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Oakland, MD Homes for Sale — Page 3 | Realty.com

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Homes for Sale in Oakland, MD

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24 of 75 Listings

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24 of 75 Listings

Price Reduced47

Homes for Sale in Oakland, MD

Hide Map

24 of 75 Listings

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Homes for Sale in Oakland, MD

24 of 75 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced47

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Active

$384,500

3 bd · 2 ba · 2,476 sqft

321 Deer Park Hotel Rd, Oakland, MD

Pamela Debnam · Houwzer, LLC

Price Reduced44Active

$1,425,000

3 bd · 2 ba · 1,695 sqft

187 Lower Penn Point Dr, Oakland, MD

Amy Webster Mangum · Railey Realty, Inc.

Price Reduced61Active

$599,999

5 bd · 5 ba · 3,300 sqft

308 Winding Trail Ln #11B, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

145Active

$3,249,000

4 bd · 5 ba · 6,036 sqft

415 Nazelrod Rd, Oakland, MD

Larry E Smith · Railey Realty, Inc.

49Active

$379,500

1 bd · 1 ba · 636 sqft

20160 Garrett Hwy #C307, Oakland, MD

Justin D Liller · Railey Realty, Inc.

Price Reduced86Active

$549,000

5 bd · 4 ba · 3,542 sqft

428 Sam Snead Cir, Oakland, MD

Justin D Liller · Railey Realty, Inc.

29Active

$195,000

3 bd · 1 ba · 1,382 sqft

2918 Oakland Sang Run Rd, Oakland, MD

Andrew L Eiswert · Railey Realty, Inc.

Price Reduced59Active

$1,089,000

4 bd · 5 ba · 2,656 sqft

122 Woodlands Hill Ln, Oakland, MD

Brian P Homberg · Taylor-Made Deep Creek Sales

Price Reduced24Active

$374,900

2 bd · 1 ba · 700 sqft

560 Glendale Rd, Oakland, MD

Lauren McCann · Railey Realty, Inc.

Price Reduced27Active

$299,000

1 bd · 1 ba · 550 sqft

20160 Garrett Hwy #H706, Oakland, MD

James Calvin Matthews · Taylor-Made Deep Creek Sales

Price Reduced48Active

$350,000

5 bd · 2 ba · 3,660 sqft

321 N 3rd St, Oakland, MD

Christina M Ford · CENTURY 21 New Millennium

Price Reduced63Active

$850,000

5 bd · 5 ba · 4,284 sqft

251 Robinwood Dr, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

58Active

$745,000

5 bd · 3 ba · 2,640 sqft

638 Glendale Rd, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

Price Reduced43Active

$1,962,000

4 bd · 2 ba · 2,190 sqft

83 Bethlehem Rd, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

31Active

$224,900

1 bd · 1 ba · 0 sqft

206 Mayhew Inn Rd, Oakland, MD

Thomas Jay Quinn · Taylor-Made Deep Creek Sales

22Active

$294,999

2 bd · 1 ba · 2,344 sqft

135 Jeffrey Ln #19a, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

55Active

$329,900

1 bd · 1 ba · 496 sqft

565 Glendale Rd #125, Oakland, MD

Jonathan D Bell · Railey Realty, Inc.

Price Reduced65Active

$279,000

3 bd · 3 ba · 2,242 sqft

163 Mitchell Dr, Oakland, MD

Andrew L Eiswert · Railey Realty, Inc.

Price Reduced53Active

$849,900

3 bd · 3 ba · 2,368 sqft

164 Grandview Dr, Oakland, MD

Elizabeth S Spiker Holcomb · Taylor-Made Deep Creek Sales

57Active

$219,000

1 bd · 2 ba · 912 sqft

141 Montana Ln, Oakland, MD

Larry E Smith · Railey Realty, Inc.

38Active

$629,000

4 bd · 3 ba · 2,280 sqft

231 Santa Fe Trl, Oakland, MD

Jay L Ferguson · Taylor-Made Deep Creek Sales

Price Reduced97Active

$1,059,900

4 bd · 6 ba · 3,032 sqft

52 Dam View Dr, Oakland, MD

Michael Fenton · Railey Realty, Inc.

Price Reduced30Active

$199,000

4 bd · 3 ba · 2,390 sqft

62 Wild Turkey Ct, Oakland, MD

Melvin E Smith Jr. · 1 Real Estate Source LLC

Price Reduced32Active

$292,000

2 bd · 1 ba · 780 sqft

565 Glendale Rd #B206, Oakland, MD

Carlos A Espinoza · Jason Mitchell Group

1 2 3 4

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-11-12 15:34:40 UTC

Oakland housing market

October 2026

Homes that sold · County records, as of Oct 27, 2026

Median sale price: $451,261$185,000–$537,000 typical range
Price per sq. ft.: $328
Sales: 25
Paid in cash: 52.0%

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $454,500
Homes for sale: 76

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,536 sq. ft.

Oakland, MD community profile

Population: 1,810
Median income: $67,177
Housing units: 929
People per sq. mi.: 8.8
Area: 205.5 sq. mi.

Source: HJN community data

Explore Oakland homes

By price

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By type

Single-Family Homes

Nearby areas

ZIP codes

21541 (84)
21550 (82)
21561 (37)
21562 (18)
21539 (8)
21521 (6)
21536 (6)
21520 (5)

Cities

Mc Henry (84)
Swanton (37)
Westernport (16)
Lonaconing (8)
Barton (6)
Accident (5)
Grantsville (5)
Friendsville (4)

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-11-12 15:34:40 UTC

Nearby areas

ZIP codes

21541 (84)
21550 (82)
21561 (37)
21562 (18)
21539 (8)
21521 (6)
21536 (6)
21520 (5)

Cities

Mc Henry (84)
Swanton (37)
Westernport (16)
Lonaconing (8)
Barton (6)
Accident (5)
Grantsville (5)
Friendsville (4)

Oakland, MD community profile

Population: 1,810
Median income: $67,177
Housing units: 929
People per sq. mi.: 8.8
Area: 205.5 sq. mi.

Source: HJN community data

Oakland housing market

October 2026

Homes that sold · County records, as of Oct 27, 2026

Median sale price: $451,261$185,000–$537,000 typical range
Price per sq. ft.: $328
Sales: 25
Paid in cash: 52.0%

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $454,500
Homes for sale: 76

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,536 sq. ft.