12,226

Homes in ZIP Code 21550

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  • /42

    $175,000 Sold May 09, 2025

    603 Oak St, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1965

    Last Sold Summary

    • $146/SF
    • 49 Days On Market

    Current Estimated Value $176,352

    Last Listing Agent Andrew Orr The KW Collective

    603 Oak St, Oakland, MD 21550
    • /35

      Est $295,196 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,854 Sq Ft

      763 Pysell Crosscut Rd, Oakland, MD 21550

      763 Pysell Crosscut Rd, Oakland, MD 21550
  • /23

    $95,000

    • Land
    • 0.62 Acre
    • $153,226 per Acre

    0 Masters View, 6, Sang Run, MD 21541

    Over half an acre of land in available in the highly sought-after Biltmore community! This stunning lot offers access to public water and sewer, and borders the Lodestone Hale Irwin-designed golf course. All members of the Lakeside Park Master Association may enjoy access to the park's Picnic Pavilion and restrooms plus enjoy limited lake access! Perfectly located in the heart of Deep Creek.

    Michelle Clark Taylor Made Deep Creek Vacations & Sales

    0 Masters View, 6, Sang Run, MD 21541
  • /21

    $115,000 Sold Nov 03, 2025

    607 K St, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Built 1920

    Last Sold Summary

    • $86/SF
    • 213 Days On Market

    Last Listing Agent Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    607 K St, Oakland, MD 21550
    • /36

      Est $234,491 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,357 Sq Ft

      2607 Maryland Hwy, Oakland, MD 21550

      2607 Maryland Hwy, Oakland, MD 21550
  • /9

    $29,900 Pending

    • Land
    • 7.51 Acres
    • $3,981 per Acre

    18 Hoye Crest Rd, Oakland, MD 21550

    Discover this beautifully wooded 7.51-acre lot located in a scenic mountain development featuring the highest point in Maryland. With an approved 5-bedroom perc, this property is ready for your dream home or mountain getaway. Enjoy the peace and privacy of nature while still being part of an established community. Exceptionally priced at just $29,900!

    Kellyann Green Railey Realty, Inc.

    18 Hoye Crest Rd, Oakland, MD 21550
  • /7

    $115,000 Sold Dec 31, 2024

    25 Acres Lot D Bailiff Ln, Oakland, MD 21550

    • Land
    • 25 Acres
    • $4,600 per Acre

    Last Sold Summary

    • 20 Days On Market

    Last Listing Agent Mike Kennedy Railey Realty, Inc.

    25 Acres Lot D Bailiff Ln, Oakland, MD 21550
    • /43

      Est $329,253 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,120 Sq Ft

      37 Laurel Brook Dr, Oakland, MD 21550

      37 Laurel Brook Dr, Oakland, MD 21550
  • /68

    $1,199,990

    • 4 Beds
    • 6 Baths
    • 4,744 Sq Ft

    444 Woodlands Hill Ln, Oakland, MD 21550

    Welcome to 444 Woodlands Hill Ln, in Oakland, MD. Nestled in the private community of The View, this custom home offers stunning lake views in a serene, private setting. Centrally located less than 4 miles from Wisp while backing up to hundreds of acres of untouched forest, this property truly offers the best that Deep Creek Lake has to offer. This luxury home has been impeccably maintained as a

    Corbin Griffith Compass

    444 Woodlands Hill Ln, Oakland, MD 21550
  • /92

    $420,000 Sold Jul 03, 2025

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541

    • 3 Beds
    • 3 Baths
    • 2,380 Sq Ft
    • Built 1989

    Last Sold Summary

    • $176/SF
    • 45 Days On Market

    Current Estimated Value $442,016

    Last Listing Agent Jon Bell Railey Realty, Inc.

    26 Bright Passage Rd Unit 3C, McHenry, MD 21541
    • /37

      Est $245,396 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,112 Sq Ft

      139 S Oakhall Dr, Oakland, MD 21550

      139 S Oakhall Dr, Oakland, MD 21550
  • /15

    $39,000

    • Land
    • 2.57 Acres
    • $15,175 per Acre

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550

    2 lots (7 & 8) totaling 2.57 acres, on gently sloping wooded area. Nestled between Cannan Valley & Deep Creek Lake, this promises to be a perfect blend of convenience and tranquility. Nature surrounds you - the perfect spot for a cozy cabin! Call agent for more information!

    Julie Mead The KW Collective

    lots 7 & 8 (2.57 ac) Valley Rd, Oakland, MD 21550
  • /39

    $210,000 Sold Aug 01, 2025

    10 Laurel Brook Dr, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • Built 1989

    Last Sold Summary

    • 421 Days On Market

    Current Estimated Value $217,818

    Last Listing Agent Michael Cumerlato Jason Mitchell Group

    10 Laurel Brook Dr, Oakland, MD 21550
    • /56

      Est $318,665 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft

      47 Mount Pleasant Ln, Oakland, MD 21550

      47 Mount Pleasant Ln, Oakland, MD 21550
  • /23

    $44,900

    • Land
    • 0.59 Acre
    • $76,102 per Acre

    LOT 13 Bray Run Rd, 14, West Oakland, MD 21550

    Build your dream home or vacation retreat on this beautiful 0.59 acre lot in Bray Run! Just a short drive to the Deep Creek Lake area, you’ll have easy access to boating, paddling, fishing, and state park facilities. This ready to build site is part of a peaceful mountain community offering excellent amenities. Enjoy a playground, basketball court, scenic hiking trails, and the beauty of Bray Run

    Nicole Jackson Railey Realty, Inc.

    LOT 13 Bray Run Rd, 14, West Oakland, MD 21550
  • /20

    $240,000 Sold Jul 11, 2025

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550

    • Land
    • 0.36 Acre
    • $666,667 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Michael Fenton Railey Realty, Inc.

    0 Boston Post Rd Unit MDGA2009736, 14, West Oakland, MD 21550
    • /56

      Est $377,560 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,440 Sq Ft

      407 Bear Dr E, Oakland, MD 21550

      407 Bear Dr E, Oakland, MD 21550
  • /7

    $115,000

    • Land
    • 0.22 Acre
    • $522,727 per Acre

    125 N 2nd St, Oakland, MD 21550

    Picture perfect level town lot on the highly sought after North 2nd Street in Oakland. Build your dream home in on the last remaining homesite on this historic and charming street located close to everything this great town has to offer! As an amazing "Feel Good" bonus, the seller is donating all proceeds from the sale to the incredible HART for Animals, Inc!!!Their mission is to help save

    Andrew Eiswert Railey Realty, Inc.

    125 N 2nd St, Oakland, MD 21550
  • /31

    $70,000 Sold Apr 07, 2025

    99 Black Diamond Ct, Mc Henry, MD 21541

    • Land
    • 0.57 Acre
    • $122,807 per Acre

    Last Sold Summary

    • 29% Below List Price
    • 835 Days On Market

    Last Listing Agent Kathy Gibson Railey Realty, Inc.

    99 Black Diamond Ct, Mc Henry, MD 21541
    • /64

      Est $1,492,094 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,548 Sq Ft

      441 Paradise Heights, Oakland, MD 21550

      441 Paradise Heights, Oakland, MD 21550
  • /114

    $999,999 Under Contract

    • 5 Beds
    • 5.5 Baths
    • 8,000 Sq Ft

    1720 Pysell Crosscut Rd, Oakland, MD 21550

    'Four Winds' is a Frank Lloyd Wright inspired masterpiece at Deep Creek Lake. Restored & renovated as recently as 2021, this 4/5BR home boasts 8000sf on nearly 5 acres of land. A small part of the home was converted to accommodate a successful medical practice - 2 patient rooms, bathroom & private office - which adds amazing potential to creatively 'work from home' in many professional fields

    Jay Ferguson Taylor Made Deep Creek Vacations & Sales

    1720 Pysell Crosscut Rd, Oakland, MD 21550
  • /41

    $485,000 Sold Sep 22, 2025

    20160 Garrett Hwy Unit D310, Oakland, MD 21550

    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft
    • Built 1975

    Last Sold Summary

    • $352/SF
    • 41 Days On Market

    Last Listing Agent Stephanie Smith Select Premium Properties, Inc

    20160 Garrett Hwy Unit D310, Oakland, MD 21550
    • /8

      Est $76,667 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft

      282 Longview Ln, Deer Park, MD 21550

      282 Longview Ln, Deer Park, MD 21550
  • /15

    $75,000

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    60 Gorman St, Oakland, MD 21550

    Bring you vision to this 3-bedroom, 1 bath home right outside of Oakland, Maryland. Features a spacious living room, updated kitchen and a cozy front deck. With a little love and final touches, the property could shine again - ideal for a renovation project or investment opportunity. There is a nice yard and off street parking. Great opportunity for buyers looking to invest or customize a home to

    Jennifer Jackson Charis Realty Group

    60 Gorman St, Oakland, MD 21550
  • /3

    $20,000 Sold Dec 19, 2025

    0 N Hammond St, Oakland, MD 21550

    • Land
    • 0.54 Acre
    • $37,037 per Acre

    Last Sold Summary

    • 398 Days On Market

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    0 N Hammond St, Oakland, MD 21550
    • /27

      Est $190,873 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,056 Sq Ft

      32 Rockville Ct, Oakland, MD 21550

      32 Rockville Ct, Oakland, MD 21550
  • /13

    $199,900 Pending

    • Land
    • 0.72 Acre
    • $277,639 per Acre

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550

    Unique opportunity to purchase an accessory building in the heart Deep Creek Lake! Property was granted special exception to use for boat storage on Penn Point Rd. Less than a mile from Pawn Run Bar + Kitchen, this level wooded lot offers .72 acres and comes fully equipped with a brand new massive 32 x 38 garage. Fully insulated with oversized 10-foot doors, wrapped with metal roof and siding to

    Jon Bell Railey Realty, Inc.

    0 Penn Point Rd Unit MDGA2010762, Oakland, MD 21550
  • /37

    $290,000 Sold Jun 05, 2025

    0 Hubbard Rd, Oakland, MD 21550

    • Land
    • 110.17 Acres
    • $2,632 per Acre

    Last Sold Summary

    • 43 Days On Market

    Last Listing Agent Justin Liller Railey Realty, Inc.

    0 Hubbard Rd, Oakland, MD 21550
    • /48

      Est $337,904 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,750 Sq Ft

      314 Allegheny Dr, Oakland, MD 21550

      314 Allegheny Dr, Oakland, MD 21550
  • /20

    $221,000

    • Land
    • 1.69 Acres
    • $130,769 per Acre

    123 Mountainview Ct, Oakland, MD 21550

    One of the best lake view lots at Deep Creek Lake! Big mountain and water views from this 1.67 acre homesite in the private community of Mountainside. Lake access with public sewer available. This lot sits at the top of the ridge with quiet surroundings, yet still close to Wisp Resort, marinas, restaurants, and local establishments. Mountainside offers a private marina club, tennis and basketball

    Jon Bell Railey Realty, Inc.

    123 Mountainview Ct, Oakland, MD 21550
  • /28

    $135,000 Sold Sep 22, 2025

    320 Coolidge Ave, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1900

    Last Sold Summary

    • $188/SF
    • 47 Days On Market

    Current Estimated Value $135,978

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    320 Coolidge Ave, Oakland, MD 21550
    • /87

      Est $756,371 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,355 Sq Ft

      34 Hooppole Ct, Oakland, MD 21550

      34 Hooppole Ct, Oakland, MD 21550
  • /8

    $119,900

    • Land
    • 0.85 Acre
    • $141,059 per Acre

    106 Snowhaven Ln, McHenry, MD 21541

    Build Your Dream Home on the Mountaintop!Don't miss this rare opportunity to own a spacious 0.85-acre lot in one of Deep Creek Lake’s most desirable communities — the Wisp mountaintop. Located on Snowhaven Lane, this lot offers the perfect setting with expansive views for your custom mountain retreat. Just minutes from Wisp Resort, ASCI Whitewater Course, Deep Creek Lake, hiking and biking

    Danielle Luscombe Taylor Made Deep Creek Vacations & Sales

    106 Snowhaven Ln, McHenry, MD 21541
  • /16

    $25,000 Sold May 27, 2025

    36 Lehman Ln, Oakland, MD 21550

    • Land
    • 0 Acre

    Last Sold Summary

    • 10 Days On Market

    Last Listing Agent Kellyann Green Railey Realty, Inc.

    36 Lehman Ln, Oakland, MD 21550
    • /87

      Est $471,906 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      2702 Mayhew Inn Rd, Oakland, MD 21550

      2702 Mayhew Inn Rd, Oakland, MD 21550
  • /37

    $289,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    511 E Green St, Oakland, MD 21550

    Completely renovated and move in ready, this charming Oakland home combines modern comfort with classic character. Every detail has been thoughtfully updated, including new wiring, insulation, roof, windows, flooring, and a beautiful kitchen, giving you peace of mind and a fresh, contemporary feel throughout. The main level features an open layout with a spacious living room that flows into the

    Eric Crawford Taylor Made Deep Creek Vacations & Sales

    511 E Green St, Oakland, MD 21550
  • /74

    $915,000 Sold Sep 15, 2025

    186 Thornberry Rd, Oakland, MD 21550

    • 5 Beds
    • 3.5 Baths
    • 2,347 Sq Ft
    • Built 1992

    Last Sold Summary

    • $390/SF
    • 48 Days On Market

    Current Estimated Value $931,789

    Last Listing Agent Betsy Spiker Holcomb Taylor Made Deep Creek Vacations & Sales

    186 Thornberry Rd, Oakland, MD 21550
    • /77

      Est $180,367 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,852 Sq Ft

      214 I St, Oakland, MD 21550

      214 I St, Oakland, MD 21550
  • /75

    $1,749,000

    • 4 Beds
    • 4.5 Baths
    • 2,605 Sq Ft

    1019 Lake Shore Dr, Oakland, MD 21550

    Tucked among the trees, Blue Spruce offers a perfect blend of modern comfort and serene natural beauty. This recently remodeled 4-bedroom, 4 and a half bathroom home invites you to relax, recharge, and reconnect with nature. With each bedroom offering an ensuite bathroom plus a half bath near the kitchen, this home was designed for comfort. Step inside to discover thoughtful updates throughout,

    Rachel Bruch Railey Realty, Inc.

    1019 Lake Shore Dr, Oakland, MD 21550
  • /22

    $145,800 Sold Apr 11, 2025

    Lot 31 Snowshoe Ct, Mc Henry, MD 21541

    • Land
    • 0.35 Acre
    • $416,571 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    Lot 31 Snowshoe Ct, Mc Henry, MD 21541

Showing Results 281 - 320, Page 8 of 18

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