Brian Duncan
Tyler Duncan Realty Partners, Inc.
(240) 549-5851
97 Total Sales
2 in Middletown
$460K - $880K Price Range
216 E Main St Middletown, MD 21769
Middletown Area
5
Beds
6
Baths
3,296
Sq Ft
0.54
Acre Lot
Highlights
- In Ground Pool
- Wood Flooring
- 1 Fireplace
- 0.54 Acre Lot
- Victorian Architecture
- No HOA
About This Home
As of June 2026***Highest & Best offers due Saturday, May 16 8PM***Featured in WASHINGTONIAN, this iconic Victorian “Painted Lady” in the heart of Middletown’s historic district, offering timeless architecture paired with modern comfort. This one-of-a-kind residence showcases striking curb appeal with its signature twin turrets, intricate woodwork, and charming front porch that sets the tone for what awaits inside. Boasting 5 bedrooms, 4 full baths, and 2 half baths, this home offers exceptional space and flexibility for everyday living and entertaining. Interior features include soaring ceilings, original hardwood floors with detailed inlay, pocket doors, and elegant millwork that highlight the home’s historic craftsmanship. Multiple living and dining areas are anchored by beautiful fireplaces, creating warm, inviting spaces throughout. A bright sunroom adds additional living space, perfect for relaxing year-round. The home has been thoughtfully updated to meet today’s lifestyle while preserving its character, including a modernized kitchen, a butler’s pantry with a wine fridge, and key system improvements. Large windows fill the home with natural light, enhancing its bright and airy feel. Step outside to a private backyard oasis featuring a pool, a 6-person hot tub, and outdoor living space, perfect for relaxing or hosting gatherings. A fenced garden space on the south side of the property offers excellent sunlight—ideal for gardening enthusiasts or those seeking a peaceful outdoor retreat. A rare 3-car garage provides ample parking and storage—an exceptional find for a property of this era. Situated on a generous lot just moments from downtown Middletown, enjoy convenient access to local shops, dining, parks, and commuter routes. A true statement property combining historic charm, functional space, and lifestyle amenities—opportunities like this are rare. Located just across the street from Middletown’s 3rd–12th grade school campus and town park—offering exceptional convenience for school drop-offs, sports, events, and activities.
Last Agent to Sell the Property
Denise Briggs
(301) 658-6186 denise.briggs@redfin.com Redfin Corp Brokerage Phone: 3016586186 Listed on: 04/29/2026
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $10,486
Year Built
- Built in 1900
Lot Details
- 23,490 Sq Ft Lot
Parking
- 3 Car Detached Garage
- Rear-Facing Garage
- Driveway
Home Design
- Victorian Architecture
- Frame Construction
Interior Spaces
- Property has 4 Levels
- Ceiling Fan
- Recessed Lighting
- 1 Fireplace
- Formal Dining Room
- Wood Flooring
- Partially Finished Basement
Kitchen
- Butlers Pantry
- Stove
- Ice Maker
- Dishwasher
- Upgraded Countertops
Bedrooms and Bathrooms
- 5 Bedrooms
- En-Suite Bathroom
- Soaking Tub
Outdoor Features
- In Ground Pool
- Porch
Utilities
- Central Air
- Radiator
- Heating System Uses Oil
- Electric Water Heater
Community Details
- No Home Owners Association
- Middletown Subdivision
Listing and Financial Details
- Assessor Parcel Number 1103139530
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Oct 4, 2019
Closed on
Aug 26, 2020
Sold by
Bought by
Seller's Agent
Terry La Scola
Welcome Home Realty Group
Buyer's Agent
Natalia Kennedy
NBI Realty, LLC
List Price
$575,000
Sold Price
$550,000
Premium/Discount to List
-$25,000
-4.35%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
5.72%
Original Mortgage
$495,000
Interest Rate
2.9%
Mortgage Type
New Conventional
Purchase Details
Listed on
Sep 5, 2013
Closed on
Feb 21, 2014
Sold by
Bought by
Seller's Agent
Rob Whalen
Long & Foster Real Estate, Inc.
Buyer's Agent
Sharon Ledbetter
Weichert, REALTORS
List Price
$639,000
Sold Price
$612,000
Premium/Discount to List
-$27,000
-4.23%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-1.62%
Original Mortgage
$489,600
Interest Rate
4.39%
Mortgage Type
New Conventional
Purchase Details
Closed on
Jun 4, 1990
Sold by
Bought by
Purchase Details
Closed on
Jun 30, 1988
Sold by
Bought by
Purchase Details
Closed on
May 19, 1986
Sold by
Bought by
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Middletown, MD
-
Brian Duncan
-
Greg Salley
Greg Salley
Long & Foster Real Estate, Inc.
(240) 693-3948
98 Total Sales
2 in Middletown
$425K - $565K Price Range
-
Heather Nahr
Heather Nahr
RE/MAX Plus
(240) 690-5564
57 Total Sales
1 in Middletown
$520,000 Price
-
Chris Dickerson
Chris Dickerson
The Glocker Group Realty Results
(814) 747-6437
254 Total Sales
1 in Middletown
$850,000 Price
-
Patrick Mayo
Patrick Mayo
RE/MAX Realty Centre, Inc.
(301) 417-5030
43 Total Sales
1 in Middletown
$715,000 Price
-
Rokhsan Fallah
Rokhsan Fallah
Samson Properties
(240) 817-2537
40 Total Sales
1 in Middletown
$385,000 Price
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $550,000 | Title One Setmnt Group Llc | |
| Deed | $612,000 | Atlantic Title & Escrow Comp | |
| Deed | $265,000 | -- | |
| Deed | $182,500 | -- | |
| Deed | $148,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $495,000 | New Conventional | |
| Previous Owner | $489,600 | New Conventional |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/29/2026 06/29/26 | Sold | $810,000 | +4.5% | $246 / Sq Ft | |
| 04/29/2026 04/29/26 | For Sale | $775,000 | +40.9% | $235 / Sq Ft | |
| 08/28/2020 08/28/20 | Sold | $550,000 | 0.0% | $135 / Sq Ft | View Prior Sale |
| 08/04/2020 08/04/20 | Pending | -- | -- | -- | |
| 08/02/2020 08/02/20 | Price Changed | $550,000 | -4.3% | $135 / Sq Ft | |
| 07/10/2020 07/10/20 | For Sale | $575,000 | 0.0% | $141 / Sq Ft | |
| 07/05/2020 07/05/20 | Pending | -- | -- | -- | |
| 06/18/2020 06/18/20 | For Sale | $575,000 | 0.0% | $141 / Sq Ft | |
| 06/06/2020 06/06/20 | Pending | -- | -- | -- | |
| 05/21/2020 05/21/20 | Price Changed | $575,000 | -4.0% | $141 / Sq Ft | |
| 02/10/2020 02/10/20 | Price Changed | $599,000 | -2.9% | $147 / Sq Ft | |
| 11/18/2019 11/18/19 | Price Changed | $617,000 | -3.1% | $151 / Sq Ft | |
| 10/04/2019 10/04/19 | For Sale | $637,000 | +4.1% | $156 / Sq Ft | |
| 02/21/2014 02/21/14 | Sold | $612,000 | -4.2% | $150 / Sq Ft | View Prior Sale |
| 12/16/2013 12/16/13 | Pending | -- | -- | -- | |
| 09/05/2013 09/05/13 | For Sale | $639,000 | -- | $156 / Sq Ft |
Source: Bright MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $10,171 | $776,000 | $119,000 | $657,000 |
| 2025 | $10,171 | $726,167 | ||
| 2024 | $9,570 | $676,333 | $0 | $0 |
| 2023 | $8,789 | $626,500 | $98,300 | $528,200 |
| 2022 | $8,675 | $618,333 | $0 | $0 |
| 2021 | $8,505 | $610,167 | $0 | $0 |
| 2020 | $8,448 | $602,000 | $78,600 | $523,400 |
| 2019 | $8,223 | $585,767 | $0 | $0 |
| 2018 | $7,996 | $569,533 | $0 | $0 |
| 2017 | $6,946 | $553,300 | $0 | $0 |
| 2016 | $5,178 | $493,833 | $0 | $0 |
| 2015 | $5,178 | $434,367 | $0 | $0 |
| 2014 | $5,178 | $374,900 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Denise Briggs
D
Seller's Agent in 2026
Denise Briggs
Redfin Corp
-
Dana Angleberger
D
Buyer's Agent in 2026
Dana Angleberger
Charis Realty Group
(410) 371-3421
53 Total Sales
-
Terry La Scola
Seller's Agent in 2020
Terry La Scola
Welcome Home Realty Group
(240) 674-8757
96 Total Sales
-
Jennifer Burns
Seller Co-Listing Agent in 2020
Jennifer Burns
Samson Properties
(301) 676-3600
38 Total Sales
-
Natalia Kennedy
Buyer's Agent in 2020
Natalia Kennedy
NBI Realty, LLC
(571) 235-8545
21 Total Sales
-
Rob Whalen
Seller's Agent in 2014
Rob Whalen
Long & Foster
(301) 788-5044
114 Total Sales
Map
Source: Bright MLS
MLS Number: MDFR2080572
APN: 03-139530
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Copyright 2026 Bright MLS, Inc.
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