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Newest Homes for Sale in Upper West Side

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  • /53

    $1,150,000

    • 4 Beds
    • 2.5 Baths
    • 3,991 Sq Ft

    804 Gilbert St, Helena, MT 59601

    Welcome to 804 Gilbert Street, a beautifully cared-for Victorian-style home in Helena’s sought-after Mansion District. Full of character and charm, this 3-bedroom, 2 1/2-bath home offers a great layout with many thoughtful updates while preserving the details that make a historic home special. Beautiful hardwood floors are featured throughout much of the home, complemented by tile in select

    Wayne Woodland Big Sky Brokers, LLC

    804 Gilbert St, Helena, MT 59601
  • /65

    $585,000

    $25K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,372 Sq Ft

    520 Madison Ave, Helena, MT 59601

    520 Madison Avenue, a well-loved home nestled in one of Helena’s cherished historic neighborhoods. Set along a beautiful tree-lined street, this home offers the character and charm Helena is known for, with downtown just minutes away. Enjoy convenient access to local shopping, restaurants, theaters, parks, and the sought-after Mount Helena trail system for hiking and mountain biking.The

    Jennifer Swartz RE/MAX Of Helena

    520 Madison Ave, Helena, MT 59601
  • /79

    $965,000

    • 7 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    Unlisted Address

    This stunning Upper West Side residence boasts a million-dollar kitchen all on its own. Extensively remodeled in 2014 with a laser-focus on cooking, hosting, and entertaining, this home truly has it all. Industry-leading Viking appliances throughout, including three ovens, a gas cooktop grille, and a warming drawer, making Thanksgiving dinner effortless. A strategically positioned main sink, two

    Anita Sherley Sherley Real Estate, LLC

    Unlisted Address
  • /35

    $289,900

    • 2 Beds
    • 1 Bath
    • 853 Sq Ft

    2872 Overlook Blvd, Helena, MT 59601

    Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

    Julie Lamb-Heller Century 21 Heritage Realty - Helena

    2872 Overlook Blvd, Helena, MT 59601
  • /34

    $289,900

    New Construction
    • 2 Beds
    • 1 Bath
    • 853 Sq Ft

    2870 Overlook Blvd, Helena, MT 59601

    Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

    Julie Lamb-Heller Century 21 Heritage Realty - Helena

    2870 Overlook Blvd, Helena, MT 59601
  • /19

    $289,900

    New Construction
    • 2 Beds
    • 1 Bath
    • 853 Sq Ft

    2874 Overlook Blvd, Helena, MT 59601

    Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

    Julie Lamb-Heller Century 21 Heritage Realty - Helena

    2874 Overlook Blvd, Helena, MT 59601
  • /29

    $1,650,000

    • Land
    • 4.4 Acres
    • $375,000 per Acre

    000 Reber Rd, Helena, MT 59601

    Rare Westside Offering — Benchmark PUD – Prime Upper Westridge Heights Development OpportunityThis pre-platted 4.4-acre tract in Phase II of the Benchmark PUD Subdivision represents the final remaining parcel in Helena’s highly sought-after Westridge Heights. As the last available development site in this established Upper Westside neighborhood, it offers a rare opportunity for builders,

    David Lemm Lemm Real Estate, LLC

    000 Reber Rd, Helena, MT 59601
  • /10

    $350,000

    • Land
    • 14,244 Sq Ft
    • $1,070,336 per Acre

    2095 Reber Rd Unit 1311, Helena, MT 59601

    Perched at the base of Mount Helena with sweeping views across the Helena Valley, this exceptional homesite offers a rare opportunity to build in one of Helena’s most remarkable settings. As the last remaining lot in Westridge Heights, the property captures million-dollar views stretching north across the valley to the iconic Sleeping Giant. The sloping terrain is ideally suited for a walkout

    Julie Lamb-Heller Century 21 Heritage Realty - Helena

    2095 Reber Rd Unit 1311, Helena, MT 59601
  • /35

    $430,000

    Open Sun 11AM - 1PM $9K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,768 Sq Ft

    2335 Cannon St, Helena, MT 59601

    Charming 1948 rancher on a spacious 0.379-acre lot, just steps from Kessler School and within walking distance of Spring Meadow Lake's trails. This 4 bedroom, 2 full bath home offers 1,768 sq ft of living space, with 2 bedrooms and a full bath on the main level plus 2 true egress bedrooms, a second living room, and a bonus non-conforming room on the finished lower level — ideal for guests, a

    Agent Photo

    Riley Kurtz

    Big Sky Brokers, LLC

    2335 Cannon St, Helena, MT 59601
  • /28

    $499,900

    $10K PRICE DROP

    1232 Hauser Blvd, Helena, MT 59601

    Investment Opportunity! Well-maintained duplex offering immediate rental income with both units currently occupied. Each unit features 2 bedrooms, 1 bathroom, functional layouts, and comfortable living spaces that appeal to long-term tenants. Pride of ownership is evident throughout, with consistent maintenance and care over the years.Owner currently provides lawn maintenance, helping

    Cortney Senecal Keller Williams Capital Realty

    1232 Hauser Blvd, Helena, MT 59601
  • /26

    $675,000

    • 3,500 Sq Ft

    407 Madison Ave, Helena, MT 59601

    Investment opportunity with many possibilities! Own a piece of Helena history while generating steady rental income. Located in the sought-after Mansion District, this classic Victorian has been converted into a fourplex, offering flexibility for both investors and owner-occupants. Rent all four units for maximum income, or easily combine two of the units to create a spacious owner's residence

    Jeff Barber Keller Williams Capital Realty

    407 Madison Ave, Helena, MT 59601
  • /81

    $974,500

    • 6 Beds
    • 3.5 Baths
    • 4,311 Sq Ft

    2531 Knight St, Helena, MT 59601

    Welcome to this beautifully maintained custom home where quality craftsmanship, thoughtful upgrades, and exceptional indoor-outdoor living come together. The remodeled main level (2021) features a bright, open floor plan with vaulted ceilings, abundant natural light, and a spacious living room that flows seamlessly into the dining area and beautifully updated kitchen. The kitchen showcases custom

    Agent Photo

    Tana Bignell

    Uncommon Ground, LLC

    2531 Knight St, Helena, MT 59601
  • /36

    $594,900

    • 3 Beds
    • 2 Baths
    • 2,754 Sq Ft

    2650 Knight St, Helena, MT 59601

    Welcome to 2650 Knight Street, a thoughtfully designed home that blends comfort, efficiency, and access to some of Helena’s best outdoor amenities and all close to a new school coming soon too!Plus, enjoy $1,000 in credits towards closing or flooring right now!This Green Built property showcases energy efficient materials and construction, offering long term savings and a more

    Amber Conger Engel & Völkers Western Frontier - Helena

    2650 Knight St, Helena, MT 59601
  • /39

    $430,000

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    2565 Overlook Blvd, Helena, MT 59601

    Welcome home to 2565 Overlook Blvd, on Helena's westside. You'll find this 3bedroom 2.5 bathroom is super-convenient to Fort Harrison, Highway 12 West, the soon-to-be (rebuilt) Kessler School, and near Mount Helena too. On the main floor, you'll find slate influences throughout, an inviting fireplace and maintenance-free flooring within the living room, nice upgraded black granite countertops

    Ryan Stavnes EXIT Realty of Helena

    2565 Overlook Blvd, Helena, MT 59601
  • /22

    $945,000

    $30K PRICE DROP

    1709 Euclid Ave, Helena, MT 59601

    Price adjusted and rent increases coming October, projected to provide a 6.39% cap rate, with additional upside potential through further rent increases, as market conditions allow! Completed in 2019, this newer construction fourplex presents a rare opportunity to acquire a low maintenance multifamily asset with immediate income and future upside potential. Designed with tenant retention and

    Bryanna Deschamps Millennium Real Estate & Management

    1709 Euclid Ave, Helena, MT 59601
  • /93

    $995,000

    $205K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 4,388 Sq Ft

    724 Monroe Ave, Helena, MT 59601

    Located in Helena's Upper Westside's Mansion District, this remarkable 1912 residence offers a rare opportunity to become the owner of one of the city's most treasured historic homes. Available for the first time in nearly 60 years, this is a home that has been deeply loved, thoughtfully updated, and carefully preserved through generations. Designed by Robert Chambers Reamer, the renowned

    Mary Ahmann Hibbard Helena Home Team

    724 Monroe Ave, Helena, MT 59601
  • /101

    $710,000

    $15K PRICE DROP
    • 6 Beds
    • 2.5 Baths
    • 2,505 Sq Ft

    2200 Cannon St, Helena, MT 59601

    A rare opportunity to own a true piece of Helena history, Appleton House #13—built in 1890 and proudly listed on the National Register of Historic Places. Situated on an expansive six city lots—nearly half an acre—this remarkable property offers a park-like setting in the heart of Helena. The outdoor space is nothing short of spectacular, featuring full fencing, underground sprinklers and drip

    Freyja Bell Uncommon Ground, LLC

    2200 Cannon St, Helena, MT 59601
  • /43

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 3,830 Sq Ft

    860 Hiawatha St, Helena, MT 59601

    NEW! $25,000 in seller concessions! What are concessions? Buyer choose to use funds toward remodel, closing costs/ prepaids or buy down rates! Home of JC Paulsen renowned architect of many Montana historical properties , including the original and stunning Montana Club, is on the market! Built in the 1800s, the stone facade and covered porches and balconies recall a bygone era. Irreplaceable

    Lane Nygren Augustine Properties

    860 Hiawatha St, Helena, MT 59601
  • /67

    $775,000

    $24K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 4,249 Sq Ft

    2028 Flowerree St, Helena, MT 59601

    Welcome home—where location and ambiance meet in perfect harmony. This stunning 4,249 sqft., 5-bdrm, 3-bath custom-built home showcases quality finishes and timeless design throughout. An impressive entry welcomes you with classic white columns, a formal sitting area, and beautiful tile flooring that sets the tone for the elegance within. From the foyer, step into the open-concept living room

    Joshua Koffler Coldwell Banker Mountainside Realty

    2028 Flowerree St, Helena, MT 59601
  • /49

    $725,000

    $70K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,976 Sq Ft

    33 Carriage Ln, Helena, MT 59601

    Stand-alone condo in a prime location at the base of Mount Helena! This spacious home features main-level living plus a full walk-out basement. The proximity to Mount Helena City Park provides abundant views and direct access to many miles of public trail systems. Enjoy the wonderful outdoor spaces providing views from the deck or shade from the covered patio. The perfect spot to live your best

    Mark Stahly Big Sky Brokers, LLC

    33 Carriage Ln, Helena, MT 59601
  • /101

    $515,000

    $120K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    1701 Cannon St, Helena, MT 59601

    A beautifully preserved 1885 brick Victorian in Helena’s coveted Upper West neighborhood, just six blocks from the Tubbs Trailhead on Mount Helena. Over the past two years, this home has been carefully transformed with a soft white palette that highlights its original, intricate woodwork and fireplaces. Notable features include fresh paint, refinished and replica hardwood floors, a spacious

    Freda Wilkinson Big Sky Brokers, LLC

    1701 Cannon St, Helena, MT 59601
  • /21

    $2,554,950

    New Construction $200K PRICE INCREASE
    • 3 Beds
    • 4 Baths
    • 3,623 Sq Ft

    442 S Park Ave, Helena, MT 59601

    Nestled at the base of the iconic Mount Helena trail system, this luxury residential townhouse is located in an area that can never be duplicated. In the heart of Helena, the locale prides itself on historic homes, world class hiking/biking, restaurants, retail shops, galleries, museums, and breweries. Enjoy all the amenities of Helena, along with nearly 80 miles of trails and wilderness out the

    Didi Peccia Augustine Properties

    442 S Park Ave, Helena, MT 59601
  • /52

    $997,000

    $22K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,686 Sq Ft

    316 S Park Ave, Helena, MT 59601

    Reflecting the real historical beginnings of Helena, the Adami Barn surely has stories to tell! Listen... can you hear them? One of a kind property nestled next to Helena's historic Reeder's Alley. One of Helena's earliest standing structures, this remarkable stone building was crafted in the 1870's from locally quarried stone, originally built as the Adami Barn. According to historical data, the

    Cindy Stevick Cindy Stevick Real Estate

    316 S Park Ave, Helena, MT 59601

Upper West Side, Helena, MT Home Prices vs. Nearby Neighborhoods

Upper West Side Upper East Side South Central North West
Median Home Price
$519,900
$479,000
$449,900
$449,700
Median Sale Price
$470,000
-6% YoY
$452,000
-4% YoY
$423,200
+6% YoY
$430,000
-1% YoY
Avg. Price per Square Foot
$251
$235
$251
$225
Median Single Family Price
$521,000
$510,000
$441,000
$438,950
Median Townhouse Price
$666,625
$370,000
$595,000
--
Median Condo Price
$289,900
$355,000
$389,500
$347,500
Total Active Listings
23 listings
20 listings
30 listings
2 listings
Market Conditions
4 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
1 Month of Supply
Seller's Market

Frequently Asked Questions

Is Upper West Side a good place to live?
Upper West Side is a good place to live. Upper West Side is considered car-dependent and very bikeable. Upper West Side has 2 parks for recreational activities.It is fairly sparse in population with 5.0 people per acre and a median age of 43. The average household income is $127,498 which is above the national average. College graduates make up 59% of residents. A majority of residents in Upper West Side are home owners, with 38% of residents renting and 62% of residents owning their home. A local real estate agent serving Upper West Side can help you decide if this neighborhood is the right one for you. Learn more on our Upper West Side neighborhood guide.
How much do you need to make to afford a house in Upper West Side?
The median home price in Upper West Side is $519,900. If you put a 20% down payment of $104,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $2,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $118K a year to afford the median home price in Upper West Side. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Upper West Side is $127K.
What are the best public schools in Upper West Side?
The best public schools that serve Upper West Side are:
  • C.R. Anderson Middle School has a B+ Niche grade, a student teacher ratio of 16:1 and an average review score of 5.0.
  • Capital High School has a B Niche grade, a student teacher ratio of 16:1 and an average review score of 3.7.
  • Helena High School has a B Niche grade, a student teacher ratio of 16:1 and an average review score of 3.6.
What are the best private schools in Upper West Side?
The best private schools that serve Upper West Side are:
  • St Andrew School has a B Niche grade, a student teacher ratio of 14:1 and an average review score of 4.0.
What are the most popular zip codes in Upper West Side, Helena, MT?
The most popular zip codes in Upper West Side, Helena, MT include 59601, 59602, 59634, 59635 and 59731.
What are the most popular neighborhoods near Upper West Side, Helena, MT?
The most popular neighborhoods near Upper West Side, Helena, MT are Lower West Side, South Central, North West, North Central and North East.
Are home prices dropping in Upper West Side?
Yes, home prices in Upper West Side are down 4% in the last 12 months.
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