Recently Sold Homes in Gentry, MD

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SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in Gentry, MD:
Rare opportunity in Homewood of Annapolis! On an oversized lot in one of the city's most sought-after neighborhoods, this 3-bedroom, 2-bathroom offers extra space for outdoor living, gardening, or future expansion. Step inside to find an inviting, oversized wraparound enclosed porch—perfect for morning coffee, evening cocktails, or a cozy reading nook year-round. Warm hardwood floors and plenty of space for the whole family, this home is ready for you to make it your own. A detached garage and private driveway, providing coveted off-street parking and extra storage. In the heart of Homewood—just minutes from downtown Annapolis, the Naval Academy, parks, restaurants, and commuter

$600,000 Last sold price

3 beds2 baths1,442 sq ft

21 Woodlawn Ave, Annapolis, MD 21401

(410) 263-9105

SOLD NOV 19, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Gentry, MD:
AMAZING NEW PRICE $1,250,000 AND TURN KEY, ALL CONTENTS CONVEY! Welcome to 14 Jefferson Place, a prime investment opportunity in the highly sought-after President’s Hill neighborhood of Downtown Annapolis, which is ranked #5 by CNN as America's Best Towns to Visit! This six-bedroom, four-bathroom duplex with four parking spots and a garage offers two complete side-by-side residences under one roof, with the potential to generate incredible annual rental income. It is located a block away from Leo, Sailor Oyster Bar, Lighthouse Bistro, Timber Pizza, Ms. Shirley's, Sea Salt and Carpaccio, and on the free Annapolis Circulator Trolley route if you want a ride down to City Dock. This pro

$1,150,000 Last sold price

6 beds4 baths2,568 sq ft

14 Jefferson Pl, Annapolis, MD 21401

(410) 263-3400

SOLD SEP 17, 2025

ABOUT THIS HOME
Recently Sold Home in Gentry, MD:
Welcome to Willow Cottage, a charming, history-rich Craftsman nestled in Eastport, just minutes from all the culture, dining, and waterfront beauty of historic downtown Annapolis. Nestled on an exceptionally large lot (. 55 acres), this beautiful 4-bedroom, 3.5-bathroom residence blends hosts modern living, timeless appeal, and ample space. The property has been meticulously maintained over the years and features a wealth of original charm, enhanced by thoughtful and stylish updates that elevate its functionality and aesthetics. The kitchen has been updated with modern amenities, offering lots of cabinet space, upgraded countertops, and stainless steel appliances. Master Bedroom: Convenient

$670,000 Last sold price

4 beds3.5 baths1,876 sq ft

1115 Tyler Ave, Annapolis, MD 21403

(410) 266-0600

SOLD OCT 28, 2025

ABOUT THIS HOME
Recently Sold Home in Gentry, MD:
CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL NANTUCKET CAPE COD IN THE HEART OF HOMEWOOD! THIS ADORABLE HOME TRANSFERS YOU BACK TO THE ISLAND OF MARTHA'S VINEYARD OR NANTUCKET AS SOON AS YOU WALK UP THE FRONT WALKWAY! SITUATED DOWN THE STREET FROM THE NAVY STADIUM, THIS HOME OFFERS 3 BEDROOMS. 2 FULL BATHS & OVERSIZED CLASSIC FRONT PORCH & A 1 CAR GARAGE WITH A LONG DRIVEWAY TO PARK SEVERAL CARS. FEATURES INCLUDE WOOD FLOORS, CLASSIC WIDE MOLDINGS & TRIM, DESIGNER TOUCHES EVERYWHERE & WELL APPOINTED W/ DESIGNER LIGHTING THROUGHOUT. THERE IS A PRIMARY BEDROOM ON THE MAIN FLOOR AS WELL AS ON THE UPPER LEVEL. THERE ARE 2 BEDROOMS UP AND ONE ON THE MAIN LEVEL. THE LOWER

$855,000 Last sold price

3 beds2 baths2,649 sq ft

20 Glen Ave, Annapolis, MD 21401

(410) 263-8686

SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in Gentry, MD:
This Murray Hill beauty has been completely renovated inside and out over the last three years, blending timeless charm with modern updates. Major improvements include new systems, roof, windows, and utilities, plus refreshed landscaping, hardscaping, and an inviting outdoor fireplace. Inside, you’ll find refinished floors, a redesigned primary suite, and a finished lower level. Every detail has been carefully updated to create a move-in ready home in one of Annapolis’s most sought-after neighborhoods.

$3,100,000 Last sold price

4 beds5 baths4,113 sq ft

2 Steele Ave, Annapolis, MD 21401

(410) 263-8686

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

$380,000 Last sold price

3 beds2 baths1,416 sq ft

211 Janwall St, Annapolis, MD 21403

(410) 793-7195

Property at 808 Carrollton Ave, Annapolis, MD 21401, 3 beds, 1.5 baths

$535,000 Last sold price

3 beds1.5 baths1,248 sq ft

808 Carrollton Ave, Annapolis, MD 21401

(410) 260-2800

Property at 1021 Cedar Ridge Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$400,000 Last sold price

3 beds2.5 baths1,320 sq ft

1021 Cedar Ridge Ct, Annapolis, MD 21403

(410) 224-2200

Property at 1028 Cedar Ridge Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$395,000 Last sold price

3 beds2.5 baths1,320 sq ft

1028 Cedar Ridge Ct, Annapolis, MD 21403

(240) 219-2422

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

$824,900 Last sold price

3 beds3 baths1,800 sq ft

42 City Gate Ln, Annapolis, MD 21401

(301) 966-0035

Property at 1109 Van Buren St, Annapolis, MD 21403, 3 beds, 2 baths

$545,000 Last sold price

3 beds2 baths1,118 sq ft

1109 Van Buren St, Annapolis, MD 21403

(410) 429-7425

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

$675,000 Last sold price

4 beds3.5 baths1,850 sq ft

407 Merryman Rd, Annapolis, MD 21401

(410) 266-0600

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

$245,000 Last sold price

2 beds1.5 baths992 sq ft

115 Merryman Ct, Annapolis, MD 21401

(443) 274-1900

Property at 34 Heritage Ct, Annapolis, MD 21401, 2 beds, 1.5 baths

$260,000 Last sold price

2 beds1.5 baths960 sq ft

34 Heritage Ct, Annapolis, MD 21401

Property at 1590 Virginia St, Annapolis, MD 21401, 4 beds, 2.5 baths

$615,000 Last sold price

4 beds2.5 baths2,189 sq ft

1590 Virginia St, Annapolis, MD 21401

(410) 263-9105

Property at 220 S Southwood Ave, Annapolis, MD 21401, 4 beds, 2 baths

$525,000 Last sold price

4 beds2 baths1,667 sq ft

220 S Southwood Ave, Annapolis, MD 21401

(410) 260-2800

Property at 602 Broach Ct, Annapolis, MD 21401, 3 beds, 2.5 baths

$330,000 Last sold price

3 beds2.5 baths1,486 sq ft

602 Broach Ct, Annapolis, MD 21401

(571) 888-2600

Property at 605 Broach Ct, Annapolis, MD 21401, 3 beds, 2.5 baths

$366,000 Last sold price

3 beds2.5 baths1,570 sq ft

605 Broach Ct, Annapolis, MD 21401

(301) 452-5691

Property at 624 Tripp Creek Ct, Annapolis, MD 21401, 4 beds, 3.5 baths

$371,000 Last sold price

4 beds3.5 baths1,782 sq ft

624 Tripp Creek Ct, Annapolis, MD 21401

(301) 854-2155

Property at 18 Sargent Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$338,000 Last sold price

3 beds2.5 baths1,450 sq ft

18 Sargent Ct, Annapolis, MD 21403

(410) 730-3456

Property at 23 Copley Ct, Annapolis, MD 21403, 2 beds, 2.5 baths

$370,000 Last sold price

2 beds2.5 baths1,822 sq ft

23 Copley Ct, Annapolis, MD 21403

(410) 263-8686

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

$425,000 Last sold price

3 beds2.5 baths1,450 sq ft

5 Rockwell Ct, Annapolis, MD 21403

(302) 539-2900

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

$660,000 Last sold price

4 beds3 baths2,342 sq ft

10 N Homeland Ave N, Annapolis, MD 21401

(866) 987-3937

Property at 4 President Point Dr Unit A3, Annapolis, MD 21403, 2 beds, 1 bath

$625,000 Last sold price

2 beds1 bath923 sq ft

4 President Point Dr Unit A3, Annapolis, MD 21403

(410) 263-8686

Property at 11 President Point Dr Unit A2, Annapolis, MD 21403, 1 bed, 1 bath

$660,000 Last sold price

1 bed1 bath923 sq ft

11 President Point Dr Unit A2, Annapolis, MD 21403

(410) 263-3400

Property at 105 Rosecrest Dr, Annapolis, MD 21403, 3 beds, 1 bath

$275,000 Last sold price

3 beds1 bath900 sq ft

105 Rosecrest Dr, Annapolis, MD 21403

(410) 304-3130

Property at 97 Quarter Landing Rd Rd, Annapolis, MD 21403, 2 beds, 2.5 baths

$1,050,000 Last sold price

2 beds2.5 baths1,920 sq ft

97 Quarter Landing Rd Rd, Annapolis, MD 21403

(410) 263-8686

Property at 290-M Hilltop Ln, Annapolis, MD 21403, 2 beds, 1.5 baths

$237,500 Last sold price

2 beds1.5 baths1,024 sq ft

290-M Hilltop Ln, Annapolis, MD 21403

(202) 255-1900

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

$320,000 Last sold price

3 beds2.5 baths1,304 sq ft

1200-F Gemini Dr, Annapolis, MD 21403

(410) 263-8686

Property at 4 Spa Creek Lndg Unit B3, Annapolis, MD 21403, 2 beds, 2 baths

$875,000 Last sold price

2 beds2 baths1,335 sq ft

4 Spa Creek Lndg Unit B3, Annapolis, MD 21403

(410) 263-8686

Property at 5 Spa Creek Landing Lndg Unit A1, Annapolis, MD 21403, 1 bed, 1.5 baths

$525,000 Last sold price

1 bed1.5 baths1,002 sq ft

5 Spa Creek Landing Lndg Unit A1, Annapolis, MD 21403

(410) 263-8686

Property at 5 Spa Creek Lndg Unit A2, Annapolis, MD 21403, 1 bed, 1.5 baths

$500,000 Last sold price

1 bed1.5 baths1,002 sq ft

5 Spa Creek Lndg Unit A2, Annapolis, MD 21403

(410) 263-8686

Property at 1005 Timber Creek Dr, Annapolis, MD 21403, 3 beds, 3 baths

$595,000 Last sold price

3 beds3 baths1,826 sq ft

1005 Timber Creek Dr, Annapolis, MD 21403

(410) 263-8686

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

$489,000 Last sold price

4 beds1.5 baths1,296 sq ft

102 Boxwood Rd, Annapolis, MD 21403

(410) 224-2200 Redfin Corp

Property at 7 Silopanna Rd, Annapolis, MD 21403, 4 beds, 3 baths

$715,000 Last sold price

4 beds3 baths2,348 sq ft

7 Silopanna Rd, Annapolis, MD 21403

(410) 260-2800

Property at 143 Spa Dr, Annapolis, MD 21403, 4 beds, 4.5 baths

$2,850,000 Last sold price

4 beds4.5 baths5,523 sq ft

143 Spa Dr, Annapolis, MD 21403

(443) 292-6767

Property at 1143 August Dr, Annapolis, MD 21403, 3 beds, 3 baths

$547,500 Last sold price

3 beds3 baths2,246 sq ft

1143 August Dr, Annapolis, MD 21403

(703) 378-8810

Property at 750 Crisfield Way, Annapolis, MD 21401, 4 beds, 4.5 baths

$800,000 Last sold price

4 beds4.5 baths4,836 sq ft

750 Crisfield Way, Annapolis, MD 21401

(410) 263-8686

Property at 1006 Primrose Rd #302, Annapolis, MD 21403, 2 beds, 2 baths

$297,500 Last sold price

2 beds2 baths1,004 sq ft

1006 Primrose Rd #302, Annapolis, MD 21403

(301) 970-2447

Property at 1009 Moss Haven Ct Unit A, Annapolis, MD 21403, 4 beds, 4.5 baths

$1,872,500 Last sold price

4 beds4.5 baths3,130 sq ft

1009 Moss Haven Ct Unit A, Annapolis, MD 21403

(410) 263-3400

Property at 5 Park Pl #430, Annapolis, MD 21401, 2 beds, 2 baths

$610,000 Last sold price

2 beds2 baths1,292 sq ft

5 Park Pl #430, Annapolis, MD 21401

(410) 224-3600

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Recently Sold Homes in Gentry

There are currently 61 recently sold homes for sale in Gentry. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Popular neighborhoods include Edgewater Beach, Bay Ridge, Cape St. John, West Annapolis, and Admiral Heights. This map is refreshed with the newest listings in Gentry every 15 minutes.

Find your dream home in Gentry 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 Gentry are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Gentry. If you're looking to sell your home in the Gentry area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Gentry with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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