Oakland Hill, MD homes for sale & real estate

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ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Beautifully Updated 4BR Colonial in Highly Sought-After Cape St. Claire! This move-in ready home has been thoughtfully modernized and offers an inviting, open flow throughout. The remodeled kitchen features updated flooring and a wall removed to create a bright, seamless connection to the family room—perfect for everyday living, hosting, and entertaining. From the kitchen, step directly onto the screened-in, covered back porch, an ideal spot to relax year-round, which leads to a spacious open deck and fenced backyard. Upstairs, you’ll find four generously sized bedrooms with great natural light, along with well-appointed bathrooms featuring ceramic tile. The finished basement pr

$670,000

4 beds2.5 baths1,888 sq ft

1181 Ramblewood Dr, Annapolis, MD 21409

9,000 sq ft lot • Garage • Built 1989

(410) 312-0000

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Make your own dream home in the charming and water-privileged community of Cape St Claire! This delightful rancher of 4 main floor bedrooms and 2.5 baths. Nestled on a large lot, the property offers plenty of outdoor space for relaxation and play. Plus, with a full basement, the possibilities for additional storage or recreational space are endless. The large deck across the back of the home makes for easy entertainment. The 2 car garage keeps your cars out of the elements. Don’t miss out on this incredible opportunity to own a beautiful home in a fantastic location!

$480,000

4 beds2.5 baths1,764 sq ft

1199 Ramblewood Dr, Annapolis, MD 21409

0.41 acre lot • 2 garage spots • Community pool

(410) 544-4000

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Welcome to 1272 Seminole Drive, an end-unit townhouse tucked among the trees in The Bluffs at Deep Creek in Arnold. This location offers quick access to College Parkway, making trips to Annapolis, Baltimore, Washington D. C. , and the Eastern Shore incredibly convenient. The neighborhood includes sought-after amenities such as a community pool, basketball courts, and a playground. Step inside to a bright, generously sized living room featuring a newly added electric fireplace, modern recessed lighting, and the convenience of a newly installed stackable washer/dryer. The adjoining kitchen offers an inviting eat-in dining nook, and the space was recently refreshed with a custom wood accent wa

$425,000

3 beds2.5 baths1,586 sq ft

1272 Seminole Dr, Arnold, MD 21012

$165 HOA • Community pool • Built 1991

(410) 263-8686

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Experience Annapolis living at its best in this move-in-ready Broadneck Colonial nestled within the waterfront community of Cape St. Claire. This 4-bedroom, 3.5-bathroom home offers approximately 2,525 square feet of living space, including a fully finished lower level. Step inside to discover refinished oak hardwood floors flowing throughout the main level, a bright and open layout, and recessed lighting that enhances the home’s natural warmth. The kitchen features stainless steel appliances and opens to the family room with a cozy wood-burning fireplace. Sliding glass doors lead to the rear deck and fenced backyard, perfect for outdoor entertaining. The primary suite boasts a privat

$619,000

4 beds3.5 baths2,667 sq ft

810 Chestnut Tree Dr, Annapolis, MD 21409

Multiple beaches • Walk-in closet • Three marinas

(410) 263-8686

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Welcome to 932 Hilltop Road, where timeless elegance meets modern luxury in the desirable Shore Acres Estates community, located within the coveted Broadneck School District. Nestled on a serene . 85-acre lot among a limited collection of executive-style homes, this 6-bedroom, 4½-bathroom brick Colonial offers nearly 6,000 total square feet of refined living space designed for comfort, style, and functionality. Step inside to discover an open and airy main level featuring new and refinished hardwood floors throughout, creating a seamless flow between rooms. The chef’s kitchen boasts stainless steel appliances, a premium island with a gas cooktop, double oven, tons of counter an

$1,295,000

6 beds4.5 baths5,865 sq ft

932 Hilltop Rd, Arnold, MD 21012

0.85 acre lot • 2 garage spots • Built 2004

(410) 224-3600

Property at 1182 Palmwood Ct, Arnold, MD 21012, 3 beds, 2 baths

$410,000

3 beds2 baths1,614 sq ft

1182 Palmwood Ct, Arnold, MD 21012

(410) 745-2596

Property at 599 Oakland Hills Dr Unit 3A, Arnold, MD 21012, 3 beds, 2 baths

$373,900

3 beds2 baths1,770 sq ft

599 Oakland Hills Dr Unit 3A, Arnold, MD 21012

(410) 255-3690

Property at 1138 Ramblewood Dr, Annapolis, MD 21409, 3 beds, 2.5 baths

$680,000

3 beds2.5 baths1,925 sq ft

1138 Ramblewood Dr, Annapolis, MD 21409

(410) 224-2200

Property at 975 Phillips Dr, Arnold, MD 21012, 3 beds, 2.5 baths

$1,900,000

3 beds2.5 baths2,731 sq ft

975 Phillips Dr, Arnold, MD 21012

Property at 478 Bay Green Dr, Arnold, MD 21012, 4 beds, 2.5 baths

$684,900

4 beds2.5 baths2,164 sq ft

478 Bay Green Dr, Arnold, MD 21012

(410) 729-7700

Property at 628 Southern Hills Dr Unit B, Arnold, MD 21012, 2 beds, 2 baths

$312,900

2 beds2 baths972 sq ft

628 Southern Hills Dr Unit B, Arnold, MD 21012

(410) 255-0000

Property at 1247 Ramblewood Dr, Annapolis, MD 21409, 4 beds, 2.5 baths

$555,000

4 beds2.5 baths1,728 sq ft

1247 Ramblewood Dr, Annapolis, MD 21409

(443) 292-6767

Property at 1447 Falcon Nest Ct #45, Arnold, MD 21012, 3 beds, 3 baths

$460,000

3 beds3 baths2,012 sq ft

1447 Falcon Nest Ct #45, Arnold, MD 21012

(410) 729-7700

Property at 921 Lake Dr, Arnold, MD 21012, 3 beds, 3 baths

$1,650,000

3 beds3 baths3,629 sq ft

921 Lake Dr, Arnold, MD 21012

(443) 372-7171

Property at 624 Southern Hills Dr Unit B-2A, Arnold, MD 21012, 2 beds, 1 bath

$304,900

2 beds1 bath943 sq ft

624 Southern Hills Dr Unit B-2A, Arnold, MD 21012

(888) 838-9044

Property at 633 Baystone Ct, Annapolis, MD 21409, 3 beds, 2 baths

$439,900

3 beds2 baths1,868 sq ft

633 Baystone Ct, Annapolis, MD 21409

(410) 544-4000

Property at 686 Southern Hills Dr Unit D-4H, Arnold, MD 21012, 2 beds, 2 baths

$299,900

2 beds2 baths966 sq ft

686 Southern Hills Dr Unit D-4H, Arnold, MD 21012

(410) 260-2800

Property at 400 Colonial Ridge Ln, Arnold, MD 21012, 3 beds, 3 baths

$440,000

3 beds3 baths2,211 sq ft

400 Colonial Ridge Ln, Arnold, MD 21012

(410) 647-8000

Property at 1165 Green Holly Ct, Annapolis, MD 21409, 3 beds, 2 baths

$535,000

3 beds2 baths2,218 sq ft

1165 Green Holly Ct, Annapolis, MD 21409

(443) 274-1900

Property at 1167 Green Holly Dr, Annapolis, MD 21409

$160,000

— beds— baths— sq ft

1167 Green Holly Dr, Annapolis, MD 21409

(443) 274-1900

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NEW CONSTRUCTION

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Experience the best of waterfront living with this new construction on the Magothy River, set on over a half-acre with expansive, stunning views and exceptional natural beauty. Enjoy effortless access to the Chesapeake Bay and a design that celebrates relaxed coastal elegance and refined comfort. An open-concept floor plan connects the gourmet kitchen, dining, and family room—all oriented to capture the breathtaking river views. The chef-inspired kitchen features quartz countertops, a spacious island, and a walk-in pantry, creating the perfect space for entertaining. The family room centers around a beautiful fireplace, offering warmth and sophistication against a backdrop of panorami

$1,985,000

4 beds2.5 baths2,800 sq ft

920 Burnett Ave, Arnold, MD 21012

0.49 acre lot • 2 garage spots • Car-dependent

(410) 255-6650

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Great 3 level duplex home in Whispering Woods that backs to community playground. Original owner! Driveway fits 2 cars. 2023 roof! Both full bathrooms updated in 2021. Stainless steel appliances, granite counter tops, recessed lights, chair rail in dining room. All flooring installed in 2022. 9year old HVAC. Well maintained landscaped fenced in backyard with deck, swing and large shed. Easy access to Route 50 and Route 2. Minutes away to grocery stores, banks, coffee shops, cleaners and restaurants. A must see to believe. Set up a showing and bring us an offer. Thank you for showing.

$395,000

3 beds2 baths1,040 sq ft

1583 Star Pine Dr, Annapolis, MD 21409

3,500 sq ft lot • $31 HOA • Car-dependent

(410) 224-2200

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Welcome to your new home in Whispering Woods! This charming duplex offers practical living with off-street parking and a two-car driveway. Home is located on a no through, dead end Cul-de-sac street minimizing traffic. The main level living room leads to an open concept kitchen, and dining area, complete with a half bath and shared laundry. Enjoy direct access to a ground-level deck, a spacious fenced yard, and a storage shed. Upstairs you’ll find the master bedroom with a walk-in closet, a second bedroom with ample storage, and a full bathroom. The home features elegant engineered wood flooring, with tile in wet areas. Enjoy recent, extensive upgrades in this home. Highlights inclu

$346,000

2 beds1.5 baths1,060 sq ft

1553 Star Pine Dr, Annapolis, MD 21409

3,341 sq ft lot • $28 HOA • Car-dependent

(410) 267-9020

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Mortgage Rates Hit a 3-Year Low - The time to buy is NOW. New Roof Sept 2025! Discover the perfect blend of comfort and convenience in this charming single-family home, on a quiet cul-de-sac in a top-rated school district. Featuring newer flooring in the living and dining rooms, fresh carpet on the upper level, and a kitchen with updated appliances—ready for weeknight dinners or weekend gatherings! The light-filled living spaces flow effortlessly, creating the perfect backdrop for making memories. Upstairs, cozy bedrooms offer peaceful retreats at the end of the day. Outside is a nature lovers paradise. Enjoy morning coffee or evening barbecues on the rear deck while watching the bi

$579,000

4 beds2.5 baths1,824 sq ft

1256 Crowell Ct, Arnold, MD 21012

7,433 sq ft lot • $13 HOA • Garage

(410) 266-9005

ABOUT THIS HOME
Oakland Hill, MD Homes for Sale
Bring your vision and create your perfect home! Conveniently located minutes from Route 50, 97 and Route 2, this is fantastic opportunity to own a home for less than rent in a highly desirable location! This spacious, rarely available end unit townhome is one of the largest 2 level homes in the neighborhood, and can easily be THE BEST home in the neighborhood! Featuring 3 bedrooms and one full bath upstairs; with an extra walk-in closet in the Primary Bedroom that could easily be converted to a primary bathroom and still have ample closet space! The main level offers a laundry area, powder room, generous sized kitchen and living room, that walks out to a large fenced-in backyard, the side i

$345,000

3 beds1.5 baths1,496 sq ft

1512 Winterberry Dr, Arnold, MD 21012

3,715 sq ft lot • $50 HOA • Car-dependent

(443) 542-2251

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