Kennedyville, MD homes for sale & real estate

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ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately . 224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the . 109-acre homesite plus an adjoining . 115-acre parcel,

$224,900

3 beds1 bath1,296 sq ft

28036 Creamery St, Kennedyville, MD 21645

Laundry utility area • Sassafras river • Large kitchen

(302) 368-1621

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage

$515,000

7 beds5 baths3,836 sq ft

11960 Flour Mill St, Kennedyville, MD 21645

Mother-in-law suite • Efficiency kitchen • Walk-in closet

(410) 778-0330

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, an

$399,000

4 beds2 baths2,156 sq ft

11944 Augustine Herman Hwy, Kennedyville, MD 21645

Laundry mudroom • Brand new siding • Updated kitchen

(410) 778-0330

FOR SALE BY OWNER

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
3 bedroom , 2 bathroom rancher that needs finishing. The home is on concrete block foundation with crawl space . Septic engineering was completed few years ago . Needs a well and septic . On half acre, last house on dead end road . Minutes from betterton beach and turner creek boat ramp . Chestertown 10 min away . Use as permanent residence or Air bnb

$105,000

3 beds3 baths— sq ft

26767 Dutchtown Rd, Still Pond, MD 21667

Crawl space • Half acre • Dead end road

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering spa

$245,000

— beds2 baths2,718 sq ft

11989 Augustine Herman Hwy, Kennedyville, MD 21645

Large backyard • Desirable location • Built 1883

(410) 275-2118

Property at 14136 Kentmore Park Rd, Kennedyville, MD 21645, 4 beds, 2 baths

$499,000

4 beds2 baths2,132 sq ft

14136 Kentmore Park Rd, Kennedyville, MD 21645

(410) 275-2118

Property at 26765 Dutchtown Rd, Still Pond, MD 21667

$99,999

Land0.50 acre (lot)

26765 Dutchtown Rd, Still Pond, MD 21667

(301) 818-0313

Property at 11930 Kennedyville Rd, Kennedyville, MD 21645

$75,000

Land0.38 acre (lot)

11930 Kennedyville Rd, Kennedyville, MD 21645

(410) 287-3629

Property at South Of Dutchtown Rd, Still Pond, MD 21667

$11,000

Land0.50 acre (lot)

South Of Dutchtown Rd, Still Pond, MD 21667

(703) 570-7307

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NEW 23 HRS AGO

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that invites tranquility and privacy. Built in 2005, this meticulously maintained home boasts 2,748 square feet of thoughtfully designed living space, perfect for those who appreciate both style and functionality. The upgraded countertops and stainless steel appliances in the kitchen elevate the culinary experience, while the formal dining room, adorned with crown moldings and exposed beams, adds a touch of sophistication. Natural light floods the interior through casement windows, enhancing the warmth of the hardwood floors th

$689,000

3 beds2 baths2,748 sq ft

13950 Huyett Ln, Galena, MD 21635

Formal dining room • Upgraded countertops • Natural light

(302) 453-3200

NEW 26 HRS AGO

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Set on 21 private acres with 3,200 feet of shoreline along the picturesque Sassafras River and Cox Creek an within easy reach of major mid-Atlantic cities, international airports & train stations. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes 6 spacious bedrooms and 4.5 baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room w

$6,250,000

6 beds4.5 baths5,151 sq ft

750 Cassidy Wharf Farm Ln, Earleville, MD 21919

Heated spa • Guest house • Pool complex

(410) 275-2118

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Welcome!!! You Will Never Need To Spend Another Vacation in Someone Else's Home - VACATION IN YOUR OWN HOME ALL SUMMER LONG!!! This is a Beautifully Cared For Home, And Is Fully Furnished, Just Show Up And Enjoy The Comfy Home, With Two Bedrooms And A Fold Out Sofa Bed Too! A Super High Ceiling Pole Building/Garage For Your Car, Golf Cart, Equipment Or Boat Storage! Indian Acres Campground Is A Boaters Dream, You Have Your Own Year Round Boat Storage! Open Access To The Community Boat Launch! Huge Screen Porch, Large Deck, Shed, Garage And Plenty Of Parking On The Spacious Corner Lot That's Located Right Around The Corner From The Community Pool, Pavilion And Recreation Area! The Indian Ac

$67,000

2 beds1 bath575 sq ft

172/173 GLEN 8 Paiute Cir, Earleville, MD 21919

Large deck • Huge screen porch • Fully furnished

(410) 398-1247

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Welcome 14 1st Avenue - a charming Victorian just steps from the Betterton bluff and public beach and with water views from the back deck and primary bedroom. Known as the Jewel of the Chesapeake, Betterton is located at the confluence of the Sassafras River and Chesapeake Bay and got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This four bedroom, two full bathroom home has been lovingly maintained and is full of historic charm: hardwood floors throughout both levels, crown, baseboard, and bullseye moldings, transom windows, the list goes on. Brand new architectural shingle roof in 2025

$399,999

4 beds2 baths1,394 sq ft

14 1st Ave, Betterton, MD 21610

Water views • Historic charm • Natural light

(410) 778-0330

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this

$589,000

5 beds2.5 baths2,320 sq ft

325 Rings End Rd, Millington, MD 21651

Open floor plan • Upper-floor laundry • Attic for storage

(717) 786-6200

FLOOR PLAN

ABOUT THIS HOME
Kennedyville, MD Homes for Sale
Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent upd

$369,900

3 beds2.5 baths2,343 sq ft

13831 Augustine Herman Hwy, Galena, MD 21635

New hot water heater • 0.5 acre lot • Built 1900

(410) 778-0330

Property at 13984 Mill Creek Ln, Galena, MD 21635, 4 beds, 2 baths

$535,000

4 beds2 baths2,167 sq ft

13984 Mill Creek Ln, Galena, MD 21635

(410) 398-1247

Property at 1 Bayview Rd Unit 19A, Betterton, MD 21610, 2 beds, 2 baths

$339,000

2 beds2 baths1,200 sq ft

1 Bayview Rd Unit 19A, Betterton, MD 21610

(410) 778-0330

Property at 214 Broad St, Crumpton, MD 21628, 3 beds, 2 baths

$249,900

3 beds2 baths1,740 sq ft

214 Broad St, Crumpton, MD 21628

(443) 627-2900

Property at 14 Third Ave, Betterton, MD 21610, 3 beds, 3 baths

$245,000

3 beds3 baths2,068 sq ft

14 Third Ave, Betterton, MD 21610

(484) 406-3004

Property at 206 Maplewood Ln, Galena, MD 21635, 3 beds, 2.5 baths

$363,000

3 beds2.5 baths1,800 sq ft

206 Maplewood Ln, Galena, MD 21635

(410) 275-8101

Property at 2321 Millington, Millington, MD 21651, 6 beds, 4.5 baths

$1,200,000

6 beds4.5 baths2,708 sq ft

2321 Millington, Millington, MD 21651

(410) 648-6844

Property at 224 Tockwogh Dr, Earleville, MD 21919, 3 beds, 2 baths

$419,900

3 beds2 baths1,600 sq ft

224 Tockwogh Dr, Earleville, MD 21919

(410) 398-9200

Property at 1-B Bayview Rd Unit 12B, Betterton, MD 21610, 3 beds, 2 baths

$565,000

3 beds2 baths2,000 sq ft

1-B Bayview Rd Unit 12B, Betterton, MD 21610

(410) 778-0330

Property at 16 Howell Point Rd, Betterton, MD 21610, 3 beds, 2.5 baths

$487,000

3 beds2.5 baths1,948 sq ft

16 Howell Point Rd, Betterton, MD 21610

(410) 778-0330

Property at 405 Rings End Rd, Millington, MD 21651, 3 beds, 2 baths

$400,000

3 beds2 baths1,056 sq ft

405 Rings End Rd, Millington, MD 21651

(217) 285-9000

Property at 14046 Tockwogh Ln, Galena, MD 21635, 4 beds, 2 baths

$1,595,000

4 beds2 baths2,538 sq ft

14046 Tockwogh Ln, Galena, MD 21635

(410) 275-2118

Property at 07 River Rd, Millington, MD 21651

$94,900

Land5.46 acres (lot)

07 River Rd, Millington, MD 21651

(240) 913-9339

Property at 273 Hoonah Ln Unit GLEN 3, Earleville, MD 21919

$7,500

Land3,484 sq ft (lot)

273 Hoonah Ln Unit GLEN 3, Earleville, MD 21919

(410) 287-1260

Property at 326,327 Mocanaqua Ln Unit GLEN 3, Earleville, MD 21919

$12,500

Land5,140 sq ft (lot)

326,327 Mocanaqua Ln Unit GLEN 3, Earleville, MD 21919

(410) 287-1260

Average home prices near Kennedyville, MD

Cities

Zip Codes

21645 homes for sale
$399,000

Kennedyville, MD real estate trends

$354K

Sale price

-20.5%
since last year

$167

Sale $/sq ft

-20.1%
since last year

Under list price

2.7%

Days on market

Down payment

—

Total homes sold

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