5440 Whippoorwill Dr, Kalamazoo, MI 49009
Property image
Property image
OFF MARKET

$666,800

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 3,964 sqft (on 1.05 acres)

5440 Whippoorwill Dr, Kalamazoo, MI 49009

Est. Refi. Payment $4,511/mo*
Refinance Your Home
Currently Off Market - Sold Jul 31, 2008 for $450,000

Home Value

Trulia Estimate
$667K
Since last month
Decreased$29K (-4.2%)
Since last year
Decreased$2K (-0.4%)
Since last sale
Increased$213K (+47.2%)
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 +58% in the last 10 years
MonthEstimated value
2026
October 2026$663K
September 2026$673K
August 2026$691K
July 2026$692K
June 2026$704K
May 2026$684K
April 2026$679K
March 2026$683K
February 2026$666K
January 2026$666K
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
5304 Whippoorwill Dr, Kalamazoo, MI
0.14
Single-Family Home
$430,000
09/29/26
4
2.5
3,414
5363 Four Seasons Dr, Kalamazoo, MI
0.24
Single-Family Home
$520,000
06/12/26
4
3.5
3,950
5420 Whippoorwill Dr, Kalamazoo, MI
0.02
Single-Family Home
$1,125,000
12/23/25
4
6
6,533
5727 W Q Ave, Kalamazoo, MI
0.28
Single-Family Home
$467,500
09/17/26
4
4
4,108
5727 Bobwhite Ave, Kalamazoo, MI
0.40
Single-Family Home
$530,000
04/13/26
5
4.5
4,621
5789 Rolling Pines Ct, Kalamazoo, MI
0.41
Single-Family Home
$498,000
09/30/26
5
4.5
3,755
7895 Deerpath Rd, Kalamazoo, MI
0.24
Single-Family Home
$495,028
10/21/25
4
2.5
3,080
5434 Saddle Club Dr, Kalamazoo, MI
0.32
Single-Family Home
$525,000
09/11/26
5
3.5
4,855
8420 S 12th St, Portage, MI
0.51
Single-Family Home
$450,000
02/13/26
4
3
3,900
7873 Shepherds Glen Ct, Kalamazoo, MI
0.39
Single-Family Home
$640,000
12/05/25
4
4.5
5,200

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
5420 Whippoorwill Dr, Kalamazoo, MI 49009
0.02
$1,125,000
4
6
6,533
Recently Sold
5458 Whippoorwill Dr, Kalamazoo, MI 49009
0.02
$456,900
5
3
3,728
Off Market
5404 Whippoorwill Dr, Kalamazoo, MI 49009
0.04
$547,300
5
4
3,978
Off Market
5482 Whippoorwill Dr, Kalamazoo, MI 49009
0.04
$638,700
Studio
3
3,668
Off Market
5391 Colony Woods Dr, Kalamazoo, MI 49009
0.06
$404,800
Studio
2
2,120
Off Market
5411 Colony Woods Dr, Kalamazoo, MI 49009
0.06
$391,400
5
3.5
3,800
Off Market
5371 Colony Woods Dr, Kalamazoo, MI 49009
0.06
$347,300
Studio
2
2,404
Off Market
5382 Whippoorwill Dr, Kalamazoo, MI 49009
0.06
$381,800
5
3
2,678
Off Market
5492 N Red Pine Cir, Kalamazoo, MI 49009
0.07
$525,000
3
3
1,668
Off Market
5492 N Red Pine Cir #10, Kalamazoo, MI 49009
0.07
$512,000
3
3
2,868
Off Market
5517 S Red Pine Cir, Kalamazoo, MI 49009
0.07
$520,800
Studio
2
2,371
Off Market
16310 S Red Pine Cir, Kalamazoo, MI 49009
0.07
-
-
-
-
Off Market
5517 S Red Pine Cir #11, Kalamazoo, MI 49009
0.07
-
-
-
-
Off Market
5351 Colony Woods Dr, Kalamazoo, MI 49009
0.07
$293,600
Studio
2
1,153
Off Market
5431 Colony Woods Dr, Kalamazoo, MI 49009
0.07
-
-
-
-
Off Market
5506 N Red Pine Cir, Kalamazoo, MI 49009
0.08
$630,000
Studio
3
2,248
Off Market
5506 N Red Pine Cir #9, Kalamazoo, MI 49009
0.08
$607,700
3
4
3,526
Off Market
5439 Whippoorwill Dr, Kalamazoo, MI 49009
0.08
$468,000
Studio
2
3,334
Off Market
5459 Whippoorwill Dr, Kalamazoo, MI 49009
0.08
$354,200
Studio
2
1,820
Off Market
5533 S Red Pine Cir #12, Kalamazoo, MI 49009
0.08
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 5440 Whippoorwill Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1971
1.05 acre lot
3,964 sqft
$168/sqft
Garage

About this House

Fantastic Colony Woods Home Situated On A Beautiful Park-Like 1+ Ac Parcel W/Stream. This Home Is Not A Drive By, You Must Get Inside. Current Owners Have Made Many Improvements Incl A 976 Sqft Addition, Prof Landscaping W/Gardens & Water Feature, Newer Roof, 75 Gal Water Heater, Furnace, A/C, Etc. This 5,400 Fin Sqft Home Is Better Than New. The Ml Offers A Foyer W/Slate Flrs, Master Suite W/3 Closets, Formal Lr & Dr, Den W/Full Ba Next To It(Would Also Make A Nice Guest Bedroom), Lg Fr W/Vlt Ceil, Stone Wood Burning Fp, Beautiful Windows & Open To The Gourmet Kirchman Kit W/All The Bells & Whistles-Sub Zero, Bosch, Convection Oven, Prep Sink In Large Center Island, Granite, & A Gorgeous Cherry Butlers Area W/Wet Bar, Icemaker & Ref An Addl Fr Or Study, Large Mudroom & Ba. Upstairs You'll Find 3 Brs & Updated Full Ba. The Bsmt Is Fin W/ More Storage Space Than Any Home I've Seen! 9' Ceils W/Egress Under Addition, Bar W/Ref Great Fr & Rr Areas. For Addl Info, Go To Www.Pprmi.Com.
5440 Whippoorwill Dr, Kalamazoo, MI 49009 is a 4 bedroom, 5 bathroom, 3,964 sqft single-family home built in 1971. It last sold for $450,000 on Jul 31, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $666,800, with a rent estimate of $4,391/month.

Home Details for 5440 Whippoorwill Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1.5

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: Single Family Home

Exterior Features

Parking & Garage
GarageParking: Garage Attached

Lot Information

Lot Area: 1.05 acres

Price and Tax history

DateEventPrice
Jul 31, 2008
Source: N/A
Sold
$450,000
May 29, 2008
Source: Agent Provided
Listed For Sale
$474,900

Market trends in Kalamazoo

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$246K
$4.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$161
$5MoM
Available listings
454
39MoM

Around this home

What Locals Say about Kalamazoo

At least 991 Trulia users voted on each feature.

  • 86 % Say it's dog friendly

  • 84 % Say car is needed

  • 80 % Say parking is easy

  • 78 % Say yards are well-kept

  • 73 % Say there are sidewalks

  • 72 % Say kids play outside

  • 70 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 60 % Say people would walk alone at night

  • 56 % Say neighbors are friendly

  • 55 % Say it's walkable to restaurants

  • 55 % Say streets are well-lit

  • 53 % Say it's quiet

  • 49 % Say it's walkable to grocery stores

  • 49 % Say they plan to stay for at least 5 years

  • 31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Cala James
    "Great neighborhood for first time home buyers or young families, it’s quiet and safe. Most houses aren’t all that big or fancy, but it is still a quietly nice neighborhood with a little park within walking distance, close to D&W and the Oakland Plaza, close to Nature’s Way preschool, and Portage. For us it’s not our forever neighborhood but it’s been a great starting off point. "
    0
    Flag
  • Virginia Kennedy
    "All these new Communities attract people who grew up in a “nice” neighborhood and meet new friends at Church,children’s schools, etc. if your not in their click your an outsider!"
    0
    Flag
  • Anetpc
    "Sidewalks, lots of people walking their dogs, friendly neighbors. People are pretty good about not letting their dogs bark for a long time outside."
    0
    Flag
  • Anetpc
    "Lots of people walk their dogs, are friendly toward dogs, and drive cautiously around people walking their dogs."
    0
    Flag
  • Brandee Sherrow
    "Lots for food and art festivals in the summer time. Davis field is the perfect place to take your dog for a little play time."
    0
    Flag
  • Ashley Clark
    "The community park events such as the lighting of the park and any pokemon gaming groups, just fun things like such"
    0
    Flag
  • Nh6tjzkwjc
    "It’s very pet friendly and lots of dog parks around the area and people put out water for them as well "
    0
    Flag
  • Karen
    "You can walk with your kids carefully and in a contained fashion, as well as your dogs, with caution. While a country road, it’s still well traveled and at 45-55 mph."
    0
    Flag
  • David E Eiben
    "We have a lot of great things. Chili cook off, Oberon day, Kalamazoo marathon, activities in Bronson Park.."
    0
    Flag
  • T5q8ytkccd
    "That the school districts is great and honestly the neighbourhood is getting worse and I don’t like the future may hold "
    0
    Flag
  • M_wendell
    "Lots of room to run around. Friendly neighbors. Beautiful area for walking. Everyone is very friendly. "
    0
    Flag
  • Trulia User
    "There are fields and parks near by that are dog friendly. Also great walking area for dogs as well. "
    0
    Flag
  • M_wendell
    "Non existent. Car required. I work in Grand Rapids the commute is manageable. I would prefer to work in Kalamazoo, but jobs are not as plentiful. "
    0
    Flag
  • Richard Dortch
    "Lots of dog people here. People are normally dog friendly even if they don’t have dogs. This place could use a dedicated dog park though. "
    0
    Flag
  • Trulia User
    "you always see people walking there dogs but they aren't nice & neither is their dog. so as long as you stay away from them you'll be ok. not everyone is a dog Person."
    4
    Flag
  • Trulia User
    "There are arts events that happen often. I usually drive by kids and people playing cards in the summer. "
    0
    Flag
  • Trulia User
    "everyone watches out for each other like a big family and I miss all my neighbors and all my sons friends I hate we had to move "
    0
    Flag
  • Trulia User
    "You are close to stores, the river walk way is great for biking, walking, family time. Police Station and fire department not far, good schools. Most of the neighbors are nice and homes well maintained. All around great neighborhood."
    0
    Flag
  • Trulia User
    "I have lived in this area for 12 years and haven’t had any issues with neighbors. I need a smaller place due to the fact that my kids are grown now"
    2
    Flag
  • Trulia User
    "loving this neighborhood just to visit it and it's a good neighborhood to live in Neighbors wonderful housing love the landlords"
    1
    Flag
  • Trulia User
    "love the naborhood it's wonderful and quiet I would love to live over here it's only me and it's nice people over here"
    3
    Flag
  • Trulia User
    "I love the neighborhood hopefully I can get in touch with the landlord of this apartment home in communicate and see where it goes from there"
    0
    Flag
  • Trulia User
    "I was born here and knit the neighborhood very well. It's very small and easy to get around, I stay to myself and I'm laid-back "
    1
    Flag
  • Trulia User
    "people are nice, bus is on time, and drivers are pleasant 99.6%of the time 😊👽I like it just fine, thanks."
    0
    Flag
  • Trulia User
    "Very quiet and everyone is nice to one another There isn’t any party’s or any gun violence Everyone respects one another too"
    5
    Flag
  • Trulia User
    "I've lived in this neighborhood for almost 17 years. I know many of my neighbors and there's a sense of community. Some keep to themselves but many are friendly and social and help one another when there is a need. We keep a contact email list for the block for easy communication. "
    0
    Flag
  • Trulia User
    "The tutors that come out and help the kids that can’t understand there work although it’s a pandemic "
    0
    Flag
  • Trulia User
    "The yards are small but the location is great. Very close to downtown and west main shopping. Great elementary and middle schools. "
    0
    Flag
  • Kidapa
    "We have annual garage sale, occasionally a block party dinner. In the norton dr/Homecrest ave area the neighbors are very close and are like part of a big famil%. We have seen a lot of younger families move in and are excited to see these families grow"
    1
    Flag
  • Aisha
    "I can get to both Interstate 94 and 131 in five minutes. It is a small quaint town where nice schools and nearby parks are in the community."
    1
    Flag
  • Haley F.
    "Pinewood Glen is a chil apt complex. Biking around here and walking is nice. Friendly people, not too many crazy cars."
    1
    Flag
  • Kidapa
    "Annual neighborhood garage sales, letters from the Milwood board updating us on water issues or misc issues"
    0
    Flag
  • Valeria T.
    "Needs to be more secure. Nice area and neighborhoods however there has been much activity that makes one questions the safety of the neighborhood "
    0
    Flag
  • Trulia User
    "This is a very friendly and safe neighborhood. It’s a good home base to raise your children! There are nearby convenience stores, gas stations, restaurants and schools. "
    0
    Flag
  • Rosalinda C.
    "I drive , I don’t use any public transportation, I have my own car that I use to go places . I know people who use it but they rather use uber "
    3
    Flag
  • Jmiltonk
    "its a easy commute. sometimes real late at night can be bit shady. the homeless are abundant in the area."
    1
    Flag
  • Sasha A.
    "It’s honestly a great part to live at you have a lot of local business connected on west main, great restaurants and few nearby elementary, middle, and high schools. It’s extremely quiet and people are friendly and outgoing."
    0
    Flag
  • Karen B.
    "This is a safe and quiet neighborhood. Houses and yards are wellcared for and Kalamazoo Promise qualified"
    0
    Flag
  • Sally L.
    "Hear gun shots every once in a while, I can't wait to relocate. We have had our cars broken into. But very nice neighbors. "
    3
    Flag
  • Mogillyy
    "this is a great area. I love living here - I always hear kids outside walking around the block, very family friendly. I would raise my family here long term - close to Kalamazoo Promise Schools. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5440 Whippoorwill Dr

  • What is 5440 Whippoorwill Dr estimated to be worth?
    Trulia's estimated value for 5440 Whippoorwill Dr in Kalamazoo, MI is $666,800.
  • What is the price history for 5440 Whippoorwill Dr?
    5440 Whippoorwill Dr in Kalamazoo, MI last sold for $450,000 in July 2008.
  • Is Kalamazoo a buyer's or seller's market?
    Kalamazoo is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Kalamazoo?
    The median sale price in Kalamazoo is $246K. That is up $4.67K from the prior month.
  • How big is the lot at 5440 Whippoorwill Dr?
    The lot at 5440 Whippoorwill Dr in Kalamazoo, MI is about 1 acre.
  • Does 5440 Whippoorwill Dr have a garage?
    Yes, 5440 Whippoorwill Dr in Kalamazoo, MI has a garage.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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