27770 Leeward Dr, Salisbury, MD 21801
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Property image
OFF MARKET

27770 Leeward Dr
Salisbury, MD 21801

  • 3 Beds
  • 2 Baths
  • 1,720 sqft (on 0.72 acres)

$344,800

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,061/mo*
Refinance Your Home

$344,800

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,061/mo*
Refinance Your Home
3 Beds
2 Baths
1,720 sqft
(on 0.72 acres)

Home Value

Trulia Estimate
$345K
Since last month
Decreased$3K (-0.9%)
Since last year
Increased$2K (+0.6%)
Since last sale
Increased$145K (+73.1%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$343K
July 2026$346K
June 2026$349K
May 2026$350K
April 2026$347K
March 2026$347K
February 2026$347K
January 2026$340K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
27243 Equestrian Dr, Salisbury, MD
0.30
Single-Family Home
$449,900
10/10/25
3
2.5
2,109
27652 Belgian Way, Salisbury, MD
0.34
Single-Family Home
$505,000
02/13/26
3
2.5
2,360
27836 Clearwater Ct, Salisbury, MD
0.61
Single-Family Home
$315,000
08/25/25
3
2.5
1,458
27768 Crooked Oak Ln, Salisbury, MD
0.46
Single-Family Home
$349,990
04/30/26
4
2.5
2,215
27620 Appaloosa Dr, Salisbury, MD
0.36
Single-Family Home
$519,000
12/15/25
4
2.5
2,555
27640 Belgian Way, Salisbury, MD
0.33
Single-Family Home
$525,000
10/31/25
4
2.5
2,645
6163 Cadagon Ct, Salisbury, MD
0.82
Single-Family Home
$351,000
08/10/26
3
2.5
1,482
5995 Bell Creek Dr, Salisbury, MD
0.76
Single-Family Home
$339,900
05/15/26
3
2
1,674
5920 Tappan Ln, Salisbury, MD
0.74
Single-Family Home
$300,000
05/28/26
3
2
1,600
5991 Bell Creek Dr, Salisbury, MD
0.75
Single-Family Home
$386,500
08/22/25
3
2
1,717

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
27715 Pemberton Dr, Salisbury, MD 21801
0.10
$383,600
3
2
1,440
Off Market
27131 Equestrian Dr, Salisbury, MD 21801
0.16
$521,100
4
2.5
2,645
Off Market
27152 Equestrian Dr, Salisbury, MD 21801
0.15
$555,000
4
3.5
2,437
For Sale
5689 Spinnaker Dr, Salisbury, MD 21801
0.15
$325,900
3
2
1,864
Off Market
5579 Channel Dr, Salisbury, MD 21801
0.27
$326,000
3
2
2,082
Off Market
27671 Belgian Way, Salisbury, MD 21801
0.30
$526,200
3
2.5
2,555
Off Market
5871 Mustang Ct, Salisbury, MD 21801
0.30
$465,200
3
2.5
2,502
Off Market
27243 Equestrian Dr, Salisbury, MD 21801
0.30
$485,000
3
2.5
2,109
For Sale
27645 Belgian Way, Salisbury, MD 21801
0.33
$612,200
4
4
3,109
Off Market
27640 Belgian Way, Salisbury, MD 21801
0.33
$525,000
4
2.5
2,645
Recently Sold
5881 Mustang Ct, Salisbury, MD 21801
0.34
$533,500
4
3
2,167
Off Market
27652 Belgian Way, Salisbury, MD 21801
0.34
$505,000
3
2.5
2,360
Recently Sold

Local Information

  • Map ViewExplore the area around 27770 Leeward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1987
Lot Size
0.72 acres
Living Area
1,720 sqft
Price/Sqft
$200
Parking
Garage

About this House

Beautifully remodeled 3 bedroom 2 bath spacious rancher located in the culdesac of a quite west side neighborhood. Home has many great features including both a living room & a large family room, formal dining room, fenced in back yard, new roof, blacktop driveway, in ground sprinkler system, large storage shed, a rear deck & a paver patio. The home also has tile floors in kitchen and in both bathrooms, a tiled shower, double sinks in master bedroom, separate utility room with walk in pantry, upgrade lights and fans, pellet stove and 3 year old appliances. This home shows very well and you will not be disappointed.Brokered And Advertised By: Vicky S WhiteheadListing Agent: Darron S Whitehead
27770 Leeward Dr, Salisbury, MD 21801 is a 3 bedroom, 2 bathroom, 1,720 sqft single-family home built in 1987. It last sold for $198,000 on Nov 4, 2011. It is currently off market. The Trulia Estimate is $344,800, with a rent estimate of $2,098/month.

Home Details for 27770 Leeward Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.72 acres

Price and Tax history

DateEventPrice
Nov 4, 2011
Source: N/A
Sold
$198,000
Aug 10, 2011
Source: Agent Provided
Listed For Sale
$198,000
Dec 23, 2008
Source: N/A
Sold
$201,000
Sep 12, 2007
Source: N/A
Sold
$175,000
Jan 15, 2003
Source: N/A
Sold
$134,500

Market trends in Salisbury

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$275K
$8.33KMoM
Sale-to-List Price
100.0%
0.8%MoM
Price per sq ft
$165
$0MoM
Available listings
260
7MoM
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Around this home

What Locals Say about Salisbury

At least 425 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 81 % Say parking is easy

  • 75 % Say yards are well-kept

  • 75 % Say it's dog friendly

  • 68 % Say there's holiday spirit

  • 62 % Say kids play outside

  • 58 % Say there are sidewalks

  • 54 % Say it's quiet

  • 47 % Say neighbors are friendly

  • 44 % Say streets are well-lit

  • 43 % Say there's wildlife

  • 41 % Say people would walk alone at night

  • 38 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to restaurants

  • 35 % Say it's walkable to grocery stores

  • 21 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Steven Harrison
    "Quite, no crime reports last year. Peaceful and safe for children to play. Dog owners respectful of others. Lawns and homes well kept."
    0
    Flag
  • Sharonroeble
    "Bike races and foot races. Monthly events on Friday including food and music. Cultural events at the college."
    0
    Flag
  • Nicole Alu-Parks
    "People do not pick up the dog poop frequently but most of the dogs are very sweet and all are on a leash. "
    4
    Flag
  • Trulia User
    "I believe the neighborhood has homeowners that have been living here for several generations. On the Westside of town, everyone knows everyone from grandparents. to grandkids"
    7
    Flag
  • Trulia User
    "I Everyone is very friendly and loves animals. If one of our animals gets loose, we immediately go online, and everyone gets together and tries to find them. A lot of animals have been returned to their owners because of that kindness of the people that live in Huntington Park. "
    3
    Flag
  • Trulia User
    "Lots of people walking dogs and picking up after them. Dogs are on leashes and not running loose. Friendly neighbors."
    0
    Flag
  • Trulia User
    "Very quiet neighborhood and safe for children. neighbors are very friendly and look out for each other. "
    3
    Flag
  • Trulia User
    "i don’t know i just go to work and go home it’s quiet for the most part i’ve also seen alot of kids around here so i guess if y’all have children i’d be fine "
    1
    Flag
  • Trulia User
    "The high crime rate and nothing too for the younger kid's to do, not many stores on this end the west and not many places too go "
    0
    Flag
  • Trulia User
    "neighborhood activities for kids during holidays, as well as contests for home decorating and community yardsales. for West Nithsdale at least"
    1
    Flag
  • TB
    "It’s a good neighborhood. And like most neighborhoods, there’s good parts and bad parts. Just do your research on where you want to live. "
    0
    Flag
  • Robin B.
    "I drive to and from everywhere I need to go. My commute is like 5 minutes. ................ what more can I say. My commute is not bad. I love it"
    7
    Flag
  • Supermegantotherescue
    "no sidewalks, no trash cans. dirt bikes and 4 wheelers in traffic and residential streets. some areas of the neighborhood are pretty rough. "
    10
    Flag
  • Robin E. J.
    "it's far enough out of the city to enjoy the quiet and relaxing neighborhood. Shopping centers and beaches are with in 30 minutes. There are local parks, restaurants nearby. Great housing within a 30 mile radius. "
    0
    Flag
  • Leif H.
    "There is a dog park a few miles down the road, not to mention Salisbury Park has great trails nearby."
    8
    Flag
  • Merri W.
    "There’s nothing to do for children from the ages of 11 to 19. The only thing there is to do is get in trouble. Salisbury does not care about its youth."
    10
    Flag
  • Brent W.
    "I feel safe in this neighborhood. Big adjustment from living in the mountains but it wasn’t so bad. Very close to some bad areas though. "
    12
    Flag
  • Neka0228
    "The school system is very good for my kids . They’re very many jobs as well . I lived here about two years and I liked it "
    0
    Flag
  • Donna P.
    "I have lived in his neighborhood for a few years now. I love that I'm close to the park and shopping. Also close to the byways and highways. Less than 30 minutes from Ocean City."
    5
    Flag
  • Daniel J.
    "I do not go to any community events. I'm not into the bar scene, movie theater is basic at best, and I'm not a university student. Part of Salisbury is college students, part is somewhat decent, and then part is just trashy crack head central! "
    0
    Flag
  • Wholeycow24
    "The Salisbury Park, Salisbury Zoo, and Civic Center have events all the time. Some are even free to the public. "
    5
    Flag
  • Stephen W.
    "There are walking trails and other people with dogs in the neighborhood. There is a wooded area where our dog runs and plays"
    3
    Flag
  • Lexi F.
    "there is absolutely positively no events in the neighborhood that are special. watch your nieghbors, theyll rob you too."
    3
    Flag
  • Trulia User
    "not far from everything and nice neighborhood, close to friends. love the area,nice yards,plenty of room "
    2
    Flag
  • Doris F.
    "There is a park and zoo in close range that does have a pet area where dogs are always welcomegreat place for dogs to romp and play to burn off some pent up energy"
    3
    Flag
  • A E.
    "My neighborhood has changed so much. what once was Mayberry is now Compton.. I cannot stand having to live in this hectic place. it is not what it used to be."
    3
    Flag
  • Deborah C.
    "Eden is a rural setting. Bull frogs get loud crickets chirp. Life is a slower pace but as for me and mine we are content. "
    0
    Flag
  • Mark P.
    "This is a quiet neighborhood. The area is close to the main shopping centers and only 30 minutes from the beach. "
    0
    Flag
  • Michele N
    "Quite,Lots of families ,close to a lot of shops ,Neighbors are friendly but stay to themselves ! Great place to talk an afternoon walk!"
    0
    Flag
  • Neil S.
    "My neighborhood is pretty decent. I feel safe enough considering how things can be these days. You really need a car however since shopping/stores too far to walk but a short in a car. "
    0
    Flag
  • Susan-cf
    "The neighborhood is friendly well maintained and safe. My husband grew up in Salisbury and he plans for us to retire there."
    0
    Flag
  • John M and Charlene Madritch
    "We are not residents of the city of Salisbury so we do not need to pay city taxes. We have very little traffic.Children can play safely outside. It's a quiet, friendly neighbourhood with a very low HOA."
    0
    Flag
  • Trulia User
    "I live close to my job and drive around town with no issues. Traffic can be heavy at times, but it’s manageable "
    2
    Flag
  • Nmalu530
    "I drive about an hour to work and am always late due to trucks, school buses and farm equipment. Not a fun commute"
    1
    Flag
  • Megan
    "many safe communities suitable to raise children, a lot of things to do such as a movie theater, trampoline park, sports center, playgrounds, a zoo, etc. abundant child care and decent schools."
    1
    Flag
  • Sjockiea
    "there are families in my neighborhood and the park and zoo are really close by. There are a lot of events for adults and social bars and places to go."
    0
    Flag
  • M.W
    "Not a bad neighborhood. The office staff are okay. Matinence is terrible and take forever to fix anything."
    0
    Flag
  • Ggardis
    "I live in an older neighbourhood. Access to public transportation is not easy. Neighborhoods are very spread out."
    0
    Flag
  • Trulia User
    "My daily commute to work is about 30 minutes. Commute to downtown about 10 minutes. Salisbury is a nice small town!!"
    0
    Flag

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Homes for sale near 27770 Leeward Dr

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Off Market Homes Near 27770 Leeward Dr

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Frequently asked questions about 27770 Leeward Dr

  • What is 27770 Leeward Dr estimated to be worth?
    Trulia's estimated value for 27770 Leeward Dr in Salisbury, MD is $344,800.
  • What is the price history for 27770 Leeward Dr?
    27770 Leeward Dr in Salisbury, MD last sold for $198,000 in November 2011.
  • Is Salisbury a buyer's or seller's market?
    Salisbury is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Salisbury?
    The median sale price in Salisbury is $275K. That is up $8.33K from the prior month.
  • How big is the lot at 27770 Leeward Dr?
    The lot at 27770 Leeward Dr in Salisbury, MD is about 0.72 acres (31,156 sq ft).
  • Does 27770 Leeward Dr have a garage?
    Yes, 27770 Leeward Dr in Salisbury, MD has a garage.