Is parking easy in Roundup, MT?

As of early 2026, 100% of users say parking is easy

Do kids play outside in Roundup, MT?

As of early 2026, 89% of users say kids play outside

Are there community events in Roundup, MT?

As of early 2026, 86% of users say there are community events

Are yards well-kept in Roundup, MT?

As of early 2026, 83% of users say yards are well-kept

Is there wildlife in Roundup, MT?

As of early 2026, 80% of users say there's wildlife

Is Roundup, MT dog-friendly?

As of early 2026, 80% of users say it's dog friendly

Are neighbors friendly in Roundup, MT?

As of early 2026, 79% of users say neighbors are friendly

Is Roundup, MT walkable to grocery stores?

As of early 2026, 75% of users say it's walkable to grocery stores

Would people walk alone at night in Roundup, MT?

As of early 2026, 75% of users say people would walk alone at night

Does Roundup, MT show holiday spirit?

As of early 2026, 73% of users say there's holiday spirit

Do residents of Roundup, MT plan to stay at least 5 years?

As of early 2026, 70% of users say they plan to stay for at least 5 years

Is Roundup, MT walkable to restaurants?

As of early 2026, 67% of users say it's walkable to restaurants

Is a car needed in Roundup, MT?

As of early 2026, 56% of users say car is needed

Is Roundup, MT quiet?

As of early 2026, 50% of users say it's quiet

Does Roundup, MT have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Are the streets well-lit in Roundup, MT?

As of early 2026, 38% of users say streets are well-lit

What is 121 Winchester Dr estimated to be worth?

Trulia's estimated value for 121 Winchester Dr in Roundup, MT is $548,400 .

Is Roundup a buyer's or seller's market?

Roundup is currently a seller's market, based on recent for-sale activity.

What do residents say about Roundup?

Residents describe Roundup, MT as easy to park in, community-oriented, and well-kept. Most residents say you need a car. See recently sold homes in Roundup, MT .

What are the closest schools to 121 Winchester Dr?

The closest schools to 121 Winchester Dr in Roundup, MT are Roundup 7-8 (Middle, rated 3/10), Roundup Elementary (Pre-K, rated 7/10), Roundup High School (rated 2/10).

OFF MARKET

$548,400

Trulia Estimate

3 Beds
3 Baths
1,824 sqft (on 29.80 acres)

121 Winchester Dr, Roundup, MT 59072

Est. Refi. Payment $3,185/mo*

Refinance Your Home

Home Value

Trulia Estimate

$548K

Since last month

$17K (-3%)

Since last year

$70K (-11.4%)

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 +111% in the last 10 years

Month	Estimated value
2026
August 2026	$543K
July 2026	$560K
June 2026	$558K
May 2026	$567K
2025
October 2025	$560K
September 2025	$561K
August 2025	$613K
July 2025	$655K
June 2025	$654K
May 2025	$656K
2024
June 2024	$497K
May 2024	$495K
April 2024	$485K
March 2024	$496K
February 2024	$478K
January 2024	$493K
2023
December 2023	$487K
November 2023	$509K
October 2023	$486K
September 2023	$500K
August 2023	$506K
July 2023	$535K
June 2023	$524K
May 2023	$495K
April 2023	$490K
March 2023	$487K
February 2023	$479K
January 2023	$499K
2022
December 2022	$485K
November 2022	$500K
October 2022	$511K
September 2022	$526K
August 2022	$521K
July 2022	$532K
June 2022	$542K
May 2022	$531K
April 2022	$521K
March 2022	$499K
February 2022	$470K
January 2022	$476K
2021
December 2021	$481K
November 2021	$482K
October 2021	$478K
September 2021	$473K
August 2021	$471K
July 2021	$477K
June 2021	$520K
May 2021	$590K
April 2021	$554K
March 2021	$444K
February 2021	$450K
January 2021	$430K
2020
December 2020	$429K
November 2020	$409K
October 2020	$370K
August 2020	$266K
July 2020	$266K
June 2020	$263K
May 2020	$257K

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
215 3rd St W, Roundup, MT	1.81	Single-Family Home	-	04/27/26	2	1	1,092
4 N Moonlight Dr, Roundup, MT	3.06	Single-Family Home	-	07/27/26	3	2	1,728
16645 US Highway 12 W, Roundup, MT	3.40	Single-Family Home	-	01/05/26	4	3	3,391
212 1st Ave W, Roundup, MT	1.68	Single-Family Home	-	12/05/25		-	-
72 Eastside Dr, Roundup, MT	5.34	Single-Family Home	-	07/01/26	3	2	1,458
50 Outlaw Trl, Roundup, MT	6.35	Single-Family Home	-	03/13/26	2	2	1,232

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
86 Winchester Mount Remington Trl, Roundup, MT 59072	0.50	$287,900	3	2	2,236	For Sale
Winchester Dr, Roundup, MT 59072	0.73	-	-	-	-	Off Market
Nhn Winchester Dr, Roundup, MT 59072	0.80	-	-	-	-	Off Market
237 Winchester Dr, Roundup, MT 59072	0.81	$537,400	3	2	2,204	Off Market
213 Winchester Dr, Roundup, MT 59072	0.84	$496,500	2	2	1,600	For Sale
Winchester Dr, Roundup, MT 59072	0.85	-	-	-	-	Off Market
25 Denali Cabin Ln, Roundup, MT 59072	1.37	$750,000	3	2.5	2,254	For Sale
Highway 87, Roundup, MT 59072	1.36	$275,000	-	-	-	For Sale

Local Information

Map ViewExplore the area around 121 Winchester Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Year Built

2005

Lot Size

29.8 acres

Living Area

1,824 sqft

Price/Sqft

$301

About this House

Wildlife Abounds On 29.8 Acre Ranchette In Hills South Of Musselshell River About 5 Min. From Roundup. Great Place To Ride Horses, Recreate & Hibernate. Beautiful Custom-Built Rancher, Cedar Siding On House & Barn (30X30). Hardwd Floors, Hickory Cabinets.

121 Winchester Dr, Roundup, MT 59072 is a 3 bedroom, 3 bathroom, 1,824 sqft unknown built in 2005. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $548,400, with a rent estimate of $2,038/month.

Home Details for 121 Winchester Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1

Exterior Features
Exterior Home Features Roof: MetalDeckExterior: WoodFoundation Type: Concrete

Property Information
Year Built Year Built: 2005
Property Type / Style Property Type: UnknownArchitecture: Ranch / Rambler

Lot Information
Lot Area: 29.80 acres

Price and Tax history

Date	Event	Price
Sep 22, 2025 Source: BMTMLS #354617	Contingent	$575,000
Sep 1, 2025 Source: BMTMLS #354617	PriceChange	$575,000 Price decreased by 8%
Jul 31, 2025 Source: BMTMLS #354617	PriceChange	$625,000 Price decreased by 7%
Apr 23, 2025 Source: BMTMLS #352267	Listed For Sale	$675,000

Year	Property tax	Tax assessment
2025	$1,063	$296,164

Additional Cost

Market trends in Roundup

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Roundup Elementary
PK-6
Public
298 Students
Roundup Elementary School District
7/10
GreatSchools Rating
Parent Rating Average
I am a student and I am twelve I am new and this school treated me like I had already been there for a long time. The students are amazing I have never met such great people. They always try there best never less. The princable is a wonderful man he always makes people laugh everyone likes him and his jolly smile. The teachers are so amazing they are always encouraging and keeping a glowing smile. Students never judge neither do teachers. I wish every school was as good as these lovely people without the teachers students wouldn't be as good as they are and without the students I would have failed they encourage and help, and they never stop.
Other Review
11y ago
3 Reviews

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 Roundup

At least 6 Trulia users voted on each feature.

100 % Say parking is easy
89 % Say kids play outside
86 % Say there are community events
83 % Say yards are well-kept
80 % Say there's wildlife
80 % Say it's dog friendly
79 % Say neighbors are friendly
75 % Say it's walkable to grocery stores
75 % Say people would walk alone at night
73 % Say there's holiday spirit
70 % Say they plan to stay for at least 5 years
67 % Say it's walkable to restaurants
56 % Say car is needed
50 % Say it's quiet
44 % Say there are sidewalks
38 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Destynee & Davin
Resident
2y ago
"Roundup goes all out for their holidays. Christmas, Halloween, Fourth of July, etc. usually parades for every holiday. "
0
Flag
Chaunty03
Resident
2y ago
"Sometimes it can take a while to fully understand/accept Roundup. It’s quant and close knit, will always be home. It’s sort of one of those towns like the movies where it’s “let me show you where I’m from” and there’s absolutely nothing but everyone is nice, and then the 4th of July R.I.D.E is an AMAZING experience to top it off."
1
Flag
rwchamberlinjr
12y ago
"Great place to live. Safe place to raise children. You can walk the street at night and not worry about anybody doing you harm. Clean air, healthy food, beautiful weather. Mostly Sunny. People are very nice. Laid back atmosphere."
4
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 121 Winchester Dr

What is 121 Winchester Dr estimated to be worth?
Trulia's estimated value for 121 Winchester Dr in Roundup, MT is $548,400.
Is Roundup a buyer's or seller's market?
Roundup is currently a seller's market, based on recent for-sale activity.
What do residents say about Roundup?
Residents describe Roundup, MT as easy to park in, community-oriented, and well-kept. Most residents say you need a car. See recently sold homes in Roundup, MT.
What are the closest schools to 121 Winchester Dr?
The closest schools to 121 Winchester Dr in Roundup, MT are Roundup 7-8 (Middle, rated 3/10), Roundup Elementary (Pre-K, rated 7/10), Roundup High School (rated 2/10).

Apartments for Rent

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Off Market Homes Near 121 Winchester Dr

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Homes for sale near 121 Winchester Dr

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NEW CONSTRUCTION
20 ACRES
$287,900
3 bd
2 ba
2,236 sqft
86 Winchester Mount Remington Trl,
Roundup, MT 59072
Kenneth Minnie, Big M Realty LLC
41.9 ACRES
$750,000
3 bd
2.5 ba
2,254 sqft
25 Denali Cabin Ln,
Roundup, MT 59072
Maggie Hansen, Meridian Real Estate LLC
5 ACRES
$496,500
2 bd
2 ba
1,600 sqft
213 Winchester Dr,
Roundup, MT 59072
Katie Klaus, Meridian Real Estate LLC
0.8 ACRES
$159,900
4 bd
2 ba
2,445 sqft
511 3rd St E,
Roundup, MT 59072
Troy Boucher, Boucher & Associates
$259,900
4 bd
2 ba
2,016 sqft
623 3rd St E,
Roundup, MT 59072
Kenneth Minnie, Big M Realty LLC
$134,900
3 bd
0.5 ba
1,977 sqft
303 1st St E #5-6,
Roundup, MT 59072
Lorie Trump, Landmark of Billings, Inc.
$395,000
3 bd
2.5 ba
1,968 sqft
1112 3rd St E,
Roundup, MT 59072
Marie Barth, Kelly Right Real Estate
0.32 ACRES
$235,000
3 bd
2 ba
2,351 sqft
420 3rd St W,
Roundup, MT 59072
Marie Barth, Kelly Right Real Estate
0.32 ACRES
$280,000
4 bd
2 ba
1,848 sqft
316 11th Ave E,
Roundup, MT 59072
Stetson Zumbrun, Berkshire Hathaway HS Floberg
$439,900
5 bd
3.5 ba
3,729 sqft
501 1st St W,
Roundup, MT 59072
Patrick Riley, LP Bar Realty
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