5 Caroline Dr, Middletown, MD 21769
Property image
Property image
OFF MARKET

$533,000

Trulia Estimate
  • 5 Beds
  • 2.5 Baths
  • 2,468 sqft (on 0.33 acres)

5 Caroline Dr, Middletown, MD 21769

Refinance Your Home
Currently Off Market - Sold Oct 14, 2022 for $425,000

Home Value

Trulia Estimate
$533K
Since last month
Decreased$6K (-1.1%)
Since last year
Decreased$10K (-1.9%)
Since last sale
Increased$109K (+25.6%)
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
August 2026$534K
August 2026$533K
July 2026$540K
June 2026$552K
May 2026$554K
April 2026$551K
March 2026$547K
February 2026$540K
January 2026$532K
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
9 Caroline Dr, Middletown, MD
0.04
Single-Family Home
$585,000
10/30/25
4
2.5
2,616
2 Lombardy Dr, Middletown, MD
0.12
Single-Family Home
$499,999
06/24/26
3
2
2,079
12 Caroline Dr, Middletown, MD
0.07
Single-Family Home
$487,500
07/07/26
3
2.5
1,722
102 Larch Ln, Middletown, MD
0.20
Single-Family Home
$492,500
09/16/25
4
3
2,084
100 Lombardy Dr, Middletown, MD
0.17
Single-Family Home
$545,000
03/31/26
3
2
2,372
101 Linden Blvd, Middletown, MD
0.25
Single-Family Home
$462,000
11/26/25
3
2
1,812
16 Linden Blvd, Middletown, MD
0.31
Single-Family Home
$410,900
06/18/26
3
2
1,684
10 Linden Blvd, Middletown, MD
0.36
Single-Family Home
$480,000
04/17/26
3
1.5
2,104
112 Locust Ct, Middletown, MD
0.28
Single-Family Home
$411,000
06/22/26
3
1.5
1,680
101 Manda Dr, Middletown, MD
0.30
Single-Family Home
$610,000
10/21/25
3
2
1,823

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
509 E Main St, Middletown, MD 21769
0.03
$413,800
2
2
1,812
Off Market
9 Caroline Dr, Middletown, MD 21769
0.04
$582,000
4
2.5
2,616
Off Market
12 Caroline Dr, Middletown, MD 21769
0.07
$487,500
3
2.5
1,722
Recently Sold
706 E Main St, Middletown, MD 21769
0.10
$685,000
5
3.5
2,202
Recently Sold
2 Lombardy Dr, Middletown, MD 21769
0.12
$499,999
3
2
2,079
Recently Sold
708 E Main St, Middletown, MD 21769
0.11
$475,000
4
2
2,036
For Sale
8 Larch Ln, Middletown, MD 21769
0.13
$530,200
3
3.5
2,536
Off Market
213 Linden Blvd, Middletown, MD 21769
0.16
$618,100
4
3.5
2,500
Off Market
100 Lombardy Dr, Middletown, MD 21769
0.17
$545,000
3
2
2,372
Recently Sold
102 Larch Ln, Middletown, MD 21769
0.20
$490,000
4
3
2,084
Off Market
110 Linden Blvd, Middletown, MD 21769
0.20
$483,700
3
2
2,355
Off Market
3 Woodmere Cir, Middletown, MD 21769
0.19
$900,400
5
4.5
6,144
Off Market

Local Information

  • Map ViewExplore the area around 5 Caroline Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
0.33 acre lot
2,468 sqft
$216/sqft
Garage

About this House

Admirable location! 5 Bedroom Home w/2.5 baths. Enormous size living room facing the front through a bay window and a cozy fireplace. Separate dining rm leading to fully equip kitchen with large breakfast bar and brick covered grill. Master bedroom suite with double walk-in closet and master bath. Downstairs family room, workshop and laundry room. Backyard entertainment area w/large deck & pool.
5 Caroline Dr, Middletown, MD 21769 is a 5 bedroom, 3 bathroom, 2,468 sqft single-family home built in 1984. It last sold for $425,000 on Oct 14, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $533,000, with a rent estimate of $3,755/month.

Home Details for 5 Caroline Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: Single Family HomeArchitecture: split entry

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price and Tax history

DateEventPrice
Oct 14, 2022
Source: Bright MLS #MDFR2024608
Sold
$425,000
Sep 2, 2022
Source: Bright MLS #MDFR2024608
Pending
$375,000
Aug 28, 2022
Source: Bright MLS #MDFR2024608
Listed For Sale
$375,000
Jan 1, 2017
Source: Agent Provided
ListingRemoved
$349,900
May 13, 2016
Source: Agent Provided
PriceChange
$349,900
Price decreased by 7%

Market trends in Middletown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
2MoM

Around this home

What Locals Say about Middletown

At least 39 Trulia users voted on each feature.

  • 96 % Say yards are well-kept

  • 93 % Say car is needed

  • 89 % Say people would walk alone at night

  • 85 % Say it's dog friendly

  • 83 % Say parking is easy

  • 82 % Say it's quiet

  • 82 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 71 % Say streets are well-lit

  • 70 % Say neighbors are friendly

  • 64 % Say it's walkable to restaurants

  • 58 % Say there are sidewalks

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

  • 51 % Say there are community events

  • 47 % Say there's wildlife

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Chloe Bishop
    "It’s a nice small-town feel with friendly neighborhoods. Great schools. People are friendly. Close to major highways with minimal traffic compared to Frederick. "
    0
    Flag
  • Trulia User
    "Very quiet, nice neighbors, many of whom grew up in the neighborhood. Siuth Mountain Creamery is a great destination for families, and even delivers. Schools are terrific--the main reason families move and stay here."
    1
    Flag
  • Trulia User
    "Owners are responsible for making sure their dogs are leashed up and under control. Also they pick up after their pets. "
    0
    Flag
  • Trulia User
    "we've lived here for 17 years. neighbors are pleasant and respectful of each otbers privacy. many of them are related, grew up in this neighborhood,(Bolivar). No complaints, except for the cars that speed on the road during rush hour. "
    1
    Flag
  • Trulia User
    "Movie night, Fourth of July celebration, golf course, ice cream parlor, mostly single-family homes, pretty rural,farmers market, good roads, great schools "
    0
    Flag
  • Haileyrockwell
    "Quiet, well kept. everyone is neighborly, small town vibe. Local farmers, schools are close together. "
    0
    Flag
  • Ctauscher10@gmail.com
    "Yes you see dog owners walking their dogs all the time. People are friendly and enjoy being in a rural area. There is also a lot of wildlife here you see deer skunks possums and foxes and I saw a bear once Ion Braddock Heights. You have quick access to interstate 70 east and west."
    0
    Flag
  • Michele M.
    "I often see plenty of dog owners walking their dogs throughout the neighborhood. Many times, you will even find families taking a walk with their pooch. It's a nice little scene. The only problem I think a dog owner might have is if his/her dog has socialization issues. Because they will run into other dogs constantly."
    0
    Flag
  • Graysonramsburg
    "20 minute drive to Frederick... about 12 miles distance. Traffic usually moving but can be heavy during school year."
    0
    Flag
  • Michele M.
    "well kept yards, safe to walk day and night, kid's community sports, award winning schools, quiet community"
    0
    Flag
  • Regis g.
    "amazing schools, great place to raise kids. great family free events all the time, such as movies at the park"
    0
    Flag
  • Gogenevago
    "I just moved here and the neighbors look out for one another. super nice area and I'm glad I own a home in this area. "
    0
    Flag
  • Robynrmason
    "Great school system and safe area. Beautiful views and great community. Very convenient to interstate and to stores. Have lived here 10 years and love it. "
    1
    Flag
  • Dotty D.
    "House is located in Brookridge neighborhood, surrounded by beautiful Wiles Branch Park. Middletown is a wonderful small town community with best schools in the area. "
    1
    Flag
  • mcbee
    "My friends live there on Tobias Run and it's a great street with a hidden open/park like area the size of 2 football fields with a spotless play area, sitting benches, and walking paths all with in 1-2 blocks of the Hollow Creek golf course, club house and Valley Grill restaurant & Sports Bar. There are beautiful views of the golf course and surrounding mountains. Plus, it is serviced by FCPS school buses that bring children to all of Middletown's schools (elementary, middle, high school) ... all of this for a fantastic home and a mere $50 HOA fee!"
    0
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  • Guillermo A. J.
    "WHY IS ANYWHERE IN MIDDLETOWN MD A POOR NEIGHBORHOOD IS BECAUSE THERE NOT ENOUGH PLACES TO WORK @ IN MIDDLETOWN MD BECAUSE YOU DON'T SEE THAT MUCH BUILDING'S IN MIDDLETOWN MD TO WORK @ AS A JOB AND BECAUSE NOBODY IN MIDDLETOWN MD MAKE'S TOO MUCH MONEY AND THERE'S NOT ENOUGH PLACE'S TO EAT @ AND WHOEVER YOU ARE NEVER EVER EVER EVER MOVE TO MIDDLETOWN MD"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5 Caroline Dr

  • What is 5 Caroline Dr estimated to be worth?
    Trulia's estimated value for 5 Caroline Dr in Middletown, MD is $533,000.
  • What is the price history for 5 Caroline Dr?
    5 Caroline Dr in Middletown, MD last sold for $425,000 in October 2022.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Middletown?
    Residents describe Middletown, MD as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Middletown, MD.
  • Does 5 Caroline Dr have air conditioning?
    Yes, 5 Caroline Dr in Middletown, MD has air conditioning.
  • How big is the lot at 5 Caroline Dr?
    The lot at 5 Caroline Dr in Middletown, MD is about 0.33 acres (14,374 sq ft).

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