09, 2026
Property Type:
Single Family Residential
Architecture Style:
Cape Cod
Subdivision:
THE WOODS AT BAYSIDE
County:
SAINT MARYS
Total Taxes:
$3,074
Courtesy of The Southside Group Real Estate
This content was last updated on November 10, 2026 22:11
Schools
| Name | Type | Level | Grades | Address | |
|---|---|---|---|---|---|
Leonardtown Middle School |
Public | Middle | 6-8 | 24015 Point Lookout Rd, Leonardtown, MD 20650 | |
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District: St. Marys County Public Schools Grade Span: 6 - 8 Admission: Public Address: 24015 Point Lookout Rd, Leonardtown, MD 20650 Phone: 301-475-0230 Website: http://schools.smcps.org/lms/ Teachers: 56 Students: 969 Ratio: 17:1 Students/Teacher Gender: 49% Male / 51% Female Lunch: 21% Free / 5% Reduced Student/Teacher ratioEnrollment |
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Chopticon High School |
Public | High | 9-12 | 25390 Colton Point Rd, Morganza, MD 20660 | |
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District: St. Marys County Public Schools Grade Span: 9 - 12 Admission: Public Address: 25390 Colton Point Rd, Morganza, MD 20660 Phone: 301-475-0215 Website: http://schools.smcps.org/chs/ Teachers: 79 Students: 1526 Ratio: 19:1 Students/Teacher Gender: 51% Male / 49% Female Lunch: 29% Free / 6% Reduced Student/Teacher ratioEnrollment |
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Benjamin Banneker Elementary School |
Public | Primary | PK-5 | 27180 Point Lookout Rd, Loveville, MD 20656 | |
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District: St. Marys County Public Schools Grade Span: PK - 5 Admission: Public Address: 27180 Point Lookout Rd, Loveville, MD 20656 Phone: 301-475-0260 Website: http://www.smcps.org Teachers: 40 Students: 543 Ratio: 14:1 Students/Teacher Gender: 52% Male / 48% Female Lunch: 31% Free / 5% Reduced Student/Teacher ratioEnrollment |
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| Name | Type | Level | Grades | Address | |
|---|---|---|---|---|---|
Busy Corner School |
Private | Elementary | 1-8 | 40385 Busy Corner Rd, Leonardtown, MD 20650 | |
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Grade Span: 1 - 8 Admission: Private Address: 40385 Busy Corner Rd, Leonardtown, MD 20650 Teachers: 1 Students: 21 Ratio: 21:1 Students/Teacher Gender: 57% Male / 43% Female Student/Teacher ratioEnrollment |
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Father Andrew White Sj School |
Private | Elementary | PK-8 | 22850 Washington St, Leonardtown, MD 20650 | |
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Grade Span: PK - 8 Admission: Private Address: 22850 Washington St, Leonardtown, MD 20650 Phone: 301-475-9795 Website: http://www.fatherandrewwhite.org/ Teachers: 15 Students: 213 Ratio: 15:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratioEnrollment |
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Leonard Hall Jr Naval Academy |
Private | Combined Elementary/Secondary | 6-12 | 41740 Baldridge St, Leonardtown, MD 20650 | |
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Grade Span: 6 - 12 Admission: Private Address: 41740 Baldridge St, Leonardtown, MD 20650 Phone: 301-475-8029 Teachers: 6 Students: 38 Ratio: 6:1 Students/Teacher Gender: 71% Male / 29% Female Student/Teacher ratioEnrollment |
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Little Seedlings Christian Preschool & Kindergarden |
Private | Elementary | PK-KG | 25550 Point Lookout Rd, Leonardtown, MD 20650 | |
|
Grade Span: PK - KG Admission: Private Address: 25550 Point Lookout Rd, Leonardtown, MD 20650 Phone: 301-475-5050 Teachers: 1 Students: 7 Ratio: 8:1 Students/Teacher Gender: 57% Male / 43% Female Student/Teacher ratioEnrollment |
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Loveville Mennonite School |
Private | Elementary | 1-8 | 40750 Parsons Mill Rd, Leonardtown, MD 20650 | |
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Grade Span: 1 - 8 Admission: Private Address: 40750 Parsons Mill Rd, Leonardtown, MD 20650 Phone: 301-475-3084 Teachers: 2 Students: 39 Ratio: 20:1 Students/Teacher Gender: 44% Male / 56% Female Student/Teacher ratioEnrollment |
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Pin Cushion Mennonite School |
Private | Elementary | 1-8 | 24983 Pincusion Rd, Leonardtown, MD 20650 | |
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Grade Span: 1 - 8 Admission: Private Address: 24983 Pincusion Rd, Leonardtown, MD 20650 Teachers: 1 Students: 27 Ratio: 27:1 Students/Teacher Gender: 56% Male / 44% Female Student/Teacher ratioEnrollment |
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St Mary S Ryken High School |
Private | Secondary | 9-12 | 22600 Camp Calvert Rd, Leonardtown, MD 20650 | |
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Grade Span: 9 - 12 Admission: Private Address: 22600 Camp Calvert Rd, Leonardtown, MD 20650 Phone: 301-373-4198 Teachers: 57 Students: 639 Ratio: 11:1 Students/Teacher Gender: 55% Male / 45% Female Student/Teacher ratioEnrollment |
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