1 Winter Dr, Ashland, OR 97520
Property image
Property image
OFF MARKET

$2,004,100

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 6,332 sqft (on 19.47 acres)

1 Winter Dr, Ashland, OR 97520

Est. Refi. Payment $11,462/mo*
Refinance Your Home
Currently Off Market - Sold Dec 3, 2019 for $1,457,500

Home Value

Trulia Estimate
$2M
Since last month
Increased$15K (+0.7%)
Since last year
Decreased$15K (-0.7%)
Since last sale
Increased$567K (+38.9%)
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 +17% in the last 10 years
MonthEstimated value
2026
August 2026$2.02M
July 2026$2.01M
June 2026$2.04M
May 2026$1.98M
April 2026$1.99M
March 2026$2.04M
February 2026$2M
January 2026$1.94M
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
514 Granite St, Ashland, OR
0.23
Single-Family Home
$979,500
03/17/26
4
4
2,890
683 Ashland Creek Dr, Ashland, OR
0.10
Single-Family Home
$950,000
01/16/26
3
3
2,067
435 Granite St, Ashland, OR
0.25
Single-Family Home
$850,000
05/08/26
3
3
2,111
162 Hitt Rd, Medford, OR
0.61
Single-Family Home
$1,760,000
03/31/26
5
3
5,139
551 Strawberry Ln, Ashland, OR
0.74
Single-Family Home
$1,050,000
04/22/26
3
4
4,435
355 Granite St, Ashland, OR
0.26
Single-Family Home
$812,000
03/20/26
3
2
2,015
161 Sunnyview Dr, Ashland, OR
1.00
Single-Family Home
$1,560,000
09/19/25
4
5
4,733
520 Glenview Dr, Ashland, OR
0.45
Single-Family Home
$690,000
07/24/26
3
3
2,627
99 Granite St, Ashland, OR
0.75
Single-Family Home
$3,800,000
08/17/26
5
6
6,903
107 Granite St, Ashland, OR
0.73
Single-Family Home
$945,000
09/05/25
4
3
2,974

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
603 Ashland Creek Dr, Ashland, OR 97520
0.09
-
-
-
-
Off Market
683 Ashland Creek Dr, Ashland, OR 97520
0.10
$950,000
3
3
2,067
Recently Sold
599 Ashland Creek Dr, Ashland, OR 97520
0.11
$1,213,700
3
4
3,906
Off Market
514 Granite St, Ashland, OR 97520
0.23
$979,500
4
4
2,890
Recently Sold
385 Granite St, Ashland, OR 97520
0.23
$1,125,200
4
3
3,372
Off Market
435 Granite St, Ashland, OR 97520
0.25
$850,000
3
3
2,111
Recently Sold
355 Granite St, Ashland, OR 97520
0.26
$812,000
3
2
2,015
Recently Sold
545 Ashland Creek Dr, Ashland, OR 97520
0.29
$1,250,000
3
3
3,108
For Sale
309 Granite St, Ashland, OR 97520
0.30
$1,650,000
5
5
6,332
For Sale
251 Granite St, Ashland, OR 97520
0.36
$294,000
-
-
-
For Sale
Granite St, Ashland, OR 97520
0.37
-
-
-
-
Off Market
237 Granite St, Ashland, OR 97520
0.37
$3,800,000
5
6
6,396
For Sale

Local Information

  • Map ViewExplore the area around 1 Winter Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1998
Lot Size
19.47 acres
Living Area
6,332 sqft
Price/Sqft
$317
Parking
Garage

About this House

This single-family home is located at 1 Winter Dr, Ashland, OR. 1 Winter Dr is in Ashland, OR and in ZIP code 97520. This property has 4 bedrooms, 5 bathrooms and approximately 6,332 sqft of floor space. This property has a lot size of 19.47 acres and was built in 1998.
1 Winter Dr, Ashland, OR 97520 is a 4 bedroom, 5 bathroom, 6,332 sqft single-family home built in 1998. It last sold for $1,457,500 on Dec 3, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,004,100, with a rent estimate of $6,502/month.

Home Details for 1 Winter Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
Refrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

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

Property Information

Year Built
Year Built: 1998Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 19.47 acres

Additional Information

Greenhouse

Price and Tax history

DateEventPrice
Dec 3, 2019
Source: Oregon Datashare #102986091
Sold
$1,457,500
Jun 30, 2019
Source: Agent Provided
PriceChange
$1,775,000
Price decreased by 9%
May 24, 2018
Source: Agent Provided
PriceChange
$1,950,000
Price decreased by 20%
Feb 19, 2018
Source: Agent Provided
Listed For Sale
$2,450,000
Jun 3, 2010
Source: N/A
Sold
$1,350,000

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

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

Frequently asked questions about 1 Winter Dr

  • What is 1 Winter Dr estimated to be worth?
    Trulia's estimated value for 1 Winter Dr in Ashland, OR is $2,004,100.
  • What is the price history for 1 Winter Dr?
    1 Winter Dr in Ashland, OR last sold for $1,457,500 in December 2019.
  • 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 1 Winter Dr have air conditioning?
    Yes, 1 Winter Dr in Ashland, OR has air conditioning.
  • How big is the lot at 1 Winter Dr?
    The lot at 1 Winter Dr in Ashland, OR is about 19.5 acres.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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