266 Gresham St, Ashland, OR 97520
Property image
Property image
OFF MARKET

266 Gresham St
Ashland, OR 97520

  • 4 Beds
  • 2 Baths
  • 1,600 sqft

$524,000

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,064/mo*
Refinance Your Home

$524,000

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $3,064/mo*
Refinance Your Home
4 Beds
2 Baths
1,600 sqft

Home Value

Trulia Estimate
$524K
Since last month
Decreased$10K (-1.8%)
Since last year
Decreased$20K (-3.7%)
Since last sale
Increased$25K (+4.9%)
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 +38% in the last 10 years
MonthEstimated value
2026
August 2026$524K
July 2026$522K
June 2026$534K
May 2026$536K
April 2026$543K
March 2026$543K
February 2026$534K
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
770 Iowa St, Ashland, OR
0.28
Multi-Family Home
$615,000
11/25/25
5
2
2,012
1208 Iowa St, Ashland, OR
0.66
Multi-Family Home
$483,500
08/29/25
4
2
1,550
237 B St, Ashland, OR
0.56
Multi-Family Home
$625,000
11/25/25
4
2
1,725
574 E Main St, Ashland, OR
0.31
Multi-Family Home
$955,000
11/10/25
5
2
3,342
155 Central Ave, Ashland, OR
0.81
Multi-Family Home
$577,100
01/07/26
3
2
1,088
549 B St, Ashland, OR
0.52
Multi-Family Home
$925,000
10/29/25
8
4
3,264
252 B St, Ashland, OR
0.52
Multi-Family Home
$925,000
01/05/26
5
4
3,339
144 N 2nd St, Ashland, OR
0.47
Multi-Family Home
$1,100,000
09/29/25
7
5
3,088
545 A St, Ashland, OR
0.60
Multi-Family Home
$1,165,000
07/31/26
3
1
4,950
684 Chestnut St, Ashland, OR
1.49
Multi-Family Home
$550,000
09/26/25
3
2
1,824

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
459 Holly St, Ashland, OR 97520
0.05
$624,200
3
3
2,235
Off Market
455 Holly St, Ashland, OR 97520
0.05
$540,000
3
3
1,844
For Sale
461 Holly St, Ashland, OR 97520
0.05
$590,000
3
3
2,206
Recently Sold
575 Auburn St, Ashland, OR 97520
0.07
$1,035,000
3
3
4,120
Recently Sold
207 Gresham St #207-209-211, Ashland, OR 97520
0.07
$669,900
6
2
2,304
For Sale
259 Idaho St, Ashland, OR 97520
0.08
$625,000
3
2
1,776
Recently Sold
269 Idaho St, Ashland, OR 97520
0.08
$645,000
3
2
1,667
Recently Sold
499 Iowa St, Ashland, OR 97520
0.08
$769,700
3
2
2,150
Off Market
145 Union St, Ashland, OR 97520
0.08
$551,600
3
2
1,588
Off Market
325 Taylor St, Ashland, OR 97520
0.09
$535,000
3
2
1,205
Recently Sold
121 Union St, Ashland, OR 97520
0.10
$442,900
3
2
1,272
Off Market
350 Guthrie St, Ashland, OR 97520
0.10
$748,200
3
3
2,484
Off Market

Local Information

  • Map ViewExplore the area around 266 Gresham St.
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1970
Living Area
1,600 sqft
Price/Sqft
$328
Parking
Garage

About this House

Charming two bedroom duplex... close to town!
266 Gresham St, Ashland, OR 97520 is a 4 bedroom, 2 bathroom, 1,600 sqft multi-family built in 1970. It last sold for $499,900 on Mar 26, 2021. More recently, it was listed as a rental in October 2022 with an asking price of $1,450 per month. That rental listing was removed on October 22, 2022. It is currently off market. The Trulia Estimate is $524,000, with a rent estimate of $1,920/month.

Home Details for 266 Gresham St

Interior Features

Heating & Cooling
Heating: Other, Radiant, Wall, Electric, GasCooling System: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Laminate
Interior Details
Number of Rooms: 12Types of Rooms: Breakfast Nook, Family Room
Appliances & Utilities
Cable ReadyDryerWasher

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: Wood ProductsGardenPatio
Parking & Garage
GarageParking: Carport, Garage

Property Information

Year Built
Year Built: 1970Year Updated: 2006
Property Type / Style
Property Type: Multi FamilyArchitecture: Ranch / Rambler

Community

Units in Building: 2

Lot Information

Lot Area: 6534 sqft

Price and Tax history

DateEventPrice
Oct 22, 2022
Source: Zillow Rental Manager
ListingRemoved
Oct 3, 2022
Source: Zillow Rental Manager
Listed For Rent
$1,450
Mar 26, 2021
Source: Oregon Datashare #220117495
Sold
$499,900
Mar 15, 2021
Source: Oregon Datashare #220117495
Pending
$499,900
Mar 3, 2021
Source: Oregon Datashare #220117495
Listed For Sale
$499,900

Market trends in Ashland

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$541K
$18.33KMoM
Sale-to-List Price
98.8%
0.2%MoM
Price per sq ft
$313
$10MoM
Available listings
194
7MoM
Skip to last item
  • Results are loading
Skip to first item

Around this home

What Locals Say about Ashland

At least 116 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 84 % Say people would walk alone at night

  • 79 % Say it's walkable to grocery stores

  • 77 % Say it's walkable to restaurants

  • 77 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 67 % Say neighbors are friendly

  • 67 % Say parking is easy

  • 67 % Say car is needed

  • 66 % Say it's quiet

  • 64 % Say there are sidewalks

  • 60 % Say kids play outside

  • 55 % Say streets are well-lit

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

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Larm1
    "I’ve lived here for three years now. The neighbours are friendly and accommodating. Disputes are rare and solved between the disgruntled- outside help is not sought. Kids free range and enjoy the bountiful outdoor life. It’s quite ideal for singles, families alike. "
    1
    Flag
  • Larm1
    "The open outdoor space is plentiful. The parks are safe and clean. The inhabitants are helpful and polite. "
    0
    Flag
  • Larm1
    "It’s a pet friendly place. The bears are not puff ball fans mind you - but the bipeds are. Plenty of running places. Dog walking paths and feee running water. "
    0
    Flag
  • Larm1
    "There is a lot of outdoor space. Hiking trails. Playgrounds. Ball courts. The locals use the space widely and often. Great place for families to enjoy fresh air and sunshine. "
    0
    Flag
  • Fionao.robinette
    "There’s so many places to walk your dogs. There is a lot of pet friendly cafés. If you’re a service dog owner like me you’re very welcome all over Ashland. And most dogs you encounter are friendly."
    0
    Flag
  • Larm1
    "This is the home of the Oregon Shakespeare festival. It has not been a summer only thing for years now. It runs from March through November. In addition there are numerous other play houses and troupes. Always something g to do. "
    0
    Flag
  • Larm1
    "Multiple trails for dogs (and people). Loads of things to chase - from deer to turkeys - steer them clear of the bears though - they might chase back. "
    0
    Flag
  • Larm1
    "The area is full of people who want to be a part of community. They are proud of their land and of the town they have nourished. They enjoy the great outdoors "
    0
    Flag
  • Kaylin
    "The people are kind and care about the community. It’s a lovely place to spend holidays as well. The town has a very nice appeal."
    0
    Flag
  • Larm1
    "Good public schools. Good restaurants. People are kind Good environment for children and families. "
    0
    Flag
  • Pratt_5
    "People are walking their dogs daily. Plenty of sidewalks and trails for fun times with your companion."
    0
    Flag
  • Alicia Rowe
    "Ashland is a lovely community for families and retirees. Peaceful, safe, and naturally beautiful. A true gem of a town. "
    0
    Flag
  • Larm1
    "4th of July parade. Pride parade. Halloween parade. Lighting of the lights in December. Shakespeare festival plays. Music on the green and at the shellback. "
    0
    Flag
  • Larm1
    "This area sports many great attributes for both parents and children. Good schools. Safe neighbourhoods. Easy bike roads. Low crime. Plenty of children to make friends. Art programs. "
    0
    Flag
  • Larm1
    "Piece of cake. I can walk most places. Small town - and I live in town. Not much traffic. Roads are low speed - which is kind of lovely. "
    0
    Flag
  • Pratt_5
    "I am just moving to Ashland. Ideally my commute will be by EBike or a short drive. Even outside city limits, you are easily back in the city quick. "
    0
    Flag
  • lme
    "lithia park and other community parks with playgrounds are nice, safe. we often encounter young families. this is great for our kids who have been impacted by the covid isolation "
    0
    Flag
  • Larm1
    "On foot a lot. Also, by car. I live near shops restaurants and parks. These I walk to. Missing is a decent public transport that is frequent enough to rely on. Also needs a commuter to airport. "
    3
    Flag
  • Brianangelo369
    "some places are dog friendly and a lot of people have dogs. leashes are required most everywhere in town"
    0
    Flag
  • Aaron G.
    "Most things are walkable or bikeable. The town is very easy to get around. Public transit is somewhat sporadic. Uber is almost non-existent."
    0
    Flag
  • Jeff T.
    "I think they like the idea that it was a really dog friendly area as long as they pick up their Doodoo. There are lots of dogs here and people seem to be dog friendly."
    1
    Flag
  • Onelove2285
    "Everyone has dogs. They are very popular. We let them run around, and they are friends. We live in Tolman Heights. "
    1
    Flag
  • Jeff T.
    "Awesome and short. No traffic and friendly drivers. It’s hard to describe it as a true commute compared to the Bay Area "
    0
    Flag
  • Jeff T.
    " I love Ashland it is a very friendly place. It is the best move I have made coming from the bay area which is so rude and entitled. The people are friendly happy and very relaxed."
    0
    Flag
  • Ashland resident
    "It’s important to keep kids active in Ashland and luckily there are lots of different types of things to do. Sports, art, music, theater camps "
    0
    Flag
  • Peterfithian
    "Quiet, friendly neighborhood, sports park and nature preserve nearby. Easy access to downtown, and Lithia Park and hiking trails"
    0
    Flag
  • LVogel
    "Close to an elaborate trail system that is unique in flora and fauna. Very safe neighborhood and free of theft. To live so close to theater, art, restaurants and a great coop, and yet be able to head out the backdoor into hundreds of miles of trails is truly astonishing. It's also quiet, which is increasingly rare in this world."
    0
    Flag
  • lev
    "Parades, music, dance, and tons of nature. An involved and active community. A great coop, and lots of restaurants. Especially love the teahouse. The Britt Fest in Jacksonville is only 20 minutes away, and the coast Redwoods are two hours and 20 minutes by car. "
    1
    Flag
  • Antonio c
    "accepting and loving area, ergonomic and organic choices all around. Everyone is very friendly and helpful. All stores are nearby"
    0
    Flag
  • Chloe C.
    "I live close to many things and can get around easily. It’s very simple public transport and nice local places to go."
    0
    Flag
  • Sallywiggins
    "Halloween First Friday Art Show OSF SOU university nearby with sports, plays and music Near the Peace House "
    0
    Flag
  • Rc97404
    "I don’t find Ashland very friendly. Very unaccepting of me during my time here. If you’re not into walking everywhere or are a smoker, you get stared at. "
    0
    Flag
  • Tammymlord35
    "i have lived here for the past 20 yrs and I live the sense of community. it's a great place to have a family. Ashland is a very unique town, it is surrounded by beauty."
    0
    Flag
  • Demecioortiz
    "I’ve lived in this neighborhood off and on again for the last 19 years. I love it and this side of Ashland. The families that live here are very friendly. "
    4
    Flag
  • Haley j.
    "Safe friendly and centrally local to everything. Close safe parks near by for kids and adult recreation "
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

21 pet-friendly rentals in Ashland, OR

Explore by feature - Garage

15 rentals with a garage in Ashland, OR

Explore by feature - Air Conditioning

66 rentals with air conditioning in Ashland, OR

Explore by feature - Washer/dryer

43 rentals with a washer/dryer in Ashland, OR

Explore by feature - Outdoor Space

10 rentals with an outdoor space in Ashland, OR

Homes for sale near 266 Gresham St

Skip to last item
Skip to first item

Off Market Homes Near 266 Gresham St

Skip to last item
Skip to first item

Frequently asked questions about 266 Gresham St

  • What is 266 Gresham St estimated to be worth?
    Trulia's estimated value for 266 Gresham St in Ashland, OR is $524,000.
  • What is the price history for 266 Gresham St?
    266 Gresham St in Ashland, OR last sold for $499,900 in March 2021.
  • Is Ashland a buyer's or seller's market?
    Ashland is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Ashland?
    The median sale price in Ashland is $541K. That is down $18.33K from the prior month.
  • Does 266 Gresham St have air conditioning?
    Yes, 266 Gresham St in Ashland, OR has air conditioning.
  • Does 266 Gresham St have laundry facilities?
    Yes, 266 Gresham St in Ashland, OR has in-unit laundry.