OFF MARKET

Off market jul 2020 for $2.8M

$4,380,339

Est. refi paymentEst. refi $18,524/mo

•

7,907

sq ft

27188 Baileys Neck Rd, Easton, MD 21601

About this home

An exceptional address with a seamless blend of privacy and outstanding amenities on 9+ acres. The tree-lined lane brings you to the impressive brick main house where the entrance hall provides instant views of the Tred Avon River and Trippe's Creek. Gracious living room, incredible formal dining room with service area, stately paneled library/study, large family room with fireplace, beautifully appointed kitchen, butler's pantry, large laundry room, first-floor master suite with lounge area and office, large master bath, two walk-in closets. Second floor: reached by grand circular staircase has three bedrooms all with waterfront balconies, large bathrooms and enormous storage rooms. Second House/ Guesthouse is a separate residence with full kitchen, living room, dining area, first-floor bedroom, full bath, laundry room. The second floor has 2/ 3 bedrooms, Balconies, full bath. There is a complete Exercise Room as well as professional-grade Sauna. Exterior: Large Swimming Pool, Gazebo with refrigerator sink granite countertop and large outdoor Flat Screen TV, first-rate Tennis Court with backboard and basketball. Enclosed Outdoor Shower with Bath, Sports Equipment room, brick surround Hot Tub, raised Garden Beds, Mature Trees. Dock with 3 Boat Lifts, Water, Electricity, and floating dock. Secure rip wrapped shoreline. Click on Property Tour. By Appointment Only.

Single-familyProperty Type

1920Year Built

9.42 acresLot Size

$554Est. Price/Sq.Ft.

4 car garageParking

Listed by Chata Smith • Coldwell Banker Chesapeake Real Estate Company

•410-822-9000 (broker)

Bought with Barbara Watkins • Benson & Mangold, LLC

•410-822-1415 (broker)

•info@bensonandmangold.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDTA137604

Redfin Estimate

$4,380,339

$1.6M since sold in July 2020$54K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 141.7% higher than the average sale price ($1.81M) of 6 comparable homes.

SOLD JUL 30, 2026
$900,000
A
4 beds3.5 baths3,200 sq ft
6372 Country Club Dr, Easton, MD 21601
SOLD SEP 8, 2026
$1,800,000
B
4 beds4 baths2,986 sq ft
106 E Division St, Oxford, MD 21654
SOLD JUN 18, 2026
$2,000,000
C
4 beds5 baths5,207 sq ft
26090 Royal Oak Rd, Royal Oak, MD 21662
SOLD SEP 11, 2026
$2,100,000
D
4 beds4 baths4,469 sq ft
27877 Bent Farm Ln, Oxford, MD 21654
SOLD SEP 4, 2026
$1,325,000
E
5 beds4.5 baths4,610 sq ft
28091 Oaklands Cir, Easton, MD 21601
SOLD SEP 23, 2026
$2,750,000
F
4 beds3.5 baths3,088 sq ft
5837 Irish Creek Rd, Royal Oak, MD 21662

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

Earn from this home

Sell

$2,166,823

Est. take-home

List your home with Redfin and save $43,803

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,868/mo

Redfin rental estimate

List your home for rent

Market trends in 21601, MD

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

97.3%

0.6% MoM

Median sale price

$444K

$11K MoM

Avg. days on market

97d

7 days MoM

Recently sold homes

6 MoM

New listings for sale

NEW 2 HRS AGO
$269,500
2 beds1 bath982 sq ft
302 W Oak Ave, Easton, MD 21601
(410) 822-7556
$499,900
3 beds3 baths2,342 sq ft
29709 Lyons Dr, Easton, MD 21601
(410) 643-2244
$365,000
4 beds2 baths1,880 sq ft
29430 Corbin Pkwy, Easton, MD 21601
(202) 528-9245
COMING SOON
$459,900
4 beds2.5 baths2,200 sq ft
8496 Colony Cir, Easton, MD 21601
(410) 822-6665
$135,000
2 beds1.5 baths1,282 sq ft
17 Downing St, Easton, MD 21601
(410) 228-0800
3D WALKTHROUGH
$495,000
2 beds2 baths2,184 sq ft
7311 Madaline Ave, Easton, MD 21601
(410) 822-6665
$445,000
2 beds2 baths1,485 sq ft
117 E Dover St E #207, Easton, MD 21601
(410) 822-6665
$480,000
4 beds2.5 baths2,000 sq ft
8760 Black Dog Aly, Easton, MD 21601
(410) 224-2200
$465,000
4 beds2.5 baths2,120 sq ft
8362 Colony Cir, Easton, MD 21601
(410) 822-6665
3D WALKTHROUGH
$1,595,000
4 beds3.5 baths4,618 sq ft
6385 Canterbury Dr, Easton, MD 21601
(410) 822-6665
See all

Provided by Redfin

Sale history for 27188 Baileys Neck Rd

Year

Property tax

Land + Additions

Assessment*

2026

$28,984 (+5.2%)

$1,577,000 + $1,554,200

$3,131,200

2025

$27,559 (+5.0%)

$1,577,000 + $1,554,200

$3,131,200

2024

$26,241 (+18.7%)

2023

$22,110 (+8.5%)

2022

$20,374 (+3.2%)

$1,577,000 + $1,016,300

$2,593,300

2021

$19,738 (+4.3%)

2020

$18,932

2019

$18,932 (+3.4%)

$1,564,200 + $968,300

$2,532,500

2018

$18,306 (−6.4%)

$1,564,200 + $968,300

$2,532,500

2017

$19,560 (−2.2%)

$1,952,000 + $895,100

$2,847,100

2015

$20,005 (+2.4%)

$2,202,000 + $910,000

$3,112,000

2014

$19,539 (+3.5%)

2013

$18,885 (−17.8%)

2012

$22,966 (+39.1%)

2011

$16,512 (+1.1%)

2010

$16,329 (−1.4%)

2009

$16,556

Tax history for 27188 Baileys Neck Rd

Year

Property tax

Land + Additions

Assessment*

2026

$28,984 (+5.2%)

$1,577,000 + $1,554,200

$3,131,200

2025

$27,559 (+5.0%)

$1,577,000 + $1,554,200

$3,131,200

2024

$26,241 (+18.7%)

2023

$22,110 (+8.5%)

2022

$20,374 (+3.2%)

$1,577,000 + $1,016,300

$2,593,300

2021

$19,738 (+4.3%)

2020

$18,932

2019

$18,932 (+3.4%)

$1,564,200 + $968,300

$2,532,500

2018

$18,306 (−6.4%)

$1,564,200 + $968,300

$2,532,500

2017

$19,560 (−2.2%)

$1,952,000 + $895,100

$2,847,100

2015

$20,005 (+2.4%)

$2,202,000 + $910,000

$3,112,000

2014

$19,539 (+3.5%)

2013

$18,885 (−17.8%)

2012

$22,966 (+39.1%)

2011

$16,512 (+1.1%)

2010

$16,329 (−1.4%)

2009

$16,556

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

Public record

Public record
Zoning

Beds

—

Baths

4.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

9.42 Acres

Year renovated

—

Sq. Ft.

5,373

Year built

1920

Style

Single Family Residential

County

Talbot County

APN

03 123197

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 26, 2026.

Resource Conservation District

The RC District is characterized by natural environments (wetlands, forests, or abandoned fields) and resource development activities (agriculture, forestry, fisheries, or aquaculture). This district conserves the irreplaceable agricultural, forested, and natural environmental character of the County. Agricultural activities shall be preserved, encouraged and protected. Development activities are to be in the form of large lots or clustered lots outside of habitat protection areas, without public water or sewer service. Development in this district shall: Maintain and, wherever possible, improve the quality of runoff and groundwater entering the Chesapeake Bay and its tributary streams; Conserve and protect agricultural lands and uses; Protect environmentally sensitive lands and Preserve rural character through conservation of open space and agricultural lands.

Permitted uses

Include but are not limited to:

Agriculture
Greenhouse / nursery
Livestock production
Day care facility
Housing-Group
Housing-Single unit
Infrastructure
Fire house
Police station
Communications tower

Property details

Parking

Parking Information
# of Detached Garage Spaces: 4
Garage Features: Additional Storage Area
# of Total Garage and Parking Spaces: 4
Has Garage
# of Garage Spaces: 4
Detached Garage, Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On Main Level: 1

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3

Interior Information
Flooring Type: Hardwood
Living Area Sq.Ft. Source: Assessor

Fireplace Information
Has Fireplace

Basement Information
Basement: Yes
Combination

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $968,300
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Brick
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Balconies- Multiple, Brick, Deck(s), Enclosed, Patio(s), Porch(es), Terrace
Roof: Asphalt
Structure Type: Detached
Other Structures: Cabana/Pool House, Gazebo, Guest House, Pool Equipment Shed, Other

Exterior Information
BBQ Grill, Exterior Lighting, Flood Lights, Hot Tub, Outbuilding(s), Outside Shower, Private Beach

Pool Information
Personal Pool

Lot Information
Navigable Water

Land Information
Land Assessed Value: $1,564,200

Dock Information
Dock Type and Features: Hoist/Lift Electric, Material - Treated Lumber, Multiple Slip, Pier, Private
Dock/Slip Conveyance: Exclusive Use
# of Docks: 1
Dock/Slip Conveys: Yes

Above Grade Information
Finished Sq.Ft.: 7,907
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $18,973
Tax Assessed Value: $2,532,500
Tax Year: 2019
Tax Annual Amount: $18,973

Assessments Information
Year Assessed: 2019

Utilities

Utilities Information
Cooling Type: Heat Pump(s)
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Oil
Water Source: Well

Location

School Information
School District Name: TALBOT COUNTY PUBLIC SCHOOLS
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: Oxford Road to Bailey's Neck Road , continue to almost end of road. Where road splits stay left to private lane on right. (Do not enter without appointment)

Waterfrontage Information
Water Access
On Waterfront
Water Oriented
Water Body Type: River
Water Body Name: Tred Avon/Trippe Creek

Public facts

Beds: —
Baths: 4.5
Sq. Ft.: 5,373
Stories: 1.5
Lot Size: 9.42 acres
Style: Single Family Residential
Year Built: 1920
Year Renovated: —
County: Talbot County
APN: 03 123197

Home facts updated by county records on Aug 26, 2026

Around this home

Schools

White Marsh Elementary School

Public PreK-5 • Assigned • 5.0mi

8/10

Easton Middle School

Public 6-8 • Assigned • 4.5mi

5/10

Easton High School

Public 9-12 • Assigned • 4.6mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

7/10 Flood Factor

Estimated 72-80% 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

9/10 Heat Factor

7 days above 103° expected this year, 16 days in 30 years

6/10 Wind Factor

57% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Easton, MD • 21601

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 4.9 hours in December, which is comparable to the U.S. average for solar exposure.

9.3 hrs

4.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.16M – $5.04M

Reach more buyers when you sell with Redfin. Save up to $43,803 in fees. 3 minutes to get started.

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

Nearby similar homes

NEW 2 HRS AGO

$269,500

2 beds1 bath982 sq ft

302 W Oak Ave, Easton, MD 21601

One story living • Picture window • Spacious lot

(410) 822-7556

3D WALKTHROUGH

$2,695,000

4 beds4 baths3,589 sq ft

4440 Baildon Rd, Trappe, MD 21673

Private dock • Deepwater point • Guest apartment

(410) 745-0415

$525,000

3 beds2 baths1,404 sq ft

105 Pier St E, Oxford, MD 21654

Front porch • Back porch • Town park

(410) 643-2244

$513,000

3 beds3 baths3,506 sq ft

7316 Casey Ave, Easton, MD 21601

Corner lot • Large loft area • New hvac

(410) 543-4545

OPEN SUN, 11:30AM TO 1PM

$749,990

4 beds3.5 baths4,201 sq ft

8095 N Fork Blvd, Easton, MD 21601

Open floor plan • Generous island • Gas fireplace

(301) 355-0510

$2,375,000

5 beds4.5 baths3,670 sq ft

25705 Edgeview Rd, Royal Oak, MD 21662

Five-foot-wide pier • Nature walking-trail • Park-like setting

(410) 822-6665

New listings for sale in 21601

NEW 2 HRS AGO

$269,500

2 beds1 bath982 sq ft

302 W Oak Ave, Easton, MD 21601

One story living • Picture window • Spacious lot

(410) 822-7556

$499,900

3 beds3 baths2,342 sq ft

29709 Lyons Dr, Easton, MD 21601

Corner lot • Formal dining room • Great room

(410) 643-2244

$365,000

4 beds2 baths1,880 sq ft

29430 Corbin Pkwy, Easton, MD 21601

Local amenities • 0.3 acre lot • 4 parking spots

(202) 528-9245

COMING SOON

$459,900

4 beds2.5 baths2,200 sq ft

8496 Colony Cir, Easton, MD 21601

0.33 acre lot • Pool • Built 1996

(410) 822-6665

$135,000

2 beds1.5 baths1,282 sq ft

17 Downing St, Easton, MD 21601

Three-season room • Walking trails • Dog park

(410) 228-0800

3D WALKTHROUGH

$495,000

2 beds2 baths2,184 sq ft

7311 Madaline Ave, Easton, MD 21601

Flexible floor plan • Built-in shelving • Granite countertops

(410) 822-6665

$445,000

2 beds2 baths1,485 sq ft

117 E Dover St E #207, Easton, MD 21601

Ten-foot ceilings • New hvac • Hot water tank

(410) 822-6665

$480,000

4 beds2.5 baths2,000 sq ft

8760 Black Dog Aly, Easton, MD 21601

Modern kitchen • White cabinets • Quartz countertops

(410) 224-2200

$465,000

4 beds2.5 baths2,120 sq ft

8362 Colony Cir, Easton, MD 21601

Open space views • Soaking tub • Large walk in closet

(410) 822-6665

Home values near 27188 Baileys Neck Rd

Data from public records.

Address	Redfin Estimate
27310 Baileys Neck Road, Easton, MD - Beds \| 2 Baths \| 2620 Sq. Ft.	$1,239,788
27151 Baileys Neck Road, Easton, MD 5 Beds \| 6.5 Baths \| 10000 Sq. Ft.	$4,975,702

Address	Redfin Estimate
27214 Baileys Neck Road, Easton, MD 7 Beds \| 7.5 Baths \| 7418 Sq. Ft.	$3,357,852
27159 Baileys Neck Road, Easton, MD - Beds \| 2.5 Baths \| 2627 Sq. Ft.	$1,803,174

Address	Redfin Estimate
27211 Baileys Neck Road, Easton, MD 5 Beds \| 5.5 Baths \| 5942 Sq. Ft.	$2,821,859
27318 Baileys Neck Road, Easton, MD - Beds \| 3.5 Baths \| 2988 Sq. Ft.	$1,569,419

Property information provided by BRIGHT MLS when last listed in 2020. This data may not match . Learn more.

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

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

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.

Houses for rent in Easton	Agents near me	Frederick, MD homes for sale	Easton Housing Market
Houses for sale near me	Baltimore, MD homes for sale	Rockville, MD homes for sale
Land for sale near me	Bethesda, MD homes for sale	Columbia, MD homes for sale
Open Houses near me	Bowie, MD homes for sale	Easton Property Records
Condos for sale near me	Silver Spring, MD homes for sale	MD New Listings

St. Michaels homes for sale
Stevensville homes for sale
Cambridge homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 21601, MD

Sale history for 27188 Baileys Neck Rd

Tax history for 27188 Baileys Neck Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21601

Home values near 27188 Baileys Neck Rd

More real estate resources