Kent County Public Schools Real Estate

Kent County Public Schools Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Kent_County_Public_Schools and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

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Newest Listings in Kent County Public Schools

2 Beds ⋅ 2 Baths

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

List Price is opening bid. Online Auction Only! Bidding begins Saturday, August 15 and ends Thursday, August 20, 2026 at 1:00 PM. Exceptional Multi-Family Investment Opportunity in Chestertown! Introducing 104 Maple Avenue, a beautifully updated 6-unit apartment building ideally located in Kent County's desirable Chestertown area. Thoughtfully renovated, this income-producing property seamlessly blends modern finishes with practical functionality, making it an outstanding addition to any investment portfolio. Each unit has been carefully improved to provide attractive, comfortable living spaces designed to appeal to today's renters. The extensive updates enhance both the property's aesthetic appeal and long-term value while helping to minimize future maintenance concerns. Upon full occupancy, the property offers an impressive Gross Annual Rent of $129,300±, presenting an exceptional opportunity for investors seeking strong cash flow and long-term appreciation. Conveniently situated near Washington College, University of Maryland Medical Center, & downtown Chestertown's restaurants, shops, waterfront, and local amenities, the location further enhances its desirability for tenants. Whether you're expanding your real estate portfolio or acquiring a high-performing multi-family asset, 104 Maple Avenue represents a rare opportunity to own a updated six-unit building in one of Kent County's most charming and sought-after communities. Features and Highlights: • (6) Apartments • Thoughtfully Updated & Beautifully Maintained Building • Stabilized Asset in a Prime Location • Gross Annual Rent of $129,300± • 7 Electric Meters • 7 Electric Panels • 3 Forced Hot Air Units • 7,296± SF Building • 8± Onsite Parking Spaces Property Breakdown: Main Level -Central A/C -Forced Hot Air Heat Unit 1 Rented for $2,225/ mo 2 Bedrooms, 1 Full Bathroom Unit 2 Rented for $1,890/ mo 2 Bedrooms, 1 Full Bathroom Second Level -Mini Split A/C & Heating System(s) Unit 3 Rented for $1,520/ mo 2 Bedrooms, 1 Full Bathroom Unit 4 Rented for $1,820/ mo 2 Bedrooms, 1 Full Bathroom Note: tenant vacating at end of August. Third Level -Central A/C -Forced Hot Air Heat Unit 5 Rented for $1,400/ mo 2 Bedrooms, 1 Full Bathroom Unit 6 Rented for $1,920/ mo 2 Bedrooms, 2 Full Bathrooms Lower Level Unfinished Basement housing utilities & storage space. The information contained herein was obtained from sources deemed to be reliable, but is offered for informational purposes only. Neither the auctioneer or the owner make any representations or warranties with respect to the accuracy of information.

104 Maple Ave, Chestertown

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

3 Beds ⋅ 3 Baths

Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

189 Birchwood, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

3 Beds ⋅ 2 Baths

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075

3 Beds ⋅ 3 Baths

Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a wood-burning fireplace, and an enclosed sunroom overlooking the water. Step outside to the expansive Trex deck with a recessed hot tub, then follow the path directly to the river. With three bedrooms, three full bathrooms, a walkout lower level, two bonus space, and a two-car garage, this home delivers the space, finishes, and lifestyle you’ve been waiting for. Schedule your private tour today and experience this waterfront retreat for yourself. Furniture is available for purchase as well!

14540 Stirrup Lane Ln, Galena

Listing courtesy of Keller Williams Flagship. Contact:

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

3 Beds ⋅ 1 Baths

Coming Soon in Rock Hall! Freshly renovated and ready to welcome you home. This property offers a bright new feel from the moment you step inside. Thoughtful updates and beautiful finishes create an inviting interior, while the spacious yard and mature trees provide plenty of room to enjoy the outdoors. Whether you’re searching for your first home, looking to downsize or low maintenance living, this home is one you’ll want to see! OPEN HOUSE WEEKEND : Saturday August 8th 10AM-12PM and Sunday August 9th 12PM-2PM

6179 E Dorlon Dr, Rock Hall

Listing courtesy of RE/MAX Executive. Contact: 4432741900

5 Beds ⋅ 4 Baths

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

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

2 Beds ⋅ 2 Baths

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living room, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new luxury vinyl plank flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the enclosed back porch or the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.

6022 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

3 Beds ⋅ 2 Baths

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

3 Beds ⋅ 1 Baths

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

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