1335 Windsor Dr, Gladstone, OR 97027
Property image
Property image
OFF MARKET

$536,400

Trulia Estimate
as of Aug 28, 2026
  • 3 Beds
  • 2 Baths
  • 2,700 sqft
  • 3 Beds
  • 2 Baths
  • 2,700 sqft

1335 Windsor Dr, Gladstone, OR 97027

Home Highlights

Property Type
Single-Family Home
Living Area
2,700 sqft
Price/Sqft
$199
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 1335 Windsor Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Available Early July.

Spacious 2,700 SF Home on Large Lot with Extra Parking & Flexible Living Space

Enjoy space, comfort, and convenience in this light-filled 2,400-square-foot home located on a quiet dead-end street. Large windows and skylights provide abundant natural light throughout the home, while two wood-burning fireplaces add warmth and character.

The primary bedroom is located on the main level, and the daylight basement offers additional living space with a separate entrance-ideal for a home office, recreation room, or multi-generational living. The downstairs fourth bedroom is non-traditional and may be best suited as a guest room, office, or bonus space.

The spacious eat-in kitchen, abundant built-in storage, and attached two-car garage with overhead storage provide excellent functionality. Stay comfortable year-round with central air conditioning ready for summer.

Outside, enjoy a huge fenced yard with gated access to the street and direct proximity to the Trolley Trail for walking, jogging, and biking. Additional parking space offers room for vehicles, recreational equipment, or other storage needs.

Features Include:

Approximately 2,700 SF of living space
4 bedrooms (4th bedroom is non-traditional)
Primary bedroom on main level
Daylight basement with separate entrance
Two wood-burning fireplaces
Large windows and skylights
Eat-in kitchen
Central A/C
Attached 2-car garage with overhead storage
Extra parking area
Large fenced yard
Quiet dead-end street
Convenient access to the Trolley Trail

A spacious and versatile home offering plenty of room for living, working, and entertaining.

12 month lease.
$200.00 one time set up fee
$35.00 per adult application fee
$3295.00 Security Deposit
1335 Windsor Dr, Gladstone, OR 97027 is a 3 bedroom, 2 bathroom, 2,700 sqft single-family home. It last sold for $510,000 on Jul 12, 2021 (15,378% above the $3,295 asking price). More recently, it was listed as a rental in June 2026 with an asking price of $3,295 per month. That rental listing was removed on July 14, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $536,400, with a rent estimate of $3,246/month.

Home Details for 1335 Windsor Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central Air, Wall UnitHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 1335 Windsor Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1435 Windsor Dr, Gladstone, OR
0.05
Single-Family Home
$470,000
05/29/26
4
2
2,259 sqft
19229 SE River Rd, Milwaukie, OR
0.30
Single-Family Home
$495,000
07/20/26
3
2
1,502 sqft
232 W Hereford St, Gladstone, OR
0.29
Single-Family Home
$540,000
02/24/26
4
2
2,042 sqft
280 W Ipswich St, Gladstone, OR
0.23
Single-Family Home
$472,000
03/31/26
3
2
1,200 sqft
5085 SE Britton Ave, Milwaukie, OR
0.37
Single-Family Home
$494,000
03/09/26
3
2
1,864 sqft
384 W Dartmouth St, Gladstone, OR
0.46
Single-Family Home
$511,000
04/27/26
3
2
2,211 sqft
470 W Dartmouth St, Gladstone, OR
0.46
Single-Family Home
$460,500
06/12/26
3
2
2,990 sqft
1640 Manor Dr, Gladstone, OR
0.16
Single-Family Home
$540,000
10/03/25
4
3
1,700 sqft
140 Nelson Ln, Gladstone, OR
0.30
Single-Family Home
$425,000
04/08/26
3
2
1,465 sqft
5035 SE Glen Echo Ave, Milwaukie, OR
0.38
Single-Family Home
$525,000
10/07/25
3
2
1,620 sqft

Nearby homes

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Around this home

What Locals Say about Gladstone

At least 66 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 85 % Say parking is easy

  • 82 % Say kids play outside

  • 75 % Say car is needed

  • 74 % Say yards are well-kept

  • 72 % Say there are sidewalks

  • 71 % Say there's holiday spirit

  • 64 % Say it's walkable to grocery stores

  • 63 % Say people would walk alone at night

  • 61 % Say it's walkable to restaurants

  • 60 % Say neighbors are friendly

  • 59 % Say they plan to stay for at least 5 years

  • 57 % Say it's quiet

  • 51 % Say streets are well-lit

  • 48 % Say there's wildlife

  • 36 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Summer Myers
    "Keep on a leash pickup poop and then throw it away don’t just tie the bag and throw it back on ground keep off others property "
    0
    Flag
  • Tracy Hill
    "It’s important to get inviting you want to make a difference in this community. However, it’s a wonderful community to bring your children up in. I grew up here and brought my daughter back here in her late teens. It’s a mostly beautiful and peaceful community, and hopefully getting better and better."
    0
    Flag
  • Nroseatwood
    "There are dog parks for the dogs to run freely and a lot of trails around the neighborhood and along both the Willamette River and Clackamas River. "
    0
    Flag
  • Mnostrander
    "I commute all the way to Vancouver on the I205 and my commute is much shorter than friends who live in Portland, even though Portland technically is closer. it's an easy on/off the freeway! "
    0
    Flag
  • Tracy
    "I’m not a big “dog walker” as my dog doesn’t like walks so much. However, it seems like a very dog-friendly area."
    0
    Flag
  • Jon H.
    "Lots of dog owners, and a great paved hiking area near Clackamas River. Lots of complaints by neighbors though, of owners not picking up after their pets. "
    0
    Flag
  • Mchris
    "I've lived here for 10 years and I'm getting ready to move. Taxes are exorbitantly high and the neighbors are rude. "
    2
    Flag
  • Bobbijokane
    "I commute with bus and wish we had weather protector on WEBSTER RD. I wish there was more options when it comes to buses on WEBSTER RD"
    0
    Flag
  • Rebecca M.
    "price is too high to live here. sorry I have to say. but school are good. depends on how you and they raised their kids"
    0
    Flag
  • glad not happy
    "It’s turning into a drug haven and people that steal out of yards, police do nothing they sit inside the police station that’s all. "
    2
    Flag
  • Mchris
    "We'll be moving in a couple months. can't wait to get out of Gladstone. Prices are way too high for this neighborhood. property taxes have more than doubled in the 10+years I've lived here and now our water bill is going up by 300%. It's beyond ridiculous."
    0
    Flag
  • Kannliebert
    "It very walkable. Nice parks and overall a friendly place to live. It’s got a small town feel next to the big city. "
    0
    Flag
  • Breahnadv
    "My boyfriend lives in this neighborhood and it’s an amazing community feel. Everyone feels like family and it’s beautiful to see. Feel at home "
    1
    Flag
  • Danyabrien
    "I've been living in Gladstone for 4 years now. I love the families and friendly community. Great neighborhood to raise a family or settle down into retirement."
    0
    Flag
  • Jaclynsull
    "Small good community. We love it here and have lived here for 12 years. We will probably stay in Gladstone for a really long time. "
    0
    Flag
  • suedan588
    "Will be living there. Our daughter and family are living there now. Wonderful quiet neighbor hood. House on Cul-de-sac."
    0
    Flag
  • musacchio
    "This is a very quiet, peaceful, low traffic neighborhood. Easy to go for morning stroll or bike around. Small children's play area. Good mix of young families and older neighbors. No walkable shops or restaurants and public transportation is a little bit of a challenge to access. Great place to walk pets but no walkable dog parks."
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jul 14, 2026
Source: Zillow Rentals
ListingRemoved
$3,295
Jun 30, 2026
Source: Zillow Rentals
Listed For Rent
$3,295
Nov 10, 2023
Source: Zillow Rentals
ListingRemoved
Oct 27, 2023
Source: Zillow Rentals
Listed For Rent
$2,795
Oct 26, 2023
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 1335 Windsor Dr

  • What is 1335 Windsor Dr estimated to be worth?
    Trulia's estimated value for 1335 Windsor Dr in Gladstone, OR is $536,400.
  • What is the price history for 1335 Windsor Dr?
    1335 Windsor Dr in Gladstone, OR last sold for $510,000 in July 2021.
  • Is Gladstone a buyer's or seller's market?
    Gladstone is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Gladstone?
    Residents describe Gladstone, OR as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Gladstone, OR.
  • Does 1335 Windsor Dr have air conditioning?
    Yes, 1335 Windsor Dr in Gladstone, OR has air conditioning.
  • Does 1335 Windsor Dr have parking?
    Yes, 1335 Windsor Dr in Gladstone, OR has on-site parking.

Homes for rent near 1335 Windsor Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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