21550, MD homes for sale & real estate

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NEW 4 HRS AGO

ABOUT THIS HOME
21550, MD Homes for Sale
Check out the views from the deck and even inside!! Everything has been completely updated! It is being sold completely turnkey so just bring your toothbrushes and move right in. This is priced to sell so call today for a showing.

$260,000

2 beds1 bath520 sq ft

36 Jeffrey Ln Unit 6A, Oakland, MD 21550

$320 HOA • Built 1990

(866) 525-3466

COMING SOON

ABOUT THIS HOME
21550, MD Homes for Sale
Contractors, flippers, or anyone ready to put in the work—this one is for you. Just minutes outside of Oakland in a small, peaceful community, this 4-bedroom home offers a rare chance to create something special. Most of the materials needed to finish the remodel are already on-site, saving you both time and money. What’s left is the TLC and finishing touches that will bring it all together. Sitting on 1.12 flat acres—something hard to come by in this area—you’ll find a full tennis court ready for new life, a covered porch perfect for relaxing, and a private balcony off the owner’s suite that offers peaceful views. Inside, the layout has one finished bath

$170,000

4 beds3 baths2,288 sq ft

306 Shady Acre Ln, Oakland, MD 21550

1.12 acre lot • Car-dependent

(866) 525-3466

COMING SOON

ABOUT THIS HOME
21550, MD Homes for Sale
A magnificent waterfront retreat in The Reserve at Holy Cross on the shores of Deep Creek Lake, representing the pinnacle of lake life living. This incomparable estate captures the essence of refined waterfront with a private dock, expansive outdoor entertaining spaces, and tranquil lakeside ambiance. Featuring 7 total bedrooms, 5 of which are en-suites, this home was thoughtfully designed with privacy, comfort, and flexibility in mind. Nature and luxury converge in perfect harmony with beautifully landscaped grounds creating an unmatched backdrop for lakefront gatherings, comfort and peace of mind.

$3,600,000

7 beds6.5 baths5,681 sq ft

870 Holy Cross Dr, Oakland, MD 21550

1.32 acre lot • $167 HOA • 3 garage spots

(301) 387-2000

NEW 35 HRS AGO

ABOUT THIS HOME
21550, MD Homes for Sale
Welcome to "Latitude Adjustment", a 3-level townhome in the desirable Roman Ridge Community, perfectly located in the heart of Deep Creek Lake. This is an active short-term rental that sleeps 9 and averages $46k to $54k in annual rentals with an ADR of $380! 2025 already has 78 days booked for $30k that can be conveyed or canceled; the choice is yours! This 3 BR, 3.5 BA property is being sold turnkey after a complete refresh in 2022, including new high-end furnishings, luxury vinyl plank flooring, updated décor, accessories, bedding, and kitchenware, plus a modernized kitchen with granite counters and stainless steel appliances. Stylish, move-in ready, and rental-ready &mda

$475,000

3 beds3.5 baths1,820 sq ft

118 Roman Ridge Rd, Oakland, MD 21550

Cozy gas fireplace • Modernized kitchen • Granite counters

(443) 574-1600

NEW 35 HRS AGO

ABOUT THIS HOME
21550, MD Homes for Sale
If you are looking for a low maintenance home with stunning lake views, this is it. This condo offers two bedrooms and a wood burning fireplace. You are able to enjoy views of Deep Creek lake from almost every room. Centrally located to local restaurants, state parks, WISP Resort, and Deep Creek Lake. Call today to preview.

$250,000

2 beds1 bath660 sq ft

157 Jeffrey Ln Unit 21A, Oakland, MD 21550

Lake views • Centrally located • $320 HOA

(301) 387-4700

Property at 72 Cliff Dr, Oakland, MD 21550, 3 beds, 2 baths

$585,000

3 beds2 baths2,176 sq ft

72 Cliff Dr, Oakland, MD 21550

(301) 387-2000

Property at 78 Mountainside Ct, Oakland, MD 21550, 5 beds, 3 baths

$950,000

5 beds3 baths3,492 sq ft

78 Mountainside Ct, Oakland, MD 21550

(301) 387-4700

Property at 220 N 11th St, Oakland, MD 21550, 4 beds, 2.5 baths

$474,900

4 beds2.5 baths3,159 sq ft

220 N 11th St, Oakland, MD 21550

(301) 387-2000

$65,000

— beds— baths792 sq ft

809 N St, Oakland, MD 21550

(301) 387-2000

Property at 565 Glendale Rd Unit 210A, Oakland, MD 21550, 1 bed, 1 bath

$175,000

1 bed1 bath382 sq ft

565 Glendale Rd Unit 210A, Oakland, MD 21550

(301) 387-2000

Property at 272 Mccomas Beach Ter, Oakland, MD 21550, 5 beds, 3.5 baths

$1,690,000

5 beds3.5 baths2,448 sq ft

272 Mccomas Beach Ter, Oakland, MD 21550

(301) 387-2000

Property at 20160 Garrett Hwy Unit G507, Oakland, MD 21550, 2 beds, 1 bath

$429,000

2 beds1 bath912 sq ft

20160 Garrett Hwy Unit G507, Oakland, MD 21550

(301) 387-2000

Property at 197 Black Angus Dr, Oakland, MD 21550, 5 beds, 3.5 baths

$2,600,000

5 beds3.5 baths4,156 sq ft

197 Black Angus Dr, Oakland, MD 21550

(301) 387-2000

Property at 1989 Lake Shore Dr, Oakland, MD 21550, 4 beds, 3.5 baths

$1,699,000

4 beds3.5 baths3,008 sq ft

1989 Lake Shore Dr, Oakland, MD 21550

(301) 387-2000

Property at 1010 Holy Cross Dr, Oakland, MD 21550, 8 beds, 8.5 baths

$5,150,000

8 beds8.5 baths10,300 sq ft

1010 Holy Cross Dr, Oakland, MD 21550

(301) 387-2000

Property at 127 S Oakhall Dr, Oakland, MD 21550, 4 beds, 2 baths

$310,000

4 beds2 baths2,174 sq ft

127 S Oakhall Dr, Oakland, MD 21550

Property at 2311 Boy Scout Rd, Oakland, MD 21550, 4 beds, 3 baths

$1,699,900

4 beds3 baths3,517 sq ft

2311 Boy Scout Rd, Oakland, MD 21550

(301) 387-2000

Property at 66 Paradise Ridge Rd, Oakland, MD 21550, 4 beds, 4 baths

$650,000

4 beds4 baths2,550 sq ft

66 Paradise Ridge Rd, Oakland, MD 21550

(410) 413-3575

Property at 88 Knoll Crest Hts, Oakland, MD 21550, 3 beds, 2.5 baths

$219,000

3 beds2.5 baths1,867 sq ft

88 Knoll Crest Hts, Oakland, MD 21550

(301) 387-2000

Property at 1720 Pysell Crosscut Rd, Oakland, MD 21550, 5 beds, 5.5 baths

$999,999

5 beds5.5 baths8,000 sq ft

1720 Pysell Crosscut Rd, Oakland, MD 21550

(301) 387-4700

Property at 425 Mountainview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$829,000

3 beds2.5 baths1,586 sq ft

425 Mountainview Dr, Oakland, MD 21550

(301) 387-4700

Property at 16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550, 4 beds, 3 baths

$589,000

4 beds3 baths2,700 sq ft

16 Silver Ridge Ct Unit 41/2, Oakland, MD 21550

(301) 387-2000

Property at 104 Pine Top Trl, Oakland, MD 21550, 4 beds, 4.5 baths

$425,000

4 beds4.5 baths1,596 sq ft

104 Pine Top Trl, Oakland, MD 21550

(301) 387-8300

Property at 503 E Alder St E, Oakland, MD 21550, 4 beds, 2 baths

$270,991

4 beds2 baths2,496 sq ft

503 E Alder St E, Oakland, MD 21550

(703) 763-1950

Property at 98 Bear Run Rd, Oakland, MD 21550, 3 beds, 2 baths

$268,900

3 beds2 baths1,080 sq ft

98 Bear Run Rd, Oakland, MD 21550

(304) 788-5540

Property at 565 Glendale Rd #116, Oakland, MD 21550, 1 bed, 1 bath

$179,000

1 bed1 bath484 sq ft

565 Glendale Rd #116, Oakland, MD 21550

(301) 387-2000

Property at 5202 Hutton Rd, Oakland, MD 21550, 3 beds, 1 bath

$239,000

3 beds1 bath1,199 sq ft

5202 Hutton Rd, Oakland, MD 21550

(301) 387-2000

Property at 1056 Sunrise Dr, Oakland, MD 21550, 4 beds, 2.5 baths

$295,000

4 beds2.5 baths1,528 sq ft

1056 Sunrise Dr, Oakland, MD 21550

(301) 387-2000

Property at 415 Nazelrod Rd, Oakland, MD 21550, 4 beds, 5 baths

$3,249,000

4 beds5 baths6,036 sq ft

415 Nazelrod Rd, Oakland, MD 21550

(301) 387-2000

Property at 1875 Pysell Crosscut Rd, Oakland, MD 21550, 5 beds, 5 baths

$818,000

5 beds5 baths3,664 sq ft

1875 Pysell Crosscut Rd, Oakland, MD 21550

(301) 387-4700

Property at 939 Glendale Rd #19, Oakland, MD 21550, 3 beds, 2 baths

$785,000

3 beds2 baths1,432 sq ft

939 Glendale Rd #19, Oakland, MD 21550

(410) 241-3725

Property at 198 Grandview Dr, Oakland, MD 21550, 3 beds, 3 baths

$825,000

3 beds3 baths2,744 sq ft

198 Grandview Dr, Oakland, MD 21550

(410) 224-4400

Property at 1260 Gnegy Church Rd, Oakland, MD 21550, 3 beds, 3 baths

$449,000

3 beds3 baths4,420 sq ft

1260 Gnegy Church Rd, Oakland, MD 21550

(301) 387-2000

Property at 1570 Garrett Rd, Oakland, MD 21550, 3 beds, 1 bath

$300,000

3 beds1 bath1,408 sq ft

1570 Garrett Rd, Oakland, MD 21550

(301) 387-8300

Property at 60 Gorman St, Oakland, MD 21550, 2 beds, 1 bath

$110,000

2 beds1 bath1,488 sq ft

60 Gorman St, Oakland, MD 21550

(410) 740-7100

Property at 565 Glendale Rd Unit 106 B, Oakland, MD 21550, 1 bed, 1 bath

$269,900

1 bed1 bath— sq ft

565 Glendale Rd Unit 106 B, Oakland, MD 21550

(301) 387-2000

Property at 873 Paradise Hts, Oakland, MD 21550, 5 beds, 4 baths

$829,000

5 beds4 baths2,934 sq ft

873 Paradise Hts, Oakland, MD 21550

(301) 387-2000

Property at 126 Leo Friend Rd, Mchenry, MD 21550, 4 beds, 3 baths

$529,900

4 beds3 baths2,235 sq ft

126 Leo Friend Rd, Mchenry, MD 21550

(301) 387-2000

Property at 163 Crestview Dr, Oakland, MD 21550, 3 beds, 2.5 baths

$335,000

3 beds2.5 baths1,416 sq ft

163 Crestview Dr, Oakland, MD 21550

(301) 387-2000

Property at 17 Driftwood Ln, Oakland, MD 21550, 3 beds, 2 baths

$345,000

3 beds2 baths2,092 sq ft

17 Driftwood Ln, Oakland, MD 21550

(301) 387-2000

Property at 511 E Green St, Oakland, MD 21550, 4 beds, 2 baths

$309,000

4 beds2 baths1,880 sq ft

511 E Green St, Oakland, MD 21550

(301) 387-4700

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Average home prices near 21550, MD

Cities

Zip Codes

21550, MD real estate trends

$385K

Sale price

+17.6%
since last year

$230

Sale $/sq ft

+13.3%
since last year

Under list price

5.5%

Days on market

Down payment

—

Total homes sold

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