5711 Waterside Dr
Berlin, MD 21811
6 Beds
5.5 Baths
6,312 sqft (on 6.39 acres)
6 Beds
5.5 Baths
6,312 sqft
(on 6.39 acres)
Local Information
- Map ViewExplore the area around 5711 Waterside Dr.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Most waterfront properties give you a view. This one gives you an entire Peninsula. Set on 6.39 private acres in the prestigious South Point Farms community, this extraordinary waterfront estate offers more than 700 feet of direct bayfront and a setting that feels worlds away from everything, yet minutes from the best of the Eastern Shore. Properties like this are not simply waterfront. They are surrounded by it. From its rare peninsula-style position, the estate captures sweeping, unobstructed water views in nearly every direction. Sunrises over the bay. Evening light reflecting across open water. Quiet mornings where the only sound is the tide moving along the shoreline. The custom built property was designed to blur the line between indoor comfort and outdoor living. Anchoring the estate is a 4,165 square foot main residence, thoughtfully positioned to take full advantage of the panoramic waterviews and endless skyline. Inside, nearly every room faces the bay. Soaring ceilings frame a grand great room with a traditional fireplace, while the chef’s kitchen, dining area, and sitting spaces flow naturally toward the surrounding decks and water views. The main-home offers four bedrooms, four and a half baths, two dedicated home offices, and multiple gathering spaces designed for both everyday living and large waterfront entertaining. Step outside and the experience continues. IPE Brazilian hardwood decks stretch along the waterfront side of the home, creating an ideal setting for sunset dinners, crab feasts, and long summer evenings overlooking the bay. A thoughtfully placed bay-facing 'bonus' garage provides convenient storage for boating gear, waterfront equipment or a perfect place for a home gym. Just steps away from the main-house is the 1,619 square foot guest-home, creating a private retreat for visiting family and friends. Two bedrooms, a full bath with sauna, a vaulted wood ceiling family room with fireplace, and a professional-grade kitchen allow guests to settle in comfortably for extended stays. The guest house overlooks the estate’s 50' x 24' bay-facing in-ground pool, where wide water views become the perfect backdrop for both relaxing and entertaining. A fully conditioned oversized-garage and game room adds another layer of entertainment space and is attached to the back of the guest house. For boaters, the waterfront infrastructure is equally impressive. A 250 foot private pier extends into the bay, providing quick access to open water, with more than enough room for your boat and your wave-runners. More than 700 feet of newly installed rip-rap shoreline protects the property while preserving its natural beauty. The grounds themselves are as memorable as the waterfront. Professionally landscaped acreage surrounds the home, highlighted by a half-acre deep-water pond, expansive lawn areas, and a circular drive that creates a grand yet welcoming arrival. And while the estate feels remarkably private, the location keeps you connected to the region’s most celebrated destinations. Assateague Island National Seashore is just minutes away, offering protected beaches, wild ponies, and miles of untouched coastline. The shops, restaurants, and charm of Historic Downtown Berlin, consistently ranked among America’s best small towns, are nearby. And when you want the energy of the coast, the beaches, boardwalk, and marinas of Ocean City are only a short drive away. Waterfront estates of this scale, privacy, and peninsula positioning rarely become available in Worcester County, or anywhere on Marylands Eastern Shore. Especially not with this combination of acreage, infrastructure, and proximity to the coast. For those who understand what a property like this represents, it is more than a home. It is a legacy waterfront setting that simply cannot be recreated.
Home Highlights
Parking
8 Car Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$618
Listed
180+ days ago
Home Details for 5711 Waterside Dr
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Interior Details Number of Rooms: 1Types of Rooms: Basement |
Beds & Baths Number of Bedrooms: 6Main Level Bedrooms: 2Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1Number of Bathrooms (main level): 3 |
Dimensions and Layout Living Area: 6312 Square Feet |
Appliances & Utilities Utilities: CableAppliances: Dishwasher, Dryer, Exhaust Fan, Double Oven, Oven/Range - Electric, Range Hood, Refrigerator, Freezer, Stainless Steel Appliance(s), Washer, Water Treat System, Electric Water HeaterDishwasherDryerLaundry: Dryer In Unit,Washer In UnitRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Electric,GeothermalHas CoolingAir Conditioning: Central Air,Electric,GeothermalHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 4Fireplace: Gas/Propane, Stone, Wood Burning, Wood Burning StoveSpa: Hot TubHas a FireplaceHas a Spa |
Windows, Doors, Floors & Walls Flooring: Hardwood, Wood |
Levels, Entrance, & Accessibility Stories: 2.5Levels: Two and One HalfAccessibility: NoneFloors: Hardwood, Wood |
View Has a ViewView: Bay, Other, Panoramic, Pond, Scenic Vista, Water |
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Exterior Home Features Roof: Architectural ShinglePatio / Porch: Deck, Patio, Porch, ScreenedOther Structures: Above Grade, Below Grade, OutbuildingExterior: Extensive Hardscape, Lighting, Lawn Sprinkler, Outdoor Shower, Private Beach, Other, BalconyFoundation: Concrete Perimeter, Crawl SpaceHas a Private Pool |
Parking & Garage Number of Garage Spaces: 8Number of Covered Spaces: 8Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 14Parking: Storage,Garage Door Opener,Garage Faces Front,Garage Faces Rear,Inside Entrance,Oversized,Circular Driveway,Driveway,Private,Attached,Detached,Off Street |
Pool Pool: In Ground, PrivatePool |
Frontage WaterfrontWaterfront: Rip-Rap, Sandy Beach, Bayfront, Fishing Allowed, Boat - Powered, BayOn Waterfront |
Water & Sewer Sewer: Private Septic TankWater Body: Chincoteague Bay, Sinepuxent Bay, Newport Bay |
Farm & Range Frontage Length: Water Frontage Ft: 700 |
Finished Area Finished Area (above surface): 6312 Square Feet |
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Days on Market: 180+ |
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Year Built Year Built: 1998Year Renovated: 2011 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary,Art Deco,Coastal |
Building Building Name: None AvailableConstruction Materials: FrameNot a New Construction |
Property Information Not Included in Sale: See Inventory AddendumIncluded in Sale: See Inventory AddendumParcel Number: 2410324432 |
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Price List Price: $3,900,000Price Per Sqft: $618 |
Status Change & Dates Possession Timing: Close Of Escrow |
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MLS Status: ACTIVE |
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Direction & Address City: BERLINCommunity: South Point Farms |
School Information Elementary School District: Worcester County Public SchoolsJr High / Middle School District: Worcester County Public SchoolsHigh School District: Worcester County Public Schools |
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Listing Agent Listing ID: MDWO2029066 |
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Building Details Builder Name: M&O Builders 2009-2011 remodel and Guest Home |
Building Area Building Area: 6312 Square Feet |
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Not Senior Community |
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No HOA |
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Lot Area: 6.39 Acres |
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Special Conditions: Standard |
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Listing Agreement Type: Exclusive Right To Sell |
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Energy Efficiency Features: HVAC |
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Business Information Ownership: Fee Simple |
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Mls Number: MDWO2029066Water ViewWater View: Bay, Pond, WaterAbove Grade Unfinished Area: 6312 |
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Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y |
Last check for updates: about 6 hours ago
Listing courtesy of Grant Fritschle, (410) 430-5880
Keller Williams Realty Delmarva, (410) 524-6400
Listing Team: The Fritschle Barker Group
Source: Bright MLS, MLS#MDWO2029066
Also Listed on Bright MLS.
Market trends in Berlin
Last updated June 2026
Avg. sale price
$469K
$15KMoM
Sale-to-List Price
99.2%
0.8%MoM
Price per sq ft
$249
$9MoM
Available listings
247
7MoM
Price History for 5711 Waterside Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 03/19/2026 | $3,900,000 | Listed For Sale | Bright MLS #MDWO2029066 |
| 12/08/2025 | $4,100,000 | ListingRemoved | Bright MLS #MDWO2029066 |
| 03/01/2025 | $4,100,000 | Listed For Sale | Bright MLS #MDWO2029010 |
| 06/25/2020 | $2,950,000 | ListingRemoved | Agent Provided |
| 03/15/2020 | $2,950,000 | Listed For Sale | Agent Provided |
| 11/23/1999 | $267,500 | Sold | N/A |
| 02/12/1999 | $260,000 | Sold | N/A |
| 03/26/1996 | $250,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $12,506 |
| Assessment | $1,584,000 |
Home facts updated by county records
Comparable Sales for 5711 Waterside Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.28 | Single-Family Home | $3,200,000 | 08/21/25 | 4 | 5 | 8,372 | |
1.02 | Single-Family Home | $600,000 | 08/08/25 | 3 | 2 | 2,325 | |
0.89 | Single-Family Home | $625,000 | 11/12/25 | 2 | 2 | 1,792 | |
1.16 | Single-Family Home | $640,000 | 04/17/26 | 3 | 2 | 2,102 | |
1.32 | Single-Family Home | $1,250,000 | 12/12/25 | 3 | 3.5 | 2,637 | |
1.51 | Single-Family Home | $515,017 | 02/28/26 | 3 | 2 | 1,300 | |
1.09 | Single-Family Home | $500,000 | 08/04/25 | 3 | 4.5 | - |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETCoastal Life Realty Group LLC
SOLDNOV 12, 2025Long & Foster Real Estate, Inc.
OFF MARKETBerkshire Hathaway HomeServices PenFed Realty - OP
OFF MARKETHileman Real Estate-Berlin
OFF MARKETAtlantic Shores Sotheby's International Realty
Assigned Schools
These are the assigned schools for 5711 Waterside Dr.
- Stephen Decatur Middle School
- 7-8
- Public
- 665 Students
10/10GreatSchools RatingParent Rating AverageTheres no discipline at all. Theres a constant bullying problem. I haven't learned anything sincr 5th grade. Constant physical fights. The teachers have little or no support for people with (Autism, ADHD, etc...) and they get bullied as well. The school food sucks and its overpriced. Teachers practically just read off a book and call it a day of teaching. And they also don't remind you at all if you forgot any work. Some of teachers are way too strict or way too lenient. (One teacher took away my summerfest for playing games in class once, even though I had 1/3 strikes.) (One teacher did absolutely nothing when kids were running around yelling in the middle of teaching)Student Review3y ago - Berlin Intermediate School
- 5-6
- Public
- 613 Students
7/10GreatSchools RatingParent Rating AverageMy daughter attended 5th grade in BIS last year and she thrived! The environment is awesome! We relocated to the area after my older children had completed 6th grade, so last year was our first experience with BIS. And it's been the best school I've experienced for 5th and 6th grades. Communication from the school is plentiful, educational experience is wonderful, and my daughter loves going to school each day!Parent Review1y ago - Ocean City Elementary School
- PK-4
- Public
- 566 Students
10/10GreatSchools RatingParent Rating AverageMy experience at OCES is mostly a bitter one. As a former student I would go back for a lot of reasons. The teachers are usually on power trip most of the time and don't seem to care about students. In third grade I had a rough experience with a friend telling the entire grade my crush. My classmates were talking and the teacher overheard it. Want to know what she told me. That I was too young to have a crush when it's perfectly normal at that age. It put a burden on me that I was wrong and what I felt was wrong and that I shouldn't be feeling what I was feeling. I didn't want to talk with the school consular because the admin would always take teachers sides. It puts a rift from feeling safe to walking on eggshells. No kid should have to experience that. Would not recommend going to OCES just go to Buckingham or Showell you will be better off there.Other Review7mo ago - Stephen Decatur High School
- 9-12
- Public
- 1462 Students
7/10GreatSchools RatingParent Rating Averagebest school 10/10 i like coach colemanStudent Review1y ago 
Check out schools near 5711 Waterside Dr.
What Locals Say about Berlin
At least 220 Trulia users voted on each feature.
89 % Say car is needed
89 % Say it's dog friendly
82 % Say yards are well-kept
81 % Say parking is easy
80 % Say there's holiday spirit
73 % Say it's quiet
73 % Say people would walk alone at night
66 % Say kids play outside
63 % Say there's wildlife
61 % Say neighbors are friendly
53 % Say they plan to stay for at least 5 years
49 % Say it's walkable to restaurants
42 % Say there are community events
38 % Say it's walkable to grocery stores
30 % Say streets are well-lit
25 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Grant Fritschle, Keller Williams Realty Delmarva, (410) 524-6400
Agent Phone: (410) 430-5880
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Copyright 2026 Bright MLS, Inc. Click here for more information
5711 Waterside Dr, Berlin, MD 21811 is a 6 bedroom, 6 bathroom, 6,312 sqft single-family home built in 1998. This property is currently available for sale and was listed by Bright MLS on Mar 18, 2026. The MLS # for this home is MLS# MDWO2029066.