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2452 Bennett Point Rd, Queenstown
$4,900,000
4 Beds ⋅ 5 Baths
Experience luxury waterfront living at its finest at this stunning 2.7-acre estate on Greenwood Creek. Meticulously constructed on a double lot with over 300’ of shoreline, a private sandy beach, infinity-edge saltwater heated pool with water features & tanning ledge, and protected views across preserved land, this property is a rare find. Custom-built and completed in 2024, this home offers 10’ ceilings throughout, soaring to 21’ in the great room, 8” English oak floors, and walls of Anderson windows that showcase panoramic water views. The chef’s kitchen features dual islands, a Wolf 6-burner range with grill and griddle, stunning quartz countertops, Sub-Zero fridge, and a large butler’s pantry with prep sink and full-size fridge. The main level includes a luxurious waterside primary suite with spa bath and walk-in closet with island. Upstairs are 3 large ensuite bedrooms with custom finished closets, a private office, 26 ' x 55' bonus room, and multiple storage areas. The bonus room is very large, has closets and shares a bath jack and Jill style with the 3rd bedroom. Exterior highlights include new 120’ pier with 12K lb lift, floating jet ski dock, electric, water, and fish cleaning station. 6-car garage parking including detached garage with roughed-in guest house above. Mechanical features include 4 zone HVAC, 3 air handlers, 4 heat pumps and tankless water heater. There is propane for heat backup, water, pool and cooking and reverse osmosis system in Kitchen. The lower level is unfinished with 3200 SF with 9' ceilings and impressive fully sealed block system and plumbed for wet bar and full bath. An excellent location for boaters with a 10 minute ride from your dock to either St. Michaels or the Narrows. A special property with the most gorgeous sunsets imaginable. Golf, clubhouse and restaurant memberships available at nearby Prospect Bay.

2452 Bennett Point Rd, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

3027 Bennett Point Rd, Queenstown
$3,300,000
5 Beds ⋅ 6 Baths
Reduced below replacement cost!! This spectacular 5-1/2 acre, deep water Wye River estate has so much to offer that it's almost hard to know where to start. Designed and built by a family of custom home builders, the attention to detail and regular care exhibited over time will impress the most discriminating buyer. The main house was built for people that LOVED to entertain. The open floor plan invites everyone to pitch in and then carry meals to a sunny enclosed sunroom or back onto an awesome screened porch that overlooks a custom concrete pool with a stone outdoor fireplace. You'll be impressed with the kitchen as well with its high quality appliances and enormous butler's pantry. Like to craft? Then you'll find your dream craft room that shares space with a wonderful laundry room. The impressive entry leads to a more formal part of the home with a stunning formal dining room and a clubby den with its own gas fireplace. Beyond those rooms is a 1st floor main suite with an impressive dressing room for the lovers of clothing and accessories, a lovely main bath and ultimately, a breathtaking view of the Wye River. From the main suite, you can step out to the backyard pool or into the sun room. Upstairs are 4 additional spacious bedrooms and 3 bathrooms. One of the most luxurious guest suites has a river view that is sure to captivate your guests. One is oversized and more private with its own entrance through the three car garage, perfect for staff. Across the paved driveway is the building that makes this home particularly unique - a massive garage and shop sized to fit the largest RVs and boats. If you LOVE big garages, this one is for you! When your boats aren't stored indoors, the dock has two lifts and ample water depth to dock a substantial yacht. Got RV friends that like to visit? There is a dedicated RV pad with water, electric and sewer hookups. If longer term visits are in your mind, there is an awesome guest apartment above the garage that offers Wye River views that will have them talking long after they leave. Please allow ample time to visit this home. There is no shortage of wonderful things to see.

3027 Bennett Point Rd, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Benson & Mangold, LLC.

3207 Bennett Point Rd, Queenstown
$3,200,000
5 Beds ⋅ 7 Baths
Welcome to 3207 Bennett Point, a breathtaking Norman Jaffe–designed waterfront estate set on over 5 private acres along the widest stretch of the Wye River. Designed to maximize its setting, the home offers floor-to-ceiling glass, seamless indoor-outdoor living, and panoramic water views from nearly every room. The main residence showcases timeless craftsmanship with Tennessee Quarry FlagStone, rich hardwoods, and warm wood-clad ceilings and walls. Expansive living areas and a waterfront screened porch highlight the home’s indoor-outdoor flow, while a home office, elevator, and a gourmet kitchen that was renovated in 2017 with an oversized island, contemporary cabinetry, and premium finishes that add comfort and function. Upstairs, the primary suite offers a stunning wall of glass framing the river, a fireplace, dual walk-in closets, and a spa-inspired bath. The estate’s separate 4-bedroom, 4-bath guest house was taken down to the studs and completely reimagined in 2017. The renovation added two bedrooms and two bathrooms, a full kitchen, and a spacious living area all with sweeping water views. Providing luxurious accommodations for family and guests. Outdoors, the property delivers resort-style amenities at every turn: a 22’x44’ PebbleTec heated pool with pool house, a Bradford hot tub designed for year-round relaxation, and a 340’ pier with 8’ MLW, boat lift, davits, and deep-water access for boating, fishing, and swimming. Recent upgrades (2017) include kitchen and bath renovations, the guest house addition, elevator installation, whole-house generator for the main and guest house, new insulation, HVAC, electric service, lighting, and flooring- ensuring peace of mind for years to come. With expansive shoreline, mature landscaping, and sunset views over the Wye, this estate pairs architectural pedigree with resort-like amenities that is just minutes from the Chesapeake Bay Bridge. Experience the pinnacle of Eastern Shore living at 3207 Bennett Point.

3207 Bennett Point Rd, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

3021 Bennett Point Rd, Queenstown
$2,800,000
5 Beds ⋅ 6 Baths
Set on more than five tranquil acres with deep water and over 900 feet plus of protected shoreline, this custom-built waterfront residence new finished square footage 7,129 feet offers timeless design, enduring quality, and a setting unlike any other. With five full en-suites and newly finished spaces for a second family room & kitchenette, it provides flexibility for multi-generational living or exceptional guest accommodation. Originally built in 1981 and completely reimagined in 2006, every detail reflects craftsmanship and artistry. A gated entry and private drive lined with seasonal blooms lead to a circular drive and covered brick porch, where glass entry doors open to reveal soaring vaulted ceilings, skylights, and a wall of windows framing the breathtaking Wye River views. Throughout the home, custom cherry millwork elevates fireplaces, built-ins, and displays with warmth and richness. At the heart of the open floor plan, the gourmet kitchen is outfitted with Alder cabinetry, Sub-Zero refrigeration, three wall ovens, a five-burner cooktop with grill, and a warming oven—designed for both entertaining and everyday living. Formal dining beneath a vaulted ceiling, casual meals at the breakfast bar, or dining al-frescos on the composite deck all capture sweeping water views. Outdoors, cascading deck stairs open to a lush lawn and private pier with boat lift in deep water, offering endless opportunities for boating, kayaking, and sunrise views. Inside, thoughtfully designed spaces accommodate every lifestyle need. A professional office with private entry is ideal for working from home, while a separate en-suite suite with private stair access provides perfect quarters for guests or an au pair. The main-level primary suite features soaring ceilings, panoramic river views, and a spa-inspired bath with onyx floors, jetted tub, walk-in shower, and dual vanities. Upstairs, two additional en-suites and a cedar closet complete the private wing. The walk-out lower level expands the living experience with a recreation room, gas fireplace, full daylight windows, a full bath, and covered patio access. Flex rooms, abundant storage, and a generously sized workshop/studio make the home as practical as it is luxurious. In addition, there is 776 sq. in basement that could be finished if necessary or used as storage.

3021 Bennett Point Rd, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: TTR Sotheby's International Realty.

1150 Cheston Ln, Queenstown
$2,050,000
4 Beds ⋅ 3 Baths
This amazing property is like no other. Private w/ deep water. The winding driveway leads to tennis court & 2-story tennis house w/ it's own driveway or stay on the main driveway to the main house. The main part of the main house was built w/ materials from a 1730 barn. Incredible beams, floor, doorways & more! 3 story great room w/ full stone chimney w/ gas fireplace. This dwelling provides 4 bedrooms & 2.5 baths spanning 3 stories, plus a lookout tower. There is also an efficiency apt. over the garage w/ its own water views. Roof & HardiPlank siding are reasonably new. There is an accessible crawl space & house generator. Interior is very unique & special, still ready for your upgrades. The tennis house has 4 rooms, reception area, a kitchenette, full bath & sauna. It is far enough away from the main house to provide its own sandy beach front, great views & privacy. DO NOT ENTER PROPERTY W/O APPOINTMENT!

1150 Cheston Ln, Queenstown

Listing courtesy of RE/MAX One. Contact:

Selling Office: Coldwell Banker Waterman Realty.

416 Cove Rd, Queenstown
$1,890,000
3 Beds ⋅ 4 Baths
Welcome to “This is Wye”! Set on a spectacular elevated lot overlooking the Wye River, this Exceptional property captures breathtaking views of both the river and Wye Island. This beautifully designed one-level residence offers 3 bedrooms and 3.5 baths, delivering effortless waterfront living with a refined, thoughtful layout. Completely renovated in 2018 and enhanced with ongoing updates through 2026, the home features hardwood flooring throughout, along with abundant windows and skylights that fill the interiors with natural light and showcase expansive water views from nearly every room. The renovated gourmet eat-in kitchen is both stylish and functional, equipped with top-of-the-line appliances, a generous center island, convenient mudroom, and seamless flow into the main living spaces. The living room opens naturally to the dining area and is anchored by a wood-burning stove insert, creating a warm and inviting focal point. A separate yet connected family room provides additional gathering space, and both rooms feature sliding glass doors that lead to the waterside patio, pool, and deck—ideal for indoor-outdoor living. The primary suite is a private retreat, set in its own wing and thoughtfully appointed with dual walk-in closets and two en suite baths. One bath features a double-sink vanity, soaking tub, and glass-enclosed shower, while the second offers a single-sink vanity and glass-enclosed shower. Two additional bedrooms share a well-designed Jack-and-Jill bath, and a charming powder room completes the interior. Outdoors, the property is equally impressive, with a waterside gunite pool, expansive decking, and approximately 450 feet of bulkheaded shoreline. The new protected pier offers 5+'MLW and includes a lift, three slips, and a floating dock, making it ideal for boating enthusiasts. A detached, oversized garage, connected by a breezeway, includes a spacious office and workshop, while two additional storage sheds provide ample space for equipment and tools. Mature landscaping, trees, and extensive hardscaping create a private, picturesque setting. Recent improvements include the renovated kitchen and baths, refurbished pool, Andersen windows and doors, encapsulated crawlspace, generator, and tankless water heater and so much more—offering a truly turnkey waterfront lifestyle.

416 Cove Rd, Queenstown

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

Selling Office: Benson & Mangold, LLC.

133 Kilby Pt, Queenstown
$1,875,000
4 Beds ⋅ 3 Baths
Imagine waking up to breathtaking sunrises over Eastern Bay and the Wye River at 133 Kilby Point Road, a stunning waterfront retreat nestled within the private community of Kilby Point at the tip of Bennett Point. This beautifully renovated 4-bedroom, 2.5-bath residence boasts approximately 3,156 sq. ft. of living space, perfectly blending timeless elegance with modern comforts. Please do not venture down without an appointment - this is a private point - thank you . As you step inside, you'll be greeted by the warmth of Provenza engineered hardwood floors, a custom solid wood entry door, and big views that frame the captivating water views steps away. The fully renovated chef's kitchen is a culinary dream, featuring quartz countertops, stainless steel appliances, dual wall ovens, and 6-burner gas range that's sure to delight even the most discerning cooks. Imagine sipping your morning coffee or enjoying a glass of wine while cooking up a storm, with the serene water views as your backdrop. The main level's open layout seamlessly connects the dining room, living areas, and kitchen, creating an ideal space for entertaining and making memories with family and friends. The intimate porch off the dining room is the perfect spot to enjoy a quiet morning or a sunset cocktail, with the water views providing a serene atmosphere. Upstairs, the primary suite is a tranquil retreat, complete with a newly built Duradeck balcony (2025) that offers panoramic views of the surrounding waters. The additional three bedrooms, all with water-facing windows, and a renovated hall full bath make this level the perfect haven for family and guests. The true magic happens outdoors, where the nearly 5-acre property unfolds into a stunning oasis. The heated saltwater pool (2021) is the perfect spot for pool parties and relaxation, surrounded by patios for lounging and landscaped grounds. There are so many more opportunities to add gardens, pergolas, chicken coop and more. As you gaze out across the water in multiple directions, you'll be treated to picturesque views of a lighthouse and a charming old-time windmill, views of the boats sailing to St. Michaels, adding to the property's natural beauty. And, if you're lucky, you might even catch a glimpse of the two resident white swans on the pond and 2 bald eagles perched on the lighthouse that call the property home, or gliding effortlessly across the water. Imagine hosting unforgettable gatherings, with an extra pool enclosure that can be easily converted into a vibrant pool club room or outdoor kitchen. The fireplace is already there. The possibilities are endless, from sunset soirees to family reunions, weddings, and the serene water views provide a breathtaking backdrop for any celebration. As a resident of Kilby Point, you'll enjoy a 1-mile waterfront walking/golf cart path, and a pier/dock, 1 available boat slip (not deeded, subject to availability). The property's convenient location, to Route50 and the Bay Bridge, makes it easy to explore Annapolis, Washington, D.C., and the charming destinations on Maryland's Eastern Shore, Easton, St Micheals, Oxford and more. This is a rare opportunity to own such a unique waterfront retreat with extensive upgrades, captivating views, and endless possibilities for entertainment and relaxation. Come make your memories today.

133 Kilby Pt, Queenstown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: RLAH @properties.

313 Wye Rd, Queenstown
$1,600,000
5 Beds ⋅ 6 Baths
Experience a true “wow” moment the instant you arrive at this meticulously maintained estate in the exclusive Bennett Point community, set on a private street with views of the renowned Wye River. Step into the grand foyer and be greeted by soaring ceilings, elegant columns, lighted niches, graceful arches, and a stunning curved staircase. The home opens into a formal dining room perfect for entertaining, flowing seamlessly into a dramatic two-story family room with a wall of windows overlooking the patio, saltwater Gunite pool, fenced backyard, and barn. A floor-to-ceiling stone gas fireplace anchors the space—ideal for cozy winter nights or gathering for the big game. The open-concept layout continues into a chef’s dream kitchen, featuring granite countertops, abundant Merillat Masterpiece solid cherry cabinetry, and premium appliances including a Sub-Zero refrigerator/freezer, commercial-grade Viking cooktop with hood and pot filler, double wall ovens, built-in microwave, beverage cooler, dishwasher, and ice maker. A spacious island, built-in desk, appliance cabinet, hidden cutting board, and corner pantry make this kitchen as functional as it is beautiful. The main level offers two luxurious owner’s suites. The primary suite includes a wet bar, private sitting area, dual walk-in closets, and a spa-inspired bath with heated soaking tub, dual-head shower, travertine floors, and marble countertops. The second suite features a gas fireplace, built-in desk, and an accessible ensuite bath with roll-in shower and elegant finishes—ideal for multi-generational living or guests. A main-level laundry room adds everyday convenience. Throughout the home, you’ll find rich teak flooring, tray ceilings, and abundant recessed lighting. Upstairs, three spacious bedrooms each feature private ensuite baths, along with a large game room. A generous unfinished third level offers endless possibilities for expansion, including an au pair suite or additional bedrooms. Outdoor living is equally impressive. Enjoy the fenced saltwater pool with water feature, a screened porch with Easy-Breeze windows for year-round use, and a beautifully maintained yard with underground irrigation, vegetable garden, and whole-house generator. The conditioned crawl space adds efficiency and peace of mind. Equestrian enthusiasts will appreciate the adjacent horse training facility with covered arena. The property includes a 3-stall barn with heat sensor, two pastures, dry lot, heated water, electric, and vinyl fencing—perfect for year-round care and riding. This exceptional property offers luxury, functionality, and lifestyle—all in one remarkable setting.

313 Wye Rd, Queenstown

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

Selling Office: Coldwell Banker Realty.

500 Nesbit Rd, Queenstown
$1,400,000
5 Beds ⋅ 5 Baths
This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle amenities have improved since then with nationally renowned Queenstown Harbor Golf Resort and the marinas/dining options in Kent Narrows all minutes away. Privacy is paramount here with a wooded and gated entry lane but without sacrificing access due to the exit on Route 50 still less than a mile away. The sweeping views here are unmatched with the protected lands of Eastern Neck Wildlife Refuge across the Chester from the residence also guaranteeing this peace and tranquility for years to come. The home itself is a historic masterpiece with hardwood floors, hand blown glass windows, and grand center hall staircase. The connection with the water is celebrated here with multiple sunrooms boasting big water views for those special moments. A rough cut timber 2 car garage and workshop provides old Eastern Shore charm. Wildlife here is abundant for the outdoorsman and nature lover due to it being one of the first large parcels after crossing through the hustle and bustle of Kent Island. Invest wisely while improving your quality of life with your own waterfront sanctuary to create those special memories for generations.

500 Nesbit Rd, Queenstown

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

Selling Office: Potomac Country Real Estate.

212 Dutcher Rd, Queenstown
$1,340,000
4 Beds ⋅ 4 Baths
Welcome to Storybook charm meets waterfront living at 212 Dutcher Rd in Queenstown… and this one is something truly special 🌊🏡 Nestled on a stunning 1.34-acre waterfront lot, this Cape Cod offers the kind of Eastern Shore lifestyle people dream about—complete with a updated private pier, electric boat lift, and even your own sandy beach. Days on the water, evenings by the shoreline… this is what it’s all about.The main home (2,425 sq ft.) features 4 bedrooms and 3 full baths, filled with warmth, character, and timeless design. And just when you think it couldn’t get better—there’s a separate 1 bedroom, 1 bath guest house, perfect for visitors, extended family, or a private retreat. With nearly 3,000 sq ft of total living space and located in the desirable Belle Point community (low HOA!), this property offers both privacy and connection—just minutes to the Bay Bridge, marinas, and everything the Shore has to offer.

212 Dutcher Rd, Queenstown

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

405 Cove Rd, Queenstown
$1,050,000
4 Beds ⋅ 4 Baths
PLEASE CLICK ON VIRTUAL TOUR ICON TO VIEW INTERACTIVE FLOOR PLAN!!**Welcome to 405 Cove Road on the Wye River in Queenstown Maryland** NO HOA!!!**This 4600 + SF Home is Ready to be Loved by New Owners**Large Dining Room made for BIG Family Gatherings**Upgraded Kitchen w/Leathered Countertops**Quaint Sitting Room or Breakfast Nook Facing the Water**First Floor Primary w/Water Views and Additional Two Bedrooms on Main Level**Spacious Family Room w/Screened Porch and Bar for Parties or Watching Football Games**Upper Level has Large Primary Bedroom Suite w/Private Bath and Balcony**Two Car Garage on Lower Level just Steps into Main Home**Basement Under Original Home**Set Out to Catch Some of Maryland's Best Crabs on the Wye River**Come Explore the Beauties of the Wye River and Surrounding Towns of Saint Michaels and Easton**

405 Cove Rd, Queenstown

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

Selling Office: Redfin Corp.

315 Nottingham Ln, Queenstown
$970,000
5 Beds ⋅ 5 Baths
Beautiful Custom-Built Home with Income Potential or Multi-Generational Built in 2019, this stunning custom home offers over 5,100 square feet of finished living space with even more room to expand. Perfectly positioned on a beautiful lot backing to open farmland, it blends modern comfort with peaceful rural views. Designed with versatility in mind, the home features two separate apartments—ideal for rental income, and or an in-law suite, or extended family seeking independent living space. Also, there is a possibility for a first-floor bedroom with a full bathroom if needed. Inside the main home, you’ll find a gourmet kitchen with granite countertops, stainless steel appliances, a center island, and a spacious open layout that flows seamlessly into the family room, complete with a gas fireplace and designer accent wall. The main level also includes a formal dining room, a breakfast area, a full bathroom, and a flexible spa room that could easily serve as a first-floor bedroom or home office. Upstairs, the main home offers three bedrooms and three full bathrooms, providing plenty of space, comfort, and privacy. Step outside to a screened porch, paver patio with hot tub, and a covered gazebo—all overlooking the fenced backyard, perfect for entertaining or unwinding. Car enthusiasts and hobbyists will love the three-car garage, with one bay currently used by tenants of the apartment above. The property includes two one-bedroom apartments, each with private entrances, creating excellent options for multi-generational living or income-producing opportunities that can help support your mortgage. With its thoughtful design, high-quality upgrades, and exceptionally flexible layout, this home delivers a rare combination of luxury, functionality, and value.

315 Nottingham Ln, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Redfin Corp.

111 Mt Mills Ln, Queenstown
$950,000
4 Beds ⋅ 4 Baths
**Seller to Provide $25,000 Credit for Desired Updates with a Full Price Offer.** The Sally Harris Mill House was once part of the Bloomingdale Estate is one of the remaining 18th Century masterpieces on the Eastern Shore. This peaceful farmette boasts over 31 acres with a blend of open pasture and wooded seclusion. The property sits on the Western banks of Madam Alices Branch, a tributary of the Wye River. Mature evergreens line the entrance creating a dramatic feel and historic charm is displayed throughout the home with 5 fireplaces, Flemish bond brickwork, and a gambrel roof. Modern amenities have been incorporated with the 2 story North wing which was completed around 2000 to include a first floor primary suite with en suite bathroom, makeup room, and 2 separate walk-in closets on the first floor and 2nd floor family room. The updated kitchen, partially finished basement with kitchenette, and heated pool are also highlighted upgrades. Outdoor living is celebrated here with a screened in rear porch for dinners in nature, a front porch to sit and watch the wildlife, and pool deck for making memories. Bring your machines and toys because there is plenty of storage in the outbuildings. The 2 story machine shop has been impeccably maintained and is perfect for any type of project. The open pasture would be perfect for horses and though they haven't been maintained in a few years, the forest contains nature trails for disconnecting from the hustle and bustle or hunting opportunities. This is your chance to make a piece of Eastern Shore's history your own peaceful retreat.

111 Mt Mills Ln, Queenstown

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

Selling Office: Coldwell Banker Realty.

301 Nottingham Ln, Queenstown
$835,000
4 Beds ⋅ 4 Baths
Elegant Brick Home on One Acre with salt pool, gazebo and 5,510 feet of living space. First time on the market, this stately brick home—three sides brick—offers timeless elegance on a beautifully landscaped 1.12-acre lot. The fully fenced backyard features a sparkling pool, charming gazebo, and plenty of space for outdoor enjoyment. Inside, nearly 3,800 square feet of finished living space showcases rich hard wood floors on the main level, a gourmet kitchen with stainless steel appliances, tile backsplash, and abundant cabinetry. The main level also features a family room with fireplace and tray ceilings, a private office, formal living and dining areas, and a bright bonus sunroom ideal for year-round enjoyment. Upstairs you'll find four spacious bedrooms and three and a half baths, including a luxurious primary suite with a private full bath. The expansive unfinished basement 1715 sq. ft offers potential for future living space or storage with ruff in for full bath and walk out basement to back yard. A two-car oversized garage adds to storage for pool toys and your favorite car. A rare opportunity to own this well-appointed home—offered for the first time and ready to welcome its new owners.

301 Nottingham Ln, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Redfin Corp.

2107 Bennett Point Rd, Queenstown
$750,000
4 Beds ⋅ 3 Baths
OFFER DEADLINE OF SUNDAY 3/1 5pm. Nestled in the prestigious Bennett Point community, “Deerwood” is a stunning Colonial offering over 3,200 sq. ft. of thoughtfully designed living space on a picturesque 5-acre lot. Blending elegance with everyday comfort, this home is ideal for relaxed living and entertaining alike. The interior features a gourmet kitchen with abundant storage, two ovens, and a sunlit casual dining area that flows seamlessly into the main living spaces. Three wood-burning fireplaces and a gas wood stove, living and dining rooms, and a library/office provide both charm and functionality. A bright sunroom overlooks the custom freeform pool, patios, and tranquil wooded surroundings. The generous floor plan includes four bedrooms, highlighted by a luxurious primary suite with fireplace, heated-floor bath, walk-in shower, soaking tub, large walk-in closet and even a laundry chute! A versatile bonus/flex room with an alternate separate entrance offers options for a home gym, office, nursery, or creative space. HVAC updated in 2022, roof in 2024, upgraded well pump in 2024, freshly painted and new carpet 2026. Step outside to your private retreat, surrounded by mature trees and lush landscaping. Enjoy entertaining on multiple patios, relaxing by the pool, or quiet moments by the waterfall and pond. Additional features include a new wooden fence, whole-house generator, security system, laundry chute, extra storage, and a separate mudroom with garage access. This exceptional property combines space, privacy, and sophistication—creating a true sanctuary to call home with easy access to dining, shopping, Route 50, Kent Island and Easton. Don't wait to make this house your home!!

2107 Bennett Point Rd, Queenstown

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

108 Carriage Ln, Queenstown
$735,000
4 Beds ⋅ 2 Baths
This stunning contemporary home in the desirable Hickory Ridge subdivision offers a perfect blend of comfort and convenience. Built in 1999 and extensively renovated starting in 2017, this 1,700 sq. ft. +/- residence features four spacious bedrooms and two full bathrooms, ensuring ample space for relaxation and entertainment. Step inside to discover an open floor plan that seamlessly connects the family room and kitchen, ideal for gatherings. The modern kitchen, new in 2019, boasts stainless steel appliances and a dining area, while the living room features a striking wood-burning fireplace with glass doors, perfect for cozy evenings. Additional highlights include hardwood and ceramic tile flooring, an attic for extra storage, and a convenient upper-floor laundry. The exterior is equally impressive, set on a generous 2.17-acre lot with 200 +/- feet of waterfront on the picturesque Wye River. Enjoy outdoor living with a personal in-ground pool, extensive hardscape, and multiple patios, a deck, and porches, including a balcony for serene views from your primary bedroom. The property also includes a private dock, perfect for canoeing, kayaking, or fishing. Located just steps from the headwaters of the Wye River, this home offers easy access to local amenities and recreational activities. With an attached garage and ample parking, the property combines convenience with a tranquil lifestyle. Experience the best of riverfront living in this exceptional home in Queenstown, Maryland. Call to schedule your appointment today!

108 Carriage Ln, Queenstown

Listing courtesy of Realty Navigator. Contact:

Selling Office: Meredith Fine Properties.

1410 Bennett Point Rd, Queenstown
$725,000
5 Beds ⋅ 3 Baths
This immaculate, 5-bedroom, 3-bath Colonial is ideally positioned on the coveted Bennett Point peninsula, set on a private 2+ acre partially wooded homesite. Thoughtfully upgraded inside and out, the home now offers smart home functionality, fresh interior paint, and a truly move-in ready experience. Outdoor living shines with a heated saltwater pool, elegant paver patio, and built-in gas fire pit—enhanced by privacy fencing, professional landscaping, and curated lighting. A shed provides stylish storage for pool and lawn essentials. Inside, the chef’s kitchen flows seamlessly into the dining area with slider access to the screened porch—ideal for elevated entertaining. Wood-look tile floors anchor the main level, which also includes a first-floor bedroom with full bath, a sun-filled family room, and updated lighting throughout. Upstairs, the spacious primary suite offers a walk-in closet and en-suite bathroom, complemented by three additional generously sized bedrooms and a full hall bathroom. An oversized driveway provides ample parking. Enjoy nearby water access at Bryantown Landing on the Wye River. Only minutes to Prospect Bay Country Club and Queenstown Harbor Golf Club. Easy commuting access to Easton, Kent Island, and Annapolis. A refined blend of privacy, modern comfort, and Eastern Shore lifestyle—this exceptional home is ready for its next chapter.

1410 Bennett Point Rd, Queenstown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

117 Overlook Dr, Queenstown
$690,000
5 Beds ⋅ 4 Baths
117 Overlook (1.15 Acres) is ideally located in Queenstown, Maryland—just 30 minutes to Annapolis and only 15 minutes to Easton—offering both convenience and a peaceful setting. This spacious home features 2,672 square feet of finished living space above, along with the basement area of 1270 sf/ 400 sf finished, providing ample opportunity for customization or future expansion. The property includes 5 bedrooms, with two serving as primary suites. One of the main-level bedrooms can also function as a private in-law suite, offering flexibility for multi-generational living or guest accommodations. Throughout the home, you’ll find custom molding, granite counter tops, hardwood flooring, custom build-in, ceramic tile, and two wood-burning fireplaces, adding warmth and character. A two-car attached garage provides added convenience. The roof is only 2.5 yrs young. The large barn at the rear of the property is a standout feature, offering a workshop, office space, and second-floor storage that could easily be transformed into a studio. Electricity is already in place, enhancing its functionality. The barn also provides ample space for RV or large boat storage, along with room for lawn equipment and more.

117 Overlook Dr, Queenstown

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

Selling Office: Taylor Properties.

219 Overlook Dr, Queenstown
$667,500
4 Beds ⋅ 3 Baths
Welcome to Overlook at Carmichael. This beautiful home shows true pride of ownership, from the well-kept exterior with mature plantings and blooming flowers, including raised strawberry garden beds, to the spacious interior with well-appointed rooms for everyone. Hardwood floors and tile span the first floor. Enjoy the view from the kitchen and living area, overlooking the fully fenced backyard and inground pool. The kitchen features granite countertops and updated appliances. There’s a separate dining room and a large family room with a wood-burning fireplace. Added touches like chair rail and crown molding are found throughout. Rest easy with a 10-year-old roof and a brand-new HVAC in 2025. The open, unfinished basement already has exterior walls framed, ready for your personal touch. The pool will be open soon.

219 Overlook Dr, Queenstown

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

Selling Office: Samson Properties.

319 Wye Rd, Queenstown
$655,000
3 Beds ⋅ 3 Baths
Set on more than 5 tranquil acres with woods, open space, and a partially fenced yard, this inviting one-level home offers a peaceful setting along the Wye River with glimpses of the water. Enjoy morning coffee or evening cocktails from the welcoming front porch while taking in the serene surroundings. Inside, the thoughtfully designed floor plan features an open kitchen with granite countertops, a center island, and seamless flow into the spacious living room. A separate dining room sits just off the main living area, while the screened porch overlooks private farmland views and offers the perfect place to relax. The oversized primary suite includes a vaulted ceiling, walk-in closet, and private bath. Two additional bedrooms feature hardwood flooring and share a full bath, with a convenient half bath and laundry area nearby. This well-maintained home includes a brand-new roof, new heating and air units with warranty, a new nitrogen septic system designed for long-term use, and high-end vinyl siding for low-maintenance living. The bathrooms have been updated, and a screen porch was added when the roof was replaced. Additional highlights include minimal steps for easy accessibility, an attached two-car garage, a detached one-car garage, and comfortable spaces throughout. Full of possibilities and move-in ready, this is a home you can truly enjoy for years to come.

319 Wye Rd, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

115 Choice Ct, Queenstown
$650,000
5 Beds ⋅ 4 Baths
If you’ve been looking for space, privacy, and a great setting with room to make it your own, this 5-bedroom, 3.5-bath Colonial might be the one. Tucked at the end of a cul-de-sac and sitting on nearly an acre (.92), the home backs to open farmland, giving you peaceful views and a little extra breathing room. Inside, there’s a classic layout with formal living and dining rooms, plus a cozy family room with a gas fireplace right off the kitchen—perfect for everyday hangouts. There’s also a dedicated office, a laundry room, and plenty of space for everyone with five bedrooms upstairs.Out back is where this home really shines—a saltwater gunite pool ready for summer, and a yard set up with an underground invisible fence for pets. It’s a great spot to relax or entertain.Some of the big-ticket items have already been taken care of, including a roof less than 3 years old, Trane HVAC systems under 10 years old, and a gas hot water heater that’s just 1 year old.There’s also an unfinished basement with tons of potential, plus a 2-car garage for storage and convenience.The home could use a little TLC, but it’s a solid property in a great location with so much to offer—come see the possibilities!

115 Choice Ct, Queenstown

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Rosendale Realty.

100 Marlborough Rd, Queenstown
$649,999
5 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION — Now $649,999! Motivated seller brings this exceptional opportunity to the market . NEW PRICE — $649,999 Check out this exceptional property located in Queenstown on a private 1.15-acre lot. This spacious 5-bedroom, 3-bath home offers the perfect blend of comfort, flexibility, and Eastern Shore charm. The upper level features brand-new flooring, giving the home a fresh, modern feel. Multiple living areas provide plenty of space for entertaining, relaxing, or hosting guests, and there is a dedicated home office—ideal for today’s lifestyle. Enjoy peaceful outdoor living on the back porch overlooking your expansive yard, plus the convenience of a two-car garage and ample parking. A home warranty is included for added peace of mind. Experience everything the Eastern Shore lifestyle has to offer—privacy, space, and a beautiful setting—all at an incredible new value. Don’t miss this opportunity to own over an acre in Queenstown for under $650,000!

100 Marlborough Rd, Queenstown

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

Selling Office: Long & Foster Real Estate, Inc..

103 Trevors Ct, Queenstown
$649,900
4 Beds ⋅ 3 Baths
Located on a quiet corner lot in Bishops Meadow, this 4-bedroom, 2.5-bath home offers 2,200 sq. ft. of living space with easy access to Routes 301 and 50. The open floor plan features a kitchen with granite countertops, stainless steel appliances, and a large island that flows into the living room with a gas fireplace. Upstairs, the primary suite includes a walk-in closet with a full IKEA closet system and private bath. New carpet has just been installed throughout the entire top floor, including the bedrooms and stairway. The 1,254+/- sq. ft. insulated basement is unfinished, plumbed for a full bathroom, and ready for your vision. Outside, enjoy a private backyard oasis with a custom pool featuring a waterfall, a gazebo, and full fencing—ideal for entertaining or relaxing. This home offers a great location, a private setting, and is truly move-in ready.

103 Trevors Ct, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: CENTURY 21 New Millennium.

618 Pigpen Point Rd, Queenstown
$625,000
3 Beds ⋅ 2 Baths
Whether for a weekend getaway or full-time residence, this well elevated waterfront property offers deep water and wide views at an affordable price. Sited at the end of a peninsula on Maryland’s pristine Wye River in Queen Annes County, 618 Pigpen Point is located just 15 minutes from the Chesapeake Bay Bridge and 25 minutes to Easton. Situated directly cross the river from Wye Island, a serene sanctuary of unspoiled wetlands, hardwood forests, and nature-rich trails, you will enjoy broad, rap-around views of one of the Eastern Shore’s most beautiful and scenic waterways. With spectacular expansive riverfront leading out to Eastern Bay on one side and a quiet cove on the other, this property offers convenient one-story living with 3 bedrooms, 2 baths, large living room, eat-in kitchen, laundry and tiled family room with fireplace. In addition, there is an expansive walk-out basement with plenty of room for a workshop, storage or finishing into extra living space. Please see Virtual Tour "Wye River Cottage" included in this listing to appreciate the surrounding beauty of this rare location on the Wye River. The property is in need of renovation and is offered AS-IS, all desired inspections should be completed prior to offer. Septic inspection & repair receipt available, recommended repairs made (filter and riser installed). A/C repaired and in good working order.

618 Pigpen Point Rd, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Bright MLS.

235 Wye Knot Ct, Queenstown
$605,000
4 Beds ⋅ 3 Baths
Welcome to 235 Wye Knot Court! A beautifully maintained 4 bedroom, 2.5 bath rancher located in the sought-after Wye Knot Farms community of Queenstown. This single-level home features an open floor plan that seamlessly connects the kitchen, dining, and living areas, ideal for entertaining and everyday comfort. The interior is bright and inviting, offering spacious bedrooms including a private primary suite with an ensuite bath. Outside, you’ll find a well-manicured lawn, paved driveway, and a two-car garage. The property sits on a private lot enhanced by mature shrubs that provide natural privacy and curb appeal. Enjoy the peace and quiet of Eastern Shore living while remaining just minutes from Route 50, local marinas, and shopping and dining options on Kent Island and in Easton.

235 Wye Knot Ct, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: HomeSmart.

119 Wye Knot Rd, Queenstown
$604,000
3 Beds ⋅ 3 Baths
Thoughtfully updated in 2025 from top to bottom, this beautiful home welcomes you with curb appeal and fresh landscaping. The charming front porch with a porch swing overlooks the expansive front and side yards of the 1.44+/- acre parcel. Inside, luxury vinyl plank flooring spans both the first and second floors. The completely redesigned kitchen features custom countertops, a stylish tile backsplash, stainless steel appliances and a central island. The adjoining dining area overlooks the living room, while the kitchen also opens directly to the family room with a gas-stove fireplace and sliding glass doors leading to the rear patio. Upstairs, the private primary suite offers a newly completed bath showcasing a glass corner shower, separate soaking tub and access to a walk-in closet, plus two additional closets within the bedroom. Two spacious guest bedrooms, a full hall bath with a glass shower and a convenient laundry room complete the second level. A partially finished basement provides flexible space ready to be tailored to your needs, whether for recreation, work or hobbies. The oversized two-car garage offers ample room for vehicles and a workshop/storage space. Outdoors, enjoy a beautiful backyard overlooking farmland, complete with a rear patio and in-ground pool, it’s perfect for both entertaining and relaxing. Recent upgrades also include a new roof and a new on-demand Rinnai hot water heater.

119 Wye Knot Rd, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: KW Metro Center.

7112 Maryland Ave, Queenstown
$600,000
This exceptional four‑unit property sits in the heart of Queenstown and makes a fantastic addition to any rental portfolio. The building features a well‑designed mix of units, including a one‑bedroom with an office, a three‑bedroom unit, and two spacious two‑bedroom units, along with a detached two‑car garage that adds valuable flexibility and potential for additional income. The property currently grosses $6,075 per month, with renewals bringing that figure closer to $6,300 per month starting in June. It is home to outstanding tenants who take pride in where they live, and there is always a strong pool of interested renters for these units, ensuring consistently low vacancy. The location is a major draw, with Queenstown Golf just moments away, the Queenstown Premium Outlets right nearby, and a welcoming community atmosphere that includes Food Truck Fridays at the start of each month, walkable access to the local park, a lively summer concert series, and plenty more to enjoy. This is a rare opportunity to own a stable, income‑producing property in a thriving and highly desirable town. Must See!

7112 Maryland Ave, Queenstown

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Unrepresented.

1700 Bennett Point Rd, Queenstown
$585,000
3 Beds ⋅ 2 Baths
Welcome home to this beautifully updated contemporary offering water views, flexible living space, and a community pier practically in your backyard! With 3 bedrooms and 2 full baths, this home features a primary bedroom on each level, making the layout ideal for a variety of living arrangements.The heart of the home is the gourmet kitchen, complete with granite countertops, a stylish glass backsplash, stainless steel appliances, a center island, breakfast bar, and plenty of space for a kitchen table. Just beyond, the dramatic two-story living room features a cozy gas fireplace, refinished hardwood floors, and a beautiful stained-glass window that adds character and charm. Enjoy the convenience of a main-level primary bedroom, while upstairs, the entire second floor is dedicated to an expansive primary suite with beautiful views of Greenwood Creek. Outdoor living is just as inviting. Relax on the screened porch, large deck, enjoy the fenced rear yard, or head just steps away to the community pier, where an available boat slip puts days on the water within easy reach. You get the Chesapeake lifestyle and beautiful water views without the waterfront taxes! The entire home has been freshly painted and the hardwood floors beautifully refinished, making it ready for its next owner. Additional features include an encapsulated crawl space and a spacious 2-car garage.Water views, boating access, beautiful updates, and a unique contemporary design—this is Eastern Shore living without the waterfront price tag.

1700 Bennett Point Rd, Queenstown

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Next Step Realty.

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