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$910,000
5 Beds ⋅ 5 Baths
Welcome to 13532 Rustling Oaks Drive: where meticulous pride of ownership truly shows on this classic Cape Cod in the land of pleasant living on the Eastern Shore. Situated on over an acre of land with towering pines providing excellent shade and privacy, this 5 bedroom, 5,500+ square foot home has been recently upgraded and offers something for the whole family. 10 foot ceilings, hardwood floors, arched hallways, crown moldings, columns, chair rails, are just a few of the timeless interior finishes while a brand new saltwater gunite pool elevates the exterior space. Inside, an expansive first floor primary suite offers total main level living and complete privacy. With a tray ceiling, bay window and double walk-in closets, it is a retreat in its own; punctuated by an updated ensuite bath with double vanity, soaking tub, and oversized glass walk-in shower. The true heart of the main level is the upgraded kitchen and living room areas. These large complementing spaces are perfect for entertaining and everyday living. The kitchen has all new stainless steel appliances including a double wall oven and is finished with wood cabinets and granite countertops. The large island has a propane cooktop and overhanging bar seating. A breakfast area looks through a large bay window to the back yard. A new wood burning stove insert with wood mantel is the centerpiece of the living room just off the kitchen. A formal dining room and separate laundry/mud room complete the first floor. The main living area seamlessly flows into everyone's favorite space: the back yard, anchored by a brand new saltwater gunite pool and sweeping patio with lounging, grilling and fire pit areas. An additional screened-in porch with a tv is perfect for summertime crab feasts or morning coffee. Back inside, the basement is another world of its own with 9 foot ceilings and over 2,000 finished square feet. A 2nd full kitchen opens the possibilities to a private guest space or mother-in-law suite. There is a large game area, a private home office, a 5th bedroom with full bath and an unfinished utility space with room for more storage or workout equipment. Moving upstairs to the 2nd floor, one will find an additional primary bedroom with ensuite bath, two more generously sized guest bedrooms, a shared bath and a comfortable reading area atop the stairs. In addition to the two-car attached garage, a detached two-car garage with space above offers additional storage and workshop potential. A large garden shed and underground sprinkler system completes the backyard. A few of the recent updates include a saltwater gunite pool (2024), all new stainless steel kitchen appliances (2024), updated primary bath (2025), first floor dual-fuel 5-ton high efficiency heat pump (2025), fireplace wood stove insert (2023), leaf gutter guards (2025). Minutes away from a public boat ramp serving the picturesque Wye River and the enduring beauty of the Wye Island Nature Preserve. Major marinas are close by at Kent Narrows, St Michaels, or Oxford. This centrally located Eastern Shore getaway serves the lower beaches and the Chesapeake's tributaries well yet is still an easy commute to Annapolis, Baltimore or D.C. 10 minutes to downtown Easton and all the shopping you might need. The property across the street is open community space and will not be built upon. This tastefully updated and diligently maintained home offers a unique blend of amenities and functionality for the laid-back Eastern Shore lifestyle. Much more info and professional photos to come. Stay tuned!!

13532 Rustling Oaks Drive, Wye Mills

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: .

$850,000
3 Beds ⋅ 2 Baths
Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

492 Pear Tree Point Road, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: .

$820,650
5 Beds ⋅ 5 Baths
Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving and cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Sellers have a $450,000 assumable VA Loan at a 2% interest rate. Recent updates include: roof tune up, exterior paint, interior hard floor refinish, interior paint, hvac service, and more.

3908 Street Road, Street

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: .