Talbot County Public Schools Homes with Garage - Side Entry Garage Description

Talbot County Public Schools Homes with Garage - Side Entry Garage Description

Welcome to Talbot County, Maryland, where the charm of small-town living meets the excellence of quality education! Nestled in the heart of the Eastern Shore, Talbot County Public Schools is renowned for its commitment to fostering academic achievement and personal growth. The school district boasts a diverse array of educational programs, dedicated teachers, and a strong sense of community, making it an ideal place for families looking to settle down.

Parents can feel confident in the educational opportunities available within this district, which includes a mix of elementary, middle, and high schools that focus on innovative teaching methods and student engagement. With a strong emphasis on both academics and extracurricular activities, Talbot County Public Schools prepare students for success in an ever-changing world.

As you explore the real estate options in this picturesque region, you'll discover an array of beautiful homes featuring side entry garages—a coveted feature that adds both functionality and curb appeal. These thoughtfully designed garages not only provide ample space for your vehicles but also enhance the overall aesthetic of your property, making it a perfect fit for families who appreciate convenience and style.

Imagine coming home to a lovely residence with a side entry garage, allowing for easy access while maintaining a clean and inviting facade. Whether you’re hosting friends or simply enjoying a quiet evening at home, these homes cater to your lifestyle needs.

Embrace the charm of Talbot County, where exceptional schools and beautiful homes with side entry garages await you. Discover your dream home in this vibrant community today!

Newest Talbot County Public Schools Homes with Garage - Side Entry Garage Description

$1,095,000
3 Beds ⋅ 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$250,000
4 Beds ⋅ 3 Baths
Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

3759 Rumsey Dr, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$5,295,000
4 Beds ⋅ 7 Baths
First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$849,000
3 Beds ⋅ 4 Baths
An Exceptional Opportunity! Unexpectedly available once again due solely to a change in the buyers' personal circumstances, this exceptional property is available through no fault of the home. If you missed it the first time, here's your opportunity to own one of the area's most distinctive and beautifully maintained residences. Ideally situated just four miles from the heart of charming St. Michaels, this timeless home offers peaceful country living with easy access to boutique shopping, exceptional dining, marinas, and the Chesapeake Bay lifestyle. Just moments from Claiborne Landing, you'll enjoy convenient public boat access for effortless days on the water, whether your passion is cruising, fishing, crabbing, or simply exploring the beauty of the Chesapeake Bay. Built in the early 1900s and thoughtfully renovated over the past two decades, this remarkable residence seamlessly blends historic character with today's modern conveniences. Situated on a picturesque half-acre lot, the home offers three spacious bedrooms, each with its own private bath, plus the flexibility for a fourth bedroom, home office, or guest suite. Several bedrooms also enjoy access to private balconies, adding to the home's unique charm and appeal. The beautifully updated kitchen features granite countertops, stainless steel appliances, tile flooring, and generous workspace, making it ideal for both everyday living and entertaining. Gleaming hardwood floors flow throughout the home, showcasing its warmth, craftsmanship, and attention to detail. Step outside to enjoy the beautifully landscaped grounds, complete with a charming potting shed and an additional storage building. The true showpiece, however, is the extraordinary 1,500-square-foot attached garage. This impressive two-story space features three oversized garage bays, a dedicated office, and abundant room for multiple vehicles, boats, workshop space, hobbies, collections, and projects of every kind. Whether you're a car enthusiast, woodworker, craftsman, artist, entrepreneur, or someone who simply enjoys tinkering and creating, this exceptional space offers endless possibilities rarely found in a property of this caliber. Rich in history, impeccably maintained, and completely move-in ready, this one-of-a-kind property offers the perfect blend of timeless elegance, modern comfort, and exceptional versatility. Whether you're searching for a full-time residence, a weekend retreat, or a home with unmatched garage and workspace, this remarkable property delivers. Don't miss this exceptional opportunity to make it yours.

10494 Rich Neck Rd, Claiborne

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$850,000
4 Beds ⋅ 4 Baths
Easton Club. This beautiful 3300 sq. ft. home has been almost entirely renovated. Living room, formal dining room, renovated kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

28391 Masters Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,995,000
3 Beds ⋅ 4 Baths
Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. Adding even greater value, the property includes fully approved architectural, structural, and interior design plans for an extraordinary three-story Modern Country French estate. Every detail has been thoughtfully curated to create a truly remarkable waterfront residence featuring: ● Five bedrooms, including a luxurious waterfront primary suite on the first floor ● Four-stop elevator ● Six full baths and two half baths (powder room and dedicated pool bath) ● Five fireplaces ● Grand staircase ● Dramatic vaulted living room ● Glass-enclosed dining room with black iron NanoWall doors opening to breathtaking Miles River views ● Spacious family room seamlessly connected to an entertainer’s dream kitchen ● Bar, butler’s pantry, and separate catering kitchen with silver vault ● Expansive lower level with a temperature-controlled wine cellar, billiards room, home theater, oversized fitness center, full bath with dog wash, and abundant storage ● Covered 440-square-foot vaulted timber patio with an outdoor wood-burning fireplace and television, creating the ultimate year-round outdoor living space The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted locations.

9338 Bantry Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$495,000
3 Beds ⋅ 2 Baths
Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

8658 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$3,595,000
5 Beds ⋅ 6 Baths
Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$379,000
3 Beds ⋅ 2 Baths
This is a Great Opportunity to make this your Forever Home. Great remodel and expansion potential in this Brick home on a large corner lot with Water Views. Home is in need of a Total Renovation. Just off of St. Michaels Rd. looking across to Oak Creek. With nearly 3/4 of an acre and no Flood Zone this is centrally located between Easton and St. Michaels. Property is being offered "As Is" !

25911 River Rd, Newcomb

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,595,000
4 Beds ⋅ 3 Baths
Nestled on Peachblossom Creek in Easton is a property that won’t disappoint if you are one who expects the unexpected. From the one-hundred-year-old oak standing sentinel over the tides to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both Easton and Oxford while providing a peaceful waterfront setting. Designed for comfortable one-floor living, with a full second floor, you can expect a lifetime of enjoyment. This home offers 4-bedrooms, 3 full baths, beautiful wood floors throughout, 2 sitting/living room areas, a gas fireplace, an office with built ins, an attractive eat-in kitchen, a beautiful waterside sunroom with separate HVAC, and tons of storage space. There’s even a hot tub! A huge attached garage provides abundant room for vehicles, hobbies, and storage. A yard implemented by an expert environmental gardener (an author on the subject) crafts a haven for birds that is less maintenance—and more attractive to neighbors—than the oh, so very common “all lawn” approach. Watch bluebirds and butterflies while you sip your morning coffee on the expansive Azek deck or large paver patio overlooking the water. Smile at lightning bugs flitting about the yard as you watch the stars come out at night in your private back yard retreat. The open floor plan and large windows keep the home full of light and allow endless views of the water. State-of-the-art solar with 2 large Tesla storage batteries, whole house water purification system and zoned HVAC systems make for healthy living, too. A denitrifying septic system - designed for 4-6 bedrooms - helps keep the Bay clean—in fact, this home's low carbon footprint and thoughtfully designed landscape and rain gardens actually help the environment. Several walk-in storage areas, plus huge unfinished space over the garage. An unforeseen property, even if you expect the unexpected. Don't miss this fabulously easy-care, low maintenance home. All the hard work is done - all that's left is to ENJOY!

28674 Edgemere Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$950,000
4 Beds ⋅ 3 Baths
*INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island, this delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with a charming screened porch perfect for enjoying warm breezes and waterfront views. A connected wing was elevated 10 feet and now features a spacious two-car garage on the main level, offering abundant storage for boats, kayaks, and gear. The rear wing provides exceptional versatility with a private studio apartment—currently a licensed B&B with its own entrance—ideal for guests, rental income, or multigenerational living. Inside the main home, a wood-burning fireplace invites you to curl up on cool days and evenings, while the screened porch becomes the heart of the home during warmer months. With 4 bedrooms and 3 baths, this property offers comfort, flexibility, and the relaxed coastal lifestyle that defines the Eastern Shore. Appointment-only showings. Do not enter the property without an appointment.

4938 Fairbank Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$1,795,000
3 Beds ⋅ 2 Baths
A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291
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