Homes with Pools for Sale in 21658, MD

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ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
This amazing property is like no other. Private w/ deep water. The winding private driveway leads to tennis court & 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 1700s barn. Incredible beams, floor, doorways & more! 3 story great room w/ full stone fireplace & chimney. 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 & s

$2,700,000

4 beds2.5 baths5,023 sq ft

1150 Cheston Ln, Queenstown, MD 21658

10.29 acre lot • 2 garage spots • Built 1986

(410) 224-4400

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
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

$599,000

4 beds2.5 baths2,632 sq ft

235 Wye Knot Ct, Queenstown, MD 21658

0.8 acre lot • 2 garage spots • Built 2001

(443) 988-0483

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
Discover the perfect blend of comfort, style, and space in this pristine single-family detached home set on a full acre. Flooded with natural light and thoughtfully designed throughout, this 4-bedroom, 2.5-bath residence offers exceptional living for every lifestyle. Step inside to a gourmet eat-in kitchen featuring a large island, pantry, and plenty of workspace—ideal for both everyday meals and entertaining. The kitchen opens seamlessly to a warm family room with a cozy fireplace, while a separate living room, formal dining room and den/home office provide flexible spaces to suit your needs. Upstairs, the grand primary suite impresses with its spacious layout, luxurious primary bath

$675,000

4 beds3.5 baths3,462 sq ft

518 Bryce Rd, Queenstown, MD 21658

Large island • Cozy fireplace • En-suite bathroom

(301) 298-1001

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boater’s dream — complete with 3 boat lifts and 2 jet-ski lifts — perfect for crabbing, fishing, or setting out for a sunset cruise. The home’s Royal Blue Terracotta roof and accents make a bold architectural statement, while the full wrap-around deck ensures you’ll never miss a moment of the breathtaking waterfro

$1,500,000

4 beds3 baths2,721 sq ft

2006 Bennett Point Rd, Queenstown, MD 21658

6.68 acre lot • 20 parking spots • Built 1998

(443) 274-1900

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
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 appliance

$997,000

5 beds5 baths5,152 sq ft

315 Nottingham Ln, Queenstown, MD 21658

1.08 acre lot • 3 garage spots • Built 2019

(410) 224-2200

Property at 108 Carriage Ln, Queenstown, MD 21658, 4 beds, 2 baths

$789,654

4 beds2 baths1,700 sq ft

108 Carriage Ln, Queenstown, MD 21658

(410) 643-3404

Property at 119 Wye Knot Rd, Queenstown, MD 21658, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,028 sq ft

119 Wye Knot Rd, Queenstown, MD 21658

(410) 745-0415

Property at 108 Wall St, Queenstown, MD 21658, 2 beds, 2 baths

$349,900

2 beds2 baths1,033 sq ft

108 Wall St, Queenstown, MD 21658

(410) 827-4663

Property at 100 Marlborough Rd, Queenstown, MD 21658, 5 beds, 3 baths

$699,500

5 beds3 baths2,488 sq ft

100 Marlborough Rd, Queenstown, MD 21658

(410) 643-2244

Property at 3207 Bennett Point Rd, Queenstown, MD 21658, 5 beds, 6.5 baths

$3,495,000

5 beds6.5 baths7,065 sq ft

3207 Bennett Point Rd, Queenstown, MD 21658

(410) 822-6665

Property at 100 Wall St, Queenstown, MD 21658, 6 beds, 2 baths

$450,000

6 beds2 baths2,486 sq ft

100 Wall St, Queenstown, MD 21658

(443) 274-1900

Property at 144 River Run, Queenstown, MD 21658, 4 beds, 3 baths

$849,000

4 beds3 baths3,200 sq ft

144 River Run, Queenstown, MD 21658

(410) 643-2244

Property at 915 Sportsman Neck Rd, Queenstown, MD 21658

$399,900

— beds— baths— sq ft

915 Sportsman Neck Rd, Queenstown, MD 21658

(410) 827-6163

Property at 6107 Ocean Gtwy, Queenstown, MD 21658

$97,000

— beds— baths— sq ft

6107 Ocean Gtwy, Queenstown, MD 21658

(410) 822-6665

Property at 248 Harbor Ln, Queenstown, MD 21658

$320,000

— beds— baths— sq ft

248 Harbor Ln, Queenstown, MD 21658

(410) 643-2244

Property at Hess Frontage Rd, Grasonville, MD 21638

$875,000

— beds— baths— sq ft

Hess Frontage Rd, Grasonville, MD 21638

(301) 970-2447

Property at Route 301, Queenstown, MD 21658

$199,900

— beds— baths— sq ft

Route 301, Queenstown, MD 21658

(410) 827-6163

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ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
Your Spacious Retreat Awaits: 4 (with potential for a 5th) BR Home in Greenwood Community! Step into this truly charming and expansive 5-bedroom, 3.5-bathroom home nestled in the tucked-away community of Greenwood. If space is what you crave, this is it, everywhere you look, you'll find room to breathe, live, and create a memorable experience perfectly catered to your lifestyle. This layout displays space and welcomeness. Step inside to an atmosphere of refined elegance, where generously sized, beautifully appointed bedrooms offer tranquil retreats. The home's design seamlessly blends classic charm with modern living, showcased by the inviting formal dining and living rooms, both distinguis

$754,999

4 beds3.5 baths3,668 sq ft

621 Caspian Dr, Grasonville, MD 21638

0.23 acre lot • 2 garage spots • Built 2004

(410) 729-7700

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
Don't miss the opportunity to own this beautifully renovated home that offers peaceful country living with exceptional convenience. This three-bedroom, two-full-bathroom rancher has been completely transformed from top to bottom. Everything is BRAND NEW, including the roof, siding, windows, electric, plumbing, doors, gutters, flooring, HVAC system etc etc. .. .. Additionally, the crawlspace has been professionally encapsulated for enhanced efficiency. The interior has been thoughtfully remodeled to blend modern luxury with comfort and functionality. The home includes a primary suite with an ensuite bathroom, and the spacious living area is bright and airy, connecting seamlessly to the dinin

$405,000

3 beds2 baths1,064 sq ft

1109 Grasonville Cemetery Rd, Grasonville, MD 21638

0.29 acre lot • Built 1962 • Listed 13 days

(410) 827-4663

COMING SOON

$400,000

3 beds2 baths1,320 sq ft

104 Windsor Ave, Centreville, MD 21617

6,098 sq ft lot • 3 parking spots • Built 1916

(301) 970-2447

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
DEEDED BOAT SLIP - Seller offering a 2-1 buy down -✨ What’s a 2-1 Buydown? ✨ It’s a temporary mortgage rate reduction that lowers your payment for the first two years. ✔️ Year 1: Rate is 2% lower ✔️ Year 2: Rate is 1% lower . Year 3+: Back to your original fixed rate 💰 This means lower monthly payments upfront and an easier transition into homeownership. -LIVE EVERYDAY LIKE YOUR ON VACATION in this completely renovated, designer-inspired two-level end-unit water view townhome offering 2 bedrooms, 2.5 baths, and 2,031 sq ft of coastal luxury! Shows like a model home—every detail has been thoughtfully curated. Enjoy breathtaking sunsets from one of the three private decks.

$580,000

2 beds2.5 baths2,031 sq ft

112 Bayview, Grasonville, MD 21638

$650 HOA • Garage • Community pool

(410) 643-2244

OPEN SAT, 12PM TO 2PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 21658, MD:
MOTIVATED SELLERS!!!! Welcome to 218 Winchester Drive — a stunning Centreville gem where comfort, charm, and outdoor living come together beautifully! This 4-bedroom, 2.5-bath home offers an inviting layout with hardwood floors throughout the main level and a spacious bonus room over the garage that’s perfect as a fifth bedroom, playroom, or home office. The main level provides a seamless flow between the kitchen, dining, and living spaces—ideal for gatherings and everyday living. Step outside to your own private oasis! Enjoy a screened-in porch overlooking the fenced backyard, complete with an in-ground pool featuring a built-in seating area, new cover, and a 2024 pump re

$525,000

4 beds2.5 baths2,093 sq ft

218 Winchester Dr, Centreville, MD 21617

1.04 acre lot • 2 garage spots • Pool

(410) 705-6295

$329,998

3 beds2 baths1,152 sq ft

113 Moes Ln, Grasonville, MD 21638

0.61 acre lot • Built 1977 • Listed 25 days

(410) 220-4648

Property at 714 Harmony Way #714, Centreville, MD 21617, 4 beds, 3 baths

$579,000

4 beds3 baths2,804 sq ft

714 Harmony Way #714, Centreville, MD 21617

(410) 643-2244

Property at 1326 Perrys Corner Rd, Grasonville, MD 21638, 4 beds, 2 baths

$445,000

4 beds2 baths1,784 sq ft

1326 Perrys Corner Rd, Grasonville, MD 21638

(443) 988-0483

Property at 111 Beach Harbor F, Grasonville, MD 21638, 2 beds, 1 bath

$89,000

2 beds1 bath950 sq ft

111 Beach Harbor F, Grasonville, MD 21638

(443) 250-4707

Property at 108 Perrys Retreat Blvd, Grasonville, MD 21638, 4 beds, 2.5 baths

$614,950

4 beds2.5 baths2,450 sq ft

108 Perrys Retreat Blvd, Grasonville, MD 21638

(410) 479-3993

Property at 807 Harmony Way, Centreville, MD 21617, 4 beds, 3 baths

$595,000

4 beds3 baths2,804 sq ft

807 Harmony Way, Centreville, MD 21617

(443) 274-1900

Property at 12654 Ocean Gtwy, Cordova, MD 21625, 4 beds, 3 baths

$705,000

4 beds3 baths2,184 sq ft

12654 Ocean Gtwy, Cordova, MD 21625

(410) 822-6272

Property at Grasonville Cemetery Rd Lot 1, Grasonville, MD 21638, 4 beds, 2 baths

$664,650

4 beds2 baths1,710 sq ft

Grasonville Cemetery Rd Lot 1, Grasonville, MD 21638

(888) 860-7369

Property at Grasonville Cemetery Rd Lot 2, Grasonville, MD 21638, 4 beds, 2.5 baths

$662,550

4 beds2.5 baths1,664 sq ft

Grasonville Cemetery Rd Lot 2, Grasonville, MD 21638

(888) 860-7369

Property at 902 Long Point Rd, Grasonville, MD 21638, 4 beds, 3.5 baths

$1,150,000

4 beds3.5 baths3,556 sq ft

902 Long Point Rd, Grasonville, MD 21638

(410) 827-6163

Property at 107 Whitby Ln, Centreville, MD 21617, 3 beds, 3 baths

$535,000

3 beds3 baths2,440 sq ft

107 Whitby Ln, Centreville, MD 21617

(410) 827-4663

Property at 125 Price St, Centreville, MD 21617, 3 beds, 1 bath

$290,000

3 beds1 bath1,080 sq ft

125 Price St, Centreville, MD 21617

(866) 987-3937

Property at 3729 Main St, Grasonville, MD 21638, 2 beds, 1 bath

$320,000

2 beds1 bath1,056 sq ft

3729 Main St, Grasonville, MD 21638

(866) 987-3937

Property at Vfw Ave, Grasonville, MD 21638

$1,400,000

— beds— baths— sq ft

Vfw Ave, Grasonville, MD 21638

(410) 643-2244

Property at 149,141,155 Sawmill Ln Lot 1, 2 & 3, Grasonville, MD 21638

$445,000

— beds— baths— sq ft

149,141,155 Sawmill Ln Lot 1, 2 & 3, Grasonville, MD 21638

(443) 256-3773

Homes with Pools for Sale in 21658

There are currently 17 homes with pools for sale in 21658 at a median listing price of $900K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21658 stay on the market for 66 days. This map is refreshed with the newest listings in 21658 every 15 minutes.

In the past month, 4 homes have been sold in 21658. In addition to houses in 21658, there were also 0 condos, 1 townhouse, and 0 multi-family units for sale in 21658 last month. Find your dream home in 21658 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21658 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21658. If you're looking to sell your home in the 21658 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21658 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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