Google satellite image for 129 S Winchester Rd, Annapolis, MD 21409

Off market aug 1988 for $450K

$1,686,486

Est. refi paymentEst. refi $3,123/mo

—

•

2.5 ba

•

2,018

sq ft

129 S Winchester Rd, Annapolis, MD 21409

About this home

129 S Winchester Rd is a 2,018 square foot house on a 2.25 acre lot with 2.5 bathrooms. - it last sold on August 31, 1988 for $450,000. Based on Redfin's Annapolis data, we estimate the home's value is $1,686,486.

Single-familyProperty Type

1933Year Built

2.25 acresLot Size

$836Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,686,486

$1.2M since sold in August 1988$1,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 107.2% higher than the average sale price ($814K) of 5 comparable homes.

SOLD SEP 10, 2026
$1,100,000
A
3 beds2.5 baths1,802 sq ft
111 Wardour Dr, Annapolis, MD 21401
SOLD SEP 16, 2026
$680,000
B
3 beds2 baths2,200 sq ft
1505 Riverdale Dr, Annapolis, MD 21409
SOLD MAY 22, 2026
$715,000
C
3 beds3 baths1,947 sq ft
1438 Ridgeway E, Arnold, MD 21012
SOLD SEP 17, 2026
$799,000
D
4 beds3 baths2,249 sq ft
1518 Winchester Rd, Annapolis, MD 21409
SOLD JUL 22, 2026
$775,000
E
3 beds2.5 baths2,282 sq ft
1740 Long Green Dr, Annapolis, MD 21409

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Earn from this home

Sell

$1,587,597

Est. take-home

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Est. cash available

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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

2 MoM

New listings for sale

COMING SOON
$985,000
5 beds3.5 baths2,504 sq ft
1928 Pendennis Dr, Annapolis, MD 21409
(410) 263-8686
$699,000
2 beds2 baths1,682 sq ft
76 Old Mill Bottom Rd N #201, Annapolis, MD 21409
(410) 224-2200
$1,750,000
3 beds3 baths3,502 sq ft
314 Kingsberry Dr, Annapolis, MD 21409
(410) 224-4400
$345,000
3 beds1.5 baths1,200 sq ft
339 Elderwood Ct, Annapolis, MD 21409
(410) 263-8686
COMING SOON
$550,000
4 beds2.5 baths1,108 sq ft
976 Mount Holly Dr, Annapolis, MD 21409
(410) 255-3690
3D WALKTHROUGH
$799,900
4 beds2.5 baths2,072 sq ft
700 N Holly Dr, Annapolis, MD 21409
(410) 461-2800
$385,000
2 beds2 baths1,235 sq ft
1501 Broadneck Pl #303, Annapolis, MD 21409
(888) 860-7369
OPEN NOV 12, 11AM TO 1PM
$250,000
3 beds3 baths1,820 sq ft
721 Fairway Dr, Annapolis, MD 21409
(703) 636-7300
$749,999
5 beds3.5 baths2,048 sq ft
962 Woodland Cir, Annapolis, MD 21409
(410) 758-0333
LISTED BY REDFIN
$617,000
4 beds2 baths1,964 sq ft
1193 Hampton Rd, Annapolis, MD 21409
See all

Provided by Redfin

Sale history for 129 S Winchester Rd

Year

Property tax

Land + Additions

Assessment*

2026

$10,894 (+1.7%)

2025

$10,717 (+1.7%)

2024

$10,536 (+2.4%)

2023

$10,292 (+6.2%)

$1,565,000 + $188,000

$1,753,000

2022

$9,693 (+1.9%)

2021

$9,516 (+3.2%)

2020

$9,218 (+2.8%)

$1,485,000 + $176,600

$1,661,600

2019

$8,965 (+5.9%)

2018

$8,465 (+1.1%)

$1,185,000 + $149,400

$1,334,400

2017

$8,372 (−2.5%)

$1,185,000 + $149,400

$1,334,400

2016

$8,589

$1,485,000 + $169,400

$1,654,400

2015

$8,582 (+1.1%)

$1,485,000 + $169,400

$1,654,400

2014

$8,488 (+4.6%)

2013

$8,117 (+6.3%)

2012

$7,635 (+6.7%)

2011

$7,156

2010

$7,156 (+11.1%)

2009

$6,441

Tax history for 129 S Winchester Rd

Year

Property tax

Land + Additions

Assessment*

2026

$10,894 (+1.7%)

2025

$10,717 (+1.7%)

2024

$10,536 (+2.4%)

2023

$10,292 (+6.2%)

$1,565,000 + $188,000

$1,753,000

2022

$9,693 (+1.9%)

2021

$9,516 (+3.2%)

2020

$9,218 (+2.8%)

$1,485,000 + $176,600

$1,661,600

2019

$8,965 (+5.9%)

2018

$8,465 (+1.1%)

$1,185,000 + $149,400

$1,334,400

2017

$8,372 (−2.5%)

$1,185,000 + $149,400

$1,334,400

2016

$8,589

$1,485,000 + $169,400

$1,654,400

2015

$8,582 (+1.1%)

$1,485,000 + $169,400

$1,654,400

2014

$8,488 (+4.6%)

2013

$8,117 (+6.3%)

2012

$7,635 (+6.7%)

2011

$7,156

2010

$7,156 (+11.1%)

2009

$6,441

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

Property details

Interior

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Air Conditioning Type: Separate System
Heating Type: Radiant Hot Water

Fireplace Information
# of Fireplaces: 1
Fireplace Type: 2 Story Brick
Has Fireplace

Exterior

Exterior Information
Building Construction Quality: Fair
Exterior Wall: Frame
Building Type: Single Family

Property Information
Subdivision Name: KEMP ESTATE
Living Sq. Ft: 2,018
Building Sq. Ft: 2,018
# of Stories: 1.5
Stories Type: 1 1/2 Story With Basement
Legal Description: 2.250 ACRES 129 S WINCHESTER RD ON SEVERN RIVER

Parking & Garage Information
Parking Type: Frame Garage
Garage/Parking Sq. Ft: 896
Garage / Carport Type: Frame

Lot Information
# of Buildings: 1
Land Sq. Ft: 98,010
Legal Lot Number: 3
Acres: 2.25
Zoning Code: R1
State Use Description: RESIDENTIAL

Location Information
Parcel Location Influence: Waterfront

Utility Information
Sewer Type: Private
Water Service Type: Private

Financial

Assessor Information
Assessment Year: 2026
Tax District County: 3

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 2,018
Stories: 1.5
Lot Size: 2.25 acres
Style: Single Family Residential
Year Built: 1933
Year Renovated: —
County: Anne Arundel County
APN: 03 00033351000

Home facts updated by county records on Oct 7, 2026

Around this home

Schools

Arnold Elementary School

Public K-5 • Assigned • 1.8mi

10/10

Severn River Middle School

Public 6-8 • Assigned • 3.5mi

10/10

Broadneck High School

Public 9-12 • Assigned • 3.3mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk 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

7/10 Wind Factor

78% 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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.3 hours in June and 4.6 hours in December, which is comparable to the U.S. average for solar exposure.

9.3 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.60M – $1.94M

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New listings for sale in 21409

COMING SOON

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One level living • Secure building • Elevator access

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Home values near 129 S Winchester Rd

Data from public records.

Address	Redfin Estimate
125 South Winchester Rd, Annapolis, MD - Beds \| 4.5 Baths \| 4260 Sq. Ft.	$5,377,823
1718 Winchester Rd, Annapolis, MD - Beds \| 3 Baths \| 2762 Sq. Ft.	$3,979,493

Address	Redfin Estimate
105 South Winchester Rd, Annapolis, MD - Beds \| 2.5 Baths \| 3300 Sq. Ft.	$1,813,403
1720 Winchester Rd, Annapolis, MD 3 Beds \| 2.5 Baths \| 2314 Sq. Ft.	$1,832,920

Address	Redfin Estimate
71 South Winchester Rd, Annapolis, MD 4 Beds \| 3 Baths \| 3330 Sq. Ft.	$2,002,946
55 South Winchester Rd, Annapolis, MD - Beds \| 2 Baths \| 2468 Sq. Ft.	$839,973

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