1744 Winston Ave, Upland, CA 91784
OFF MARKET

1744 Winston Ave
Upland, CA 91784

  • 4 Beds
  • 3 Baths
  • 2,192 sqft

$940,200

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $5,694/mo*
Refinance Your Home

$940,200

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $5,694/mo*
Refinance Your Home
4 Beds
3 Baths
2,192 sqft

Local Information

  • Map ViewExplore the area around 1744 Winston Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 1744 Winston Ave, Upland, CA. 1744 Winston Ave is in Upland, CA and in ZIP code 91784. This property has 4 bedrooms, 3 bathrooms and approximately 2,192 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1985.
1744 Winston Ave, Upland, CA 91784 is a 4 bedroom, 3 bathroom, 2,192 sqft single-family home built in 1985. It last sold for $380,000 on May 15, 2003. It is currently off market. The Trulia Estimate is $940,200, with a rent estimate of $4,580/month.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1744 Winston Ave

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
FireplaceHot Tub or Spa

Property Information

Year Built
Year Built: 1985Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Modern

Exterior Features

Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 1744 Winston Ave

DatePriceEventSource
05/15/2003$380,000Sold
N/A

Market trends in Upland

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$809K
$333MoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$438
$2MoM
Available listings
174
16MoM
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Property Tax and Assessment

Year2025
Tax$6,359
Assessment$573,371
Home facts updated by county records

Comparable Sales for 1744 Winston Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1764 Winston Ave, Upland, CA
0.05
Single-Family Home
$940,000
11/04/25
4
2
1,867
1778 Sunnybrook Ave, Upland, CA
0.10
Single-Family Home
$1,015,000
05/19/26
4
3
2,173
1732 Winston Ave, Upland, CA
0.03
Single-Family Home
$869,000
08/01/25
3
2
1,687
1754 N 2nd Ave, Upland, CA
0.20
Single-Family Home
$1,025,000
10/27/25
4
3
2,668
1754 N 1st Ave, Upland, CA
0.26
Single-Family Home
$825,000
08/04/25
4
2.5
2,111
460 E Nicole Ct, Upland, CA
0.24
Single-Family Home
$1,100,000
09/26/25
4
3
2,995
1785 N 3rd Ave, Upland, CA
0.20
Single-Family Home
$1,250,000
09/19/25
4
3.5
2,486
1679 N 2nd Ave, Upland, CA
0.29
Single-Family Home
$870,000
11/07/25
4
2
1,846
1685 Francis Ave, Upland, CA
0.18
Single-Family Home
$990,000
06/22/26
3
2
1,867
1844 N 1st Ave, Upland, CA
0.36
Single-Family Home
$855,000
08/08/25
4
2.5
2,432

Nearby homes

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Assigned Schools

These are the assigned schools for 1744 Winston Ave.
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 Upland

At least 652 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 89 % Say there are sidewalks

  • 82 % Say car is needed

  • 75 % Say yards are well-kept

  • 74 % Say there's holiday spirit

  • 68 % Say parking is easy

  • 63 % Say streets are well-lit

  • 63 % Say it's walkable to grocery stores

  • 62 % Say it's walkable to restaurants

  • 62 % Say it's quiet

  • 62 % Say people would walk alone at night

  • 58 % Say they plan to stay for at least 5 years

  • 58 % Say kids play outside

  • 52 % Say there's wildlife

  • 51 % Say neighbors are friendly

  • 25 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • A.corryn22
    "It's a really great community and area to raise or start a family. I also think it's great for an older couple or family. "
    0
    Flag
  • Trulia User
    "Very calm. And very friendly. Always felt safe and quiet the area was very quiet to downtown and other shopping centers"
    0
    Flag
  • Dauraluko
    "It is generally quiet, peaceful and safe. The neighbors hardly bother you. Kid friendly, safe for walks and relatively clean. "
    0
    Flag
  • Twitchboxing
    "Sometimes dog owners do not pick up after their animals. That’s itself is infuriating when I take a wrong step smh"
    0
    Flag
  • Guillermonperez
    "t's a good neighborhood to grow the kids and I'm sure above all welcome to be to upland God bless you"
    0
    Flag
  • Shannwally
    "The Lemon festival is one of the biggest events that we have in old town upland! They also do a harvest type Halloween festival and a forth of July parade. I also love that we are in between Rancho and Claremont because there’s more of a variety of events. But our most favorite thing about living in upland is mt baldy. We go up there every week"
    2
    Flag
  • Jasmine Parrilla
    "Well is a nice area but I been seeing a lot homeless little by little and I live in an apartment for 4 year and now they been stealing out side my porch and that’s because I live on the second floor and the lobby is closed but the new neighbors don’t close it sometimes and they come in and take stuff homeless people "
    4
    Flag
  • Akhernandez
    "Lots of parks and restaurants for kids. But there’s also several bars in the area. Also noticed an increase in homeless "
    4
    Flag
  • Sndayu
    "They would like the long trail made for pet owners as well as for people biking and exercising. They dislike some of the parts on the trail does not provide enough shades."
    0
    Flag
  • Kenda kershah
    "I like live in upland , it’s quite and clean , I like the mountains and trees and the weather. I hope to find a good home to buy because I want to live in upland "
    2
    Flag
  • Trulia User
    "Very clean and safe for dogs. There is a great park for walking dogs in this complex. I don’t own pets but many residents do and they seem very happy. "
    0
    Flag
  • Riverrat368
    "Good schools, local and convenient shopping. Parks and dog parks. Walking up Euclid is nice for families. "
    6
    Flag
  • Sherriandlaura
    "I have easy access to several freeways, and streets are simple to navigate. My commute is still very long but living out here makes it worth’s "
    1
    Flag
  • Manny T.
    "very friendly to dogs especially in the downtown area. Store owners leave out food or water for dogs "
    0
    Flag
  • Brandon B.
    "I’m not sure but Upland has always been a solid place to live. Very safe, great people, and peaceful."
    2
    Flag
  • Indy2118
    "People keep their dogs on leashes & clean up after them more often than not. People also seem happy "
    0
    Flag
  • High
    "Our particular neighborhood is green and quiet. Wide streets. Well manicure yards. Off a busier street but little noise. "
    0
    Flag
  • Kim J.
    "the downtown events such as fairs festivals and other community events so families can come out and get to know what's going on in the community and so family please can come out and get to know other families in the community. "
    0
    Flag
  • Shannon P.
    "Walking distance to anything and everything, schools restaurants, shopping, laundromats, churches, banks, pharmacies, parks, grocers, mall (when they reopen). All in such close proximity that you could walk to them if necessary)."
    0
    Flag
  • Celine W.
    "Nothing to not like everyone including the dogs are friendly and it’s a very safe and tolerable atmosphere "
    1
    Flag
  • Anaslvrnblck
    "Love my city! Have lived here for 13 years and don't want to move anywhere else. I love my no drama neighbors and my son loves play outside with his friends. We like the school district. Most shopping is walking distance. The city is very quiet and clean. Police department is quick to answer calls. I feel very safe here."
    0
    Flag
  • Innocent A.
    "Downtown upland festivals held by city and local business owners and local community events and overall support by law enforcement and fire department is well "
    0
    Flag
  • Alexis M.
    "The parks are small but well-maintained, and you can rent out some park spaces like at McCarthy park for birthday parties and things. Mostly quiet neighborhood! "
    3
    Flag
  • Nando243
    "Horrible only cause I travel everywhere but not during work hours it great. Overall it a good experience. "
    1
    Flag
  • Dyonnepeterson
    "Quiet no drama and very friendly neighbors. I would recommend this area to many people. If you are looking for a place that’s peaceful then Upland is the place for you"
    0
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  • Ja5923197
    "good people and good respects all store there nearby and school there very nice and street there good "
    0
    Flag
  • Shannon P.
    "Lemon festival is a gathering of vendors though the price of food and drinks are exorbitant. We are not far from Pomona fairplex where the county fair is held."
    0
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  • Meg R.
    "Upland is great in general however certain parts of upland are sketchy. If looking for a decent home in a nice area I would consider above foothill. People are nice, love all the different cultures, and and great for evening walks especially down Euclid. "
    1
    Flag
  • Krissyko57
    "Old neighborhood !! NOT well lit. City trees overgrown, sidewalks cracked uneven due to roots from overgrown trees. Constantly hear sirens, street racing, "
    1
    Flag
  • Riverrat368
    "I commute 39 min to work now. However I did work in Santa Monica and the Metrolink was very simple to use. The upland station is clean and safe. "
    0
    Flag
  • Jenellemillan7
    "It’s definitely a suburban area . Lots of people walk out with their kids / dogs it’s very historic looking but I love it . & there’s convenient stores all around "
    0
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  • Daisy M.
    "I've lived in this neighborhood for 20 years , I grew up here and back in the days it was great families everywhere kids enjoying themselves and now you see crazy drug addicts and lots of crime and rude people "
    0
    Flag
  • Rudy G.
    "It a quiet area, there’s gonna be crime everywhere but it’s not too bad here, always something going on in old town upland and it’s within walking distance, lots of places to eat out. 5 min walk to metro link station."
    2
    Flag
  • CRYSTAL
    "Fine a little backed up when school is in but other then that great I love it here I wouldn’t want to move away "
    0
    Flag
  • Kris L.
    "Small town that’s trying to clean up the homeless and crime issue. Has rustic old home feel. There’s evens down town that’s fun to attend with friends or family such as lemon festival, beer fest, etc."
    0
    Flag
  • D_wright04
    "The Lemon festival in downtown is fun and community centered. Upland is a family centered community "
    0
    Flag
  • Disappointed in upland
    "I live in an area in upland that has been forgotten. The apartments are not taken care of & the streets are falling apart. "
    0
    Flag
  • Kayleewytcherley
    "This neighborhood sucks there’s homeless walking on every street, I’ve seen hookers, and it’s not safe walking around at night or sometimes even during the day with out some form of protection "
    1
    Flag
  • Zami F.
    "We have festivals at downtown. Irish, lemon festival, Halloween and many others. We have a 5k too. We have a run trail and we can run up To the mountain on The Euclid path. "
    0
    Flag
  • Alyssa N.
    "Upland is a great place to live , I am happy to raise my three kids here ... schools and shops . They have nice parks Close to all freeways "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Homes for sale near 1744 Winston Ave

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Off Market Homes Near 1744 Winston Ave

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