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21123 Striper Run, Rock Hall
$344,900
3 Beds ⋅ 3 Baths
NEW PRICE — $344,900! MORE SPACE, MORE FLEXIBILITY & NO HOA! Discover an exceptional opportunity in the charming waterfront town of Rock Hall! Offering approximately 2,040 square feet of living space, an oversized lot and a versatile floor plan, this beautifully maintained home has so much more to offer than meets the eye! Featuring 3 bedrooms, 2 full baths, a powder room and an impressive oversized sunroom/flex space that’s even larger than the primary suite! With its own private exterior entrance and direct kitchen access, this incredible bonus space offers endless possibilities for a home office, guest retreat, hobby room or additional living area. Inside, you’ll find beautiful hardwood flooring, a cozy gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your personal touch. Outside, enjoy ample parking, room for your golf cart and the added freedom of NO HOA FEES! Imagine enjoying everything Rock Hall has to offer! Explore nearby marinas, boating, fishing, waterfront restaurants, coffee shops, live music, local shops and the relaxed Eastern Shore lifestyle. Whether you’re searching for a year-round residence or a weekend getaway, this home offers the space and versatility to make it your own. ANOTHER OPTION WORTH EXPLORING! Seller will also consider a short-term SIX-MONTH RENTAL, subject to mutually acceptable terms. NOW OFFERED AT $344,900! Generous living space, a unique bonus room, an oversized lot, NO HOA and flexible options make this a home worth seeing in person. Schedule your private tour today and discover the possibilities!

21123 Striper Run, Rock Hall

Listing courtesy of Chaney Homes, LLC. Contact:

5815 Clam Cv, Rock Hall
$340,000
3 Beds ⋅ 3 Baths
Nestled in charming Watermans Estates, this traditional duplex home offers a perfect blend of comfort and style. With 1,720 sq ft, the inviting interior features warm wood flooring throughout the main level. Nine foot ceilings, crown molding and fresh paint give the living areas an open, airy feel. Stainless kitchen appliances and solid wood cabinets are complemented by Corian countertops in the kitchen. Upstairs you'll find an inviting primary suite with jetted tub and separate tile shower, plus two generous size bedrooms and another full bath. Step outside to a covered front porch or screened patio, both ideal for morning coffee or evening relaxation. The community is known for its friendly atmosphere and close proximity to the town's waterfront harbor and amenities. Experience the warmth and charm of Watermans Estates.

5815 Clam Cv, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

1 Bayview Rd Unit 19A, Betterton
$339,000
2 Beds ⋅ 2 Baths
Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Many furnishings can be included! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

1 Bayview Rd Unit 19A, Betterton

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

5862 N Main St, Rock Hall
$334,900
3 Beds ⋅ 2 Baths
Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main floor offers a large entry with a view of the living room, dining room, stunning kitchen, and a beautiful open wood staircase. The stunning kitchen boasts a vaulted ceiling, ample cabinets finished with crown moldings, stainless steel appliances (including an electric cooktop and lower wall oven), granite countertops, and a double stainless sink. Just off the entryway is a full bath with laundry. On the second floor are two sizable secondary bedrooms, a larger primary bedroom with access to one of the secondary bedrooms, and a full bath featuring a walk-in shower with a spa feature. From the kitchen's sliding doors, step onto a spacious wood deck overlooking the semi-fenced yard, which offers green space, numerous possibilities, and a detached garage. This move-in-ready home is ideal for any new homeowner and is located near shopping, restaurants and commuter routes.

5862 N Main St, Rock Hall

Listing courtesy of LPT Realty, LLC. Contact:

321 West St, Millington
$334,900
3 Beds ⋅ 2 Baths
321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with stackable washer & dryer included. Down the spiral staircase to the ground level you'll discover a one-car garage and a full unfinished basement with daylight windows - perfect for extra storage or future possibilities. Situated on a level rectangular .23 acre lot, this property offers both comfort and potential. Settlement date is negotiable and we kindly ask for a 1 hour prior notice for all showings. This home DOES HAVE an FHA assumable mortgage.

321 West St, Millington

Listing courtesy of RE/MAX Associates - Newark. Contact:

21121 Striper Run, Rock Hall
$330,000
3 Beds ⋅ 3 Baths
Nestled in the serene enclave of Watermans Estates, this exquisite end-of-row townhouse offers a harmonious blend of contemporary design and luxurious living. Spanning 1,628 square feet, this home is a sanctuary of comfort and style, perfect for those seeking an elevated lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, enhanced by plush carpeting and a cozy gas fireplace that beckons for intimate gatherings. The kitchen is a culinary enthusiast's dream, featuring upgraded countertops, a built-in microwave, and a gas range, all designed to inspire your inner chef. Enjoy casual meals in the kitchen's table space or host dinners in the dedicated dining area. This residence boasts three spacious bedrooms, including a convenient entry-level bedroom, ensuring comfort and privacy for all. Each of the three bathrooms is thoughtfully designed, with the master bath featuring a luxurious soaking tub, perfect for unwinding after a long day. The allure of this home extends beyond its interior. Step outside onto the expansive deck or balcony, where you can savor morning coffee or evening sunsets amidst the tranquil sounds of nature. The partly wooded lot, adorned with mature trees, offers a peaceful retreat. Located just three blocks from the stunning Chesapeake Bay, this property invites you to embrace a lifestyle enriched by water-oriented activities. Whether it's a leisurely stroll along the shore or a day of boating, the beauty of the bay is always within reach. Parking is a breeze with a private driveway and an attached garage, ensuring convenience for you and your guests. The home is equipped with modern amenities, including a washer and dryer, ensuring that daily tasks are handled with ease. This property is not just a house; it's a place to create lasting memories. With its blend of luxury, comfort, and natural beauty, this townhouse in Watermans Estates is a rare find, offering an exclusive lifestyle that truly feels like home. Looking for a cash flowing investment? The property has performed exceptionally well as a short-term rental. With no restrictions, this property could be the perfect option. Experience the perfect balance of elegance and tranquility-your dream home awaits.

21121 Striper Run, Rock Hall

Listing courtesy of Astoria Realty Advisors LLC. Contact:

33741 Galena Sassafras Rd, Galena
$325,000
3 Beds ⋅ 2 Baths
ONE-LEVEL LIVING IN GALENA—SELLER WELCOMES ALL REASONABLE OFFERS! This three-bedroom, two-bath ranch offers a practical layout, manageable homesite, and the opportunity to make it your own. Built in 2007 and situated on a cleared 0.47-acre lot in the Sassafras subdivision, the home features luxury vinyl plank flooring, abundant natural light, and an open living area that connects easily to the kitchen and breakfast space. The country-style kitchen includes generous cabinet storage, an electric range, built-in microwave, and dishwasher. The primary bedroom features a private bath with a soaking tub and separate stall shower, while the remaining bedrooms can accommodate additional sleeping space, an office, hobbies, or other needs. Outside, the front, side, and rear yards provide room for gardening, recreation, outdoor gatherings, or relaxing in the peaceful surroundings. A detached shed offers convenient storage for tools, lawn equipment, and seasonal belongings. Schedule your private showing and bring the seller your reasonable offer!

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. Contact:

22974 Bay Shore Rd, Chestertown
$315,000
2 Beds ⋅ 2 Baths
Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

21232 Rock Hall Ave, Rock Hall
$310,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

21232 Rock Hall Ave, Rock Hall

Listing courtesy of RE/MAX Advantage Realty. Contact:

24775 Langford Rd, Chestertown
$305,000
3 Beds ⋅ 1 Baths
PRICE IMPROVEMENT!! Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas. Call to set up an appointment!

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

234 N Kent St, Chestertown
$300,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

21305 Haven Rd, Rock Hall
$299,999
4 Beds ⋅ 2 Baths
Selller has made a Major price reduction to move this propperty! Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

21305 Haven Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

9126 Fairlee Rd, Chestertown
$299,500
3 Beds ⋅ 2 Baths
UPDATED HOME, 1.66 ACRES, public water and sewer, and NO HOA - ALL FOR $299,500! Discover the value of this beautifully updated 3-bedroom, 1.5-bath home. Featuring a BRAND-NEW ROOF, NEW HVAC SYSTEM, and a ONE-YEAR HOME WARRANTY, this property offers major improvements already completed and the convenience of one-level living. In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and cabinet space. Outside, the expansive lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a vacation home, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

11037 Bottom Rd, Worton
$299,000
3 Beds ⋅ 2 Baths
The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

11037 Bottom Rd, Worton

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

21279 W Sharp St, Rock Hall
$299,000
Discover a unique opportunity in the heart of the Town of Rock Hall with this commercial property, built in 1960 and situated on a 0.189-acre lot. This versatile space, constructed with durable block and featuring concrete flooring, offers a solid foundation for a variety of commercial or retail uses. The Town of Rock Hall is renowned for its vibrant community spirit, with local shops, restaurants, and waterfront attractions just a stone's throw away. Residents and visitors enjoy access to Main Street events and activities, with abundant recreational opportunities for outdoor enthusiasts. The property is walkable to public parking areas and is served by the free "Rock Hall Rides" Shuttle. This property presents an exceptional chance to invest in a thriving community, where business potential meets local charm.

21279 W Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

26670-26680 Maple Ave, Still Pond
$290,000
3 Beds ⋅ 2 Baths
The Kent County State Health Department have approved percs for the following three properties: 26670 Maple Avenue Tax Map 13/Parcel 16/Deed Reference 77/422 with the recording of a 1920 dwelling, 26680 Maple Avenue Tax Map 13/Parcel 17/identified as Parcel #1 Deed Reference 249/96 with the recording of a 1940 dwelling and .5 acre parcel of land Tax Map 13/Parcel 9/identified as Parcel #2 Deed Reference 249/96 . Both homes are in need of major repair however the parcels are lovely. These residentially zoned properties present a great investment opportunity. The parcels are of a generous size, featuring front and side yards that offers great outdoor space. Still Pond is just minutes from Betterton Beach. Total size of three parcels is 1.66 +/- acre.

26670-26680 Maple Ave, Still Pond

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

8732 Elm Rd, Chestertown
$289,000
3 Beds ⋅ 2 Baths
Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

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

no property photo
$289,000
Bring your vision to this rare 15-acre property offering privacy, natural beauty, and endless possibilities. Mostly wooded with a picturesque pond, this property is an ideal setting for those seeking a private retreat, recreational getaway, or future homesite. An original structure dating back to 1980 remains on the property and includes a full basement. The condition existing home is believed unknown and is being sold strictly as-is. Do not enter any structures on the property. Whether you dream of restoring or rebuilding within the existing footprint (subject to county approvals), creating a hunting or fishing retreat, harvesting the mature hardwoods, or simply enjoying the peace and quiet of nature, this property offers exceptional potential. A perfect place to live, play, or both, with convenient access to Route 301 for an easy commute to Maryland, Delaware, and beyond. Buyer to verify all zoning, land use, and building possibilities.

31001 Chesterville Bridge Rd, Millington

Listing courtesy of RE/MAX Executive. Contact:

4818 Piney Neck Rd, Rock Hall
$289,000
3 Beds ⋅ 1 Baths
Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

4818 Piney Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

8820 Cumberland St, Chestertown
$281,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

Cannon Street, Chestertown
$281,000
Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. No property address has yet been assigned to the 9,381 sq ft lot; the 3,097 parcel is designated as 620 Cannon Street. Buyer to verify zoning, permitted uses, building requirements, and utility availability. Each lot is listed separately in separate listings.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

104 Lincoln Dr, Chestertown
$275,000
3 Beds ⋅ 1 Baths
**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price improvement and a seller ready to make a move, now is the time to explore the possibilities. Imagine settling into your new home before the holidays and potentially making your first mortgage payment in 2027! This charming Chestertown rancher offers bright, updated interiors, comfortable single-level living, a spacious corner lot, newer paver patio, fenced backyard and no community HOA. Whether you're purchasing your first home, looking to simplify or searching for an easy-to-maintain property, there's plenty to love here. Schedule your tour, bring your offer and let's make a move!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

104 Acorn Dr, Chestertown
$275,000
3 Beds ⋅ 3 Baths
Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

25213 Porters Grove Rd, Worton
$270,000
3 Beds ⋅ 2 Baths
Recently Renovated Rancher with Inviting Outdoor Living! Welcome to 25213 Porters Grove Road in Worton, Maryland! This beautifully refreshed 3-bedroom, 2-full-bath ranch-style home offers the perfect combination of modern updates, comfortable living, and inviting outdoor space. With its open-concept layout, recent renovations, and spacious yard, this home is ready for its next chapter! Step inside and enjoy a bright, welcoming living area that flows seamlessly into the eat-in kitchen, creating an ideal setting for everyday living and entertaining. Recent updates, including carpeting and tile finishes in the kitchen and bathrooms, add a fresh touch throughout the home. The thoughtfully designed floor plan makes excellent use of the space while maintaining an open and inviting atmosphere. The home features three comfortably sized bedrooms, including a primary bedroom with its own attached full bathroom, offering added privacy and convenience. A second full bathroom provides functionality for guests and everyday living. Step outside and discover even more to love! The generous backyard and side yard offer plenty of green space to enjoy outdoor activities, gardening, entertaining, or simply relaxing in the fresh air. The patio creates a wonderful spot for outdoor dining, while the fire pit provides the perfect gathering place for evenings under the stars. Whether you're hosting a weekend cookout or enjoying a quiet afternoon outdoors, this property offers space to make lasting memories. A large driveway provides convenient off-street parking with room for multiple vehicles. Located in Worton, Maryland, with convenient access to nearby Chestertown and the surrounding Kent County area, this home offers an appealing blend of comfort, practicality, and outdoor enjoyment. With recent improvements, an open floor plan, three bedrooms, two full bathrooms, and inviting outdoor living areas, this property is an opportunity you won't want to miss. Schedule your private tour today and see all that 25213 Porters Grove Road has to offer!

25213 Porters Grove Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact:

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