Gentry, MD homes for sale & real estate

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NEW 7 HRS AGO3D WALKTHROUGH

26 Pleasant St, Annapolis, MD 21401
26 Pleasant St, Annapolis, MD 21401
26 Pleasant St, Annapolis, MD 21401
ABOUT THIS HOME
Gentry, MD Homes for Sale
Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife. Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025. Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft a

$349,900

2 beds1 bath972 sq ft

26 Pleasant St, Annapolis, MD 21401

Built 1940

(443) 901-2200

NEW 9 HRS AGO

5 Park Pl #602, Annapolis, MD 21401
5 Park Pl #602, Annapolis, MD 21401
5 Park Pl #602, Annapolis, MD 21401
ABOUT THIS HOME
Gentry, MD Homes for Sale
Beautiful 2 bedroom 2 bath condo in Park Place. This unit faces the fountain and courtyard. Stainless appliances, beautiful hardwood floors. Top tier amenities in The Residence at Park Place makes this the ideal location for in town living. A 24-hour staffed from desk in lobby. Secured lobby with controlled access. Outdoor pool with lifeguard during the season. Hot tub, Party Room, club room, library, Gym, Dog Park, garden courtyard with grills. An active social committee organizes events and gatherings. Secure underground parking garage with 2 deeded parking spaces. Enjoy the historic charm of Annapolis combined with modern luxury! Walk to restaurants and shopping. There is a one time Move

$675,000

2 beds2 baths1,213 sq ft

5 Park Pl #602, Annapolis, MD 21401

Outdoor pool • Hot tub • Fountain

(410) 263-3400

COMING SOON

11 President Point Dr Unit A2, Annapolis, MD 21403
11 President Point Dr Unit A2, Annapolis, MD 21403
11 President Point Dr Unit A2, Annapolis, MD 21403
ABOUT THIS HOME
Gentry, MD Homes for Sale
Location, Location, Location! Rare opportunity to own in The Point, one of Annapolis’ premier waterfront condominium communities. This one-bedroom, one-bath residence offers breathtaking views of Spa Creek and the iconic Maryland State Capitol. Step inside to find a beautifully updated gourmet kitchen featuring quartz countertops, sleek stainless-steel appliances, and custom cabinetry. The bright and open living space showcases gleaming hardwood floors, a cozy wood-burning fireplace, and newer windows and sliding glass doors that frame the views. Enjoy two covered decks—perfect for relaxing or entertaining—as well as an updated bath, generous walk-in closet, and a storage

$675,000

1 bed1 bath923 sq ft

11 President Point Dr Unit A2, Annapolis, MD 21403

$584 HOA • Community pool • Car-dependent

(410) 263-3400

1411 Stonecreek Rd, Annapolis, MD 21403
1411 Stonecreek Rd, Annapolis, MD 21403
1411 Stonecreek Rd, Annapolis, MD 21403
ABOUT THIS HOME
Gentry, MD Homes for Sale
Nicely renovated single family contemporary in sought after Stonecreek (The Landings). 4 bedrooms, 2.5 bath. Stainless appliances and granite in the sunny kitchen. Minutes to downtown Annapolis, shops, parks, dining. Remodeled kitchen and all bathrooms. New HVAC, brand new architectural shingle roof. This home is move in ready! Properties rarely come up in this sidewalk neighborhood with community pool and tennis courts.

$575,000

4 beds3 baths1,920 sq ft

1411 Stonecreek Rd, Annapolis, MD 21403

Community pool • New hvac • Tennis courts

(410) 263-3400

290-M Hilltop Ln, Annapolis, MD 21403
290-M Hilltop Ln, Annapolis, MD 21403
290-M Hilltop Ln, Annapolis, MD 21403
ABOUT THIS HOME
Gentry, MD Homes for Sale
Open House Sunday, Sept 7, 1-3 PM. Nice Townhome at the Saltaire in Annapolis. 2 bedroom, 1.5 Bath with a fireplace and large back deck. Well priced, vacant, and freshly painted in a popular community. Home is a great investment as a starter home, or rental in an investor friendly community. Across the street from Truxton Park with includes "The Pip Moyer Recreation Center, ball fields, tennis and pickleball courts, a skateboard park, swim center and boat ramp are spread across the park. But what is often overlooked are the trails that wind through the park. To walk a two mile loop through the woods and along the creek, park behind the rec center near a fun new playground and look for

$249,950

2 beds1.5 baths1,024 sq ft

290-M Hilltop Ln, Annapolis, MD 21403

Large back deck • Wooded trail head • New pool

(202) 255-1900

Property at 5 Park Pl #514, Annapolis, MD 21401, 2 beds, 2 baths

$565,000

2 beds2 baths1,056 sq ft

5 Park Pl #514, Annapolis, MD 21401

(410) 266-0600

Property at 115 Merryman Ct, Annapolis, MD 21401, 2 beds, 1.5 baths

$245,000

2 beds1.5 baths992 sq ft

115 Merryman Ct, Annapolis, MD 21401

(443) 274-1900

Property at 5 Rockwell Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths1,450 sq ft

5 Rockwell Ct, Annapolis, MD 21403

(302) 539-2900

Property at 52 Primrose Hill Ln, Annapolis, MD 21403, 5 beds, 4.5 baths

$985,000

5 beds4.5 baths3,978 sq ft

52 Primrose Hill Ln, Annapolis, MD 21403

(443) 292-6767

Property at 14 Jefferson Pl, Annapolis, MD 21401, 6 beds, 4 baths

$1,375,000

6 beds4 baths2,568 sq ft

14 Jefferson Pl, Annapolis, MD 21401

(410) 263-3400

Property at 5 Park Pl #224, Annapolis, MD 21401, 2 beds, 2 baths

$670,000

2 beds2 baths1,188 sq ft

5 Park Pl #224, Annapolis, MD 21401

(410) 224-2200

Property at 111 Janwall St, Annapolis, MD 21403, 3 beds, 2.5 baths

$649,900

3 beds2.5 baths1,754 sq ft

111 Janwall St, Annapolis, MD 21403

(410) 398-1247

Property at 211 Janwall St, Annapolis, MD 21403, 3 beds, 2 baths

$389,000

3 beds2 baths1,416 sq ft

211 Janwall St, Annapolis, MD 21403

(410) 793-7195

Property at 42 City Gate Ln, Annapolis, MD 21401, 3 beds, 3 baths

$839,000

3 beds3 baths1,800 sq ft

42 City Gate Ln, Annapolis, MD 21401

(301) 966-0035

Property at 198 Clay St, Annapolis, MD 21401, 2 beds, 1.5 baths

$429,000

2 beds1.5 baths902 sq ft

198 Clay St, Annapolis, MD 21401

(443) 292-6767

Property at 13 Elliott Rd, Annapolis, MD 21403, 4 beds, 3.5 baths

$1,175,000

4 beds3.5 baths3,292 sq ft

13 Elliott Rd, Annapolis, MD 21403

(888) 860-7369

Property at 730 Crisfield Way, Annapolis, MD 21401, 5 beds, 4.5 baths

$899,000

5 beds4.5 baths3,586 sq ft

730 Crisfield Way, Annapolis, MD 21401

(410) 260-2800

Property at 5 Park Pl #107, Annapolis, MD 21401, 2 beds, 2 baths

$625,000

2 beds2 baths1,272 sq ft

5 Park Pl #107, Annapolis, MD 21401

Property at 93 Clay St, Annapolis, MD 21401, 4 beds, 2.5 baths

$399,999

4 beds2.5 baths2,022 sq ft

93 Clay St, Annapolis, MD 21401

(410) 220-5745

Property at 102 Boxwood Rd, Annapolis, MD 21403, 4 beds, 1.5 baths

$510,000

4 beds1.5 baths1,296 sq ft

102 Boxwood Rd, Annapolis, MD 21403

(410) 224-2200

Property at 1831 Drew St, Annapolis, MD 21401, 5 beds, 2 baths

$575,000

5 beds2 baths2,236 sq ft

1831 Drew St, Annapolis, MD 21401

(410) 263-3400

Property at 5 Park Pl #626, Annapolis, MD 21401, 2 beds, 2 baths

$699,000

2 beds2 baths1,314 sq ft

5 Park Pl #626, Annapolis, MD 21401

(410) 263-3400

Property at 407 Merryman Rd, Annapolis, MD 21401, 4 beds, 3.5 baths

$699,999

4 beds3.5 baths1,850 sq ft

407 Merryman Rd, Annapolis, MD 21401

(410) 266-0600

Property at 637 Chase St, Annapolis, MD 21401, 3 beds, 2 baths

$1,168,000

3 beds2 baths2,064 sq ft

637 Chase St, Annapolis, MD 21401

(410) 263-8686

Property at 5 Park Pl #431, Annapolis, MD 21401, 1 bed, 1 bath

$489,900

1 bed1 bath839 sq ft

5 Park Pl #431, Annapolis, MD 21401

(410) 224-3600

Property at 5 Park Pl #217, Annapolis, MD 21401, 2 beds, 2 baths

$699,900

2 beds2 baths1,343 sq ft

5 Park Pl #217, Annapolis, MD 21401

(302) 360-0300

Property at 917 Arbutus Rd, Annapolis, MD 21403, 5 beds, 3.5 baths

$5,250,000

5 beds3.5 baths3,945 sq ft

917 Arbutus Rd, Annapolis, MD 21403

(410) 263-8686

Property at 1200-F Gemini Dr, Annapolis, MD 21403, 3 beds, 2.5 baths

$324,999

3 beds2.5 baths1,304 sq ft

1200-F Gemini Dr, Annapolis, MD 21403

(410) 263-8686

Property at 66 Franklin St #20, Annapolis, MD 21401, 1 bed, 1.5 baths

$750,000

1 bed1.5 baths1,342 sq ft

66 Franklin St #20, Annapolis, MD 21401

(410) 224-4999

Property at 399 Hilltop Ln, Annapolis, MD 21403, 4 beds, 4 baths

$595,000

4 beds4 baths3,668 sq ft

399 Hilltop Ln, Annapolis, MD 21403

(410) 224-2200

Property at 300 Hilltop Ln Unit 300K, Annapolis, MD 21403, 2 beds, 2 baths

$269,000

2 beds2 baths1,085 sq ft

300 Hilltop Ln Unit 300K, Annapolis, MD 21403

(410) 823-0033

Property at 10 N Homeland Ave N, Annapolis, MD 21401, 4 beds, 3 baths

$699,900

4 beds3 baths2,342 sq ft

10 N Homeland Ave N, Annapolis, MD 21401

(866) 987-3937

Property at 5 Park Pl #428, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,125,000

3 beds2.5 baths1,822 sq ft

5 Park Pl #428, Annapolis, MD 21401

(410) 429-7425

Property at 103 Norma Aly, Annapolis, MD 21403, 4 beds, 4 baths

$695,000

4 beds4 baths1,880 sq ft

103 Norma Aly, Annapolis, MD 21403

(410) 263-8686

Property at 9 Rusty Red Dr, Annapolis, MD 21401, 5 beds, 4.5 baths

$1,375,000

5 beds4.5 baths5,124 sq ft

9 Rusty Red Dr, Annapolis, MD 21401

(410) 263-8686

Property at 66 Franklin St #509, Annapolis, MD 21401, 3 beds, 3.5 baths

$1,850,000

3 beds3.5 baths2,477 sq ft

66 Franklin St #509, Annapolis, MD 21401

(410) 266-0600

Property at 139 Spa Dr, Annapolis, MD 21403, 4 beds, 4.5 baths

$2,900,000

4 beds4.5 baths4,628 sq ft

139 Spa Dr, Annapolis, MD 21403

(410) 505-9700

Property at 1233 Boucher Ave, Annapolis, MD 21403, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,052 sq ft

1233 Boucher Ave, Annapolis, MD 21403

(443) 292-6767

Property at 9 Edelmar Dr, Annapolis, MD 21403, 4 beds, 2 baths

$519,900

4 beds2 baths936 sq ft

9 Edelmar Dr, Annapolis, MD 21403

(410) 729-7700

Property at 5 Park Pl #507, Annapolis, MD 21401, 2 beds, 2 baths

$675,000

2 beds2 baths1,277 sq ft

5 Park Pl #507, Annapolis, MD 21401

(410) 263-8686

Property at 5 Park Pl #722, Annapolis, MD 21401, 2 beds, 2 baths

$799,000

2 beds2 baths1,285 sq ft

5 Park Pl #722, Annapolis, MD 21401

(410) 280-5600

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