Vintage homes for sale & real estate in 20816, MD

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ABOUT THIS HOME
Vintage Home for sale in 20816, MD:
Welcome to 5138 Massachusetts Avenue, an expanded and beautifully updated home offering generous living space in an exceptionally convenient Bethesda location just minutes from Washington, DC. Thoughtfully improved throughout, this home combines classic character with modern updates and a flexible floor plan designed to accommodate a variety of lifestyles. At the heart of the home is the updated kitchen, complemented by a spacious family room addition that expands the main-level living and entertaining space. Refinished hardwood floors add warmth and character, while updated bathrooms throughout provide a fresh, move-in-ready feel. The expanded footprint creates comfortable, well-proportion

$2,295,000

5 beds6 baths4,100 sq ft

5138 Massachusetts Ave, Bethesda, MD 20816

Garage • Built 1934

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ABOUT THIS HOME
Vintage Home for sale in 20816, MD:
Welcome to 5810 Overlea Road, a remarkable five-bedroom, two-full-and-two-half-bath residence in Bethesda's coveted Sumner neighborhood, where timeless mid-century modern architecture meets extraordinary privacy and beautifully curated natural surroundings. Lovingly maintained by the same owners for more than three decades, this one-of-a-kind home reflects a deep appreciation for landscape, design, and indoor-outdoor living. Inspired by extensive travels abroad, the owners thoughtfully cultivated the property's already established grounds to create a tranquil retreat that feels worlds away while remaining just minutes from the heart of Bethesda and Washington, D. C. Set within graceful land

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5 beds4 baths3,952 sq ft

5810 Overlea Rd, Bethesda, MD 20816

Gas fireplace • Pool • Built 1957

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ABOUT THIS HOME
Vintage Home for sale in 20816, MD:
Welcome to 5003 Sentinel Drive #21, a beautifully updated residence in the desirable Sumner Court Condominiums. The home features warm wood flooring throughout—including distinctive olive wood flooring in one room—updated recessed lighting, new windows, granite countertops, and stainless-steel appliances. Step outside to a private patio that provides an inviting space for relaxing, dining, or entertaining. Sumner Court offers an outdoor swimming pool, children’s playground, grilling and picnic area, community gazebo, and convenient parking. Just next door, The Shops at Sumner Place places everyday conveniences and popular dining destinations practically at your doorstep, i

$335,000

2 beds1 bath1,011 sq ft

5003 Sentinel Dr #21, Bethesda, MD 20816

Shopping center • Community amenities • Olive wood flooring

(202) 643-4687

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ABOUT THIS HOME
Vintage Home for sale in 20816, MD:
Charming, sunny, and full of personality, this expanded and beautifully updated four-bedroom Colonial offers wonderful curb appeal, generous living spaces, and designer touches throughout. The main level features hardwood floors, plantation shutters, and a gracious living room with a fireplace. The sunny white kitchen has granite countertops, abundant cabinetry, and a breakfast bar and opens to the dining room, creating a natural flow for gatherings large and small. A comfortable family room steps out to the large flagstone patio. Just off the living room, an inviting screened porch with double ceiling fans and an overhead heater extends the living space outdoors and overlooks the patio, go

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4 beds4 baths2,800 sq ft

5115 Baltimore Ave, Bethesda, MD 20816

Plantation shutters • Screened porch • Flagstone patio

ABOUT THIS HOME
Vintage Home for sale in 20816, MD:
Better than new, this exceptional custom-built six-bedroom home in the Westbrook Neighborhood checks every box without feeling like it tried. Planned and developed from the ground up, it provides more than 4,650 square feet of generous living spaces. Thoughtfully curated interiors with impeccable craftsmanship, every finish has already been chosen, every decision has already been made. All that's left is to move in and begin living. Hints of the incredible attention to detail is felt the moment you pull up. The crisp facade is bright and cheery, highlighted by professionally landscaped lawn, flowering plantings, and a stone approach. Once inside, the home unfolds naturally, with nine-foot c

$2,495,000

6 beds4 baths4,650 sq ft

5110 Baltimore Ave, Bethesda, MD 20816

Private backyard • Screened porch • Oversized windows

(301) 298-1001

Property at 4629 River Rd, Bethesda, MD 20816, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths1,764 sq ft

4629 River Rd, Bethesda, MD 20816

(202) 966-1400

Property at 5106 Duvall Dr, Bethesda, MD 20816, 4 beds, 3 baths

$1,550,000

4 beds3 baths2,800 sq ft

5106 Duvall Dr, Bethesda, MD 20816

(202) 333-3320

Property at 6117 Overlea Rd, Bethesda, MD 20816, 4 beds, 2.5 baths

$1,499,000

4 beds2.5 baths2,080 sq ft

6117 Overlea Rd, Bethesda, MD 20816

(202) 944-5000

Property at 5910 Overlea Rd, Bethesda, MD 20816, 6 beds, 5 baths

$1,725,000

6 beds5 baths2,812 sq ft

5910 Overlea Rd, Bethesda, MD 20816

(202) 234-3344

Property at 6414 Brookes Ln, Bethesda, MD 20816, 3 beds, 2.5 baths

$1,245,000

3 beds2.5 baths1,685 sq ft

6414 Brookes Ln, Bethesda, MD 20816

(301) 967-3344

Property at 5605 Overlea Rd, Bethesda, MD 20816, 5 beds, 4 baths

$2,495,000

5 beds4 baths4,582 sq ft

5605 Overlea Rd, Bethesda, MD 20816

(301) 983-6400

Property at 5016 Scarsdale Rd, Bethesda, MD 20816, 5 beds, 3 baths

$1,495,000

5 beds3 baths3,265 sq ft

5016 Scarsdale Rd, Bethesda, MD 20816

(301) 967-3344

Property at 4900 Greenway Dr, Bethesda, MD 20816, 3 beds, 2 baths

Contact for price

3 beds2 baths1,710 sq ft

4900 Greenway Dr, Bethesda, MD 20816

Property at 5301 Westbard Cir #419, Bethesda, MD 20816, 2 beds, 2 baths

$520,000

2 beds2 baths1,312 sq ft

5301 Westbard Cir #419, Bethesda, MD 20816

(301) 652-0643

Property at 5301 Westbard Cir #334, Bethesda, MD 20816, 3 beds, 2 baths

$485,000

3 beds2 baths1,896 sq ft

5301 Westbard Cir #334, Bethesda, MD 20816

(301) 298-1001

Property at 5301 Westbard Cir #328, Bethesda, MD 20816, 1 bed, 1 bath

$245,000

1 bed1 bath993 sq ft

5301 Westbard Cir #328, Bethesda, MD 20816

(410) 321-8800

Property at 5301 Westbard Cir #224, Bethesda, MD 20816, 1 bed, 1 bath

$255,000

1 bed1 bath951 sq ft

5301 Westbard Cir #224, Bethesda, MD 20816

(202) 319-1303

Property at 5301 Westbard Cir #208, Bethesda, MD 20816, 2 beds, 2 baths

$409,900

2 beds2 baths1,302 sq ft

5301 Westbard Cir #208, Bethesda, MD 20816

(202) 243-7700

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EARLY ACCESSCOMPASS COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
A classic Washington residence with gracious proportions, architectural character and remarkable potential in AU Park, offered for the first time in nearly 50 years. This handsome brick home on Massachusetts Avenue has a distinctive stone-arched entrance and welcoming covered front porch and is a surprisingly spacious home with approximately 3,200 square feet, including approximately 2,450 square feet above grade, with four bedrooms, three full baths, a two-car garage and a deep 6,000-square-foot lot. The wide entry foyer introduces the home's wonderful scale and original character. Arched openings lead to generously proportioned living and dining rooms with hardwood floors, abundant natura

$1,350,000

4 beds4 baths2,450 sq ft

4939 Massachusetts Ave NW, Washington, DC 20016

Covered front porch • Glass paned door • Hardwood floors

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ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
Welcome to 4420 Chesapeake St NW, a beautifully updated detached single-family home offering exceptional space, character, and outdoor living in sought-after AU Park. This home features a large fenced backyard, rear patio, private upper-level deck, and detached one-car garage—all just minutes from Tenleytown, Metro, shopping, dining, and everyday conveniences. Step through the bright vestibule into a welcoming main level where original charm blends seamlessly with thoughtful modern updates. The spacious living room features large windows and a cozy fireplace, while the separate dining room flows into an updated kitchen with white cabinetry, stainless steel appliances, and direct acces

$1,474,900

5 beds2 baths1,992 sq ft

4420 Chesapeake St NW, Washington, DC 20016

Updated kitchen • Finished lower level • Tree-lined setting

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
Behind 4414 Lowell Street's classic Tudor façade lies an unexpectedly expansive residence. Originally developed in the early 1920s with impressive, well-built single-family homes, Wesley Heights remains one of Northwest DC’s most desirable neighborhoods. Recognized as one of the first planned communities in the United States, Wesley Heights was thoughtfully designed with large, rectangular lots, a variety of architectural materials, and an emphasis on craftsmanship and detail. Today, the neighborhood retains its distinctive character with a beautiful collection of Tudors, Colonials, bungalows, and Cape Cods. Continuing this tradition, 4414 Lowell Street NW is a han

$2,695,000

5 beds4.5 baths3,600 sq ft

4414 Lowell St NW, Washington, DC 20016

Formal dining room • Large renovated bath • 7,500 sq ft lot

(202) 387-5555

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
Spacious Two-Bedroom at The Towers Condominium Welcome to The Towers Condominium, where spacious living meets exceptional full-service convenience. This approximately 1,100-square-foot two-bedroom, one-and-a-half-bath residence offers a comfortable and inviting floor plan with a generous dining area, updated modern kitchen, and ample closet space throughout. Enjoy the ease of full-service condominium living with a doorman and 24 hour front desk, along with an impressive selection of on-site amenities including a gym, grocery store, flower shop, library, beauty shop, community room, tennis court, and in-ground swimming pool. Garage parking adds an extra level of convenience, with bus service

$375,000

2 beds1.5 baths1,146 sq ft

4201 Cathedral Ave NW Unit 202E, Washington, DC 20016

24 hour front desk • Ample closet space • Generous dining area

(202) 966-1400

ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
Experience the perfect harmony of timeless elegance and contemporary living at 4611 43rd Place NW. Brought to life by the expert team at Dogwood Restoration LLC, this exceptional residence is being transformed into a sophisticated home offering five bedrooms and four and a half bathrooms across four expansive levels and two car parking. Upon entering, you are greeted by a gracious living area that flows effortlessly into an inviting and spacious dining room, creating the perfect setting for both entertaining guests and enjoying family meals. At the heart of the home lies the beautifully designed kitchen, featuring Thermador appliances, a generous island, a stylish wine bar, and seamless acc

$1,995,000

5 beds4.5 baths3,254 sq ft

4611 43rd Pl NW, Washington, DC 20016

Private rooftop deck • Spacious dining room • Built 1925

(202) 448-9002

ABOUT THIS HOME
Vintage Home for sale in 20816, DC:
A wonderful opportunity in the heart of Wesley Heights. This spacious and sun-filled 2-bedroom, 2-bath corner residence offers approximately 1,090 square feet of comfortable living space in a quiet, well-established condominium building. Natural light fills the home from its corner exposure, while wood floors throughout create a warm and inviting feel. The generous floor plan features two well-proportioned bedrooms, two full baths, and excellent closet and storage space. Enjoy the convenience of one outdoor parking space and utilities included in the monthly condominium fee, adding meaningful value and simplicity to everyday living. Residents also enjoy an on-site fitness center, front desk

$245,000

2 beds2 baths1,090 sq ft

4200 Cathedral Ave NW #106, Washington, DC 20016

Quiet atmosphere • Front desk service • Convenient to dining

(240) 497-1700

Property at 6500 Pyle Rd, Bethesda, MD 20817, 4 beds, 2.5 baths

$1,430,000

4 beds2.5 baths2,815 sq ft

6500 Pyle Rd, Bethesda, MD 20817

(301) 304-8444

Property at 4811 Albemarle St NW, Washington, DC 20016, 4 beds, 4.5 baths

$1,895,000

4 beds4.5 baths5,250 sq ft

4811 Albemarle St NW, Washington, DC 20016

(301) 298-1001

Property at 4412 Butterworth Pl NW, Washington, DC 20016, 3 beds, 3.5 baths

$1,300,000

3 beds3.5 baths1,918 sq ft

4412 Butterworth Pl NW, Washington, DC 20016

(877) 366-2213

Property at 6163 Kellogg Dr, Mclean, VA 22101, 4 beds, 3 baths

$1,349,000

4 beds3 baths2,817 sq ft

6163 Kellogg Dr, Mclean, VA 22101

(703) 760-8880

Property at 4723 Upton St NW, Washington, DC 20016, 5 beds, 3.5 baths

$1,995,000

5 beds3.5 baths3,024 sq ft

4723 Upton St NW, Washington, DC 20016

(202) 944-5000

Property at 4200 Cathedral Ave NW #1009, Washington, DC 20016, 1 bed, 1 bath

$229,000

1 bed1 bath765 sq ft

4200 Cathedral Ave NW #1009, Washington, DC 20016

(202) 483-6300

Property at 3036 New Mexico Ave NW, Washington, DC 20016, 4 beds, 4 baths

$1,750,000

4 beds4 baths2,277 sq ft

3036 New Mexico Ave NW, Washington, DC 20016

Property at 5515 Trent St, Chevy Chase, MD 20815, 3 beds, 3 baths

$1,125,000

3 beds3 baths2,190 sq ft

5515 Trent St, Chevy Chase, MD 20815

(301) 299-6000

Property at 4940 Indian Ln NW, Washington, DC 20016, 4 beds, 4.5 baths

$9,995,000

4 beds4.5 baths6,600 sq ft

4940 Indian Ln NW, Washington, DC 20016

(202) 975-0873

Property at 5611 Belmont Ave, Chevy Chase, MD 20815, 4 beds, 3 baths

$1,400,000

4 beds3 baths3,039 sq ft

5611 Belmont Ave, Chevy Chase, MD 20815

(202) 386-6330

Property at 4347 Hawthorne St NW, Washington, DC 20016, 5 beds, 6.5 baths

$4,995,000

5 beds6.5 baths7,500 sq ft

4347 Hawthorne St NW, Washington, DC 20016

(202) 975-0873

Property at 4700 Sedgwick St NW, Washington, DC 20016, 3 beds, 2 baths

$1,150,000

3 beds2 baths1,695 sq ft

4700 Sedgwick St NW, Washington, DC 20016

(202) 386-6330

Property at 4606 Nottingham Dr, Chevy Chase, MD 20815, 3 beds, 3.5 baths

$1,400,000

3 beds3.5 baths3,140 sq ft

4606 Nottingham Dr, Chevy Chase, MD 20815

Property at 4201 Cathedral Ave NW Unit 220E, Washington, DC 20016, 1 bed, 1 bath

$270,000

1 bed1 bath898 sq ft

4201 Cathedral Ave NW Unit 220E, Washington, DC 20016

Vintage Homes for Sale in 20816

There are currently 18 vintage homes for sale in 20816 at a median listing price of $1.29M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 20816 stay on the market for 39 days and receive 5 offers. This map is refreshed with the newest listings in 20816 every 15 minutes.

In the past month, 17 homes have been sold in 20816. In addition to houses in 20816, there were also 24 condos, 8 townhouses, and 0 multi-family units for sale in 20816 last month. Find your dream home in 20816 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 20816 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 20816. If you're looking to sell your home in the 20816 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 20816 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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