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Real estate in Kalamazoo’s Oakland / Winchell neighborhood.

Compare top Oakland / Winchell real estate agents.

Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 2026.*


*Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.

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Oakland / Winchell real estate Market Report.

Information and statistics on the latest trends in the Oakland / Winchell real estate market. *

Latest Rolling 3-Month Snapshot

Jul 1, 2026 - Sep 30, 2026

Median sale price
$366K
+11% from Q2 '26
Median list price
$374K
+25% from Q2 '26
Active listings
23
-18% from Q2 '26
Homes sold
21
+50% from Q2 '26
New pendings
15
-32% from Q2 '26
New listings
18
-14% from Q2 '26

Quarterly Pricing Trends for Oakland-Winchell

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Oakland-Winchell Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $259K Median sale price in Jan 2022 - Mar 2022: $263K Median sale price in Apr 2022 - Jun 2022: $282K Median sale price in Jul 2022 - Sep 2022: $258K Median sale price in Oct 2022 - Dec 2022: $310K Median sale price in Jan 2023 - Mar 2023: $255K Median sale price in Apr 2023 - Jun 2023: $340K Median sale price in Jul 2023 - Sep 2023: $315K Median sale price in Oct 2023 - Dec 2023: $240K Median sale price in Jan 2024 - Mar 2024: $260K Median sale price in Apr 2024 - Jun 2024: $306K Median sale price in Jul 2024 - Sep 2024: $290K Median sale price in Oct 2024 - Dec 2024: $295K Median sale price in Jan 2025 - Mar 2025: $313K Median sale price in Apr 2025 - Jun 2025: $343K Median sale price in Jul 2025 - Sep 2025: $325K Median sale price in Oct 2025 - Dec 2025: $303K Median sale price in Jan 2026 - Mar 2026: $325K Median sale price in Apr 2026 - Jun 2026: $329K Median sale price in Jul 2026 - Sep 2026: $366K Median list price in Oct 2021 - Dec 2021: $250K Median list price in Jan 2022 - Mar 2022: $290K Median list price in Apr 2022 - Jun 2022: $280K Median list price in Jul 2022 - Sep 2022: $300K Median list price in Oct 2022 - Dec 2022: $250K Median list price in Jan 2023 - Mar 2023: $315K Median list price in Apr 2023 - Jun 2023: $335K Median list price in Jul 2023 - Sep 2023: $300K Median list price in Oct 2023 - Dec 2023: $260K Median list price in Jan 2024 - Mar 2024: $257K Median list price in Apr 2024 - Jun 2024: $330K Median list price in Jul 2024 - Sep 2024: $295K Median list price in Oct 2024 - Dec 2024: $300K Median list price in Jan 2025 - Mar 2025: $317K Median list price in Apr 2025 - Jun 2025: $345K Median list price in Jul 2025 - Sep 2025: $335K Median list price in Oct 2025 - Dec 2025: $379K Median list price in Jan 2026 - Mar 2026: $330K Median list price in Apr 2026 - Jun 2026: $300K Median list price in Jul 2026 - Sep 2026: $374K Oct 2021 - Dec 2021 Median sale price $259K Median list price $250K Jan 2022 - Mar 2022 Median sale price $263K Median list price $290K Apr 2022 - Jun 2022 Median sale price $282K Median list price $280K Jul 2022 - Sep 2022 Median sale price $258K Median list price $300K Oct 2022 - Dec 2022 Median sale price $310K Median list price $250K Jan 2023 - Mar 2023 Median sale price $255K Median list price $315K Apr 2023 - Jun 2023 Median sale price $340K Median list price $335K Jul 2023 - Sep 2023 Median sale price $315K Median list price $300K Oct 2023 - Dec 2023 Median sale price $240K Median list price $260K Jan 2024 - Mar 2024 Median sale price $260K Median list price $257K Apr 2024 - Jun 2024 Median sale price $306K Median list price $330K Jul 2024 - Sep 2024 Median sale price $290K Median list price $295K Oct 2024 - Dec 2024 Median sale price $295K Median list price $300K Jan 2025 - Mar 2025 Median sale price $313K Median list price $317K Apr 2025 - Jun 2025 Median sale price $343K Median list price $345K Jul 2025 - Sep 2025 Median sale price $325K Median list price $335K Oct 2025 - Dec 2025 Median sale price $303K Median list price $379K Jan 2026 - Mar 2026 Median sale price $325K Median list price $330K Apr 2026 - Jun 2026 Median sale price $329K Median list price $300K Jul 2026 - Sep 2026 Median sale price $366K Median list price $374K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
15
Seller’s Market
Seller’s Market
Buyer’s Market
0
25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).

Oakland / Winchell currently leans toward sellers, with a clear seller’s market reading. Months of supply is just 0.9, far tighter than Kalamazoo overall at 2.6 months. Homes also go under contract quickly, with a median of only 6 days on the market in this rolling three-month window.

Prices have pushed higher over the past year, with the typical home value up about 13 percent year over year and similar gains in the median list price. Compared with the wider Kalamazoo city market, Oakland / Winchell’s typical value sits well above the city median, highlighting its relatively higher price point. Even with these rising prices, the average sale-to-list ratio is near 97 percent, showing that most sellers are still negotiating some from their asking prices rather than seeing extreme bidding wars.

On the activity side, homes sold in the latest three-month period are up roughly 26 percent from a year ago, even as active listings dipped slightly and months of supply fell by about a third. Fewer new listings and a lower share of homes selling above list than last year suggest buyers may be a bit more price-sensitive, but strong demand is still moving inventory quickly. In a fast-paced, low-supply environment like Oakland / Winchell, Agent Pronto can connect both buyers and sellers with an agent who understands these dynamics and can guide their next move.



Learn more about what Oakland / Winchell has to offer.

Oakland / Winchell offers residents a welcoming, walkable community with tree-lined streets, nearby parks, reliable local amenities, and a strong sense of neighborhood pride.

Oakland / Winchell stands out in Kalamazoo for its rare mix of wooded ravines, walkable streets, and quick access to both downtown and Western Michigan University. Centered along Oakland Drive and Winchell Avenue, the neighborhood feels established and settled, yet continues to attract new residents who value strong schools and everyday convenience.

Families are drawn to Winchell Elementary, part of Kalamazoo Public Schools and the Kalamazoo Promise district. Students and professionals appreciate the short trip to Kalamazoo College and the cultural options near Bronson Park. Nearby Asylum Lake Preserve and Kleinstuck Preserve offer miles of trails and wetlands, giving Oakland / Winchell a remarkably natural feel inside city limits.

Daily life is practical and connected. Oakland Drive links residents to grocery options, neighborhood favorites like O’Duffy’s Pub, and medical centers around Westnedge Hill. Sidewalks, mature trees, and a mix of mid century homes and updated properties support both long term homeowners and first time buyers looking for a stable setting.

For sellers, steady demand and limited inventory mean preparation and pricing strategy matter. For buyers, being ready with local insight and a clear plan is key in such a competitive pocket of the city. Agent Pronto can connect both buyers and sellers in Oakland / Winchell with a real estate professional who understands timing, value, and the nuances of this neighborhood.

Find your Oakland / Winchell real estate agent today →


Trusted by over 500,000 buyers and sellers.

See why so many people rely on Agent Pronto to make their real estate journey a success.

“Kelley Di Martino recently assisted us in the purchase of a home in Kalamazoo for our daughter, who has been going through a difficult time, and decided to begin a new chapter in her life. On both the personal and professional level, Kelley was wonderful to work with. She was warm, kind and supportive. She is knowledgeable and easy to communicate with. Kelley was an effective liaison between the seller, who had listed their home by owner, our daughter, and my husband and me. Kelley helped to foster a cooperative relationship between all parties. The sellers needed a more flexible closing date, so a provision to remain in the home for up to two weeks past closing was agreed upon. When the need for an expensive but necessary electrical repair turned up in the inspection, the sellers agreed to cover 100% of the estimate that was submitted. Thanks to Kelley’s diligence, the purchase was completed successfully and our daughter is now enjoying her new home. We confidently recommend Kelley Di Martino and plan to use her services for real estate transactions in the future.”

vmlammers ·

Photo of Kelley Di Martino
eXp Realty
“Dennis helped sell a tough one due to itss age and needed repairs, he didnt shy away tho and took it on, great work”

C. Rafffile · Cassopolis, MI

Photo of Dennis Bamber
Cressy & Everett Real Estate
“Eric is such a joy to work with! I made him drive all over the place and look at some strange houses and he did it all with a smile on his face. He'll give it to you straight and was always there to answer questions any time of day. My husband and I are so glad we had Eric at our side along the way of buying and selling!”

EmilyVer Mulm ·

Photo of Brian McDonald
RE/MAX Executive
“Traci was wonderful to work with. This was our second time working with her and even though it wasn't our first home purchase it had been a while and Traci was great answering what seemed like all my "new home buyer" questions. Couldn't be happier with the service we got and would NEVER think of going with another agent. Thanks Traci”

JoshNelson78 ·

Photo of The Aspen Group
Five Star Real Estate
“Thomas was absolutely wonderful to work with. He sold my dad’s home quickly and made the entire process so much easier for us. He was professional, knowledgeable, and always on top of everything. He walked us through every step and was always available when we had questions. What I appreciated most was that Thomas is ethical, honest, and truly does the right thing. We are extremely happy with his service and would highly recommend him to anyone looking for a realtor!”

Suzy Farr ·

Photo of Thomas Switek
Exp Realty Michigan
“Cedric did a great job all the way around he went over and beyond helping my family secure a home I would definitely be passing his name to anyone who is looking to secure a home in the future”

cory shepard84 ·

Photo of Cedric Wicks
RE/MAX Executive
“Barketa is fantastic! She walked with us and pointed out things that maybe an issue. She was great at figuring out what met our needs. Barketa is straightforward and honest. We felt super comfortable when working with her. Barketa is a wonderful agent and if we have anything like this again, I would 100% work with her again. I would recommend her to anyone looking in the area”

Kerry Lawhorn · South Bend, IN

Photo of Barketa Kerns
Century 21 Affiliated
“We had an incredible experience working with Bryant Stuut to both buy and sell our home. Bryant was attentive, honest, incredibly responsive, and always willing to answer our many questions throughout the process. What stood out most was how well Bryant understood exactly what we were looking for. He never made us feel pressured and consistently gave us thoughtful, straightforward advice. When it came time to sell, he recommended several small, practical changes that we feel helped our home sell faster and for a higher price. Buying and selling a home can be very stressful, but Bryant made the entire experience feel manageable and gave us complete confidence along the way. I truly cannot say enough good things about him and would recommend Bryant to anyone looking to buy or sell a home.”

Kyle Centers · Kalamazoo, MI

Photo of Bryant Stuut
Next Realty Group, LLC
“Ben did a fantastic job making sure all my questions were answered and giving real feedback on the homes we toured; I never felt like he was trying to convince me to buy. His genuine care for clients is clear, and he had great knowledge throughout the process. Highly recommend Ben to anyone looking to buy a home.”

connor salerno10 ·

Photo of the Lucas Howard Group
Lucas Howard Group - Keller Williams Grand Rapids
“I cannot recommend Ashley highly enough. She originally helped me secure a home during an incredibly high-demand market, navigating the complexities of waived inspections and competitive bidding wars with absolute expertise. Ashley is remarkably well-connected within the community; her extensive network provides her with a constant stream of off-market opportunities that most buyers never see. When it came time to sell our home in Plainfield, we wanted to avoid the stress of constant showings. Ashley managed a seamless off-market sale that exceeded our expectations. She then helped us find our perfect new home, patiently walking us through every detail, including the nuances of HOA regulations. Ashley is honest, driven, and a fierce advocate for her clients. If you want a realtor who handles the legwork and refuses to let you be misled, Ashley is the professional you need."”

Chelsea Fansler ·

Photo of Ashley Bodell
Bellabay
“Amazing! This was my first time buying a home, he was very knowledgeable about the whole process and so helpful. He made a stressful thing very unstressful. Highly recommend and I will personally use in the future!”

karinna irwin ·

Photo of Jeff Newberg
Lake Homes Realty
“Justin was so knowledgeable and helpful. He was always available when I needed him and he and went above and beyond to make my first time buying a home smooth and stress free.”

Amanda V · Kalamazoo, MI

Photo of Justin Lena
Century 21 Affiliated
“Rob did an excellent job helping us sell our house. He took the time to understand our needs and desired timeline. He thoroughly analyzed comparable home sales in our area and helped us set an appropriate price. He helped us prepare the house for showing and then conducted an effective marketing campaign including postings to marketplace sites, individual showings, open houses, etc. Once we received an appropriate offer, Rob managed the entire post sale / closing process. Rob was always available to answer questions and follow up on various details. We are totally pleased with Rob's work on our behalf!”

Mike Ritter ·

Photo of Rob Conat
Exp Realty Grand Rapids
“Gavin did a great job with helping us sell our old home and purchase our new home. He was very professional, punctual, and responsive. He gave a lot of great advice getting us the best bang for our buck. I would recommend Gavin to anyone when purchasing or selling your home.”

Cody Tone ·

Photo of Gavin Homer
The Homer Group with eXp Realty
“I had a great experience working with Megan! She was knowledgeable and always very quick to respond, and was super helpful with referrals for all sorts of services I needed. I will absolute seek her out again if I ever need a realtor.”

SarahCorstange ·

Photo of Megan Hill
Five Star Real Estate - Ada
“Dan did an amazing job. He was quick to set up appointments for walk throughs, he was always honest on things he saw at each house which was very helpful, and he was on top of all the requirements to close on the house. Overall Dan has a lifetime customer with us.”

AshleyLynneFreed ·

Photo of Dan Thornton
Advanced Realty Group
“We moved to Grand Rapids from St Louis. Jeff was great at getting us in houses and using FaceTime to walk us through virtually. We started looking in Jan 2020 and continued through the start of the Covid pandemic. Due to low supply and high demand we went through multiple offers before finally getting our house. Jeff was quick to get paperwork going and prompt to follow up throughout the process. We didn't miss out on a thing even while being out of state during a pandemic, it really speaks to Jeff's dedication, understanding of what we wanted and knowing the local area. I would highly recommend Jeff to friends and family.”

JaynieElle ·

Photo of Grassroots Properties KW
Keller Williams GR East
“Chase was truly one of the best and easiest realtors I’ve ever worked with. He’s hard working, quick to respond with questions/concerns. But most of all his upbeat and positive attitude toward everything. Very happy to have had the opportunity to work with him . HIGHLY recommend Chase.”

zuser20170723072224339 ·

Photo of Coughlin Home Group
Five Star Real Estate
“Julie is a fun and energetic person who wants to get you the home that you are looking for. Julie cares about her clients and will go out of her way to do whatever she can for them.”

user1876571 ·

Photo of Julie Hribar
Berkshire Hathaway Home Services

Frequently Asked Questions

There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Oakland / Winchell. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.


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