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Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of Ashland. R2 zoning offers versatile living: A gracious private residence, a home with Airbnb units, or a B&B with owner-occupied quarters. Once the beloved Midsummer Night's Dream B&B, it's now a private home with 2 vacation rentals in a stunning detached annex. The main house (2375 SF) features hardwood floors, a lovely living room with fireplace, parlor/game room, formal dining room, chef's kitchen, laundry room, & small office. Three luxurious suites are in the main home, with two more in the annex (1092 SF), each with a fireplace, spa bath, shower & a private deck. Expansive lush lawn areas with mature flowering trees & mountain views, creates a peaceful & picturesque setting. Unbeatable location near theaters, dining, & the magic that is Ashland. Off street parking. Most furnishings included. An exceptional opportunity for a family home, extended family living or income. Request information.

5 Beds ⋅ 6 Baths ⋅ 220230213 MLS

Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of Ashland. R2 zoning offers versatile living: A gracious private residence, a home with Airbnb units, or a B&B with owner-occupied quarters. Once the beloved Midsummer Night's Dream B&B, it's now a private home with 2 vacation rentals in a stunning detached annex. The main house (2375 SF) features hardwood floors, a lovely living room with fireplace, parlor/game room, formal dining room, chef's kitchen, laundry room, & small office. Three luxurious suites are in the main home, with two more in the annex (1092 SF), each with a fireplace, spa bath, shower & a private deck. Expansive lush lawn areas with mature flowering trees & mountain views, creates a peaceful & picturesque setting. Unbeatable location near theaters, dining, & the magic that is Ashland. Off street parking. Most furnishings included. An exceptional opportunity for a family home, extended family living or income. Request information.

496 Beach Street, Ashland

$515,000

Searching for a sweat equity project in rural Ashland? If so, this is the one for you! This charming single level property (needs TLC) features a spacious 3 bed, 2 bath, 2366 sq ft home that offers an open floor plan, bamboo flooring throughout, large (partially covered) deck, woodstove in the living room, 6+ wooded acres, circular driveway, multiple sheds, & much more! In addition, you also have a detached 2018 built, 2 bed, 1 bath manufactured home (very livable) that offers an open floor plan, covered deck, and chef's kitchen. Manufactured home was installed under a medical hardship as well. Buyer to perform their own due diligence pertaining to usability of the manufactured home. Perfect opportunity for a contractor looking for their next project and/or anyone that wants to get lost in the woods and enjoy the ambiance of rural Southern Oregon. This one won't last long on the market, so contact your agent today for a personal tour, before it's too late!

3 Beds ⋅ 2 Baths ⋅ 220230033 MLS

Searching for a sweat equity project in rural Ashland? If so, this is the one for you! This charming single level property (needs TLC) features a spacious 3 bed, 2 bath, 2366 sq ft home that offers an open floor plan, bamboo flooring throughout, large (partially covered) deck, woodstove in the living room, 6+ wooded acres, circular driveway, multiple sheds, & much more! In addition, you also have a detached 2018 built, 2 bed, 1 bath manufactured home (very livable) that offers an open floor plan, covered deck, and chef's kitchen. Manufactured home was installed under a medical hardship as well. Buyer to perform their own due diligence pertaining to usability of the manufactured home. Perfect opportunity for a contractor looking for their next project and/or anyone that wants to get lost in the woods and enjoy the ambiance of rural Southern Oregon. This one won't last long on the market, so contact your agent today for a personal tour, before it's too late!

1311 Neil Creek Road, Ashland

$425,000

Darling, turn-key single-level 1950's cottage is situated on a good-sized .17 acre lot with views. This home offers 772 sq ft of well lit living space with 2 bedrooms, 1 bath, welcoming living room, kitchen with a dining nook & red oak hardwood floors. 235 E Hersey is conveniently located just blocks from town with easy access to shopping and schools. The property features a large, private, fully fenced backyard with a beautiful lawn, cedar deck, 2 raised garden beds, abundant drip irrigated flowers, mature fruit trees, table grapes & a 2 part compost station. There is a 10x20 shed with built-in storage shelving. Enjoy views of Grizzly Peak from the kitchen and backyard. 2023 updates: Fridge, windows, exterior paint and insulation in the attic. 2025: new HVAC unit, solid core doors. 2026: cedar deck, new gutters, new roof on the shed, 3 tier patio, organic garden beds, landscaping, irrigation & permitted back flow preventer.

2 Beds ⋅ 1 Baths ⋅ 220230032 MLS

Darling, turn-key single-level 1950's cottage is situated on a good-sized .17 acre lot with views. This home offers 772 sq ft of well lit living space with 2 bedrooms, 1 bath, welcoming living room, kitchen with a dining nook & red oak hardwood floors. 235 E Hersey is conveniently located just blocks from town with easy access to shopping and schools. The property features a large, private, fully fenced backyard with a beautiful lawn, cedar deck, 2 raised garden beds, abundant drip irrigated flowers, mature fruit trees, table grapes & a 2 part compost station. There is a 10x20 shed with built-in storage shelving. Enjoy views of Grizzly Peak from the kitchen and backyard. 2023 updates: Fridge, windows, exterior paint and insulation in the attic. 2025: new HVAC unit, solid core doors. 2026: cedar deck, new gutters, new roof on the shed, 3 tier patio, organic garden beds, landscaping, irrigation & permitted back flow preventer.

235 E Hersey Street, Ashland

$605,000

This charming 3 bed / 2 bath 1890 Victorian farmhouse is on a beautiful tree-lined street close to downtown Ashland. The covered front porch leads you into the 1658 sq ft home with original fir floors, high ceilings and period light fixtures. There are generous windows and skylights bringing wonderful light into the parlor, large kitchen and living room. French doors off the kitchen lead to the covered side porch and a large backyard including 4 fig trees, 10 raised beds and your own potting sunroom. The big jobs have been completed in this well maintained home- the foundation and roof were replaced in 2015. The HVAC system is new as of 2022 and ductless mini-splits were added upstairs in 2019.

3 Beds ⋅ 2 Baths ⋅ 220229966 MLS

This charming 3 bed / 2 bath 1890 Victorian farmhouse is on a beautiful tree-lined street close to downtown Ashland. The covered front porch leads you into the 1658 sq ft home with original fir floors, high ceilings and period light fixtures. There are generous windows and skylights bringing wonderful light into the parlor, large kitchen and living room. French doors off the kitchen lead to the covered side porch and a large backyard including 4 fig trees, 10 raised beds and your own potting sunroom. The big jobs have been completed in this well maintained home- the foundation and roof were replaced in 2015. The HVAC system is new as of 2022 and ductless mini-splits were added upstairs in 2019.

726 Iowa Street, Ashland

479 Russell Street 202 Unit 202, Ashland

$265,000

Escape to the great town of Ashland. Easy access to College, Bus line, shopping, eateries and theater. The location is so close to Downtown and the sought after Railroad District of Ashland. Urban living with views from this end unit condo with balcony; Motivated Seller! This would be Super for second home, or easy affordable living. Elevator and small storage area are great for those who don't take stairs. Storage will hold bikes and other recreational items etc. Open floor plan with high ceilings lots of natural light, end unit with private balcony, up/down blinds, ceaser stone counters. Stainless appliances, interior ceiling fire sprinklers, and stackable washer and dryer are included. This condo is located on a private street with off-street parking for guests and residents. HOA is building up funds which cover all exterior matinence, landscaping, sewer, water garbage and roof.

1 Beds ⋅ 1 Baths ⋅ 220229841 MLS

Escape to the great town of Ashland. Easy access to College, Bus line, shopping, eateries and theater. The location is so close to Downtown and the sought after Railroad District of Ashland. Urban living with views from this end unit condo with balcony; Motivated Seller! This would be Super for second home, or easy affordable living. Elevator and small storage area are great for those who don't take stairs. Storage will hold bikes and other recreational items etc. Open floor plan with high ceilings lots of natural light, end unit with private balcony, up/down blinds, ceaser stone counters. Stainless appliances, interior ceiling fire sprinklers, and stackable washer and dryer are included. This condo is located on a private street with off-street parking for guests and residents. HOA is building up funds which cover all exterior matinence, landscaping, sewer, water garbage and roof.

479 Russell Street 202 Unit 202, Ashland

$1,395,000

Some homes are addresses. This one was a destination. Set high in the Ashland hills, this connected double geodesic dome was the longtime home of internationally influential author Jean Houston. Inside, faceted ceilings soar overhead, pierced by triangular skylights that move light through the day. Fresh paint, restored floors, and a bold gold hearth in the great room. Below, a self-contained multi-generational suite with its own entrance, plus a 2,000 sq ft finished bonus room, once a private library. Working elevator, ramps, and accessible design throughout. Outside, a wraparound deck opens to nearly twelve acres: orchard, gardens, and matured vines on the property's own well. New septic, upgraded electrical, and completed wildfire mitigation. Bordered by BLM and protected city land, the valley views stay private and pristine. A home with a soul, ready for its next chapter.

4 Beds ⋅ 5 Baths ⋅ 220229205 MLS

Some homes are addresses. This one was a destination. Set high in the Ashland hills, this connected double geodesic dome was the longtime home of internationally influential author Jean Houston. Inside, faceted ceilings soar overhead, pierced by triangular skylights that move light through the day. Fresh paint, restored floors, and a bold gold hearth in the great room. Below, a self-contained multi-generational suite with its own entrance, plus a 2,000 sq ft finished bonus room, once a private library. Working elevator, ramps, and accessible design throughout. Outside, a wraparound deck opens to nearly twelve acres: orchard, gardens, and matured vines on the property's own well. New septic, upgraded electrical, and completed wildfire mitigation. Bordered by BLM and protected city land, the valley views stay private and pristine. A home with a soul, ready for its next chapter.

2200 Lupine Drive, Ashland

$317,000

Charming 2004 built Victorian-style townhouse offering the perfect blend of classic character and modern convenience. This inviting end unit features 2 bedrooms and 1½ baths, with wood floors extending through the entry and living room. The comfortable floor plan offers a warm, welcoming living space with plenty of natural light and easy flow. Step outside to the back deck, ideal for relaxing, enjoying your morning coffee, or entertaining friends. As an end unit, this home offers added privacy and a desirable setting. Conveniently located near schools, shopping, dining, and everyday amenities, this delightful townhouse is a wonderful opportunity for comfortable, low-maintenance living with plenty of charm. Note, all tenant possessions have been removed from all photos.

2 Beds ⋅ 2 Baths ⋅ 220229021 MLS

Charming 2004 built Victorian-style townhouse offering the perfect blend of classic character and modern convenience. This inviting end unit features 2 bedrooms and 1½ baths, with wood floors extending through the entry and living room. The comfortable floor plan offers a warm, welcoming living space with plenty of natural light and easy flow. Step outside to the back deck, ideal for relaxing, enjoying your morning coffee, or entertaining friends. As an end unit, this home offers added privacy and a desirable setting. Conveniently located near schools, shopping, dining, and everyday amenities, this delightful townhouse is a wonderful opportunity for comfortable, low-maintenance living with plenty of charm. Note, all tenant possessions have been removed from all photos.

49 California Street, Ashland

$585,000

Welcome to the other side of Ashland! Set on 30 acres within a private gated community, this property offers an incredible sense of seclusion while still providing convenient access to everything Ashland has to offer. Surrounded by natural beauty and expansive views, the setting creates a peace beyond explanation. Whether you're looking for a quiet Southern Oregon retreat, room to enjoy the land, manage livestock, or simply a property where privacy is hard to come by, this unique Ashland acreage is one you won't want to miss!

3 Beds ⋅ 2 Baths ⋅ 220228064 MLS

Welcome to the other side of Ashland! Set on 30 acres within a private gated community, this property offers an incredible sense of seclusion while still providing convenient access to everything Ashland has to offer. Surrounded by natural beauty and expansive views, the setting creates a peace beyond explanation. Whether you're looking for a quiet Southern Oregon retreat, room to enjoy the land, manage livestock, or simply a property where privacy is hard to come by, this unique Ashland acreage is one you won't want to miss!

3150 Butler Creek Road, Ashland

$375,000

Just minutes from downtown Ashland, this light-filled single-level home offers comfort, convenience, and room to grow. The living and dining areas feel unexpectedly spacious thanks to the natural light, while laminate flooring and ductless heating and air add everyday ease. Two large bedrooms and a framed-in porch create flexible living and storage options. The refreshed kitchen makes cooking simple, and the generous yard, parking space, and detached shed support all your outdoor hobbies. Development potential, buyers to verify options with the city.

2 Beds ⋅ 1 Baths ⋅ 220227291 MLS

Just minutes from downtown Ashland, this light-filled single-level home offers comfort, convenience, and room to grow. The living and dining areas feel unexpectedly spacious thanks to the natural light, while laminate flooring and ductless heating and air add everyday ease. Two large bedrooms and a framed-in porch create flexible living and storage options. The refreshed kitchen makes cooking simple, and the generous yard, parking space, and detached shed support all your outdoor hobbies. Development potential, buyers to verify options with the city.

1342 E Main Street, Ashland

$400,000

Charming cottage just minutes from downtown Ashland, filled with great natural light. This two-bedroom, one-bath home features updated vinyl flooring and windows throughout. The oversized kitchen offers white cabinetry, an electric range/oven, and abundant storage. Enjoy surrounding mountain views from the front deck, or relax in the large fenced backyard with garden space and a concrete patio ideal for outdoor entertaining. Development potential--buyers to perform their own due diligence with the city regarding options.

2 Beds ⋅ 1 Baths ⋅ 220227289 MLS

Charming cottage just minutes from downtown Ashland, filled with great natural light. This two-bedroom, one-bath home features updated vinyl flooring and windows throughout. The oversized kitchen offers white cabinetry, an electric range/oven, and abundant storage. Enjoy surrounding mountain views from the front deck, or relax in the large fenced backyard with garden space and a concrete patio ideal for outdoor entertaining. Development potential--buyers to perform their own due diligence with the city regarding options.

1340 E Main Street, Ashland

$379,900

Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Advantage-certified cottage offers an easy, comfortable way to live. The bright, open interior features vaulted ceilings, abundant natural light, and contemporary finishes throughout. The kitchen pairs quartz countertops with stainless steel appliances and a convenient breakfast bar, creating a stylish and functional heart of the home. Outside, the fully fenced yard is an exceptional extension of the living space, with a private patio and room for gardening, dining, or simply enjoying the mountain views. As part of a shared solar community, the home is designed with energy efficiency and lower operating costs in mind. With its manageable size, low-maintenance design, outdoor space, and modern construction, this two-bedroom, one-bath home is a smart opportunity for anyone looking for a newer home without the upkeep of a larger property.

2 Beds ⋅ 1 Baths ⋅ 220227252 MLS

Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Advantage-certified cottage offers an easy, comfortable way to live. The bright, open interior features vaulted ceilings, abundant natural light, and contemporary finishes throughout. The kitchen pairs quartz countertops with stainless steel appliances and a convenient breakfast bar, creating a stylish and functional heart of the home. Outside, the fully fenced yard is an exceptional extension of the living space, with a private patio and room for gardening, dining, or simply enjoying the mountain views. As part of a shared solar community, the home is designed with energy efficiency and lower operating costs in mind. With its manageable size, low-maintenance design, outdoor space, and modern construction, this two-bedroom, one-bath home is a smart opportunity for anyone looking for a newer home without the upkeep of a larger property.

583 Coffee Lane, Ashland

$384,900

GREAT opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 15 mins from downtown Ashland. This existing permitted general purpose building, is ready to be converted into a 1-bed, 1-bath layout. Property features outdoor sauna, small seasonal pond, & high-producing well (11 GPM w/ pump, 41 GPM raw). Built in 2014, the existing permitted structure currently includes an unfinished kitchen & dining room. Purchase property as-is w/ cash (see MLS listing # 220226037) for $249,900 or finance the construction using a rehab loan w/ this listing. List price is an estimate on the the total costs including the land purchase & the amount needed to finish it, based on estimate by our contractor ($129,000). Buyer to due their own due-diligence. Buyer to enter into a separate building contract with suggested contractor or contractor of their choice outside of escrow. Final price to be determined at a later date when Rehab package is finalized.

1 Beds ⋅ 1 Baths ⋅ 220226151 MLS

GREAT opportunity to own 2.14 acres and finish building a newer, 688-sqft tiny home nestled on private acreage, just 15 mins from downtown Ashland. This existing permitted general purpose building, is ready to be converted into a 1-bed, 1-bath layout. Property features outdoor sauna, small seasonal pond, & high-producing well (11 GPM w/ pump, 41 GPM raw). Built in 2014, the existing permitted structure currently includes an unfinished kitchen & dining room. Purchase property as-is w/ cash (see MLS listing # 220226037) for $249,900 or finance the construction using a rehab loan w/ this listing. List price is an estimate on the the total costs including the land purchase & the amount needed to finish it, based on estimate by our contractor ($129,000). Buyer to due their own due-diligence. Buyer to enter into a separate building contract with suggested contractor or contractor of their choice outside of escrow. Final price to be determined at a later date when Rehab package is finalized.

4712 Old Highway 99 S, Ashland

$489,000

DRAMATIC PRICE REDUCTION TO $489,000. Looking for a home in Ashland that offers more than just a place to live? 508 N Main Street offers a unique opportunity to own a distinctive Victorian property with two separate living spaces. Currently arranged as two 1-bedroom, 1-bath living areas, this versatile property offers the opportunity to live in one space while exploring rental income from the other, subject to applicable regulations. It could also be ideal for multigenerational living, guests, or a dedicated home office. Enjoy mountain and territorial views, charming patio and garden areas, off-street parking, additional storage, and a dry sauna-- all less than a mile from downtown Ashland. REDUCED By $55,900. If you've been waiting for an opportunity to own property in Ashland with flexible living options and potential income-producing space, this is one to explore.

3 Beds ⋅ 2 Baths ⋅ 220225550 MLS

DRAMATIC PRICE REDUCTION TO $489,000. Looking for a home in Ashland that offers more than just a place to live? 508 N Main Street offers a unique opportunity to own a distinctive Victorian property with two separate living spaces. Currently arranged as two 1-bedroom, 1-bath living areas, this versatile property offers the opportunity to live in one space while exploring rental income from the other, subject to applicable regulations. It could also be ideal for multigenerational living, guests, or a dedicated home office. Enjoy mountain and territorial views, charming patio and garden areas, off-street parking, additional storage, and a dry sauna-- all less than a mile from downtown Ashland. REDUCED By $55,900. If you've been waiting for an opportunity to own property in Ashland with flexible living options and potential income-producing space, this is one to explore.

508 N Main Street, Ashland

$425,000

Rare opportunity to own an updated end-unit less than one mile from Lithia Park. This move-in ready home features engineered hardwood flooring, quartz countertops, a beautifully remodeled kitchen, new roof and premium Janke HVAC system. HOA covers water, sewer, trash, exterior maintenance, landscaping and access to the community's solar-heated pool, creating an exceptionally low-maintenance lifestyle. Enjoy nearby restaurants, shops, parks and all the charm of downtown Ashland without the upkeep of a detached home. Owner carry option available.

3 Beds ⋅ 3 Baths ⋅ 220225375 MLS

Rare opportunity to own an updated end-unit less than one mile from Lithia Park. This move-in ready home features engineered hardwood flooring, quartz countertops, a beautifully remodeled kitchen, new roof and premium Janke HVAC system. HOA covers water, sewer, trash, exterior maintenance, landscaping and access to the community's solar-heated pool, creating an exceptionally low-maintenance lifestyle. Enjoy nearby restaurants, shops, parks and all the charm of downtown Ashland without the upkeep of a detached home. Owner carry option available.

426 Chestnut Street, Ashland

$749,000

Rolling pastures, gentle hills & gorgeous Mt. Ashland views create an exceptional setting for this beautifully updated single-level home on 6.85 acres. Rebuilt from the studs in 2004, it blends timeless craftsmanship with a light-filled, open design where every room connects to the surrounding landscape. Vaulted ceilings, expansive view windows, maple hardwood floors, custom Shaker-style woodwork, fir doors, built-ins & two fireplaces add warmth and character. The spacious kitchen with sunny breakfast nook opens to wraparound decking & gardens, inviting outdoor living amid sweeping views, colorful seasonal blooms, spectacular sunsets & brilliant star-filled skies. The rebuild included updated plumbing, electrical, Milgard windows, raised ceilings, remodeled kitchen & baths, added living space, on-demand hot water & underground utilities. Outbuildings with animal shed & approx. 850-sf shop complete this peaceful, private retreat, above the fog, below the snow & just 10 minutes to town

3 Beds ⋅ 2 Baths ⋅ 220225306 MLS

Rolling pastures, gentle hills & gorgeous Mt. Ashland views create an exceptional setting for this beautifully updated single-level home on 6.85 acres. Rebuilt from the studs in 2004, it blends timeless craftsmanship with a light-filled, open design where every room connects to the surrounding landscape. Vaulted ceilings, expansive view windows, maple hardwood floors, custom Shaker-style woodwork, fir doors, built-ins & two fireplaces add warmth and character. The spacious kitchen with sunny breakfast nook opens to wraparound decking & gardens, inviting outdoor living amid sweeping views, colorful seasonal blooms, spectacular sunsets & brilliant star-filled skies. The rebuild included updated plumbing, electrical, Milgard windows, raised ceilings, remodeled kitchen & baths, added living space, on-demand hot water & underground utilities. Outbuildings with animal shed & approx. 850-sf shop complete this peaceful, private retreat, above the fog, below the snow & just 10 minutes to town

2815 Dead Indian Memorial Road, Ashland

$799,000

It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1 Beds ⋅ 2 Baths ⋅ 220224982 MLS

It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 400-600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, Ashland

$2,140,000

Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

5 Beds ⋅ 5 Baths ⋅ 220223401 MLS

Rare 203-acre Ashland estate with sweeping south-facing views offers a resort setting tucked away at the end of a mountain road. Completed in 2015, the 7,468 sq ft Craftsman residence was designed for beauty and function. The main level showcases two primary suites, two additional oversized bedrooms, expansive living and family rooms, and a gourmet kitchen. One walnut staircase leads to a private loft while a second stairway leads to a spacious upper level bonus room. The partially finished daylight basement has exterior and patio access. The original 1,812 sq ft home is now an amazing fully finished flex space, ideal for guests, office, studio, or recreation. Surrounded on three sides by the Siskiyou Cascade National Monument for vast recreational opportunities. The property offers pasture, wooded terrain, and creek frontage. This rare legacy estate delivers self sufficiency, seclusion, and unparalleled outdoor access while remaining within reach of Ashland's renowned amenities.

22494 Jefferson Road, Ashland

$699,000

Check out this Chalet-style triplex with R-2 zoning offering both short- and long-term rental possibilities just minutes from downtown Ashland. Units 1 & 3 are one-bedroom, unit 2 is 2 bedroom, all units have tile flooring, a kitchen with granite countertops and breakfast bar, a full bathroom with tile shower, and generous living area. Private decks provide outdoor living space, while the upper unit enjoys spectacular views. The property includes off-street parking, one space per unit, plus basement with shared laundry facilities and additional storage. Two units are currently vacant, creating flexibility for an owner-occupant, investor, or those seeking a combination. Updates completed in 2016 include ductless heating and cooling system, electrical improvements, and interior finishes. The metal roof has been recently painted, decks have been updated and water heaters were new in '23. This is a rare opportunity to own a versatile income-producing property in a desirable location.

220223307 MLS

Check out this Chalet-style triplex with R-2 zoning offering both short- and long-term rental possibilities just minutes from downtown Ashland. Units 1 & 3 are one-bedroom, unit 2 is 2 bedroom, all units have tile flooring, a kitchen with granite countertops and breakfast bar, a full bathroom with tile shower, and generous living area. Private decks provide outdoor living space, while the upper unit enjoys spectacular views. The property includes off-street parking, one space per unit, plus basement with shared laundry facilities and additional storage. Two units are currently vacant, creating flexibility for an owner-occupant, investor, or those seeking a combination. Updates completed in 2016 include ductless heating and cooling system, electrical improvements, and interior finishes. The metal roof has been recently painted, decks have been updated and water heaters were new in '23. This is a rare opportunity to own a versatile income-producing property in a desirable location.

326 N Main Street, Ashland

$589,000

Timeless mid-century home just a block above Lithia Park and only a short jaunt to the plaza. Sitting in a quiet location with views, this home offers serenity while still being close in. Exposed beam ceilings on the lower level offers warmth and charm. A bank of picture windows in the living room allows one to take in the mountain views as well as overlooking the backyard. The kitchen opens to the spacious back deck which is perfect for entertaining and indoor/outdoor living. An oversized mudroom/pantry as well as an office nook round out the downstairs. Upstairs sit 4 bedrooms, including a spacious primary suite that opens to a private deck with views to take in the natural beauty. One bedroom with vaulted ceiling could be used as a media room or flex space. Outside, the yard is fully fenced and has garden beds and room to play. With a solar array and backup battery, this home is well-equipped. All of this is so close to town, Lithia Park and the incredible trail network of Ashland!

4 Beds ⋅ 3 Baths ⋅ 220220812 MLS

Timeless mid-century home just a block above Lithia Park and only a short jaunt to the plaza. Sitting in a quiet location with views, this home offers serenity while still being close in. Exposed beam ceilings on the lower level offers warmth and charm. A bank of picture windows in the living room allows one to take in the mountain views as well as overlooking the backyard. The kitchen opens to the spacious back deck which is perfect for entertaining and indoor/outdoor living. An oversized mudroom/pantry as well as an office nook round out the downstairs. Upstairs sit 4 bedrooms, including a spacious primary suite that opens to a private deck with views to take in the natural beauty. One bedroom with vaulted ceiling could be used as a media room or flex space. Outside, the yard is fully fenced and has garden beds and room to play. With a solar array and backup battery, this home is well-equipped. All of this is so close to town, Lithia Park and the incredible trail network of Ashland!

34 Scenic Drive, Ashland

$425,000

Builder/developer opportunity in one of Ashland's most sought-after neighborhoods. Exceptional redevelopment potential on a .35 acre corner lot just blocks from the Ashland Plaza. Elevated position captures sweeping mountain, city, and territorial views in an area of high-end homes. Existing structure is likely best suited for removal, creating a rare chance to build a stunning custom home on a large in-town lot or explore the potential for a lot split and development of two residences (buyer to complete all due diligence with the City of Ashland). Prime location near Lithia Park, OSF, and downtown amenities. Opportunities like this with size, views, and proximity to town are increasingly rare.

3 Beds ⋅ 2 Baths ⋅ 220218469 MLS

Builder/developer opportunity in one of Ashland's most sought-after neighborhoods. Exceptional redevelopment potential on a .35 acre corner lot just blocks from the Ashland Plaza. Elevated position captures sweeping mountain, city, and territorial views in an area of high-end homes. Existing structure is likely best suited for removal, creating a rare chance to build a stunning custom home on a large in-town lot or explore the potential for a lot split and development of two residences (buyer to complete all due diligence with the City of Ashland). Prime location near Lithia Park, OSF, and downtown amenities. Opportunities like this with size, views, and proximity to town are increasingly rare.

166 Nob Hill Street, Ashland

$139,900

Welcome to your perfect Southern Oregon Retreat at 16170 Highway 66 in Ashland! This charming 2-bedroom, 1-bathroom single-wide home offers 840 square feet of comfortable living space on a generous .59-acre lot, providing the ideal blend of cozy functionality and outdoor potential. Whether you're seeking a peaceful vacation getaway just minutes from Ashland's renowned cultural attractions, wineries, and outdoor recreation, or looking for a smart investment property in one of Oregon's most desirable destinations, this well-proportioned home delivers exceptional value. The spacious lot offers room for gardening, outdoor entertaining, or simply enjoying the natural beauty of the Rogue Valley, while the efficient floor plan ensures easy maintenance and comfortable year-round living. Don't miss this rare opportunity to own an affordable piece of Ashland's lifestyle at an attractive price point!

2 Beds ⋅ 1 Baths ⋅ 220212880 MLS

Welcome to your perfect Southern Oregon Retreat at 16170 Highway 66 in Ashland! This charming 2-bedroom, 1-bathroom single-wide home offers 840 square feet of comfortable living space on a generous .59-acre lot, providing the ideal blend of cozy functionality and outdoor potential. Whether you're seeking a peaceful vacation getaway just minutes from Ashland's renowned cultural attractions, wineries, and outdoor recreation, or looking for a smart investment property in one of Oregon's most desirable destinations, this well-proportioned home delivers exceptional value. The spacious lot offers room for gardening, outdoor entertaining, or simply enjoying the natural beauty of the Rogue Valley, while the efficient floor plan ensures easy maintenance and comfortable year-round living. Don't miss this rare opportunity to own an affordable piece of Ashland's lifestyle at an attractive price point!

Ashland

$1,249,000

Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

8 Beds ⋅ 9 Baths ⋅ 220212846 MLS

Just blocks from downtown, this historic gem blends charm and flexibility. Original fir floors, built-ins, high ceilings, and abundant natural light pair with modern updates. Enjoy the welcoming lawn, pollinator garden, and large covered front porch. The main level offers spacious living and dining areas, kitchen, half bath, and generous entry spaces. A 1-bedroom apartment with interior and private exterior access--includes a kitchen, laundry and full bathroom--a separate additional en-suite bedroom with exterior entry adds versatility. Upstairs are four lovely en-suite bedrooms, one with a balcony, all with updated Renewal by Andersen windows and balcony door. A detached 704 sq ft, 2 bedroom, 1.5 bath, single level cottage with its own address and electric meter provides added flexibility or income potential. With six paved off-street parking spaces, sheds, on-street parking, and alley access, this property offers exceptional possibilities for multi-generational living or investors.

451 N Main Street, Ashland

$799,000

It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1 Beds ⋅ 2 Baths ⋅ 220200581 MLS

It's all about the beautiful 13.39 contiguous acres with 12.6 acres of TID irrigation, panoramic views and just minutes to downtown Ashland. Family owned since 1964, the original home was built in 1915. There are 3 separate tax lots, one with the original home,8-stall horse barn and workshop (5.81 acres), one that has a non-expiring homesite (confirm with county) with fantastic panoramic views (4.53 acres) and the third with a large barn (3.05 acres) and separate access. All 3 may be sold separately (check with Jackson County Planning). Tax lot #700 has a small home, large shop, a 8-stall barn, tack room and small living quarters in the back. There is a 2-story barn on tax lot #300. The portion of the property growing grass and clover for hay produces approximately 600 bales and has wheel line irrigation. There are many other potentials for this EFU property.

1249 N Valley View Road, Ashland

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