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$695,000
Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportunity to create your own private estate while enjoying outstanding recreational and hunting opportunities. The current owners have strategically developed and maintained the property for exceptional deer and turkey hunting through their partnership with HuntingPlots.com. Thoughtful habitat and land management includes established travel corridors, bedding areas, food plots, an artificial water pond, and carefully planned tree management, creating an ideal environment for wildlife. The property is subject to a Maryland Environmental Trust conservation easement; however, the easement permits the construction of one homestead, offering the opportunity to build a private residence surrounded by acreage and natural beauty. Please refer to the Kent County Health Department percolation letter and additional easement information included in the documents. Location is truly a standout feature of this rare offering. Situated within approximately 1.5 miles of downtown Chestertown, the property provides convenient access to Chester River boat ramps, Washington College, the Chester River Yacht & Country Club, shopping, dining, and all that Chestertown has to offer. Included are 3 Ten Point box deer stands, several tacticam deer cameras, and several other ladder stands. A rare combination of acreage, privacy, recreational value, and proximity to town, an exceptional opportunity on Maryland’s Upper Eastern Shore.

Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$50,000
This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.

Towhee Rd, Chestertown

Listing courtesy of The Parker Group. Contact: 3022176692
$55,000
1 Beds ⋅ 1 Baths
Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

34155 Bradford Johnson Rd, Galena

Listing courtesy of Taylor Properties. Contact:

$290,000
3 Beds ⋅ 2 Baths
Discover a remarkable investment opportunity in Kent County with this charming 3-bedroom, 2-bathroom manufactured ranch-style home, built in 2006. Spanning 1,680 sq. ft. , this property offers a spacious layout perfect for comfortable living or rental potential. Nestled on a generous 1.15-acre lot, enjoy serene views of trees and woods, creating a peaceful retreat for residents. The inviting living space features a cozy fireplace, ideal for gatherings or quiet evenings. With ample parking options, including a driveway and off-street spaces, accessibility is a breeze. This property's location and features position it well for appreciation in value, making it a smart addition to any investment portfolio. Embrace the potential for steady returns while providing a warm and inviting home for future occupants. Don't miss out on this exceptional opportunity!

10804 Big Stone Rd, Millington

Listing courtesy of Century 21 Gold Key Realty. Contact: 3023695397
$325,000
3 Beds ⋅ 2 Baths
Nestled in the serene SASSAFRAS subdivision, this ranch-style residence offers a harmonious blend of comfort and elegance. Built in 2007, this home showcases a thoughtful design that emphasizes an open floor plan, perfect for both relaxation and entertaining. Step inside to discover a warm and inviting atmosphere, highlighted by luxury vinyl plank flooring that flows seamlessly throughout the living spaces. The heart of the home is the country-style kitchen, equipped with modern appliances including a built-in microwave, dishwasher, and electric oven/range. The kitchen effortlessly transitions into a cozy breakfast area, making it an ideal spot for morning coffee or casual meals. The spacious living area is designed for gatherings, featuring ample natural light from double-hung windows that frame picturesque views of the garden and lawn. The layout includes three well-appointed bedrooms, with the primary suite offering a private oasis complete with a soaking tub and a stall shower in the en-suite bathroom. Each bedroom provides a tranquil retreat, ensuring comfort and privacy for all. This property boasts a generous 0.47-acre lot, meticulously cleared to create a beautiful outdoor space. The front yard welcomes you with lush greenery, while the rear yard offers a perfect canvas for gardening or outdoor activities. With side yards that provide additional space, the possibilities for outdoor enjoyment are endless. Enjoy the peaceful surroundings and the charm of the neighborhood, where the views of the street and garden create a picturesque backdrop for your daily life. The additional shed on the property provides extra storage, enhancing the functionality of this lovely home. This residence is not just a house; it's a lifestyle. Experience the perfect blend of modern amenities and serene living, all within a community that values comfort and tranquility. Embrace the opportunity to make this exceptional property your own, where every detail has been crafted for a life of ease and enjoyment.

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$599,900
3 Beds ⋅ 3 Baths
Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

13981 Mill Creek Ln, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

$1,500,000
3 Beds ⋅ 3 Baths
Stunningly renovated home in Shorewood Estates. Your back yard is Swantown Creek. Professional pics and rest of the details are coming. Expected on market date is 9/25. Everything inside and out has been renovated to 11 out of 10. A truly incredibly rare opportunity that will need to be seen to be believed....but believe it!

13876 Swantown Creek Rd, Galena

Listing courtesy of Patterson-Schwartz - Greenville. Contact: 3024294500
$89,000
Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

27942 Old Morgnec Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$897,000
3 Beds ⋅ 3 Baths
Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

25411 Paradise Point Ln, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$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:

$229,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$363,000
3 Beds ⋅ 3 Baths
Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

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

$325,000
4 Beds ⋅ 1 Baths
This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Hall’s restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall.

20705 Wilkins Ave, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$275,000
3 Beds ⋅ 1 Baths
Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy, and a great neighborhood setting. Location is a bonus! Just minutes from historic downtown Chestertown, offering convenient access to local shopping, restaurants, movies, and a variety of waterfront activities. Enjoy the peaceful feel of a quiet neighborhood while being close to everything Chestertown has to offer. Schedule your tour today!

7482 Poplar Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

$55,000
Wooded building lot on Judefind Ave in Rock Hall town limits. No flood plain, no critical area, no wetlands. Water & sewer hook ups will be required. Lot is 75 ft wide by 165 ft deep. Nice walkable in-town location on a quiet, private street. Just minutes to the Main Street shopping district and the Mainstay.

Judefind Ave Unit #LOT 2, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$315,000
3 Beds ⋅ 1 Baths
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.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$300,000
3 Beds ⋅ 1 Baths
**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside. Set on a spacious corner lot, you'll find a long driveway, new paver patio, vinyl privacy fencing, playset and room to roam, while the inside features a beautiful kitchen, spacious living room and updated bathroom. Cute, low maintenance and just the right size to come make your own!!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$25,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026, 10:00 AM. Bidding ends 99/28/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in Worton, MD, in Kent County. The property is in close proximity to Worton Park and the Kent County Community Center. It offers easy access to Worton Road (MD 297), a major local traffic artery, with nearby community services and surrounding amenities. Public water and sewer connections are believed to be available at the buyer’s expense.

Lambs Meadow Rd, Worton

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$369,000
3 Beds ⋅ 2 Baths
Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

374 Hurtt Ave, Millington

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

$270,000
3 Beds ⋅ 2 Baths
Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for gatherings and everyday living. The spacious kitchen features a convenient island, perfect for casual meals or entertaining guests. Equipped with stainless steel appliances, including a built-in microwave, dishwasher, and washer/dryer, this kitchen is both stylish and practical. The breakfast area is a lovely spot to enjoy your morning coffee while basking in the natural light that fills the space. This home boasts three well-appointed bedrooms, including a primary suite with an en-suite bathroom that features a tub shower, providing a serene retreat at the end of the day. Ceiling fans throughout the home ensure comfort year-round, while the combination of living and dining spaces enhances the sense of togetherness. Outside, the property is equally inviting. The exterior is adorned with low-maintenance vinyl siding and features exterior lighting that adds a warm glow to the evenings. A spacious deck invites you to enjoy outdoor living, whether it's hosting summer barbecues or simply unwinding with a good book. The lot backs to trees, offering a peaceful backdrop and a sense of privacy that is hard to find. The 0.14-acre lot provides ample space for gardening or play, while a handy shed offers additional storage for tools and outdoor equipment. Parking is a breeze with a dedicated driveway, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where comfort meets functionality. With its excellent condition and modern amenities, it's ready for you to make it your own. Don't miss the opportunity to experience the warmth and charm of this beautiful property in WORTON.

25213 Porters Grove Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,195,000
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$675,000
5 Beds ⋅ 3 Baths
Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor living. Complete with a 2-car garage.

212 Washington Ave, Chestertown

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

$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! 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:

$38,200,000
4 Beds ⋅ 2 Baths
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$250,000
Nestled in a serene enclave, this exceptional 0.55-acre lot offers a rare opportunity to create your dream retreat, perfectly positioned just a block away from the tranquil waters of Swan Creek and The Chesapeake Bay. and just across the street from The Haven on Swan Creek. The property boasts a level, cleared landscape, with water-views of The Haven. Perfect for a permanent residence or a seasonal escape. Keep your boat at any one of several marinas nearby, just a stroll or bike ride away. Town water and sewer both available on Hynson Road. The lot is flagged. A survey plat is available upon request.

Hynson Rd., Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,195,000
2 Beds ⋅ 1 Baths
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$1,495,000
5 Beds ⋅ 4 Baths
Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Creek. Mature trees, landscaping and hardscaping surround this waterfront oasis.  In addition to your own private dock and waterfront, Kinnairds Point offers two waterfront community areas with a beach, pavilion, kayak rack and a boat ramp. Located just outside of Chestertown and within easy reach of points north and south.

23911 Kinnards Point Dr, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$359,000
3 Beds ⋅ 2 Baths
Discover the charm of coastal living in the heart of the town of Rock Hall. just three blocks from the public beach! This beautifully maintained ranch-style home offers the perfect combination of comfort, style, and an exceptional location. Situated on a generous 0.34-acre lot, the property features beautifully landscaped grounds, cedar-impression vinyl siding, and a detached garage providing excellent storage and convenience. Step inside to find warm hardwood flooring and newer carpeting throughout the main living areas, creating an inviting and timeless atmosphere. The thoughtfully designed floor plan offers three spacious bedrooms and one-and-a-half bathrooms, providing comfortable living for full-time residents or an ideal weekend retreat. The outdoor living spaces truly set this home apart. Relax on the screened porch with your morning coffee, gather with friends on the patio, or enjoy al fresco dining surrounded by beautifully landscaped grounds. There is plenty of space to entertain, garden, or simply unwind and enjoy the relaxed pace of Rock Hall living. Located just minutes from local restaurants, marinas, shops, and the Chesapeake Bay, this property offers an incredible opportunity to enjoy all that this charming waterfront town has to offer. Whether you're looking for a full-time residence, vacation getaway, or weekend escape, this inviting Rock Hall home is ready to welcome you. Come experience the lifestyle and make this special property your own!

5780 Kent Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$649,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

22400 Great Oak Landing Rd., Chestertown

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

$305,000
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: 4109724000