Olde Town Issaquah homes for sale
Find Olde Town Issaquah homes — the Eastside's most authentic historic downtown neighborhood.
RexMont helps buyers search Olde Town Issaquah craftsmen, bungalows, and mid-century homes — with guidance on Front Street walkability, Village Theatre access, Gilman Park proximity, Issaquah School District, and $800K–$2.2M+ opportunities where the character, history, and small-town feel of the Eastside's most distinctive neighborhood are irreplaceable.
Page author
Adriano Tori
Designated Broker, Founder & CEO — RexMont Real Estate · WA Lic. #21220
Adriano leads RexMont Real Estate — the most-reviewed real estate brokerage in Seattle and the Eastside. 1,200+ closed transactions, $1B+ in production, and 1,238 five-star Google reviews.
Market context
Olde Town is the only neighborhood on the Eastside where a century of real history shows in every block.
Every other neighborhood on the Eastside was built to a plan. Olde Town Issaquah wasn't — it grew organically from a coal mining and logging town through the twentieth century into the city it is today, and that history is legible in the streetscapes, the craftsman architecture, the creek that still runs through the center of it, and the performing arts theater that has been a cultural anchor for decades. You cannot replicate that character by developing a hillside master plan. Buyers who want authentic neighborhood identity rather than HOA-curated uniformity have exactly one choice in the Issaquah market.
The walkability is structural, not incidental. Front Street's independent restaurant row, the Village Theatre, Gilman Park, and the Issaquah Creek trail system all exist because they were built when Issaquah was a walkable small town — and they survived because the community protected them. Most Eastside suburbs demolished their historic cores in the 1970s and 1980s and replaced them with strip malls. Issaquah didn't. That protection is now a genuine real estate asset.
RexMont helps Olde Town buyers evaluate the specific housing stock — craftsmen and bungalows that require different inspection criteria than standard suburban construction, mid-century homes with renovation potential, and the occasional larger home on a lot where the school district and walkability story is as strong as anything on the Plateau at a significant price discount.
Coverage
Service area at a glance
RexMont represents buyers and sellers across these Seattle and Eastside markets. Click any city for the full local guide.
Bellevue, WA
ZIPs: 98004 · 98005 · 98006 · 98007 · 98008
Schools: Bellevue SD
Medina, WA
ZIP: 98039
Schools: Bellevue SD
Clyde Hill, WA
ZIP: 98004
Schools: Bellevue SD
Mercer Island, WA
ZIP: 98040
Schools: Mercer Island SD
Kirkland, WA
ZIPs: 98033 · 98034
Schools: Lake Washington SD
Redmond, WA
ZIPs: 98052 · 98053
Schools: Lake Washington SD
Sammamish, WA
ZIPs: 98074 · 98075
Schools: Lake Washington / Issaquah SD
Issaquah, WA
ZIPs: 98027 · 98029
Schools: Issaquah SD
Newcastle, WA
ZIPs: 98056 · 98059
Schools: Renton SD
Woodinville, WA
ZIPs: 98072 · 98077
Schools: Northshore SD
Kenmore, WA
ZIP: 98028
Schools: Northshore SD
Seattle, WA
ZIPs: 98101 · 98109 · 98112 · 98115 · 98118
Schools: Seattle Public Schools
For Olde Town buyers
Evaluate craftsman and bungalow-era housing, walkability by block, Issaquah SD school assignments, and how Olde Town's value compares to Issaquah Highlands for buyers who care about neighborhood character over master-plan amenities.
Start Olde Town searchFor Olde Town sellers
Market your home to buyers who have specifically chosen Olde Town's authentic character over the uniformity of master-planned alternatives — a buyer pool willing to pay a premium for what Olde Town uniquely offers.
Request a home valueLive NWMLS data
Active homes for sale in the 98027 area (Olde Town Issaquah)
Live NWMLS listings in the 98027 ZIP that includes Olde Town Issaquah, refreshed hourly.
- Median price
- $1.1M
- Median $/sqft
- $505
- Avg days on market
- 33
- Listings for sale
- 134+
ActiveNew today$1,187,000
MLS# 257007326415 Se 154th Place
Issaquah, WA 98027
4 bd3.25 ba2,750 sqftListing courtesy of RE/MAX Northwest
ActiveNew today$599,000
MLS# 256633814410 Issaquah Hobart Road Se
Issaquah, WA 98027
3 bd1.75 ba1,350 sqftListing courtesy of Coldwell Banker Bain
Active1 day on market$865,000
MLS# 25670871946 Newport Way Nw #16
Issaquah, WA 98027
2 bd1.75 baListing courtesy of John L. Scott, Inc.
Active3 days on market$1,165,000
MLS# 25674581109 Lewis Lane Se
Issaquah, WA 98027
4 bd2.75 ba1,993 sqftListing courtesy of Windermere Real Estate/East
Active3 days on market$920,000
MLS# 25679111934 Riva Lane Nw #27
Issaquah, WA 98027
2 bd2.75 baListing courtesy of John L. Scott, Inc.
Active4 days on market$1,558,980
MLS# 256824625007 Se Mirrormont Way
Issaquah, WA 98027
5 bd4 ba4,000 sqftListing courtesy of RE/MAX Northwest
Active5 days on market$473,100
MLS# 2567520206 Mountain Park Boulevard Sw #d203
Issaquah, WA 98027
3 bd2 baListing courtesy of Windermere Real Estate/East
Active3 days on market$997,500
MLS# 256734916530 237th Avenue Se
Issaquah, WA 98027
3 bd1.75 ba2,380 sqftListing courtesy of COMPASS
Active7 days on market$1,250,000
MLS# 2557007700 6th Avenue Nw
Issaquah, WA 98027
4 bd2.5 ba2,551 sqftListing courtesy of Realogics Sotheby's Int'l Rlty
Active5 days on market$1,000,000
MLS# 256610615650 Issaquah Hobart Road Se
Issaquah, WA 98027
4 bd2 ba2,000 sqftListing courtesy of Windermere Real Estate/East
Active5 days on market$1,599,950
MLS# 256072918811 Se 44th Way
Issaquah, WA 98027
4 bd2.25 ba2,210 sqftListing courtesy of Redfin
Active10 days on market$634,900
MLS# 25648792157 Nw Talus Drive
Issaquah, WA 98027
2 bd1.75 ba1,120 sqftListing courtesy of Engel & Volkers Snoqualmie Vly
Active3 days on market$2,275,000
MLS# 256489024926 Se 162 Street
Issaquah, WA 98027
5 bd4.25 ba3,860 sqftListing courtesy of Windermere Bellevue Commons
Active4 days on market$1,600,000
MLS# 256476826233 Se 162nd Place
Issaquah, WA 98027
5 bd2.75 ba2,991 sqftListing courtesy of COMPASS
Active5 days on market$1,175,000
MLS# 256481726340 Se 158 Street
Issaquah, WA 98027
3 bd2.25 ba2,580 sqftListing courtesy of Windermere Real Estate/East
Active5 days on market$2,275,000
MLS# 256520324926 Se 162nd Street
Issaquah, WA 98027
5 bd4.25 ba3,860 sqftListing courtesy of Windermere Bellevue Commons
Active10 days on market$360,000
MLS# 2562871700 Front St. S #e110
Issaquah, WA 98027
2 bd2 baListing courtesy of Windermere Real Estate/East
Active5 days on market$1,239,990
MLS# 2566473968 7th Ave Nw (homesite #5)
Issaquah, WA 98027
2 bd2.25 ba1,654 sqftListing courtesy of Windermere Real Estate/East
Active5 days on market$1,239,990
MLS# 2564385968 7th Ave Nw (homesite #5)
Issaquah, WA 98027
2 bd2.25 baListing courtesy of Windermere Real Estate/East
Active6 days on market$225,000
MLS# 25631550 123xxx 202nd Place Se
Issaquah, WA 98027
0 bd0 baListing courtesy of Best Choice Realty LLC
Active12 days on market$2,950,000
MLS# 256219224282 Se 147th Place
Issaquah, WA 98027
4 bd5.25 ba4,760 sqftListing courtesy of Best Choice Realty LLC
Active12 days on market$149,500
MLS# 25634240 252nd Avenue Se
Issaquah, WA 98027
0 bd0 baListing courtesy of HomeSmart Real Estate Assoc
Active15 days on market$639,000
MLS# 255700693 Sky Ridge Road Nw #505
Issaquah, WA 98027
2 bd1.75 baListing courtesy of Realogics Sotheby's Int'l Rlty
Active4 days on market$899,999
MLS# 25615411078 Cabin Creek Lane Sw
Issaquah, WA 98027
3 bd2.5 baListing courtesy of John L. Scott, Inc.
- Active4 days on market
$899,999
MLS# 25665281078 Cabin Creek Lane Sw
Issaquah, WA 98027
3 bd2.5 ba1,885 sqftListing courtesy of John L. Scott, Inc.
- Active5 days on market
$1,249,950
MLS# 2560396845 3rd Avenue Nw
Issaquah, WA 98027
3 bd1.75 ba1,720 sqftListing courtesy of Windermere R.E. Mill Creek
- Active5 days on market
$689,000
MLS# 2561831162 Cougar Ridge Road Nw #1104
Issaquah, WA 98027
2 bd2.5 baListing courtesy of eXp Realty
- Active3 days on market
$1,650,000
MLS# 25616892210 Nw Harmony Way
Issaquah, WA 98027
4 bd3.25 ba2,818 sqftListing courtesy of COMPASS
- Active3 days on market
$599,000
MLS# 256160814509 Cedar Grove Road Se #e201
Issaquah, WA 98027
2 bd1.75 baListing courtesy of Windermere Real Estate/M2, LLC
- Active5 days on market
$1,299,950
MLS# 256237317432 Issaquah Hobart Road Se
Issaquah, WA 98027
4 bd2.5 ba2,864 sqftListing courtesy of John L. Scott, Inc.
- Active5 days on market
$1,299,950
MLS# 256576017432 Issaquah Hobart Road Se
Issaquah, WA 98027
4 bd2.5 ba2,864 sqftListing courtesy of John L. Scott, Inc.
- Active10 days on market
$399,900
MLS# 25605034641 W Lake Sammamish Parkway Se #f305
Issaquah, WA 98027
2 bd1.75 baListing courtesy of Coldwell Banker Bain
- Active11 days on market
$995,000
MLS# 2561411450 Mount Defiance Circle Sw
Issaquah, WA 98027
3 bd1.75 ba1,040 sqftListing courtesy of Windermere Real Estate/M2, LLC
- Active14 days on market
$250,000
MLS# 2560158230 Sw Clark Street #c-104
Issaquah, WA 98027
1 bd1 baListing courtesy of Real Broker LLC
- Active3 days on market
$1,525,000
MLS# 25611641520 Sycamore Drive Se
Issaquah, WA 98027
4 bd2.75 ba2,980 sqftListing courtesy of KW Greater Seattle
- Active3 days on market
$384,950
MLS# 2543423700 Front Street S #a108
Issaquah, WA 98027
2 bd2 baListing courtesy of Windermere R E Mount Baker
- Active17 days on market
$1,495,000
MLS# 255916314808 260th Avenue Se
Issaquah, WA 98027
3 bd2.75 ba3,620 sqftListing courtesy of Coldwell Banker Bain
- Active3 days on market
$899,999
MLS# 255921428102 Se 63rd Street
Issaquah, WA 98027
3 bd1.5 ba1,650 sqftListing courtesy of Windermere Real Estate Central
- Active4 days on market
$1,150,000
MLS# 255838971 Sunset Court Nw
Issaquah, WA 98027
3 bd2.75 ba1,730 sqftListing courtesy of COMPASS
- Active4 days on market
$3,500,000
MLS# 25591174814 194th Avenue Se
Issaquah, WA 98027
4 bd4 ba4,070 sqftListing courtesy of Windermere Real Estate/East
- Active25 days on market
$2,495,000
MLS# 2558544510 Viewcrest Drive Nw
Issaquah, WA 98027
6 bd4.75 ba4,300 sqftListing courtesy of Skyline Properties, Inc.
- Active1 day on market
$1,398,800
MLS# 255643016430 266th Avenue Se
Issaquah, WA 98027
4 bd3 ba3,580 sqftListing courtesy of Bentley Properties
- Active3 days on market
$1,235,000
MLS# 2556458525 Mount Everest Lane Sw
Issaquah, WA 98027
4 bd2.5 ba2,140 sqftListing courtesy of Coldwell Banker Bain
- Active21 days on market
$165,000
MLS# 255600724829 Se Mirrormont Boulevard
Issaquah, WA 98027
0 bd0 baListing courtesy of Windermere Real Estate/East
- Active4 days on market
$489,000
MLS# 2553616700 Front Street S #b206
Issaquah, WA 98027
2 bd1.5 baListing courtesy of Coldwell Banker Bain
- Active7 days on market
$499,950
MLS# 2553740601 12th Avenue Nw #e1
Issaquah, WA 98027
2 bd2.25 baListing courtesy of Black Knight Real Estate LLC
- Active10 days on market
$1,089,950
MLS# 2554937756 Nw Holly Street
Issaquah, WA 98027
4 bd4 ba2,025 sqftListing courtesy of Teambuilder KW
- Active10 days on market
$1,499,950
MLS# 2554930795 7th Avenue Nw
Issaquah, WA 98027
4 bd3.25 ba1,949 sqftListing courtesy of Teambuilder KW
Active10 days on market$899,999
MLS# 2554916749 7th Avenue Nw
Issaquah, WA 98027
3 bd2.75 ba1,566 sqftListing courtesy of Teambuilder KW
Active10 days on market$1,249,950
MLS# 2554123781 7th Avenue Nw
Issaquah, WA 98027
5 bd4 ba2,112 sqftListing courtesy of Teambuilder KW
Active11 days on market$1,400,000
MLS# 25540294560 186th Avenue Se
Issaquah, WA 98027
3 bd2 ba1,950 sqftListing courtesy of Emerald Sound Realty
Active32 days on market$274,950
MLS# 2555770273 Xx Se 164th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of Kronos Real Estate
Active1 day on market$620,000
MLS# 25374742145 Nw Pacific Elm Drive #2145
Issaquah, WA 98027
2 bd2.25 baListing courtesy of Kohtoku Enterprise Inc.
Active25 days on market$799,000
MLS# 25522575 Xxx 229th Avenue Se
Issaquah, WA 98027
0 bd0 baListing courtesy of RE/MAX Elite
Active4 days on market$1,485,000
MLS# 255219324017 Se 111th Street
Issaquah, WA 98027
4 bd2.5 ba2,860 sqftListing courtesy of The Cascade Team
Active2 days on market$1,450,000
MLS# 25469045931 290th Avenue Se
Issaquah, WA 98027
3 bd2.25 ba2,690 sqftListing courtesy of Windermere Real Estate Co.
Active21 days on market$1,199,999
MLS# 255215760 2nd Avenue Ne
Issaquah, WA 98027
2 bd1 ba730 sqftListing courtesy of COMPASS
Active34 days on market$699,950
MLS# 2552525420 Se Sycamore Lane
Issaquah, WA 98027
0 bd0 baListing courtesy of COMPASS
Active21 days on market$445,000
MLS# 2547235202 Mountain Park Boulevard #b303
Issaquah, WA 98027
3 bd2 baListing courtesy of Pure Real Estate
Active7 days on market$1,699,000
MLS# 254897715118 262nd Avenue Se
Issaquah, WA 98027
4 bd4.25 ba4,250 sqftListing courtesy of Windermere Real Estate/East
Active23 days on market$1,500,000
MLS# 254937010911 Renton Issaquah Road Se
Issaquah, WA 98027
3 bd1.75 ba1,870 sqftListing courtesy of Jina J Real Estate
Active40 days on market$1,425,000
MLS# 2550886975 Front Street S
Issaquah, WA 98027
3 bd1.75 ba1,600 sqftListing courtesy of Windermere Real Estate/East
Active40 days on market$1,425,000
MLS# 2551552975 Front Street S
Issaquah, WA 98027
0 bd0 baListing courtesy of Windermere Real Estate/East
Active18 days on market$920,000
MLS# 254661816035 266th Avenue Se
Issaquah, WA 98027
3 bd2.5 ba2,750 sqftListing courtesy of eXp Realty
Active25 days on market$520,000
MLS# 25470572174 Newport Way Nw #4-6
Issaquah, WA 98027
2 bd2 baListing courtesy of Coldwell Banker Bain
ActiveNew today$450,000
MLS# 254583718505 Se Newport Way #f131
Issaquah, WA 98027
2 bd2.5 baListing courtesy of Keller Williams Rlty Bellevue
Active16 days on market$579,500
MLS# 254635818707 Se Newport Way #303
Issaquah, WA 98027
2 bd1.75 baListing courtesy of Kelly Right RE of Seattle LLC
Active3 days on market$1,199,000
MLS# 254241815826 266th Avenue Se
Issaquah, WA 98027
3 bd2.5 ba2,750 sqftListing courtesy of RE/MAX Integrity
Active6 days on market$475,000
MLS# 2544016204 Mountain Park Boulevard Sw #c302
Issaquah, WA 98027
3 bd1.75 baListing courtesy of Windermere Real Estate/Summit
Active26 days on market$369,950
MLS# 254493818501 Se Newport Way #m352
Issaquah, WA 98027
2 bd2 baListing courtesy of Skyline Properties, Inc.
Active5 days on market$535,000
MLS# 254407512932 231st Avenue Se
Issaquah, WA 98027
4 bd2.5 ba2,030 sqftListing courtesy of Real Broker LLC
Active2 days on market$1,250,000
MLS# 254325913020 Squak Mountain Road Se
Issaquah, WA 98027
3 bd1.75 ba2,060 sqftListing courtesy of Cook Real Estate
Active7 days on market$2,200,000
MLS# 2537095885 Front Street S
Issaquah, WA 98027
0 bd0 baListing courtesy of COMPASS
Active6 days on market$920,000
MLS# 254357624404 Se Mirrormont Boulevard
Issaquah, WA 98027
3 bd2.25 ba2,400 sqftListing courtesy of eXp Realty
Active3 days on market$1,250,000
MLS# 253712819035 Se 56th Street
Issaquah, WA 98027
4 bd2.75 ba2,420 sqftListing courtesy of Berkshire Hathaway HS NW
Active17 days on market$175,000
MLS# 25425199512 315 Avenue Se #13
Issaquah, WA 98027
2 bd0.75 baListing courtesy of John L. Scott, Inc.
Active12 days on market$850,000
MLS# 2537316275 E Sunset Way #1a
Issaquah, WA 98027
3 bd2 baListing courtesy of Coldwell Banker Bain
Active18 days on market$1,550,000
MLS# 2542832315 Se Andrews Street
Issaquah, WA 98027
5 bd2.75 ba2,207 sqftListing courtesy of Windermere RE Greenwood
Active59 days on market$510,000
MLS# 2538040515 Newport Way Nw #b3
Issaquah, WA 98027
2 bd2.25 baListing courtesy of Windermere Real Estate/East
Active4 days on market$949,950
MLS# 254006826910 Se 154th Place
Issaquah, WA 98027
3 bd2 ba1,660 sqftListing courtesy of Windermere Real Estate/East
Active4 days on market$1,850,000
MLS# 25392354414 184th Avenue Ne
Issaquah, WA 98027
3 bd2 ba3,060 sqftListing courtesy of John L. Scott, Inc.
Active61 days on market$3,700,000
MLS# 254112521099 Se 80th Street
Issaquah, WA 98027
4 bd3.5 ba4,649 sqftListing courtesy of John L. Scott HWP
Active4 days on market$1,345,000
MLS# 25321862815 Nw Pine Cone Drive
Issaquah, WA 98027
4 bd2.5 ba2,940 sqftListing courtesy of Coldwell Banker Bain
Active25 days on market$189,500
MLS# 2538210273 Xx Se 150th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of KW Mountains to Sound Realty
Active19 days on market$1,000,000
MLS# 253617523618 Se Tiger Mountain Road
Issaquah, WA 98027
3 bd4.25 ba4,027 sqftListing courtesy of Keller Williams Realty Bothell
ActiveNew today$1,300,000
MLS# 2503075529 Se Bush Street #b
Issaquah, WA 98027
4 bd3 baListing courtesy of Windermere RE West Campus Inc
ActiveNew today$1,300,000
MLS# 2539831529 Se Bush Street #b
Issaquah, WA 98027
4 bd3 ba2,198 sqftListing courtesy of Windermere RE West Campus Inc
Active6 days on market$640,000
MLS# 25324242107 Nw Moraine Place
Issaquah, WA 98027
2 bd2.5 ba1,150 sqftListing courtesy of Redfin
Active11 days on market$1,399,900
MLS# 2535639537 Nw Juniper Street
Issaquah, WA 98027
3 bd3.5 ba2,076 sqftListing courtesy of Weichert, Realtors-Pillar NW
Active11 days on market$1,379,900
MLS# 2535640539 Nw Juniper Street
Issaquah, WA 98027
3 bd3.5 ba2,076 sqftListing courtesy of Weichert, Realtors-Pillar NW
Active11 days on market$1,900,000
MLS# 2535426773 Summerhill Ridge Drive Nw
Issaquah, WA 98027
4 bd4 ba4,670 sqftListing courtesy of COMPASS
Active47 days on market$5,690,000
MLS# 25321785454 194th Avenue Se
Issaquah, WA 98027
4 bd4.75 ba7,057 sqftListing courtesy of Windermere Real Estate/East
Active5 days on market$1,395,000
MLS# 2533801600 Wildwood Boulevard Sw
Issaquah, WA 98027
3 bd1.5 ba2,280 sqftListing courtesy of Keller Williams Rlty Bellevue
Active2 days on market$1,925,000
MLS# 252964412065 206th Place Se
Issaquah, WA 98027
4 bd2.75 ba2,840 sqftListing courtesy of eXp Realty
Active5 days on market$1,429,990
MLS# 2532852962 7th Ave Nw (homesite #4)
Issaquah, WA 98027
3 bd3.25 baListing courtesy of Windermere Real Estate/East
Active5 days on market$1,429,990
MLS# 2533747962 7th Ave Nw (homesite #4)
Issaquah, WA 98027
3 bd3.25 ba2,158 sqftListing courtesy of Windermere Real Estate/East
Active10 days on market$954,950
MLS# 2529859767 7th Avenue Nw
Issaquah, WA 98027
3 bd2.75 ba1,566 sqftListing courtesy of Teambuilder KW
Active24 days on market$1,149,950
MLS# 2532238250 Se Andrews Street
Issaquah, WA 98027
4 bd1.75 ba1,450 sqftListing courtesy of Realogics Sotheby's Int'l Rlty
Active79 days on market$798,500
MLS# 253238116345 Tiger Mountain Road Se
Issaquah, WA 98027
0 bd0 baListing courtesy of John L. Scott, Inc
Active27 days on market$2,495,000
MLS# 253168812019 Issaquah-hobart Road Se
Issaquah, WA 98027
4 bd2.25 ba3,410 sqftListing courtesy of KW Mountains to Sound Realty
Active30 days on market$2,199,000
MLS# 253081521013 Se 80th Street
Issaquah, WA 98027
5 bd3.5 ba3,290 sqftListing courtesy of John L. Scott HWP
Active42 days on market$2,175,000
MLS# 25293806407 282nd Avenue Se
Issaquah, WA 98027
4 bd3.5 ba4,350 sqftListing courtesy of Windermere R.E./Snohomish
Active5 days on market$1,075,000
MLS# 253075923908 Se 168 Street
Issaquah, WA 98027
4 bd2.25 ba3,000 sqftListing courtesy of Windermere Real Estate/East
Active12 days on market$644,900
MLS# 252449418925 276th Avenue Se
Issaquah, WA 98027
2 bd1 ba1,070 sqftListing courtesy of John L. Scott, Inc
Active89 days on market$175,000
MLS# 2525783245 Xx Se 146th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of Kronos Real Estate
Active13 days on market$469,000
MLS# 2525736700 Front Street S #e206
Issaquah, WA 98027
2 bd1.5 baListing courtesy of Windermere Real Estate/East
Active8 days on market$1,550,000
MLS# 2521030541 Ne Alder Street
Issaquah, WA 98027
6 bd3.25 ba1,730 sqftListing courtesy of Hawkins Poe
Active32 days on market$389,000
MLS# 2524136700 Front Street S #b108
Issaquah, WA 98027
2 bd2 baListing courtesy of Brink Realty Group
Active7 days on market$440,000
MLS# 250285518501 Se Newport Way #h235
Issaquah, WA 98027
3 bd2 baListing courtesy of eXp Realty
Active26 days on market$1,185,000
MLS# 24798962127 Nw Far Country Lane
Issaquah, WA 98027
3 bd2.5 ba2,580 sqftListing courtesy of Keller Williams Rlty Bellevue
Active10 days on market$1,550,000
MLS# 251635413032 204th Place Se
Issaquah, WA 98027
4 bd3.75 ba3,980 sqftListing courtesy of Marketplace Sotheby's Intl Rty
Active11 days on market$1,530,000
MLS# 2508071372 Wilderness Peak Drive Nw
Issaquah, WA 98027
4 bd3.25 ba3,190 sqftListing courtesy of Kelly Right RE of Seattle LLC
Active35 days on market$199,000
MLS# 250959625116 Se 146th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of Providencia
Active20 days on market$540,000
MLS# 25057821000 Cabin Creek Lane Sw ##b106
Issaquah, WA 98027
2 bd2 baListing courtesy of Seattle Works Real Estate
Active41 days on market$1,725,000
MLS# 25070121534 Hillside Drive Se
Issaquah, WA 98027
4 bd3.25 ba3,819 sqftListing courtesy of John L. Scott, Inc.
Active53 days on market$403,000
MLS# 250560727011 Se 74th Street
Issaquah, WA 98027
2 bd1 ba830 sqftListing courtesy of Realty One Group Orca
Active53 days on market$403,000
MLS# 250561627011 Se 74th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of Realty One Group Orca
Active21 days on market$429,800
MLS# 25049401957 23rd Place Ne #203
Issaquah, WA 98027
2 bd2 baListing courtesy of Berkshire Hathaway HS NW
Active30 days on market$515,000
MLS# 2502773210 Mountain Park Boulevard Sw #f303
Issaquah, WA 98027
3 bd1.75 baListing courtesy of Real Broker LLC
Active4 days on market$2,199,000
MLS# 2494856865 Front Street S
Issaquah, WA 98027
5 bd3.25 ba3,640 sqftListing courtesy of John L. Scott Everett
Active8 days on market$88,500
MLS# 24969271317 Wildwood Boulevard Sw
Issaquah, WA 98027
0 bd0 baListing courtesy of John L. Scott, Inc
Active5 days on market$1,149,990
MLS# 2495077695 Nw Locust St (homesite #9)
Issaquah, WA 98027
2 bd2.25 baListing courtesy of Windermere Real Estate/East
Active21 days on market$199,000
MLS# 2494385116 Xx 198th Ave Se
Issaquah, WA 98027
0 bd0 baListing courtesy of eXp Realty
Active161 days on market$235,000
MLS# 24819839601 315th Avenue Se #23
Issaquah, WA 98027
2 bd1.75 baListing courtesy of William E. Johnson
Active29 days on market$1,400,000
MLS# 247057917600 Se Cougar Mountain Drive
Issaquah, WA 98027
0 bd0 baListing courtesy of Real Broker LLC
Active11 days on market$589,000
MLS# 246762532611 Se 108th Street
Issaquah, WA 98027
2 bd1 ba670 sqftListing courtesy of Redfin
ActiveNew today$60,000
MLS# 246366423800 Se Tiger Mountain Road #14
Issaquah, WA 98027
2 bd1.75 baListing courtesy of Keller Williams Eastside
Active53 days on market$303,000
MLS# 2456258146 Xx 274th Avenue Se
Issaquah, WA 98027
0 bd0 baListing courtesy of eXp Realty
Active35 days on market$2,350,000
MLS# 24471867511 271st Avenue Se #c
Issaquah, WA 98027
4 bd4.25 ba4,732 sqftListing courtesy of COMPASS
Active18 days on market$249,000
MLS# 244662511 Xx 6th Avenue Se
Issaquah, WA 98027
0 bd0 baListing courtesy of KW Mountains to Sound Realty
Active27 days on market$15,360,000
MLS# 2436427190 Xx Se 66th Street
Issaquah, WA 98027
0 bd0 baListing courtesy of Skyline Properties, Inc.
Active47 days on market$336,999
MLS# 2531326280 Nw Newport Way #b14
Issaquah, WA 98027
2 bd1.5 baListing courtesy of The Cascade Team
Active47 days on market$336,999
MLS# 2423939280 Nw Newport Way #b14
Issaquah, WA 98027
2 bd1.5 baListing courtesy of The Cascade Team
Active4 days on market$28,000
MLS# 240967223800 Se Tiger Mountain Road #39
Issaquah, WA 98027
1 bd1 baListing courtesy of Real Broker LLC
Listing data courtesy of NWMLS. Provided for the consumer's personal, non-commercial use. Market stats reflect representative market data for Issaquah; current listings and individual neighborhoods may vary.
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Issaquah Highlands homes
Master-planned Issaquah community with Liberty HS and mountain views.
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Trail-connected Cougar Mountain community with ISD schools.
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Valley-floor Issaquah with established streets and ISD quality.
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FAQ
Questions buyers and sellers ask first.
What makes Olde Town Issaquah different from Issaquah Highlands?
Olde Town is the historic heart of Issaquah — the original downtown with Front Street's independent restaurants, the Village Theatre performing arts center, Gilman Park, and Issaquah Creek. It has a genuine small-town character that the master-planned Issaquah Highlands community cannot replicate. Issaquah Highlands was designed from the ground up; Olde Town evolved over a century. The housing stock reflects that: 1920s–1950s craftsmen and bungalows close to Front Street, mid-century ranches behind. Both neighborhoods are served by the Issaquah School District, but Olde Town feeds the Issaquah High School path while Highlands feeds Liberty.
What are typical home prices in Olde Town Issaquah?
Olde Town homes typically range from $800K to $2.2M+. Historic craftsmen and bungalows on compact lots close to Front Street start around $800K–$1.3M. Mid-century homes on more generous lots behind the main street run $1.0M–$1.6M. Larger, renovated, or expanded homes on the best lots push $1.6M–$2.2M+. The neighborhood generally prices below comparable Issaquah Highlands homes, making it one of the most accessible entry points into the Issaquah School District.
What schools serve Olde Town Issaquah?
Olde Town falls within Issaquah School District, typically assigned to Issaquah Valley Elementary, Pacific Cascade Middle School, and Issaquah High School. Issaquah SD is one of Washington State's top-ranked public school districts. School assignments should always be verified by specific parcel address before purchase.
How walkable is Olde Town Issaquah?
Olde Town is the most walkable neighborhood in Issaquah — the only one where daily retail, dining, arts, and outdoor recreation are all accessible on foot. Front Street's restaurant row, the Village Theatre, Gilman Park's open green space, and Issaquah Creek's trail system are all within walking distance. This walkability is genuinely rare in Issaquah, which is otherwise dominated by car-dependent suburban development.
Is Olde Town close to I-90?
Yes. The I-90 on-ramp is approximately 5 minutes from most Olde Town addresses — one of the faster freeway-access windows in the Issaquah market. This mitigates the neighborhood's greater distance from Bellevue and Microsoft relative to Issaquah Highlands. Bellevue is 20 minutes; Seattle is 25–30 minutes; Microsoft Redmond campus is approximately 30 minutes. For buyers commuting south toward Renton, Auburn, or Kent via SR-169, Olde Town's valley-floor position is a strategic advantage.
What is the Village Theatre and why does it matter for buyers?
Village Theatre is one of the Pacific Northwest's most respected professional regional theaters — a 500-seat performing arts venue on Olde Town Issaquah's main street that draws productions and audiences from across the region. For buyers who value arts access, being able to walk to a professional theater is a quality-of-life differentiator that doesn't exist anywhere else in the Issaquah market. It's a primary reason Olde Town attracts buyers with cultural priorities alongside school-district and commute considerations.
Search Olde Town with agents who understand why historic character commands a premium.
RexMont helps you evaluate craftsman-era housing, walkability by address, Issaquah SD school paths, and the specific value that makes Olde Town irreplaceable in the Eastside market.
Talk with RexMont