Seller's Agent in 2025
Stuart Greenwell
Cummings & Co Realtors
(202) 550-5848
1 in this area
44 Total Sales
Timeless Sophistication in the Heart of Historic Guilford – 101 E Highfield Road
Nestled on one of Guilford’s most storybook blocks, 101 E Highfield Road is a masterclass in classic elegance and modern refinement. This exquisitely maintained 4-bedroom, 3.5-bath Cape Cod blends the romance of historic architecture with luxurious updates that cater to today’s discerning lifestyle.
From the moment you arrive, the home’s picturesque curb appeal and manicured landscaping set the tone. Inside, sunlit spaces unfold across gleaming pegged hardwood floors, adorned with original moldings and graceful proportions that make both daily living and entertaining feel effortlessly elevated.
The thoughtfully designed main level features a serene primary suite with a spa-inspired en-suite bath and custom built-in closets, offering true first-floor living. An additional bedroom on this level adds flexibility for a guest retreat, home office, or cozy den.
At the heart of the home lies a gourmet eat-in kitchen designed to impress. Outfitted with high-end appliances, a deep farmhouse sink, expansive counters, and abundant custom cabinetry, this chef’s haven is bathed in natural light from oversized windows—creating a warm, inviting atmosphere for everything from Sunday brunch to festive dinner parties.
The sun-drenched living room, centered around a charming fireplace, seamlessly transitions to a private covered patio through new French doors. Framed by lush landscaping and designed for year-round enjoyment, this enchanting outdoor space is perfect for al fresco dining, peaceful morning coffees, or hosting under the stars.
Upstairs, two additional bedrooms share a beautifully updated full bath and are joined by a versatile bonus room—currently serving as an inspiring art and music studio. The space is ideal for creative pursuits, a reading loft, or a playroom.
The fully finished lower level extends the home’s functionality, offering a spacious recreation room, sleek new full bath, and an expansive laundry and utility suite. Whether you're envisioning a home gym, media lounge, or second office, this level adapts to your needs with ease.
A 2-car attached garage with attic storage, an in-ground sprinkler system, and proximity to iconic Sherwood Gardens and Guilford Gateway Park further elevate this home’s appeal. Located just minutes from Johns Hopkins University, Loyola, and the boutiques and restaurants along Charles Street, this home offers the perfect blend of historic charm and city convenience.
Part of the prestigious Guilford Association, this residence is not just a home—it’s a lifestyle.
Discover the rare opportunity to own a piece of Baltimore's architectural legacy. Schedule your private tour today.
Last Agent to Sell the Property
(202) 550-5848 justaskstu@gmail.com Cummings & Co. Realtors License #667046 Listed on: 06/01/2025
Last Buyer's Agent
(410) 599-7887 gary@marylandrealestate.us Cummings & Co. Realtors License #523558
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $889,900 | None Listed On Document | |
| Deed | $830,000 | Wfg National Title | |
| Deed | $830,000 | Wfg National Title | |
| Deed | $650,000 | Sage Title Group Llc | |
| Deed | $549,000 | -- | |
| Deed | $549,000 | -- | |
| Deed | $266,500 | -- |
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $321,465 | New Conventional | |
| Previous Owner | $366,445 | New Conventional | |
| Previous Owner | $517,500 | New Conventional |
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 08/15/2025 08/15/25 | Sold | $879,900 | -1.1% | $259 / Sq Ft | |
| 07/15/2025 07/15/25 | Pending | -- | -- | -- | |
| 06/13/2025 06/13/25 | Price Changed | $889,900 | -1.1% | $262 / Sq Ft | |
| 06/01/2025 06/01/25 | For Sale | $899,900 | +8.4% | $265 / Sq Ft | |
| 07/15/2022 07/15/22 | Sold | $830,000 | +4.4% | $236 / Sq Ft | View Prior Sale |
| 06/11/2022 06/11/22 | Pending | -- | -- | -- | |
| 06/01/2022 06/01/22 | For Sale | $795,000 | 0.0% | $226 / Sq Ft | |
| 09/28/2020 09/28/20 | Rented | $3,450 | 0.0% | -- | |
| 08/20/2020 08/20/20 | For Rent | $3,450 | 0.0% | -- | |
| 05/31/2017 05/31/17 | Sold | $650,000 | -6.5% | $179 / Sq Ft | View Prior Sale |
| 04/23/2017 04/23/17 | Pending | -- | -- | -- | |
| 03/09/2017 03/09/17 | For Sale | $695,000 | -- | $191 / Sq Ft |
| 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 |
|---|---|---|---|---|
| 2025 | $14,417 | $715,100 | -- | -- |
| 2024 | $14,417 | $664,600 | $203,400 | $461,200 |
| 2023 | $15,460 | $658,233 | $0 | $0 |
| 2022 | $15,384 | $651,867 | $0 | $0 |
| 2021 | $15,234 | $645,500 | $203,400 | $442,100 |
| 2020 | $13,983 | $645,500 | $203,400 | $442,100 |
| 2019 | $13,912 | $645,500 | $203,400 | $442,100 |
| 2018 | $14,500 | $663,100 | $203,400 | $459,700 |
| 2017 | $13,956 | $633,833 | $0 | $0 |
| 2016 | -- | $604,567 | $0 | $0 |
| 2015 | $13,473 | $575,300 | $0 | $0 |
| 2014 | $13,473 | $575,300 | $0 | $0 |
Seller's Agent in 2025
Stuart Greenwell
Cummings & Co Realtors
(202) 550-5848
1 in this area
44 Total Sales
Buyer's Agent in 2025
Gary Addington
Cummings & Co Realtors
(410) 599-7887
2 in this area
128 Total Sales
Seller's Agent in 2022
Cynthia (Cindy) Conklin
Monument Sotheby's International Realty
(443) 629-0152
2 in this area
80 Total Sales
Seller Co-Listing Agent in 2022
Brandon Gaines
Berkshire Hathaway HomeServices Homesale Realty
(410) 804-9600
2 in this area
63 Total Sales
Buyer's Agent in 2022
Corey Campbell
EXP Realty, LLC
(410) 236-1339
1 in this area
183 Total Sales
Buyer Co-Listing Agent in 2022
Chris Carhart
EXP Realty, LLC
(443) 340-7597
1 in this area
83 Total Sales
Source: Bright MLS
MLS Number: MDBA2168884
APN: 3714-007