1237 Hilltop Dr, Annapolis, MD 21409
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Property image
OFF MARKET

1237 Hilltop Dr
Annapolis, MD 21409

  • 4 Beds
  • 2 Baths
  • 1,932 sqft

$556,100

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $3,328/mo*
Refinance Your Home

$556,100

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $3,328/mo*
Refinance Your Home
4 Beds
2 Baths
1,932 sqft

Home Value

Trulia Estimate
$556K
Since last month
Decreased$10K (-1.7%)
Since last year
Increased$11K (+1.9%)
Since last sale
Increased$109K (+24.4%)
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 +77% in the last 10 years
MonthEstimated value
2026
August 2026$556K
July 2026$561K
June 2026$566K
May 2026$565K
April 2026$567K
March 2026$562K
February 2026$554K
January 2026$548K
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
1248 Hilltop Dr, Annapolis, MD
0.10
Single-Family Home
$525,000
08/03/26
4
3
1,940
1227 Hampton Rd, Annapolis, MD
0.22
Single-Family Home
$585,000
10/31/25
4
2
2,068
1052 Lido Dr, Annapolis, MD
0.24
Single-Family Home
$515,000
06/29/26
4
1.5
1,488
1023 Mountain Top Dr, Annapolis, MD
0.24
Single-Family Home
$415,000
01/23/26
4
2
1,404
1247 Hilltop Dr, Annapolis, MD
0.07
Single-Family Home
$550,000
09/05/25
3
3
1,580
1245 Hilltop Dr, Annapolis, MD
0.05
Single-Family Home
$660,000
11/17/25
4
3.5
2,192
1207 Hampton Rd, Annapolis, MD
0.29
Single-Family Home
$562,500
05/01/26
4
2
2,412
1150 Little Magothy Vw, Annapolis, MD
0.26
Single-Family Home
$620,000
10/17/25
3
2
1,904
1044 Skyview Dr, Annapolis, MD
0.38
Single-Family Home
$504,000
12/03/25
3
2
1,828
1223 Hampton Rd, Annapolis, MD
0.23
Single-Family Home
$565,000
10/07/25
3
2.5
1,960

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
1245 Hilltop Dr, Annapolis, MD 21409
0.05
$660,000
4
3.5
2,192
Recently Sold
1247 Hilltop Dr, Annapolis, MD 21409
0.07
$558,900
3
3
1,580
Off Market
1248 Hilltop Dr, Annapolis, MD 21409
0.10
$525,000
4
3
1,940
Recently Sold
1011 Westway, Annapolis, MD 21409
0.12
$597,500
4
3
2,131
Off Market
1219 Hilltop Dr, Annapolis, MD 21409
0.14
$533,400
4
2.5
1,948
Off Market
1004 Westway, Annapolis, MD 21409
0.14
$725,000
4
3.5
2,607
Recently Sold
981 Westway, Annapolis, MD 21409
0.17
$507,300
4
2
2,000
Off Market
1014 Saint Charles Dr, Annapolis, MD 21409
0.16
$690,000
5
3
3,312
Recently Sold
986 Westway, Annapolis, MD 21409
0.19
$505,800
3
2
1,269
Off Market
1020 Saint Charles Dr, Annapolis, MD 21409
0.19
$585,300
4
2
2,250
Off Market
1227 Hampton Rd, Annapolis, MD 21409
0.22
$585,000
4
2
2,068
Recently Sold
1212 Highview Dr, Annapolis, MD 21409
0.20
$865,000
4
2.5
2,556
Off Market

Local Information

  • Map ViewExplore the area around 1237 Hilltop 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
1974
Living Area
1,932 sqft
Price/Sqft
$288

About this House

Nothing to do but MOVE RIGHT IN to this GORGEOUS HOME! Almost 2000 Total SQFT full of UPGRADES! Fully Finished HUGE Basement that offers a Media Room, Gym, Full Bath and a huge Bedroom with massive closet! Located in the desired Broadneck School District! The Water Accessible and Amenity Filled Community of Cape St. Claire is sure to please! Talk about LOCATION... you can walk to Schools, Parks, Playgrounds, Pool, Beaches, Piers, Marina, Picnic Areas, Club House, Broadneck Library, Trail, Waterways, Shopping, Ice Cream Shop and Ball Fields! Must See this completely Renovated Home... turn-key and ready for you! Featuring 4 Bedrooms and 2 Updated Full Bathrooms, Media/Cinema Room, Family Room, Laundry Room w/Utility Sink, Deck and Patio! Kitchen is stunning with new SS Appliances, Granite Counters, White Shaker Style Cabinets and new easy to clean LVT flooring! From the Kitchen you have easy access to the rear deck to grill out and enjoy the view overlooking the gardens of Veggies, Fruits, Herbs and Roses all within the fully fenced in Yard! The awesome Greenhouse and custom installed Shed both convey! This is a Gardner's DREAM with current harvest of Broccoli, Brussell Sprouts, Tomatoes & more!! Walk down deck stairs give access to the paved patio with a slider entrance to the lower level. Peace of mind here with the new Roof, new Hot Water Heater, new HVAC, Nest Thermostat and Gutter Covers! Well maintained and ready for YOU to make this YOUR NEW HOME!! Check out the document attached with the list of upgrades! Easy commute to Downtown Annapolis, Baltimore & DC!
1237 Hilltop Dr, Annapolis, MD 21409 is a 4 bedroom, 2 bathroom, 1,932 sqft single-family home built in 1974. It last sold for $447,000 on Jun 16, 2021. It is currently off market. The Trulia Estimate is $556,100, with a rent estimate of $3,208/month.

Home Details for 1237 Hilltop Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Hardwood, Linoleum Vinyl
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherDeckExterior: Other

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Additional Information

Greenhouse

Price and Tax history

DateEventPrice
Aug 2, 2022
Source: RE/MAX International
ListingRemoved
Jul 30, 2022
Source: Bright MLS #MDAA2036748
PendingToActive
$488,000
Jul 23, 2022
Source: RE/MAX International #MDAA2036748
Pending
$488,000
Jul 23, 2022
Source: Bright MLS #MDAA2036748
Contingent
$488,000
Jul 16, 2022
Source: Bright MLS #MDAA2036748
PriceChange
$488,000
Price decreased by 2%

Market trends in Annapolis

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$646K
$11.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$326
$7MoM
Available listings
355
3MoM
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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
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  • 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
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  • 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

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Homes for sale near 1237 Hilltop Dr

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Off Market Homes Near 1237 Hilltop Dr

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Frequently asked questions about 1237 Hilltop Dr

  • What is 1237 Hilltop Dr estimated to be worth?
    Trulia's estimated value for 1237 Hilltop Dr in Annapolis, MD is $556,100.
  • What is the price history for 1237 Hilltop Dr?
    1237 Hilltop Dr in Annapolis, MD last sold for $447,000 in June 2021.
  • 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 $646K. That is up $11.67K from the prior month.
  • Does 1237 Hilltop Dr have air conditioning?
    Yes, 1237 Hilltop Dr in Annapolis, MD has air conditioning.
  • How big is the lot at 1237 Hilltop Dr?
    The lot at 1237 Hilltop Dr in Annapolis, MD is about 0.21 acres (9,147 sq ft).