Seller's Agent in 2026
Kimberly O'Connor
Coldwell Banker (NRT-Southeast-MidAtlantic)
(410) 212-8026
17 in this area
40 Total Sales
565 Wayward Dr Annapolis, MD 21401
Parole NeighborhoodEstimated Value: $717,274 - $750,000
3
Beds
2
Baths
3,874
Sq Ft
$189/Sq Ft
Est. Value
Highlights
- Private Pool
- Wood Flooring
- No HOA
- Rambler Architecture
- 2 Fireplaces
- 2 Car Attached Garage
About This Home
As of January 2026This beautifully maintained three-bedroom home offers over 4,000 square feet of living space, combining comfort and versatility in one stunning package. Inside, you’ll find many updates. The primary suite features two large walk-in closets and a fully renovated bath with dual vanity, soaking tub, and walk-in shower—a true retreat for relaxation. Discover a spacious layout with a full finished basement, perfect for entertaining or creating your ideal home office or gym. Enjoy plenty of storage, a two-car garage, and a sparkling in-ground pool for summer relaxation. Nestled in the sought-after Rolling Knolls community, you’ll appreciate the convenience of a community elementary school. Quick and easy access to shopping, dining and the Luminus Medical Center. Enjoy a short commute to the beautiful Annapolis Historic District, shopping and dining. Easy commute to Baltimore and Washington D.C.
Last Agent to Sell the Property
(410) 224-2200 cedric.lewis@cbmove.com Coldwell Banker Realty Listed on: 12/27/2025
Last Buyer's Agent
(410) 647-8000 severnapark@penfedrealty.com Berkshire Hathaway HomeServices PenFed Realty License #520153
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,603
Year Built
- Built in 1973
Lot Details
- 20,640 Sq Ft Lot
- Vinyl Fence
- Back Yard Fenced
- Property is zoned R2
Parking
- 2 Car Attached Garage
- Front Facing Garage
Home Design
- Rambler Architecture
- Block Foundation
- Vinyl Siding
Interior Spaces
- Property has 2 Levels
- 2 Fireplaces
- Improved Basement
Flooring
- Wood
- Carpet
Bedrooms and Bathrooms
- 3 Main Level Bedrooms
- 2 Full Bathrooms
- Soaking Tub
Pool
- Private Pool
Utilities
- Forced Air Heating and Cooling System
- Heating System Uses Natural Gas
- Natural Gas Water Heater
- On Site Septic
Community Details
- No Home Owners Association
- Rolling Knolls Subdivision
Listing and Financial Details
- Tax Lot 144
- Assessor Parcel Number 020267110588603
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
Closed on
May 6, 2026
Sold by
Bought by
Current Estimated Value
Purchase Details
Listed on
Dec 27, 2025
Closed on
Jan 7, 2026
Sold by
Bought by
Seller's Agent
Kimberly O'Connor
Coldwell Banker Realty
Buyer's Agent
Christy Bishop
Berkshire Hathaway HomeServices PenFed Realty
List Price
$710,000
Sold Price
$725,000
Premium/Discount to List
$15,000
2.11%
Views
81
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
1.83%
Purchase Details
Closed on
Aug 8, 2022
Sold by
Bought by
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Home Values in the Area
Average Home Value in this Area
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 | Buyer | Sale Price | Title Company |
|---|---|---|---|
| -- | None Listed On Document | ||
| $725,000 | Eagle Title | ||
| -- | -- |
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 |
|---|---|---|---|---|
| 01/07/2026 01/07/26 | Sold | $725,000 | +2.1% | $187 / Sq Ft |
| 01/01/2026 01/01/26 | Off Market | $710,000 | -- | -- |
| 12/27/2025 12/27/25 | For Sale | $710,000 | -- | $183 / 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 |
|---|---|---|---|---|
| 2025 | $3,792 | $475,400 | -- | -- |
| 2024 | $3,708 | $453,200 | $0 | $0 |
| 2023 | $3,593 | $431,000 | $226,100 | $204,900 |
| 2022 | $3,370 | $427,200 | $0 | $0 |
| 2020 | $3,225 | $419,600 | $226,100 | $193,500 |
| 2019 | $6,210 | $409,633 | $0 | $0 |
| 2018 | $4,053 | $399,667 | $0 | $0 |
| 2017 | $2,956 | $389,700 | $0 | $0 |
| 2016 | -- | $383,467 | $0 | $0 |
| 2015 | -- | $377,233 | $0 | $0 |
| 2014 | -- | $371,000 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
Kimberly O'Connor
-
Christy Bishop
Buyer's Agent in 2026
Christy Bishop
BHHS PenFed (actual)
(443) 994-3405
9 in this area
52 Total Sales
Map
Source: Bright MLS
MLS Number: MDAA2130846
APN: 02-671-10588603
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