7737 Westerly Drive
Preston, MD, 21655 $ 568,900
Bedrooms3 Baths3.0 Sq 2,343 Monthly Estimate*
$ 3,929
for $568,900 with 3 bedrooms and 3 full baths. This 2,343 square foot home was built in 1994 on a lot size of 1.07.
*Major Price Improvement* **Thoughtfully Renovated & Move-In Ready** Welcome to a beautifully renovated home offering 3 bedrooms plus a flexible bonus space with potential for a 4th bedroom in the water front community of Two Johns. Extensively updated from top to bottom, this home offers a fresh, modern feel while maintaining a warm and inviting atmosphere. As you enter, youll immediately notice the all-new flooring and lighting throughout, freshly painted rooms, new interior doors, and crown molding featured in most spaces, creating a clean and cohesive look throughout the home. The updated kitchen combines style and functionality with beautiful quartz countertops and stainless steel appliances, making it the perfect space for everyday living and entertaining. All three bathrooms have been thoughtfully updated, including a beautifully redesigned and custom-appointed primary suite bathroom. Step outside and enjoy the best of outdoor living from the spacious screened-in porch overlooking the private rear yard. The backyard retreat features an inviting in-ground pool, fruit trees, and a 1,000-gallon pond with a tranquil waterfall, creating a peaceful setting for relaxing, entertaining, and enjoying your own private oasis. The exterior has received an impressive facelift as well, featuring brand-new siding, Azek window trim, new exterior doors, and new exterior lighting, giving the home a fresh and welcoming appearance from the moment you arrive. The spacious two-car garage offers even more versatility with a full bonus room on the second floor, complete with heat and A/C on both levelsperfect for a home office, gym, entertainment space, guest area, or potential additional living space. A lean-to extends off the back of the garage, providing even more room for storage, hobbies, equipment, or outdoor necessities. With extensive updates throughout and incredible indoor and outdoor living spaces, this home is move-in ready and waiting for its new owners!
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FeaturesGeneralLiving Area 2343
Sewer Private Septic Tank
Heating Heat Pump(s)
Cooling Central A/C
Possession Settlement
Roof Shingle
Appliances Built-In Microwave Dishwasher Refrigerator Stove Washer Dryer
Zoning R
Garage Spaces 2.00
Patio/Porch Features Deck(s) Screened Porch(es)
Architectural Style Ranch/Rambler
Pool Features In Ground
Construction Materials Combination
School District CAROLINE COUNTY PUBLIC SCHOOLS
Year Built 1994
Levels 1
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Accessibility None
County CAROLINE
New Construction N
Property Type Residential
HOA N
Subdivision Name TWO JOHNS
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 3
Status ACTIVE
Directions Google Maps
City PRESTON
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 46609.00
Tax Annual Amount 4264.0
Home Warranty Y/N N
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 3
Bathrooms Count Main Level 3.00
Price Per Sq Ft Total AG 242.81
Historic Y/N N
Lease Considered Y/N N
Vacation Rental Y/N N
Location Type Corner Lot/Unit
Standard Status Active
Year Built Source Assessor
Tax Lot 7
Association Recreation Fee N
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InteriorInterior Amenities Bathroom - Tub Shower Bathroom - Walk-In Shower Ceiling Fan(s) Combination Kitchen/Dining Family Room Off Kitchen Recessed Lighting Upgraded Countertops Walk-in Closet(s)
Heating Fuel Electric
Flooring Engineered Wood Luxury Vinyl Plank Tile/Brick
Hot Water Tankless
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N N
Above Grade Finished Area 2343
Half Baths 0
Central Air Y/N Y
Total Bedrooms 3
Below Grade Finished Area 0
Room Type Living Room Kitchen Bonus Room
Main Level Bedrooms 3
Below Grade Finished Area Unit Type Square Feet
Laundry Type Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 3
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ExteriorExterior Amenities Exterior Lighting Hot Tub Other
Pool Yes - Personal
Parking Features Asphalt Driveway
Water Source Private
Inclusions Hot Tub(unknown Condition) Pool Table & Accessories Picnic Tables
Garage Features Garage - Front Entry Garage - Side Entry Additional Storage Area Other
Type of Parking Driveway Detached Garage
Foundation Details Crawl Space
Spa N
Water View Y/N N
Lot Size Acres 1.07
Lot Size Source Assessor
Waterfront Y/N N
Horse Y/N N
Land Assessed Value 100400.00
Navigable Water Y/N N
Water Oriented Y/N N
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* Excluded FeaturesList ByKeller Williams Select Realtors Of AnnapolisBroker
Affordability Calculator
- Monthly Principal & Interest
- $3,929
- Monthly Property Taxes
- $355
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Preston, MD
Average List Price $302,439
Percent of Sale Price 47%
About Preston, MD 578 Population
6% Since 2002
$ 63,996 Median Income
42.04 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
3535583 Elementary School
3535264 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/12/2026 | $568,900 | -4.53% | Price Down |
| 9/22/2026 | $595,900 | -8.31% | Price Down |
| 8/22/2026 | $649,900 | | Listed Price |