Google street view image for 125 S Winchester Rd S, Annapolis, MD 21409

Local rules require you to be signed in to see more photos.

 or  for free with no obligation.

Sold
$5,377,823
Est. refi paymentEst. refi $6,526/mo
—
bd
•
4.5 ba
•
4,260
sq ft

125 S Winchester Rd S, Annapolis, MD 21409

map-entry

About this home

Single-familyProperty Type
1948Year Built
2.77 acresLot Size
$1,262Est. Price/Sq.Ft.
1 spaceParking
Source:Public Records

Redfin Estimate

$5,377,823
$4.1M since sold in October 2000$232K since October

This home's estimate is 121.6% higher than the average sale price ($2.43M) of 6 comparable homes.

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell
$5,067,051
Est. take-home

List your home with Redfin and save $53,778

Refinance
$0
Est. cash available

Get cash now or lower your monthly rate

Rent
$6,845/mo
Redfin rental estimate

List your home for rent

Market trends in 21409, MD

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price
100.0%

0.1% MoM

Median sale price
$677K

$27K MoM

Avg. days on market
34d

3 days MoM

Recently sold homes
69

2 MoM

New listings for sale

Provided by Redfin

Sale history for 125 S Winchester Rd S

Tax history for 125 S Winchester Rd S

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds
—
Baths
4.5
Stories
2.5
Lot width
—
Lot depth
—
Lot size
2.77 Acres
Year renovated
—
Sq. Ft.
4,260
Year built
1948
Style
Single Family Residential
County
Anne Arundel County
APN
03 00003159800
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 7, 2026.

Property details

Around this home

Schools

Arnold Elementary School

Public K-5 • Assigned • 1.7mi

10/10
Severn River Middle School

Public 6-8 • Assigned • 3.5mi

10/10
Broadneck High School

Public 9-12 • Assigned • 3.2mi

9/10
Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 106° expected this year, 15 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Annapolis, MD • 21409
Average low and high temperatures (°F)
38
26
43
30
59
41
68
51
73
58
84
68
88
73
80
67
77
64
67
52
58
44
44
31
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

Sun exposure

89/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Annapolis. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.9 hrs
6.6 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$5.11M – $6.19M

Reach more buyers when you sell with Redfin. Save up to $53,778 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$735,000
5 beds3 baths2,225 sq ft
1452 Grandview Rd, Arnold, MD 21012
Updated kitchen • Quartz countertops • Brand-new trex deck
(443) 317-8125
$89,900
2 beds1 bath2,066 sq ft
1277 Ritchie Hwy #186, Arnold, MD 21012
Remodeled home • New windows • New flooring
(804) 656-5007
3D WALKTHROUGH
$3,000,000
5 beds2 baths5,522 sq ft
1979 Baltimore Annapolis Blvd, Annapolis, MD 21409
Waterfront location • Panoramic views • Vintage kitchen
(410) 263-8686
NEW CONSTRUCTION
$950,000
5 beds3.5 baths3,104 sq ft
Beechwood Rd, Arnold, MD 21012
Modern farmhouse • Gourmet kitchen • Cozy gas fireplace
(443) 454-1470
$1,950,000
6 beds4 baths3,415 sq ft
192 Duke Of Gloucester, Annapolis, MD 21401
Historic character • Modern luxury • Single level living
(301) 755-5613
$709,900
3 beds2 baths1,440 sq ft
127 Porter Dr, Annapolis, MD 21401
Open floor plan • Upgraded kitchen • Oversized island
(410) 956-3500

New listings for sale in 21409

COMING SOON
$985,000
5 beds3.5 baths2,504 sq ft
1928 Pendennis Dr, Annapolis, MD 21409
Gourmet kitchen • Broadneck schools • 0.48 acre lot
(410) 263-8686
$699,000
2 beds2 baths1,682 sq ft
76 Old Mill Bottom Rd N #201, Annapolis, MD 21409
Designer kitchen • Rear balcony • Panoramic views
(410) 224-2200
$1,750,000
3 beds3 baths3,502 sq ft
314 Kingsberry Dr, Annapolis, MD 21409
Open floor plan • Cathedral ceilings • Hardwood floors
(410) 224-4400
$345,000
3 beds1.5 baths1,200 sq ft
339 Elderwood Ct, Annapolis, MD 21409
New roof • New siding • New flooring
(410) 263-8686
COMING SOON
$550,000
4 beds2.5 baths1,108 sq ft
976 Mount Holly Dr, Annapolis, MD 21409
Cozy fireplace • Brand new well • Upgraded well pump
(410) 255-3690
3D WALKTHROUGH
$799,900
4 beds2.5 baths2,072 sq ft
700 N Holly Dr, Annapolis, MD 21409
0.68 acre lot • 2 garage spots • Built 1972
(410) 461-2800
$385,000
2 beds2 baths1,235 sq ft
1501 Broadneck Pl #303, Annapolis, MD 21409
One level living • Secure building • Elevator access
(888) 860-7369
OPEN NOV 12, 11AM TO 1PM
$250,000
3 beds3 baths1,820 sq ft
721 Fairway Dr, Annapolis, MD 21409
Updated kitchen • Rear deck • Private well
(703) 636-7300
$749,999
5 beds3.5 baths2,048 sq ft
962 Woodland Cir, Annapolis, MD 21409
Separate living area • Gourmet kitchen • Spacious deck
(410) 758-0333

Home values near 125 S Winchester Rd S

Data from public records.

More real estate resources

Baltimore homes for sale
Upper Marlboro homes for sale
Bowie homes for sale
Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

Join us

Become an Agent
Get referrals
Careers

Find homes faster

Download the Redfin App on the Apple App Store
Download the Redfin App from the Google Play Store

About us

Why Redfin?
Community Impact
Inclusion
Culture
Press
Investors
Blog
Real Estate News

Find us

Contact Us
Help Center
Advertise

Subsidiaries

Rent.
ApartmentGuide

Affiliated Business

Rocket Close
Rocket Mortgage

Countries

US flagUnited States

Canadian flagCanada

Copyright: © 2026 Redfin. All rights reserved.

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.