# 3729 Old Highway 99 S, Ashland, OR 97520

> **TL;DR:** 3bd/4ba single family, $889,000 ($239/sqft), built 2001, 3,713 sqft.
> Fireplace, View, A/C, 3-car garage. Est. $4,754/mo. Listed 112 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $889,000 |
| Price/sqft | $239 |
| Bedrooms | 3 |
| Bathrooms | 3 full, 1 half |
| Square Feet | 3,713 |
| Year Built | 2001 |
| Lot Size | 1,413,086 sqft (32.44 acres) |
| Stories | 2 |
| Garage | 3-car |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 112 |

## Why This Home Stands Out

- **Views** - Lake, Forest
- **Large Garage** - 3-car garage

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $4,495 |
| Estimated Insurance | $259 |
| **Total** | **$4,754** |

## Nearby Schools

- **Elementary:** Bellview Elem
- **Middle:** Ashland Middle
- **High:** Ashland High

## Key Amenities

- Fireplace
- View
- A/C
- 3-car garage

## Property Highlights

- Built in 2001
- 32.44 acre lot
- 2 stories
- Fireplace

## Description

### Agent Description
Enjoy spectacular views of Emigrant Lake & the surrounding mountains from this exceptional 3,713 sf custom 3 bd 3.5 ba home on over 30 acres, just 10 min from Ashland and a short drive to Mt. Ashland. From the moment you enter through the stunning mahogany door from your wrap around deck, you are welcomed into a great room with vaulted ceilings, a floor-to-ceiling rock fireplace, & windows that fill the home with natural light. Living space blends seamlessly into your gorgeous chef's kitchen & formal dining. An office w/ custom built-ins, bonus family room, & a guest half bath round out the main living space alongside an impressive primary suite, which features a private balcony, fireplace, & newly remodeled luxurious bathroom. Downstairs, you will find a guest ensuite, another guest bedroom, full bathroom, & laundry room. A 3-car garage provides plenty of space for cars & toys. Seller has done extensive fire mitigation work & paved the driveway, making this property insurable.

## Location

- **Address:** 3729 Old Highway 99 S, Ashland, OR 97520
- **County:** Jackson
- **Coordinates:** 42.095743, -122.590734
- **Google Maps:** https://www.google.com/maps?q=42.095743,-122.590734

## Virtual Tour & Media

- **Video Tour:** https://www.zillow.com/view-imx/3b352061-b41a-424f-8405-f7b92b494ecc?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

## Listing Agent

- **Name:** Michele Fleisher
- **Brokerage:** John L Scott
- **Broker Phone:** (541) 779-3611
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/3729-Old-Highway-99-S_Ashland_OR_97520_M28024-71439?f=listhub&s=ODOR&m=220224770&c=propsimple)

## Photos

![3729 Old Highway 99 S - Photo 1](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3473134952r.jpg)

![3729 Old Highway 99 S - Photo 2](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1427803739r.jpg)

![3729 Old Highway 99 S - Photo 3](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f712805776r.jpg)

![3729 Old Highway 99 S - Photo 4](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f326509271r.jpg)

![3729 Old Highway 99 S - Photo 5](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1661340967r.jpg)

![3729 Old Highway 99 S - Photo 6](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1124673008r.jpg)

![3729 Old Highway 99 S - Photo 7](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3987912486r.jpg)

![3729 Old Highway 99 S - Photo 8](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3459191186r.jpg)

![3729 Old Highway 99 S - Photo 9](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f4176253386r.jpg)

![3729 Old Highway 99 S - Photo 10](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f736703071r.jpg)

![3729 Old Highway 99 S - Photo 11](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3504460478r.jpg)

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![3729 Old Highway 99 S - Photo 14](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2248304453r.jpg)

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![3729 Old Highway 99 S - Photo 16](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1496480324r.jpg)

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![3729 Old Highway 99 S - Photo 23](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2779934832r.jpg)

![3729 Old Highway 99 S - Photo 24](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2982837441r.jpg)

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![3729 Old Highway 99 S - Photo 32](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f600748009r.jpg)

![3729 Old Highway 99 S - Photo 33](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3350899422r.jpg)

![3729 Old Highway 99 S - Photo 34](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1413297632r.jpg)

![3729 Old Highway 99 S - Photo 35](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2327016225r.jpg)

![3729 Old Highway 99 S - Photo 36](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2222866508r.jpg)

![3729 Old Highway 99 S - Photo 37](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3507779459r.jpg)

![3729 Old Highway 99 S - Photo 38](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1717222914r.jpg)

![3729 Old Highway 99 S - Photo 39](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3707041156r.jpg)

![3729 Old Highway 99 S - Photo 40](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f311865556r.jpg)

![3729 Old Highway 99 S - Photo 41](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3750214390r.jpg)

![3729 Old Highway 99 S - Photo 42](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f352571857r.jpg)

![3729 Old Highway 99 S - Photo 43](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3330934391r.jpg)

![3729 Old Highway 99 S - Photo 44](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1828932148r.jpg)

![3729 Old Highway 99 S - Photo 45](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1877452140r.jpg)

![3729 Old Highway 99 S - Photo 46](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f141818509r.jpg)

![3729 Old Highway 99 S - Photo 47](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3148654592r.jpg)

![3729 Old Highway 99 S - Photo 48](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2402640865r.jpg)

![3729 Old Highway 99 S - Photo 49](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f326509271r.jpg)

![3729 Old Highway 99 S - Photo 50](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2321517935r.jpg)

![3729 Old Highway 99 S - Photo 51](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2554240032r.jpg)

![3729 Old Highway 99 S - Photo 52](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f85098277r.jpg)

![3729 Old Highway 99 S - Photo 53](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3764336447r.jpg)

![3729 Old Highway 99 S - Photo 54](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f4016029458r.jpg)

![3729 Old Highway 99 S - Photo 55](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3113798380r.jpg)

![3729 Old Highway 99 S - Photo 56](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f3093055102r.jpg)

![3729 Old Highway 99 S - Photo 57](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f1857579822r.jpg)

![3729 Old Highway 99 S - Photo 58](http://lh.rdcpix.com/3b74b3734a209bfe3e33dc29e7ebe68bl-f2702731747r.jpg)

---

**MLS#:** 220224770 | **Updated:** 2026-10-23
**Source:** listhub

*Copyright © 2026 Oregon Data Share. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/3729-old-highway-99-s-ashland-or-97520-df2437dd244e46dbbcd5f3e9bc1f22bb)

---

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