Are neighbors friendly in Drayden, MD?

As of early 2026, 100% of users say neighbors are friendly

Are there community events in Drayden, MD?

As of early 2026, 100% of users say there are community events

Are yards well-kept in Drayden, MD?

As of early 2026, 100% of users say yards are well-kept

Is there wildlife in Drayden, MD?

As of early 2026, 100% of users say there's wildlife

Is a car needed in Drayden, MD?

As of early 2026, 100% of users say car is needed

Would people walk alone at night in Drayden, MD?

As of early 2026, 100% of users say people would walk alone at night

Is Drayden, MD dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Do kids play outside in Drayden, MD?

As of early 2026, 50% of users say kids play outside

Is Drayden, MD walkable to restaurants?

As of early 2026, 33% of users say it's walkable to restaurants

What is 18086 Windmill Point Rd estimated to be worth?

Trulia's estimated value for 18086 Windmill Point Rd in Drayden, MD is $1,003,300 .

What is the price history for 18086 Windmill Point Rd?

18086 Windmill Point Rd in Drayden, MD last sold for $750,000 in October 2015.

Is Drayden a buyer's or seller's market?

Drayden is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 18086 Windmill Point Rd?

The closest schools to 18086 Windmill Point Rd in Drayden, MD are Leonardtown High School (rated 8/10), Piney Point Elementary School (Pre-K, rated 7/10), Spring Ridge Middle School (rated 5/10).

How big is the lot at 18086 Windmill Point Rd?

The lot at 18086 Windmill Point Rd in Drayden, MD is about 10.1 acres .

Does 18086 Windmill Point Rd have a garage?

Yes, 18086 Windmill Point Rd in Drayden, MD has a garage.

OFF MARKET

$1,003,300

Trulia Estimate

5 Beds
4 Baths
2,900 sqft (on 10.05 acres)

18086 Windmill Point Rd, Drayden, MD 20630

Est. Refi. Payment $6,176/mo*

Refinance Your Home

Currently Off Market - Sold Oct 13, 2015 for $750,000

Home Value

Trulia Estimate

$1M

Since last month

$13K (-1.3%)

Since last year

$20K (+2%)

Since last sale

$253K (+33.8%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +33% in the last 10 years

Month	Estimated value
2026
October 2026	$1M
September 2026	$1.02M
August 2026	$996K
July 2026	$1.01M
June 2026	$1.02M
May 2026	$1.01M
April 2026	$997K
March 2026	$994K
February 2026	$974K
January 2026	$970K
2025
December 2025	$967K
November 2025	$968K
October 2025	$984K
September 2025	$992K
August 2025	$997K
July 2025	$1.02M
June 2025	$1.03M
May 2025	$1.01M
April 2025	$998K
March 2025	$996K
February 2025	$975K
January 2025	$959K
2024
December 2024	$960K
November 2024	$972K
October 2024	$1M
September 2024	$1M
August 2024	$1.02M
July 2024	$1.03M
June 2024	$1.03M
May 2024	$1.03M
April 2024	$1.01M
March 2024	$996K
February 2024	$972K
January 2024	$961K
2023
December 2023	$967K
November 2023	$961K
October 2023	$962K
September 2023	$974K
August 2023	$980K
July 2023	$990K
June 2023	$989K
May 2023	$942K
April 2023	$934K
March 2023	$923K
February 2023	$904K
January 2023	$900K
2022
December 2022	$912K
November 2022	$931K
October 2022	$941K
September 2022	$945K
August 2022	$952K
July 2022	$970K
June 2022	$986K
May 2022	$985K
April 2022	$965K
March 2022	$953K
February 2022	$930K
January 2022	$917K
2021
December 2021	$914K
November 2021	$909K
October 2021	$909K
September 2021	$904K
August 2021	$902K
July 2021	$906K
June 2021	$913K
May 2021	$913K
April 2021	$883K
March 2021	$831K
February 2021	$814K
January 2021	$792K
2020
December 2020	$766K
November 2020	$755K
October 2020	$756K
September 2020	$740K
August 2020	$751K
July 2020	$744K
June 2020	$762K
May 2020	$767K
April 2020	$770K
March 2020	$766K
February 2020	$753K
January 2020	$743K
2019
December 2019	$744K
November 2019	$745K
October 2019	$744K
September 2019	$734K
August 2019	$749K
July 2019	$730K
June 2019	$719K
May 2019	$725K
April 2019	$737K
March 2019	$726K
February 2019	$729K
January 2019	$729K
2018
December 2018	$751K
November 2018	$781K
October 2018	$797K
September 2018	$814K
August 2018	$809K
July 2018	$812K
June 2018	$820K
May 2018	$805K
April 2018	$801K
March 2018	$803K
February 2018	$796K
January 2018	$788K
2017
December 2017	$763K
November 2017	$775K
October 2017	$769K
September 2017	$773K
August 2017	$766K
July 2017	$759K
June 2017	$753K
May 2017	$747K
April 2017	$741K
March 2017	$731K
February 2017	$718K
January 2017	$727K
2016
December 2016	$748K
November 2016	$751K
October 2016	$754K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
46112 Slye Way, Drayden, MD	0.85	Single-Family Home	$524,900	08/12/26	4	2.5	2,552
46442 Hyatt Ct, Drayden, MD	1.17	Single-Family Home	$635,000	02/26/26	4	3.5	3,534
18747 Vernon Ct, Drayden, MD	1.09	Single-Family Home	$640,000	05/11/26	4	2.5	3,572
19005 N Porto Bello Dr, Drayden, MD	1.58	Single-Family Home	$660,000	07/24/26	5	3.5	4,022
Address Not Disclosed, Drayden, MD	1.53	Single-Family Home	$660,000	06/15/26	4	3	2,486
46775 Frogs Marsh Rd, Drayden, MD	2.07	Single-Family Home	$699,000	04/08/26	5	3.5	3,298
17911 Rosecroft Rd, Lexington Park, MD	1.89	Single-Family Home	$850,000	11/17/25	4	2	2,548
19211 Nelson Ct, Valley Lee, MD	2.01	Single-Family Home	$555,000	06/12/26	4	2.5	2,184
45954 Burns Dr, Valley Lee, MD	2.17	Single-Family Home	$585,000	09/21/26	5	2.5	2,430
19068 Mallard Creek Ct, Valley Lee, MD	2.19	Single-Family Home	$610,000	08/10/26	4	3	2,381

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
17934 Windmill Point Rd, Drayden, MD 20630	0.15	$1,368,900	Studio	5	4,954	Off Market
18086 Windmill Point Rd, Drayden, MD 20630	0.20	-	Studio	-	-	Off Market
18018 Windmill Point Rd, Drayden, MD 20630	0.25	$767,600	Studio	3	3,186	Off Market
18100 Carthagena Ln, Drayden, MD 20630	0.25	$813,600	Studio	3	1,735	Off Market
45276 F Birch Lane, Maryland , CA 20630	0.26	$421,700	Studio	-	-	Off Market
18154 Cherryfield Rd, Drayden, MD 20630	0.29	-	-	-	-	Off Market
18154 Cherryfield Rd, Drayden, MD 20630	0.29	$571,800	Studio	-	-	Off Market
18154 Cherryfield Rd, Drayden, MD 20630	0.29	$589,000	Studio	-	-	Off Market
18016 Windmill Point Rd, Drayden, MD 20630	0.29	$839,800	Studio	3	2,383	Off Market
18278 Cherryfield Rd, Drayden, MD 20630	0.30	$335,600	Studio	2	924	Off Market
18080 Carthagena Ln, Drayden, MD 20630	0.31	$929,000	Studio	3	3,972	Off Market
18254 Cherryfield Rd, Drayden, MD 20630	0.33	$720,600	3	3.5	3,300	Off Market
18300 Cherryfield Rd, Drayden, MD 20630	0.36	$1,030,300	Studio	3	4,867	Off Market
46475 Dennis Point Way, Drayden, MD 20630	0.37	$839,600	Studio	3	3,408	Off Market
18300 Cherryfield Rd, Drayden, MD 20630	0.40	-	-	-	-	Off Market
18300 Cherryfield Rd, Drayden, MD 20630	0.40	$533,700	Studio	-	-	Off Market
18144 Cherryfield Rd, Drayden, MD 20630	0.40	$757,000	Studio	3	2,308	Off Market
18052 Cherryfield Rd, Drayden, MD 20630	0.41	$468,500	Studio	1	1,260	Off Market
18380 Windmill Point Rd, Drayden, MD 20630	0.43	$558,200	Studio	2	1,430	Off Market
46501 Cooper Creek Ln, Drayden, MD 20630	0.44	$409,400	3	2	1,932	Off Market

Local Information

Map ViewExplore the area around 18086 Windmill Point Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1989

10.05 acre lot

2,900 sqft

$346/sqft

Garage

About this House

SCHEDULE A SHOWING ONLINE AT: showmojo.com/lh/00056390d2 This large Multi-Bedroom Waterfront Home is located on Carthegena Creek just south of St. Mary's City on 4 acres of property. Master bedroom is on the first floor. The second level consists of two large bedrooms with an additional optional bedroom off of each main room. The home comes with water access, pier and storage shed. Kitchen includes electric oven/range, microwave, refrigerator and dishwasher. Wood-burning fireplace. Two bedrooms have large walk-in closets. Screened in porch.Excellent credit needed.No section 8 housing vouchers accepted.No smoking allowed.Pets accepted with owner approval.

18086 Windmill Point Rd, Drayden, MD 20630 is a 5 bedroom, 4 bathroom, 2,900 sqft single-family home built in 1989. It last sold for $750,000 on Oct 13, 2015. More recently, it was listed as a rental in January 2015 with an asking price of $1,995 per month. That rental listing was removed on January 6, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,003,300, with a rent estimate of $3,505/month.

Home Details for 18086 Windmill Point Rd

Interior Features
Heating & Cooling Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility Stories: 2
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: OtherFoundation Type: Piers
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1989
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 10.05 acres

Price and Tax history

Date	Event	Price
Oct 13, 2015 Source: N/A	Sold	$750,000
Jan 6, 2015 Source: Agent Provided	ListingRemoved	$1,995
Jan 1, 2015 Source: Agent Provided	Listed For Rent	$1,995
Oct 3, 2014 Source: Agent Provided	ListingRemoved	$1,995
Sep 10, 2014 Source: Agent Provided	PriceChange	$1,995 Price decreased by 7%
Jun 10, 2014 Source: Agent Provided	Listed For Rent	$2,150
Aug 27, 2003 Source: N/A	Sold	$770,000

Year	Property tax	Tax assessment
2025	$7,869	$723,900

Additional Cost

Market trends in Drayden

Last updated September 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

—

Sourced by Trulia Market Trends

Around this home

Piney Point Elementary School
PK-5
Public
423 Students
St. Mary's County Public Schools
7/10
GreatSchools Rating
Parent Rating Average
One of the best, if not the very best Elementary school in the county. Smallest class sizes, teachers who try and care. You can't ask you more from a public school.
Parent Review
11mo ago
8 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Drayden

At least 1 Trulia users voted on each feature.

100 % Say neighbors are friendly
100 % Say there are community events
100 % Say yards are well-kept
100 % Say there's wildlife
100 % Say car is needed
100 % Say people would walk alone at night
100 % Say it's dog friendly
50 % Say kids play outside
33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 18086 Windmill Point Rd

What is 18086 Windmill Point Rd estimated to be worth?
Trulia's estimated value for 18086 Windmill Point Rd in Drayden, MD is $1,003,300.
What is the price history for 18086 Windmill Point Rd?
18086 Windmill Point Rd in Drayden, MD last sold for $750,000 in October 2015.
Is Drayden a buyer's or seller's market?
Drayden is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 18086 Windmill Point Rd?
The closest schools to 18086 Windmill Point Rd in Drayden, MD are Leonardtown High School (rated 8/10), Piney Point Elementary School (Pre-K, rated 7/10), Spring Ridge Middle School (rated 5/10).
How big is the lot at 18086 Windmill Point Rd?
The lot at 18086 Windmill Point Rd in Drayden, MD is about 10.1 acres.
Does 18086 Windmill Point Rd have a garage?
Yes, 18086 Windmill Point Rd in Drayden, MD has a garage.

Apartments for Rent

Skip to last item

$1,390/mo
1 bd
1 ba
17476 Piney Point Rd #1d522b748,
Piney Pt, MD 20674
$1,495/mo
1 bd
1 ba
Address Not Disclosed,
Tall Timbers, MD 20690
See more homes for rent in
Drayden
Take a look

Skip to first item

Off Market Homes Near 18086 Windmill Point Rd

Skip to last item

SOLD
OCT 19, 2026
$540,000
4 bd
3.5 ba
2,964 sqft
45795 Stoney Run Dr,
Great Mills, MD 20634
Home Towne Real Estate
SOLD
OCT 2, 2026
$949,000
4 bd
4 ba
3,455 sqft
44637 Bellview Ct,
Tall Timbers, MD 20690
Infinitas Realty Group
SOLD
SEP 21, 2026
$585,000
5 bd
2.5 ba
2,430 sqft
45954 Burns Dr,
Valley Lee, MD 20692
EXP Realty, LLC
SOLD
AUG 17, 2026
$620,000
2 bd
2 ba
1,698 sqft
16144 Thomas Rd,
Piney Point, MD 20674
EXP Realty, LLC
SOLD
AUG 12, 2026
$524,900
4 bd
2.5 ba
2,552 sqft
46112 Slye Way,
Drayden, MD 20630
RE/MAX One
SOLD
AUG 10, 2026
$525,000
4 bd
1 ba
1,060 sqft
18167 River Rd,
Tall Timbers, MD 20690
EXP Realty, LLC
SOLD
AUG 10, 2026
$610,000
4 bd
3 ba
2,381 sqft
19068 Mallard Creek Ct,
Valley Lee, MD 20692
CENTURY 21 New Millennium
SOLD
JUL 29, 2026
$735,000
4 bd
3.5 ba
4,588 sqft
19305 Greens Crossing Ct,
Great Mills, MD 20634
Deep Roots Real Estate
SOLD
JUL 24, 2026
$660,000
5 bd
3.5 ba
4,022 sqft
19005 N Porto Bello Dr,
Drayden, MD 20630
Coldwell Banker Realty
SOLD
JUL 16, 2026
$1,460,000
9 bd
8 ba
9,824 sqft
45820 Highway To Heaven Ln,
Great Mills, MD 20634
EXP Realty, LLC
See more homes for sale in
Drayden
Take a look

Skip to first item

Homes for sale near 18086 Windmill Point Rd

Skip to last item

1.48 ACRES
$475,000
3 bd
2 ba
1,948 sqft
18532 Cherryfield Rd,
Drayden, MD 20630
CENTURY 21 New Millennium
189 ACRES
$3,500,000
3 bd
2 ba
4,541 sqft
45776 Boothe Rd,
Drayden, MD 20630
Century 21 Redwood Realty
NEW - 1 DAY AGO
NEW CONSTRUCTION
1.09 ACRES
$635,900
3 bd
2.5 ba
2,240 sqft
19103 Windsor Ct,
Drayden, MD 20630
RE/MAX One
1.14 ACRES
$569,900
4 bd
3.5 ba
3,436 sqft
19335 Greens Crossing Ct,
Great Mills, MD 20634
CENTURY 21 New Millennium
COMING SOON 11/20
42 ACRES
$2,250,000
4 bd
3 ba
4,228 sqft
45433 Drayden Rd,
Valley Lee, MD 20692
Century 21 Redwood Realty
NEW CONSTRUCTION
1.26 ACRES
$776,220
4 bd
3.5 ba
2,253 sqft
19166 N Porto Bello Dr,
Drayden, MD 20630
RE/MAX One
NEW - 1 DAY AGO
NEW CONSTRUCTION
1.24 ACRES
$599,900
4 bd
2 ba
2,343 sqft
19163 Porto Bello,
Drayden, MD 20630
RE/MAX One
1 ACRE
$499,000
3 bd
2 ba
1,371 sqft
47558 Lucas Cove Ln,
Lexington Park, MD 20653
Infinitas Realty Group
13.62 ACRES
$970,000
3 bd
2.5 ba
2,590 sqft
46200 Greens Rest Way,
Great Mills, MD 20634
CENTURY 21 New Millennium
0.47 ACRES
$475,000
3 bd
2.5 ba
2,350 sqft
45155 Loblolly Ct,
Tall Timbers, MD 20690
CENTURY 21 New Millennium
See more homes for sale in
Drayden
Take a look