237 Cheswick Dr, Madison, AL 35757
OFF MARKET

237 Cheswick Dr
Madison, AL 35757

  • 4 Beds
  • 3 Baths
  • 2,660 sqft (on 0.58 acres)

$418,600

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $2,313/mo*
Refinance Your Home

$418,600

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $2,313/mo*
Refinance Your Home
4 Beds
3 Baths
2,660 sqft
(on 0.58 acres)

Local Information

  • Map ViewExplore the area around 237 Cheswick Dr.
  • Schools1 Preschool School1 Elementary School2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Lovingly landscaped, this brick rancher includes 2nd master bedroom and a bonus garage with storm shelter.Home has been upgraded to include new appliances, lighting, counter tops, hardware, toilets, and flooring.Kitchen offers granite counters and glass door on corner cabinet.Breakfast bay includes crown moulding, chair rail, and built-in cabinet with glass doors and granite counter.French doors open from living room into foyer and dining room.Box ceiling and abundance of moulding add character to dining room.Recessed lighting accents gas fireplace in family room.Large sitting area, box ceiling, glamour bath & walk-in closet in master retreat.Stamped concrete patio.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 237 Cheswick Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Other, Carpet, Hardwood
Interior Details
Types of Rooms: Dining Room, Family Room, Laundry Room
Appliances & Utilities
DishwasherDisposalMicrowave
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: BrickFoundation Type: Other
Parking & Garage
GarageParking Spaces: 9Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price History for 237 Cheswick Dr

DatePriceEventSource
08/31/2020$319,000Sold
ValleyMLS #1144867
06/26/2020$319,900PendingToActiveAgent Provided
06/26/2020$319,900PendingAgent Provided
06/13/2020$319,900Listed For SaleAgent Provided
02/27/2018$240,000Sold
ValleyMLS #1086286
02/01/2018$249,900Listed For SaleAgent Provided

Market trends in Madison

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$353K
$16.67KMoM
Sale-to-List Price
99.1%
0.1%MoM
Price per sq ft
$170
$3MoM
Available listings
526
26MoM
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Property Tax and Assessment

Year2025
Tax$1,408
Assessment$402,700
Home facts updated by county records

Comparable Sales for 237 Cheswick Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
238 Cheswick Dr, Madison, AL
0.05
Single-Family Home
$522,000
01/09/26
4
3.5
3,644
224 Cheswick Dr, Madison, AL
0.15
Single-Family Home
$420,000
06/03/26
5
3.5
2,654
209 Wilson Hall Dr, Madison, AL
0.22
Single-Family Home
$575,000
11/10/25
4
4
3,816
108 Brigadoon Dr, Madison, AL
0.48
Single-Family Home
$460,000
11/18/25
3
2.5
2,926
116 Crystal Springs Dr, Madison, AL
0.44
Single-Family Home
$400,000
06/30/25
4
3
3,122
213 Wilson Hall Dr, Madison, AL
0.27
Single-Family Home
$596,500
01/09/26
4
3.5
3,434
100 Crystal Brook Ln, Madison, AL
0.46
Single-Family Home
$450,000
01/23/26
4
3
3,140
117 Sanibell Cir, Madison, AL
0.61
Single-Family Home
$342,500
08/29/25
4
3
2,027
104 Silversprings Ln, Madison, AL
0.64
Single-Family Home
$325,000
06/08/26
4
2
1,926
116 Cove Pointe Way, Madison, AL
0.80
Single-Family Home
$330,000
12/08/25
4
3
2,413

Nearby homes

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Assigned Schools

These are the assigned schools for 237 Cheswick Dr.
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 Madison

At least 474 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 90 % Say it's dog friendly

  • 84 % Say parking is easy

  • 80 % Say yards are well-kept

  • 79 % Say there are sidewalks

  • 74 % Say there's holiday spirit

  • 73 % Say it's quiet

  • 71 % Say kids play outside

  • 66 % Say people would walk alone at night

  • 63 % Say streets are well-lit

  • 54 % Say neighbors are friendly

  • 52 % Say they plan to stay for at least 5 years

  • 44 % Say there's wildlife

  • 31 % Say there are community events

  • 28 % Say it's walkable to grocery stores

  • 23 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • 8zr5kpvsgr
    "Madison is a homey city with an international flair. There are restaurants and shops offering more than the typical Southern offerings. "
    0
    Flag
  • Andy.250r
    "It’s very easy commute for me because I have to get to the interstate quick. Short trip to the school drop off. "
    0
    Flag
  • Trulia User
    "Community events in the apartment complex I live in such as food trucks, bingo nights, meet & greets "
    0
    Flag
  • Amywcannon
    "There is always something going on in this area, whether it be Madison or a short trip to Huntsville. "
    1
    Flag
  • Basheer Ghazali
    "I love Halloween because there has a bunch of kids trick-or-treating and there is good candy and really good decorations also Christmas because they have really good decorations and they’re just really nice"
    0
    Flag
  • Ny7by8sgbv
    "I have lived in this neighborhood for 9 years and really love the people and the area. Everyone is so friendly and helpful😊"
    0
    Flag
  • Nursedeb02
    "Keep your kids in eyes view at all times Keep pools secure and lock gates Have designated areas for them to play "
    1
    Flag
  • canderson3
    "Ashbery is very friendly and inviting. Ashbery has HOA and Oxford does not so take that into consideration. "
    0
    Flag
  • Swvtswzvc9
    "You see dogs and their people out walking regularly. In addition, there is a dog park about a mile from our neighborhood and multiple dog parks within the city."
    0
    Flag
  • Swvtswzvc9
    "My commute to downtown is 15-20 minutes or less from the east side of Madison in non-rush hour traffic. During rush or peak travel times, my commute is 20-30 minutes to downtown."
    6
    Flag
  • Rick
    "Getting crowded now, but still nice. Roadways inadequate for the number of vehicles. High density home projects are sprouting up everywhere. "
    2
    Flag
  • Chelsea F.
    "Safe and schools are phenomenal. Many great family fun activities nearby. Very suburban. Quick access to the interstate for travel! "
    0
    Flag
  • Jim G.
    "Yes. This is a dog/pet friendly neighborhood. Most owners have pets and it’s not a problem as long as the pet owner does the right thing."
    3
    Flag
  • Ashley V.
    "It’s very dog friendly. Most people will pick up after their dogs but as usual there are a few bad eggs. There are waste disposal areas set up."
    24
    Flag
  • Kanisha W.
    "I love living here. It’s really nice, quiet, and peaceful. It’s a sweet place. I don’t have much else to say, but do recommend it."
    1
    Flag
  • Julie W.
    "the schools are first rate. parks and communitys area are well lighted and maintained very well. there is a sense of home."
    8
    Flag
  • Kennedy J.
    "Transportation is easy & traffic is a little hectic, but the commute from my home is 3 minutes. Walking distance is easier, being that there isn’t much parking downtown."
    5
    Flag
  • Paul M.
    "Great family oriented community. Growing rapidly. House value is steadily increasing and developments going up to accommodate the growth. "
    5
    Flag
  • Alliyahannwarren
    "It’s small, full of friendly neighbors, and a variety of families. I love that our street has a Facebook page as well. Just a great place to live "
    2
    Flag
  • Whitelr6
    "Lots of people walking their dogs around the pond..so yes I believe they would enjoy walking their dogs through the neighborhood as well as the pond."
    0
    Flag
  • Ahmadhassan1977
    "People in general are nice and kind, many natural hikes and parks nearby. People here do not know how to drive, and ride your tail as much as they can"
    0
    Flag
  • Sunshine W. B.
    "It can be very loud. Lots of sweet barkers sending doggy messages throughout the neighborhood. Very dog friendly. "
    0
    Flag
  • Heathdaws
    "Everyone walks their dogs here and is very friendly I love this neighborhood of Deer Run which is probably the most quiet around "
    0
    Flag
  • Mz.tlacy
    "pleasant people and thre clean and safe atmosphere. the school's are very good and provide core curriculum to the students "
    0
    Flag
  • Talesia.1433
    "There are Children of all ages. The kids love it here. I love the area. Very well kept. Close to many shops food hospital etc "
    0
    Flag
  • Karly F.
    "Everyone is very kind and seems to take a sense of pride in keeping their homes presentable. It is a safe neighborhood and you’ll frequently see families out on a walk. Never have had any issues with unruly neighbors or anything if the sort. Comfortable with leaving my dogs in the yard for a little while too which I was not in our previous neighborhood."
    0
    Flag
  • Karly F.
    "Not bad depending on where you are going but can be heavy if you leave at peak traffic times. I just recommend to leave a little early or take the back roads and you’ll be fine."
    0
    Flag
  • Brandon
    "safe , nice homes , lot of water around , lot of schools , sidewalks, not enough restaurants though.Building plenty of new homes and businesses. "
    0
    Flag
  • Timm55
    "Fourth of July parties, Easter egg hunts and Halloween gatherings. And that’s about it. Not much else"
    0
    Flag
  • Timm55
    "Madison Street Festival where there’s a parade and community events. There’s also a firework show at the nearby park during the Fourth of July."
    0
    Flag
  • Sfhadden
    "Traffic is difficult when school takes in and dismisses. dismissal is staggered between elementary, middle and high schools so there is a steady stream of traffic in the morning- school + work and afternoon school then work. it can be sticky in spots because of this. "
    0
    Flag
  • Mccaffertycindy
    "I’ve lived in this neighborhood for 28 years. The neighbors are very friendly and take care of their homes. Wonderful community."
    0
    Flag
  • Brian B.
    "Great schools and diverse and helpful neighbors. Convenient to most events in the area and will be great area for new families coming for FBI or Toyota jobs. Infrastructure needs to be addressed. "
    13
    Flag
  • Jordan T.
    "The neighborhood provides convenient access to I-20, but traffic coming home can sometimes turn a 13 minute drive into 40. And public transit is non-existent."
    6
    Flag
  • Sfhadden
    "No publc transportation. Traffic is heaviest when school starts and ends and about 4:30-5:00. it can take about 10-15 minutes to make the 4 mile drive depending on what time I leave (doorstep to doorstep) Sunday mornings are also heavy on traffic due to the number of churches in the area. "
    0
    Flag
  • Zarazua25
    "There is a festival every October in downtown Madison that is a lot of fun. On the 4th of July there is a parade in town and fireworks at Dublin Park. During Easter there are many places that hace Easter egg hunts. Every Thursday evening during the summer there are bands that play on downtown Madison. "
    0
    Flag
  • Daphne Ellis-Floyd
    "We have firepit Fridays each month, where everyone brings their firepits, hot dogs and S'mores to the cul-de-sac for a fun time getting together. "
    0
    Flag
  • Laurel M. J.
    "Lots of community functions and events for families! Great sense of community! Safe to walk outside for the majority of the areas. Great schools!"
    0
    Flag
  • Zarazua25
    "There are lots of people that walk their dogs around the neighborhood. The neighborhood is dog friendly. "
    0
    Flag
  • Roletyde
    "It is common for people that live in our neighborhood to walk their dogs. It is expected though that you clean up after your dog and not allow it to bark frequently. Neighbors are usually friendly to dogs that are seen walking and stop to chat with the owners. "
    0
    Flag

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Apartments for Rent

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Homes for sale near 237 Cheswick Dr

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Off Market Homes Near 237 Cheswick Dr

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237 Cheswick Dr, Madison, AL 35757 is a 4 bedroom, 3 bathroom, 2,660 sqft single-family home built in 1992. This property is not currently available for sale. 237 Cheswick Dr was last sold on Aug 31, 2020 for $319,000. The current Trulia Estimate for 237 Cheswick Dr is $418,600.