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

299 Gresham St
Ashland, OR 97520

  • 2 Beds
  • 1 Bath

$369,500

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $2,190/mo*
Refinance Your Home

$369,500

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $2,190/mo*
Refinance Your Home
2 Beds
1 Bath

Local Information

  • Map ViewExplore the area around 299 Gresham St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home

About this House

Available in early January. Pets are negotiable with owner approval, an additional $500 deposit, and $35 monthly pet rent. This 2 bedroom, 1 bath home offers comfortable living space and includes a range, dishwasher, refrigerator, washer, and dryer. The home features central heating and air conditioning, as well as an electric vehicle charging station. Parking is off-street, and tenants are responsible for landscaping and all utilities. Please note: the home will be unfurnished at move-in furnishings shown in photos belong to the owner and will be removed prior to occupancy.

Security Deposit: $2,992.50
6-month lease term.
The owner will consider a co-signer.
No smoking in or on property grounds.
$55 application fee for each occupant 18 or older.
com.

DEPOSIT-FREE OPTION We are proud to offer deposit-free living to qualified renters through Obligo! We understand that moving costs can add up, so we want to extend financial flexibility to our residents. When you move in with us, you can skip paying a security deposit and keep the cash for activities you care about. Learn more about the benefits of deposit-free living with Obligo's brochure or on their website. (Disclosure: Obligo offers up to 1.5 times the rent maximum for this service; fees apply).
299 Gresham St, Ashland, OR 97520 is a 2 bedroom, 1 bathroom single-family home. It last sold for $300,000 on Aug 18, 2017 (14,938% above the $1,995 asking price). More recently, it was listed as a rental in October 2025 with an asking price of $2,100 per month. That rental listing was removed on December 6, 2025. It is currently off market. The Trulia Estimate is $369,500, with a rent estimate of $1,749/month.

Home Details for 299 Gresham St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price History for 299 Gresham St

DatePriceEventSource
12/06/2025$1,995ListingRemovedZillow Rentals
11/12/2025$1,995PriceChange
Zillow Rentals
10/22/2025$2,100Listed For RentZillow Rentals
08/18/2017$300,000Sold
N/A
07/23/2010$240,000Sold
N/A
10/20/2003$190,000Sold
N/A
03/14/2002$190,000Sold
N/A

Market trends in Ashland

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$558K
$12.83KMoM
Sale-to-List Price
99.0%
0.2%MoM
Price per sq ft
$323
$6MoM
Available listings
187
2MoM
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Property Tax and Assessment

Year2024
Tax$3,278
Assessment$271,360
Home facts updated by county records

Comparable Sales for 299 Gresham St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
71 Gresham St, Ashland, OR
0.27
Single-Family Home
$390,000
08/22/25
2
1
1,353
300 Harrison St, Ashland, OR
0.26
Single-Family Home
$450,000
12/12/25
2
1
896
65 4th St, Ashland, OR
0.42
Single-Family Home
$301,790
04/08/26
2
1
832
775 Forest St, Ashland, OR
0.45
Single-Family Home
$405,000
08/12/25
2
1
1,188
605 Liberty St, Ashland, OR
0.50
Single-Family Home
$350,000
11/10/25
2
1
1,305
75 Dewey St, Ashland, OR
0.42
Single-Family Home
$500,000
07/22/26
2
1
1,326
621 Altamont St, Ashland, OR
0.24
Single-Family Home
$475,000
05/18/26
2
2
1,440
475 Liberty St, Ashland, OR
0.41
Single-Family Home
$555,000
06/05/26
2
1
1,239
325 Taylor St, Ashland, OR
0.09
Single-Family Home
$535,000
05/28/26
3
2
1,205
494 Fairview St, Ashland, OR
0.16
Single-Family Home
$420,000
09/12/25
3
2
1,111

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 299 Gresham St.
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 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

  • 65 % Say it's quiet

  • 64 % Say there are sidewalks

  • 59 % 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

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Apartments for Rent

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Explore by feature - Pet Friendly

23 pet-friendly rentals in Ashland, OR

Explore by feature - Garage

17 rentals with a garage in Ashland, OR

Explore by feature - Air Conditioning

77 rentals with air conditioning in Ashland, OR

Explore by feature - Washer/dryer

54 rentals with a washer/dryer in Ashland, OR

Explore by feature - Outdoor Space

16 rentals with an outdoor space in Ashland, OR

Homes for sale near 299 Gresham St

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Off Market Homes Near 299 Gresham St

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Frequently asked questions about 299 Gresham St

  • What is 299 Gresham St estimated to be worth?
    Trulia's estimated value for 299 Gresham St in Ashland, OR is $369,500.
  • What is the price history for 299 Gresham St?
    299 Gresham St in Ashland, OR last sold for $300,000 in August 2017.
  • Is Ashland a buyer's or seller's market?
    Ashland is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Ashland?
    The median sale price in Ashland is $558K. That is up $12.83K from the prior month.
  • Does 299 Gresham St have air conditioning?
    Yes, 299 Gresham St in Ashland, OR has air conditioning.
  • Does 299 Gresham St have laundry facilities?
    Yes, 299 Gresham St in Ashland, OR has in-unit laundry.