583 Wayward Dr, Annapolis, MD 21401
OFF MARKET

$715,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,131 sqft (on 1.05 acres)

583 Wayward Dr, Annapolis, MD 21401

Est. Refi. Payment $4,389/mo*
Refinance Your Home
Currently Off Market - Sold Aug 4, 2020 for $565,000

Home Value

Trulia Estimate
$715K
Since last month
Decreased$14K (-2%)
Since last year
Decreased$2K (-0.3%)
Since last sale
Increased$150K (+26.6%)
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 +54% in the last 10 years
MonthEstimated value
2026
September 2026$715K
August 2026$720K
July 2026$730K
June 2026$740K
May 2026$737K
April 2026$731K
March 2026$728K
February 2026$710K
January 2026$709K
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
524 Ridge Rd, Annapolis, MD
0.12
Single-Family Home
$450,000
12/12/25
4
2.5
2,304
1961 Sigfrid Ct, Annapolis, MD
0.28
Single-Family Home
$689,000
11/04/25
4
3
2,828
2178 Glenfield Rd, Annapolis, MD
0.22
Single-Family Home
$515,000
07/13/26
4
3
1,814
602 Wayward Dr, Annapolis, MD
0.11
Single-Family Home
$505,000
12/01/25
3
3
1,936
617 Wayward Dr, Annapolis, MD
0.15
Single-Family Home
$599,000
08/14/26
3
2
1,920
2177 Glencrest Cir, Annapolis, MD
0.19
Single-Family Home
$550,000
09/22/25
3
1
1,534
565 Wayward Dr, Annapolis, MD
0.17
Single-Family Home
$725,000
01/07/26
3
2
3,874
994 Epping Forest Rd, Annapolis, MD
0.79
Single-Family Home
$730,000
01/23/26
4
2.5
2,240
2019 Valley Rd, Annapolis, MD
0.43
Single-Family Home
$470,000
04/30/26
2
2.5
1,850
622 Sean Dr, Annapolis, MD
0.61
Single-Family Home
$770,000
12/22/25
5
3.5
3,754

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
574 Wayward Dr, Annapolis, MD 21401
0.08
$645,300
4
3
3,111
Off Market
524 Ridge Rd, Annapolis, MD 21401
0.12
$450,000
4
2.5
2,304
Recently Sold
602 Wayward Dr, Annapolis, MD 21401
0.11
$505,000
3
3
1,936
Recently Sold
Address Not Disclosed, Annapolis, MD 21401
0.17
$725,000
3
2
3,874
Recently Sold
529 Ridge Rd, Annapolis, MD 21401
0.16
$579,400
3
2.5
2,040
Off Market
617 Wayward Dr, Annapolis, MD 21401
0.15
$599,000
3
2
1,920
Recently Sold
2177 Glencrest Cir, Annapolis, MD 21401
0.19
$555,900
3
1
1,534
Off Market
2175 Glencrest Cir, Annapolis, MD 21401
0.22
$950,000
5
3.5
3,081
For Sale
2198 Thoreau Ct, Annapolis, MD 21401
0.19
$517,500
5
2
1,814
Off Market
1982 Valley Rd, Annapolis, MD 21401
0.23
$679,300
5
3
2,492
Off Market
2180 Glenfield Rd, Annapolis, MD 21401
0.21
$538,200
3
2
1,264
Off Market
2178 Glenfield Rd, Annapolis, MD 21401
0.22
$515,000
4
3
1,814
Recently Sold

Local Information

  • Map ViewExplore the area around 583 Wayward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
1.05 acre lot
2,131 sqft
$336/sqft
Garage

About this House

This single-family home is located at 583 Wayward Dr, Annapolis, MD. 583 Wayward Dr is in Annapolis, MD and in ZIP code 21401. This property has 4 bedrooms, 3 bathrooms and approximately 2,131 sqft of floor space. This property has a lot size of 1.05 acres and was built in 1978.
583 Wayward Dr, Annapolis, MD 21401 is a 4 bedroom, 3 bathroom, 2,131 sqft single-family home built in 1978. It last sold for $565,000 on Aug 4, 2020. More recently, it was listed as a rental in June 2017 with an asking price of $2,500 per month. That rental listing was removed on June 15, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $715,300, with a rent estimate of $4,013/month.

Home Details for 583 Wayward Dr

Interior Features

Interior Details
BasementCeiling Fan
Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 1.05 acres

Price and Tax history

DateEventPrice
Aug 4, 2020
Source: N/A
Sold
$565,000
May 28, 2020
Source: Agent Provided
Pending
$560,000
May 4, 2020
Source: Agent Provided
PriceChange
$560,000
Price decreased by 3%
Jan 31, 2020
Source: Agent Provided
Listed For Sale
$575,000
Jun 15, 2017
Source: Agent Provided
ListingRemoved
$2,500

Market trends in Annapolis

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$643K
$1KMoM
Sale-to-List Price
100.0%
Price per sq ft
$331
$6MoM
Available listings
344
11MoM

Around this home

What Locals Say about Annapolis

At least 470 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 83 % Say car is needed

  • 75 % Say there's holiday spirit

  • 73 % Say parking is easy

  • 73 % Say there are sidewalks

  • 70 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 68 % Say kids play outside

  • 66 % Say streets are well-lit

  • 65 % Say it's quiet

  • 63 % Say there's wildlife

  • 57 % Say it's walkable to restaurants

  • 57 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly neighborhood. But not a lot of green space other than other peoples’ yards. "
    0
    Flag
  • Shannon Chatlos
    "If you like coastal living and a laid-back lifestyle, and are willing to pay for it, this a wonderful place to live."
    0
    Flag
  • Sylvie Bracke
    "It’s a very dog friendly place - I just can’t help wondering why some people don’t clean up after their pets? It’s a nice neighborhood with high end properties & I don’t get that dissonance."
    0
    Flag
  • Erin
    "Safe. On water. Paths in woods. Friendly. Dog play area. Lots of open spaces. Areas are walkable, clean. "
    0
    Flag
  • Halljanie68
    "Community Pool convenient shopping. Easy access to major routes 50/95 Easy access to downtown Annapolis "
    0
    Flag
  • Sheila Wilson
    "A lot of traffic on forest drive very hard to come onto the street. It need a red light or stop sign. Before a serious accident happens. People speed over 40mph"
    0
    Flag
  • Diana H.
    "I’m not sure, I don’t own a dog. Plenty walk by my dead end street house daily though and the neighborhood seems safe for both dogs and owners. "
    0
    Flag
  • Paul Eric Watson
    "Love the urban feel. Lots of history and near the water is a bonus. Very walkable and always something going on. "
    5
    Flag
  • Trulia User
    "Access to Route 50, the Bay Bridge, and Sandy Point State Park. Thirty minutes to Baltimore. Forty minutes to Washington D.C."
    2
    Flag
  • Trulia User
    "It’s a great neighborhood for kids and dogs Lots of walking areas, parks, water park and boat to downtown Annapolis "
    2
    Flag
  • Trulia User
    "It’s a tad busy commute rush hour traffic is something to consider small town lots of people takes about 10-15 min or so to get from one side of town to the other without traffic "
    1
    Flag
  • Trulia User
    "Great school public and private well maintained parks great public libraries close downtown Annapolis shopping for everything is conveniently close "
    0
    Flag
  • Trulia User
    "Lots of families with dogs. Poop bag stations throughout the neighborhood. Lots of woods to walk thru and sidewalks too. "
    1
    Flag
  • Trulia User
    "Nothing is special about my neighborhood. So quiet and nobody talks to anybody. The play area was demolished so no kids can hang out to play."
    4
    Flag
  • Trulia User
    "This is an excellent neighborhood for families and the neighbors are wonderful. Cape St. John gives you access to everything in Annapolis with the tranquility of living along the river."
    0
    Flag
  • Trulia User
    "While Truxton is dog friendly it would be nice to have a dedicated dog park closer than Quiet Waters. "
    0
    Flag
  • Trulia User
    "Wonderful family neighborhood. This neighborhood is very convenient to Hway 50 and all of the Annapolis area. The people here are terrific neighbors."
    0
    Flag
  • Trulia User
    "Good to walk. And parks are nice to play with kids. Stores are close by. And dog walkers all around. "
    0
    Flag
  • Trulia User
    "Summer beach parties, puppy happy hours, annual sock burning, lots of parks and the people are wonderful!"
    0
    Flag
  • Trulia User
    "the history Open napolis is amazing the people around here are kind and friendly and the schools are phenomenal"
    0
    Flag
  • Singletonad
    "the public school system in Annapolis needs to get significantly stronger overall. The private school system here is quite reliable."
    0
    Flag
  • Keren_molina
    "Lovely place and definitely good place to live and have a dog and a lot sores to go buy stuff ..........."
    5
    Flag
  • Singletonad
    "There is no community dog run here and no sidewalks so it can feel awkward letting your dog poop in someone else's yard even if you pick it up. The vast majority of neighbors are dog friendly, but not all, and that is their perogative."
    0
    Flag
  • Raddisob07
    " N/A school are great parking is great close to everything ppl are friendly and been living in Annapolis all my life "
    4
    Flag
  • Tery_hodges
    "I walk my son to elementary school. We can walk to many restaurants and “tourist” shops but do have to drive to get to a grocery store."
    2
    Flag
  • Stephanie.ward0715
    "I've been around this area for years. People are friendly and always willing to help each other. The restaurant's and shopping are also a plus. Everything you are looking for is 5 minutes away."
    0
    Flag
  • Raddisob07
    "None that I know of. The community should definitely do more collaborative events at least at least Quarterly they are family friendly."
    5
    Flag
  • Stella
    "Feel good living here Parking so easy Location very good Many things nearby Old town and new town "
    3
    Flag
  • Jennifer B.
    "It's super quiet and funny, I've leving here for 1 year and I feel safe my neighbors are nice.. Down town is amazing.. ❤️ "
    0
    Flag
  • Kwisniewski805
    "Holiday events and many boating events. There are street fairs, food markets, holiday markets. Community is very close. "
    0
    Flag
  • Cara M. E.
    "I teach at a school that is less than 10 minutes from my house. But there are times that Forest Dr gets incredibly backed up, or there is an accident that causes the road to be shut down. "
    1
    Flag
  • Beth S.
    "Bad area is close by, so kids need to understand boundaries. Private schools are important here, so save your money. Sports are good here, with lots of good coaching."
    0
    Flag
  • Linda D.
    "I've been visiting a dear close friend - helping them recuperate from serious surgery. traffic is atrocious- I miss living in the rural countryside area!"
    0
    Flag
  • Liza
    "The schools in Annapolis are not as good as they are in Severna Park which is where I grew up originally. But Annapolis has many great amenities including local places to eat and shop."
    0
    Flag
  • Rodwellsantos6
    "I like it this community is pretty good as so matters fact for elders we looking to buy in this areas I don’t know frankly about this gorgeous homes we will see."
    0
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  • Jeffrey H.
    "Lived here for 4 years. Loved the area, including the park across the street. Hate the maintenance of the building including the attention to detail of maintenance of property. "
    0
    Flag
  • jfh4k0
    "Local traffic is not too bad. Beach traffic and rush hour traffic to DC and Baltimore is pretty terrible. "
    2
    Flag
  • Nadja Maril
    "I lived in this neighborhood over 20 years and walk downtown with my dog every morning for coffee. On pretty days we visit City Dock and admire the views and the boats."
    1
    Flag
  • Markkimethanmolly
    "We’ve lived here for 18 years, and everyone is very friendly. Our neighborhood is very safe and quiet."
    0
    Flag
  • Debwill64
    "There is a bus stop close enough to walk to but I have to drive to DC. The bus only goes to Annapolis and maybe Baltimore, not sure though."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 583 Wayward Dr

  • What is 583 Wayward Dr estimated to be worth?
    Trulia's estimated value for 583 Wayward Dr in Annapolis, MD is $715,300.
  • What is the price history for 583 Wayward Dr?
    583 Wayward Dr in Annapolis, MD last sold for $565,000 in August 2020.
  • Is Annapolis a buyer's or seller's market?
    Annapolis is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Annapolis?
    The median sale price in Annapolis is $643K. That is down $1K from the prior month.
  • Does 583 Wayward Dr have air conditioning?
    Yes, 583 Wayward Dr in Annapolis, MD has air conditioning.
  • How big is the lot at 583 Wayward Dr?
    The lot at 583 Wayward Dr in Annapolis, MD is about 1 acre.

Explore by feature - Pet Friendly

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Off Market Homes Near 583 Wayward Dr

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