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$560,000
4 Beds ⋅ 3 Baths
Welcome to 135 Crossgate Drive, a beautifully maintained 4-bedroom, 2.5-bath home in Church Hill. Freshly painted throughout and truly move-in ready, this home offers a spacious, functional layout with plenty of room to settle in and make it your own. Step inside to an open, welcoming foyer framed by a graceful staircase, with a dedicated home office on one side and a formal dining room on the other. The kitchen is designed for everyday living and entertaining, featuring a large island, abundant cabinetry, and a sunny eat-in area that flows naturally into the living room, where a cozy fireplace anchors the space. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with a private bath and walk-in closet. The unfinished basement offers even more possibilities—create a second living space, home gym, playroom, workshop, or simply enjoy the additional storage. An attached two-car garage provides even more space for vehicles, tools, and gear (the walk-in cooler can be negotiated in the sale of the house). Enjoy the charm and quieter pace of Church Hill while remaining conveniently located to Centreville, Chestertown, Route 301, and all that Queen Anne's County and the Eastern Shore have to offer. Thoughtfully cared for, freshly updated, and offering room to grow, 135 Crossgate Drive is ready to welcome its next owners home.

135 Crossgate Dr, Church Hill

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

$120,000
1 Beds ⋅ 1 Baths
SEASONAL LIVING ONLY! April through November! Great camper cooperative in the Kent Narrows! SEASONAL LIVING ONLY, from April through November! Enjoy a fantastic vacation getaway and the relaxed Eastern Shore lifestyle. This updated park model camper is ready for you to enjoy life at Beach Harbor. It is fully furnished, except for the large grey sectional. The camper sleeps at least 4, and depending on the sofas, it can accommodate 6-8 people. New sunroom, new roof, new siding, updated flooring, updated heat and A/C, new windows, extra parking, and golf cart conveys with full-price offer. The golf cart is in great condition and is newer. For park purposes, it is considered a 2-bedroom. Some photos are lighting-enhanced with AI. Must make an appointment to view. Owner to arrange for showings. Parking for showings is in the guest parking outside the gate. Cash or personal loan only. No mortgage financing available, cash or personal loan onlyu. Vacation rentals are allowed, but ONLY self-managed! The owner must register guests with the office. Rules do apply!

111 Beach Harbor Dr Unit #236-E, Grasonville

Listing courtesy of Realty Navigator. Contact: 4106433404
$1,450,000
5 Beds ⋅ 5 Baths
Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the outlets, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This home features more than 4,400 square feet on three finished levels, with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work, creating an everyday space that's upscale and comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook and a redesigned island perfect for gathering. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a second primary. The second level features three additional bedrooms and a large bonus room perfect for a home office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water and glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River and Chesapeake for day trips or sunset cruises. Recent improvements include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321
$188,000
Welcome to Meadow Creek by Lacrosse Homes. Must use Lacrosse Homes to build your home. We offer severral models, from rancher to 2 story, and will also build your custom plans. This community of 16 estate homesites of 1.25 acres is surrounded by treed conservation easements for that rural feel, yet 5 minutes fron Historic Centreville. Explore the possibilites today.

117 Pasture Ct, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

$595,000
6 Beds ⋅ 3 Baths
A North Brook home like you have NEVER SEEN before! A kitchen that doesn't exist in any other home. A primary suite that you won't find in any other home. Want a RARE GEM? This is it. Get ready. This one is STUNNING!

137 Meadowcroft Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$869,000
4 Beds ⋅ 4 Baths
Welcome to 128 Lynch Court in the Brand New Starfield Farms Community. To be built with estimated completion Spring 2027 by the reputable craftsmanship of Mike's Custom Homes. This stunning 4 bedroom, 3.5 bathroom residence offers 3400 square feet of thoughtfully designed living space, with an additional 1700 sq feet of unfinished walkout basement, on a 1.4 acre lot. Get in now and customize your selections. Build your dream home with Mike's Custom Homes! Nestled in a serene setting with spacious lots, high-quality craftsmanship, and modern finishes, these homes offer the best of Eastern Shore living. Don’t miss this opportunity to build in a prime location with easy access to local amenities, schools, and major routes. Secure your lot today—contact us for more details! *Photos are of a previously sold model and may feature options that are upgrades.

128 Lynch Ct, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$505,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 2-bath home in the highly desired Bay City neighborhood! Situated on a spacious half-acre lot with community water access, this property offers the perfect blend of comfort, updated and coastal community living. Recent improvements include new windows, a new HVAC system, and new kitchen flooring and cabinets. Enjoy plenty of outdoor space with the 2 car garage and a brand new deck coming soon! This home is ready to welcome its next owner!!

912 Buckingham Dr, Stevensville

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$489,900
4 Beds ⋅ 4 Baths
Why wait for new construction when you can move right in? Welcome to 205 Jessica Lyn Ave #F20, a nearly new 4-bedroom, 3.5-bath townhome offering approximately 2,280 square feet of thoughtfully designed living space in Stevensville. Built in 2024, this home delivers the modern finishes, and open layout buyers are looking for without the wait or the price tag of competing new construction. The main level features a bright, open-concept layout with 9-foot ceilings, abundant natural light, luxury vinyl plank flooring, and a spacious kitchen that opens seamlessly to the dining and living areas. The kitchen offers generous cabinetry, stainless steel appliances, a large island with seating, and plenty of space for both everyday living and entertaining. Upstairs you'll find a spacious primary suite along with additional bedrooms and flexible living space. The other level provides even more versatility with a bedroom and full bath, ideal for guests, a home office, multigenerational living, or anyone looking for additional privacy. Located on Kent Island with convenient access to Route 50/301 and the Bay Bridge, this home puts Annapolis and the Western Shore within easy reach while still offering the Eastern Shore lifestyle. With newer construction nearby competing at significantly higher prices, 205 Jessica Lyn Ave represents an opportunity that's hard to ignore. Schedule your showing and see the value for yourself.

205 Jessica Lyn Ave Unit #F20, Stevensville

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$550,000
5 Beds ⋅ 4 Baths
Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors throughout. The entry-level bedroom offers convenience, while the walk-in closets provide ample storage. Step outside to your personal oasis with an in-ground pool (new pool pump), ideal for summer relaxation and entertaining. With a generous 0.39-acre lot and side-entry garage, this home combines space and style.

326 Castle Marina Rd, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$799,990
3 Beds ⋅ 3 Baths
THIS IS A TO BE BUILT HOME. LISTING PRICE IS THE BASE PRICE OF THE RALEIGH MODEL. Experience the exceptional craftsmanship of Schaefer Homes with the Raleigh floorplan, now offered in the highly desirable water-access community of Queen Anne’s Colony. This thoughtfully designed new construction home offers the ease of single-level living, blending timeless coastal style with modern functionality—perfect for both everyday living and effortless entertaining. The heart of the home features a designer kitchen with an oversized island, quartz countertops, and stainless steel appliances, all flowing seamlessly into a stunning vaulted family room that creates an open, airy feel. Enjoy an unbeatable location surrounded by serene water views, quiet streets, and a welcoming community atmosphere. Residents have convenient access to Queen Anne Marina—ideal for boating enthusiasts—as well as the nearby Blue Heron Golf Course for a relaxing day on the greens. Just minutes away, you’ll find a variety of waterfront dining and locally loved restaurants that capture the charm of the area. This is a rare opportunity to own a beautifully crafted Schaefer home in one of the region’s most sought-after communities—don’t miss your chance to make it yours.

204 Queens Colony High Rd, Stevensville

Listing courtesy of RE/MAX United Real Estate. Contact:

$539,990
4 Beds ⋅ 3 Baths
Discover the charm of this new construction home in Kent Island Estates, where coastal elegance meets modern comfort. With 4 spacious bedrooms and 2.5 baths, this residence features an inviting open floor plan, perfect for gatherings. The heart of the home is the kitchen, complete with a stylish island and energy-efficient stainless steel appliances, making meal prep a delight. Enjoy the luxury of partially carpeted and luxury vinyl plank flooring throughout, enhancing both warmth and durability. The family room, conveniently located off the kitchen, creates a cozy atmosphere for relaxation. Set on a generous 0.24-acre lot, this home offers ample outdoor space for future landscaping or entertaining. The community is enriched by nearby parks, excellent schools, and convenient public services, fostering a vibrant neighborhood spirit. With an attached garage and driveway parking, convenience is at your fingertips. Embrace the opportunity to make this beautiful house your home! Seller is offering $10,000 towards options or closing assistance through preferred lender and title company!

101 Oak St, Stevensville

Listing courtesy of RE/MAX United Real Estate. Contact:

$584,900
3 Beds ⋅ 2 Baths
This beautiful expanded Brick Front Rancher has upgrades galore and is situated on a professionally landscaped 1+ acre level lot. Upgrades Include...New roof 5/22, New HVAC system 11/23, New Heat Pump located in the back Sunroom 11/23, New Water Heater 9/26, New Washer/Dryer 11/24 & New Stove 3/25. Please note; Septic System was pumped and included a full service check 4/28/26. This outstanding country rancher offers so many areas to entertain friends or just find a quiet spot to sit and enjoy the peaceful surroundings and wildlife. This home shows pride of ownership throughout the property. 2hr notice on showings is requested. Buyer's should know; Owner has found home of choice with all purchase terms successfully negotiated and in place

157 Greenwood Creek Rd, Queenstown

Listing courtesy of Cummings & Co. Realtors. Contact: 4108230033
$649,990
2 Beds ⋅ 2 Baths
Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

641 Warbler Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$350,000
2 Beds ⋅ 2 Baths

200 Church St, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$595,000
4 Beds ⋅ 3 Baths
Rare opportunity to own in sought after Creek Point Estates with NO HOA. You will fall in love with this amazing colonial on 1.6 acres with gleaming hardwood floors, great room with build in bookcases, fireplace, HUGE primary bedroom with 2 WICs, deck, screened in porch, large garage and room to play and expand. Owners have updated many important things including a new roof last year, newer HVAC, appliance and so much more. There is a 1 year warranty to top it off. Only minutes from a public boat ramp/docks, parks, shopping, doctors, historic Centreville and more. Come get this one before its gone!

112 Creek Point Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

$944,900
3 Beds ⋅ 3 Baths
Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$574,900
4 Beds ⋅ 4 Baths
Luxury homes rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting, and backsplash. Escape to the spacious primary suite with a tray ceiling and spa bath or unwind on the composite deck overlooking spectacular sunset views. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails.

118 Amanda Frances Ln, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$575,000
4 Beds ⋅ 4 Baths
Room to Breathe. Space to Dream. There is something special about coming home to a place where life feels just a little slower and a bit quieter. Set on a fabulous one-acre parcel surrounded by farms and open countryside, this well-loved home offers a sense of privacy and breathing room that can be hard to find—yet it is still just minutes from the places and conveniences you need. Here, mornings can begin with coffee overlooking your own piece of land, weekends can be spent in the garden, and evenings feel removed from the noise and pace of the day. And with an acre of your own, there is room to imagine what comes next. Create the vegetable and flower gardens you have always wanted. Add an outbuilding, workshop, or hobby space. Spread out, entertain, play, plant, tinker—or simply enjoy having open space around you. The home itself has a wonderful sense of history and has clearly been loved over the years. Inside, you'll find an updated kitchen with granite countertops, warm wood floors, four full baths, a huge mudroom, and generous living spaces that offer flexibility for everyday life, guests, hobbies, or working from home. Then there is the unfinished basement—a whole additional level waiting for the next owner's vision. Perhaps a recreation room, home gym, workshop, studio, additional living space, or simply incredible storage. It is another reminder that this is a property with room not only for how you live today, but for the ideas you may have for tomorrow. Outside, an oversized garage, paved driveway, and expansive parking area provide plenty of space for vehicles, equipment, projects, and gatherings. And while this home has plenty of character and history, many of the less glamorous—but very important—systems have received significant attention in recent years, including the roof, water-conditioning system, French drains, septic system, and more. Some homes are defined by finishes and square footage. This one feels defined by something more: space, privacy, possibility, and the freedom to make it your own. A place with a past, plenty of room for the present, and so many possibilities for what comes next.

746 Hope Rd, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$750,000
1 Beds ⋅ 2 Baths
A truly special Eastern Shore property! This charming Tidewater Cape is beautifully positioned on the point of 13.78 acres, surrounded by the tidal waters of the Chester River. Built in 1950 by a father and son as a summer retreat, the home has been loved and enjoyed by generations and is filled with character and timeless charm. The setting begins to reveal itself as you travel the wooded drive and catch glimpses of the river through the trees. As you approach the homesite, the trees open and water appears on both sides, showcasing the property's unique point setting, privacy, and natural beauty. Charming and inviting from the front, the home's true presence is best appreciated from the waterside, where its distinctive three-story Tidewater elevation creates an impressive view. Inside, hardwood floors extend throughout the main and second levels, complemented by beautiful built-ins and original hardwood details. A main-level porch and lower-level patio provide wonderful spaces to relax and enjoy the peaceful surroundings. Two outbuildings along the shoreline include a one-car garage and a workshop with electric, offering additional storage and workspace. With 13.78 acres, there may be potential for subdividing. *Buyers to verify all possibilities, requirements, and approvals with the appropriate county authorities. A rare opportunity to own substantial acreage with privacy and character in a beautiful Chester River setting. Pier/dock conveys As-Is. DO NOT WALK ON DOCK. Property shown by appointment only. DO NOT ENTER PROPERTY WITHOUT AN APPOINTMENT.

200 Powers Ln, Millington

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$400,000
5 Beds ⋅ 4 Baths
List price is Opening Bid at the Online auction to be conducted on Auctioneers website. - Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the Chesapeake Bay Bridge, this property combines generous proportions with a layout designed for comfortable everyday living and entertaining. The main level makes an immediate impression with 12-foot ceilings and oversized 6-foot windows, creating bright, open living spaces throughout. The floor plan includes a spacious family room, vaulted morning room, sunroom, and an eat-in kitchen that serves as the heart of the home. The kitchen is equipped with granite countertops, a large center island, pantry, and ample cabinet and workspace. The home’s 5-bedroom, 3.5-bath configuration provides plenty of flexibility. The primary suite features a tray ceiling and private bath with a custom-tiled shower and double vanity. Four additional bedrooms are complemented by two Jack-and-Jill-style bathrooms, offering a functional arrangement for family, guests, home offices, or additional flex space. Outdoor living is another highlight, with an impressive 800± square-foot wraparound deck providing plenty of room for grilling, dining, entertaining, and relaxing. Additional features include: • Hardwood and tile flooring • Roman blinds and wood shutters • New HVAC system • Finished garage • Dedicated laundry room with New washer and dryer • Approximately 4-foot crawl-space ceiling height • Numerous custom builder upgrades • No HOA With its impressive bedroom count, expansive living areas, oversized deck, substantial storage, and convenient Chester location, 1868 Roberta Drive offers bidders a unique opportunity to purchase a custom Eastern Shore home and make it their own. Don’t miss your opportunity to bid!

1868 Roberta Dr, Chester

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

$1,250,000
3 Beds ⋅ 3 Baths
Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality. Inside, you'll find a dedicated home office and stylish engineered hardwood and tile flooring throughout, creating a seamless and low-maintenance living space. Large windows invite natural light and showcase the home's tranquil waterfront setting. Outdoor living is just as impressive, featuring two maintenance-free decks, a patio ideal for grilling and entertaining, and a fenced backyard perfect for pets, play, or simply enjoying the beautiful surroundings. Whether hosting friends or relaxing with a morning coffee, this home offers multiple spaces to take in the peaceful water views. Boating enthusiasts will appreciate the private pier equipped with both water and electric service, while the pier decking was replaced last year, providing added value and peace of mind. Enjoy easy access to boating, fishing, crabbing, kayaking, and all the activities that make waterfront living so special. Conveniently located on Kent Island near shopping, dining, marinas, and commuter routes, this exceptional waterfront property offers the perfect blend of luxury, comfort, and Chesapeake Bay lifestyle. 3 Bedrooms | 2.5 Baths | Main-Level Primary Suite | Separate Office | Waterfront on Cox Creek | Private Pier with Water & Electric | New Pier Decking (2025) | Two Maintenance-Free Decks | Grilling Patio | Fenced Backyard | Renovated Approximately 4 Years Ago

1717 Harbor Dr, Chester

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

$920,000
8 Beds ⋅ 7 Baths
Elizabeth A. Turpin House c.1872 -Purchased in 2016, (fully renovated 2019-2022) Turpin House is a beautiful, 1872 Victorian, listed on the National Register of Historic Homes, featuring an “Empire” design interior with soaring 12-foot ceilings, elegant chandeliers and handmade original plaster medallions. Recent renovations include original heartwood floors, plaster moldings, medalions and walls meticulously restored by expert craftsman. Modern upgrades include new electric, plumbing and high efficiency HVAC with, room by room, controllable mini-splits and programmable remotes making all of the spaces wonderfully comfortable, year round. Turpin House grounds include a rustic Victorian garden with fruit trees and raised vegetable beds, an outdoor kitchen for hosting garden parties, a woodworking shop and a "Carriage house" modernized with electric for off-street parking. The Turpin House features a main house with 6 bedrooms, 5 bathrooms, 5 fireplaces (3 marble), and a mother-in-law suite (2 bedrooms-2 bathrooms) that offers its own private exterior garden entrance. This home is 2 blocks from Centreville's 1782 town square, an historic town wharf, restaurants and community events including local wine & jazz festivals. One mile away is a brand new community center including indoor and outdoor pools, extensive workout gyms, an indoor track, saunas and community classes & events. Income Apartment: In addition, the Turpin property includes a garden-level one bedroom income suite with a private exterior entrance. Fully renovated and continuously leased since 2020, this space is legally permitted under R2 zoning and provides a substantial financial offset to mortgage expenses without compromising owner privacy. Ideal for commuters, Turpin is 15 minutes to the Bay Bridge and Chestertown and 38 to Annapolis, including daily commuter buses to Washington DC. Elizabeth A Turpin House is a dream home with the wonderful warm vibe of the large Victorian family who built it. This stunning home is truly a “move-in ready and an historic work of art”

201 S Liberty St, Centreville

Listing courtesy of Cottage Street Realty LLC. Contact:

$674,900
4 Beds ⋅ 3 Baths
NEW CONSTRUCTION IN QUEENSTOWN – PRIVATE WOODED SETTING! Welcome to this thoughtfully designed new construction home on beautiful John Brown Road.  This home offers nearly 2,300 square feet of high quality living space in a peaceful, private setting surrounded by towering hardwood trees and backing to the wooded portion of a 1,000+ acre farm. Step inside this bright and inviting home offering super nice kitchen, large great room with gas fireplace, large first floor laundry, and plenty of space for both everyday living and entertaining. The really spacious first-floor primary suite offers convenience and privacy with granite vanity, large tiled shower, and huge closet! Upstairs, you'll find three big bedrooms, providing plenty of room for family, guests, home offices, or additional flex space. Additional highlights include granite counters, oversized trim, LVP flooring, insulated and finished 2 car garage, with stamped concrete walks, porch, and patio really dress this home up!  Secondary driveway is perfect for parking that large RV or boat! Everyone loves that peace of mind that comes with owning a brand-new home. Quality goes well beyond what you can see – spray foam sealed crawlspace walls and concrete floor make the conditioned crawl space a dry and energy efficient feature.   The home is equipped with a whole-house water treatment system designed to address arsenic, iron, and other common well-water contaminants. All exterior walls are flash coated with closed cell insulation for maximum efficiency. If you've been searching for the perfect combination of new construction, space, privacy, and Eastern Shore living, this home deserves a look. More photos and additional details coming soon!

1306 John Brown Rd, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$485,000
3 Beds ⋅ 2 Baths
Open House: Thursday September 3 from 3:00pm - 6:30pm One-Level Living in a Quiet Cul-de-Sac with Amazing Outdoor Space! Welcome to 226 Lakeside Drive, a beautifully maintained 3-bedroom, 2-full-bath Alton E Darling Construction - built home offering timeless charm, quality craftsmanship, and 1,914 sq. ft. of comfortable one-level living in the Springview community. Situated at the end of a quiet cul-de-sac, this home features beautiful hardwood floors, crown molding, two fireplaces, and custom built-ins. The dining room is filled with natural light and features a large picture window overlooking the beautifully landscaped backyard. The spacious sunroom offers the perfect spot to relax and enjoy views of the outdoors throughout the seasons. Outside, enjoy an impressive combination of deck, brick patio with pergola, fully fenced yard, and established landscaping—providing plenty of space for entertaining, gardening, or simply enjoying the peaceful setting. Recent improvements include professionally sanded and refinished hardwood floors and a freshly repainted deck. Additional features include a 2-car garage, paved driveway, and thoughtful accessibility features including entry ramps, a roll-in shower, and bathroom grab bars. Located in Springview, residents enjoy generous open community spaces while this home's cul-de-sac location offers added privacy and tranquility. With its classic charm, thoughtful features, and exceptional indoor and outdoor living spaces, 226 Lakeside Drive is a wonderful place to call home.

226 Lakeside Dr, Millington

Listing courtesy of Taylor Properties. Contact:

$1,750,000
4 Beds ⋅ 3 Baths
712 Bay Drive isn't simply a waterfront home—it's a turnkey Chesapeake lifestyle, beautifully executed from shore to door. Just two years young, this exceptional waterfront residence combines thoughtful design, elevated finishes and impressive waterfront infrastructure with sweeping views of the Bay. The open-concept main level was designed around the view, with a dramatic wall of windows overlooking the water and a propane fireplace anchoring the living space. The kitchen delivers both beauty and function with an extra-long island, quartz countertops, high-end appliances, crisp white cabinetry, statement hood and walk-in pantry. The main-level primary suite offers a private retreat with a walk-in closet and beautifully finished bath featuring a spacious walk-in shower and shiplap detailing. Upstairs, you'll find three additional bedrooms, a bonus room and abundant walk-in storage, plus a floored, temperature-controlled attic. And then there's the waterfront. A vaulted covered side porch creates another incredible place to take in the views, complete with a hot tub that conveys, while the home's piling construction creates an expansive “Below Deck” entertaining area at ground level—perfect for waterfront gatherings, crab feasts and relaxed summer evenings. The waterfront infrastructure is equally impressive, with a newer bulkhead and pier, 12,500-lb boat lift, electric and water at the pier directly on the Chesapeake Bay. Thoughtful systems include a whole-house water filtration system, tankless water heater, two-year-old roof and HVAC, plus electric HVAC with propane backup for efficiency and peace of mind. Newer construction. Exceptional waterfront infrastructure. Thoughtfully engineered. Turnkey. And a front-row seat to life on the Bay.

712 Bay Dr, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$719,990
2 Beds ⋅ 3 Baths
Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, functionality, and stylish finishes for modern living. The main living area features an electric fireplace, creating a warm and inviting focal point, while a dry bar adds the perfect touch for entertaining. A dedicated home office with French doors provides a private and polished space for working from home, studying, or pursuing hobbies. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths for added durability and style. The primary bath offers a relaxing retreat with a spacious shower featuring a built-in seat and handheld shower wand, along with a double-sink vanity and quartz countertops. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

736 Warbler Way Unit #2733, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$415,000
3 Beds ⋅ 2 Baths
Grasonville - Property is zoned GVC, this gives you opportunity to own your own home and business. Well maintained property and home located on a corner lot with garage and extra storage sheds. Plenty of room for parking, open floor plan featuring 3 bedrooms 2 baths with luxury vinyl flooring with wonderful kitchen with upgraded commercial size refrigerator/freezer. The decks make it nice for outside entertaining with custom retractable awning and screen/shades.

101 King Store Rd, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$775,000
3 Beds ⋅ 2 Baths
SPRAWLING RANCHER IN BELLE POINT FARM! 3 Bedrooms, 2 full Baths. You're all set to make this one your own - the 'big ticket' items are done! Can't wait for you to tour it!

208 Grason Vista Dr, Queenstown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$699,900
5 Beds ⋅ 5 Baths
This stunning Victorian home, built in 1911, exudes timeless charm and modern comfort. With 5 spacious bedrooms and 3 full bathrooms, this residence offers a perfect blend of classic craftsmanship and contemporary design. The heart of the home features a gourmet kitchen with upgraded countertops, a built-in range, and a cozy breakfast area, ideal for gatherings. Elegant details like chair railings, built-ins, and hardwood floors enhance the inviting atmosphere throughout. The home's unique architectural features include a double staircase that adds a touch of drama and elegance, leading to the upper levels where the primary suite awaits. Step outside to enjoy the expansive 1.56-acre lot, complete with beautifully crafted stone retaining walls and a personal in-ground pool, perfect for summer relaxation. The expansive wrap-around porch and screened patio provide serene outdoor spaces for entertaining or unwinding. The fully finished basement includes a workshop area and convenient access to the outdoors. This home is designed for both functionality and style, making it a true sanctuary for those seeking comfort and elegance. This captivating property is conveniently located a short walk to historic downtown Centreville yet combines serene privacy with easy access to area dining and shopping.

524 Church Hill Rd, Centreville

Listing courtesy of Century 21 Downtown. Contact:

$512,000
3 Beds ⋅ 2 Baths
Welcome to 224 Wye Knot Court, a charming 3-bedroom, 2-bath home situated on a spacious lot in the peaceful Wye Knot Farms community. Step inside to a bright and inviting layout filled with natural light and comfortable, functional living spaces. This well-maintained home offers the perfect opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore. Wye Knot Farms is known for its quiet setting, generous lots, and welcoming neighborhood feel, while still providing convenient access to Route 50, shopping, dining, and the beautiful Wye River. Whether you’re purchasing your first home, looking to downsize, or simply searching for a little more space and tranquility, 224 Wye Knot Court is a must-see! Professional photographs coming soon!

224 Wye Knot Ct, Queenstown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: