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Two single-level homes on a spacious 0.16-acre lot with alley access in the heart of Ashland's Railroad District. Charming historic front home with covered porch, double-paned vinyl windows, original fir floors, high ceilings, picture rail moldings, dining with cast-iron gas stove, kitchen with glass-fronted display cabinets and butcher block counters, mudroom pantry with washer and dryer, primary bedroom with large walk-in closet, full bathroom with clawfoot tub shower, and guest bedroom with closet. Fully permitted second dwelling built in 1999 with front deck and covered entry, operable casement windows, oak hardwood flooring, spacious dining area and kitchen with wood cabinets, laundry closet, two bedrooms with closets, full bath with shower, and attached garage with second bay converted to workshop studio. New roofs, ductless mini-splits, and fully fenced private yards. Excellent investment opportunity and potential for short-term travelers' accommodations. Inquire for details!

4 Beds ⋅ 2 Baths ⋅ 220228571 MLS

Two single-level homes on a spacious 0.16-acre lot with alley access in the heart of Ashland's Railroad District. Charming historic front home with covered porch, double-paned vinyl windows, original fir floors, high ceilings, picture rail moldings, dining with cast-iron gas stove, kitchen with glass-fronted display cabinets and butcher block counters, mudroom pantry with washer and dryer, primary bedroom with large walk-in closet, full bathroom with clawfoot tub shower, and guest bedroom with closet. Fully permitted second dwelling built in 1999 with front deck and covered entry, operable casement windows, oak hardwood flooring, spacious dining area and kitchen with wood cabinets, laundry closet, two bedrooms with closets, full bath with shower, and attached garage with second bay converted to workshop studio. New roofs, ductless mini-splits, and fully fenced private yards. Excellent investment opportunity and potential for short-term travelers' accommodations. Inquire for details!

161 Fourth Street, Ashland

Courtesy of John L Scott Ashland

$599,000

The Hamaker-Taylor House, thoughtfully reimagined for modern living while preserving its Historic charm. Designed by notable architect Carlos Delgado, this 1889 cottage features a brand-new luxury kitchen with a beautiful sunroom/breakfast nook, new bathroom, updated windows, HVAC, plumbing, electrical, and roof (2026). Professionally landscaped and hardscaped front and back yards create inviting spaces for outdoor entertaining. An expansive covered front porch welcomes you home, while two bright bedrooms and beautiful Pergo flooring add warmth throughout. The full basement offers a unique art studio with lighting, hot/cold running water, and raised storage areas. Just three doors from Lithia Park, enjoy the sounds of the bandshell from your own porch. Minutes to OSF, the Plaza, and downtown Ashland. A rare opportunity to own a piece of Ashland history with modern luxury.

2 Beds ⋅ 1 Baths ⋅ 220228381 MLS

The Hamaker-Taylor House, thoughtfully reimagined for modern living while preserving its Historic charm. Designed by notable architect Carlos Delgado, this 1889 cottage features a brand-new luxury kitchen with a beautiful sunroom/breakfast nook, new bathroom, updated windows, HVAC, plumbing, electrical, and roof (2026). Professionally landscaped and hardscaped front and back yards create inviting spaces for outdoor entertaining. An expansive covered front porch welcomes you home, while two bright bedrooms and beautiful Pergo flooring add warmth throughout. The full basement offers a unique art studio with lighting, hot/cold running water, and raised storage areas. Just three doors from Lithia Park, enjoy the sounds of the bandshell from your own porch. Minutes to OSF, the Plaza, and downtown Ashland. A rare opportunity to own a piece of Ashland history with modern luxury.

63 Nutley Street, Ashland

Courtesy of Windermere Van Vleet & Assoc.

$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

Courtesy of John L Scott 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

Courtesy of John L Scott 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

Courtesy of Millen Property Group

$279,000

This Beautiful, turn key ready 2-bed / 1 bath condo, within a short walk to downtown Ashland, coffee shops , restaurants , shopping, & Southern Oregon University . Nice and bright natural light throughout with skylights in the living area. The kitchen has granite counters with stainless-steel appliances. Open floor plan flows into a spacious great room with 9ft ceilings and plenty of windows to take in the surrounding mountain views including Grizzly peak. Natural Fir doors and trim throughout. Ductless heating and air. Don't be fooled by the sq ft, this condo has a feel that it is much bigger. A modern and aesthetically pleasing living space in a small association. The furniture is included in the sale. Don't miss out on this rare opportunity to own a low maintenance home in Ashland. The unit is upstairs. Sellers are open to offers.

2 Beds ⋅ 1 Baths ⋅ 220224865 MLS

This Beautiful, turn key ready 2-bed / 1 bath condo, within a short walk to downtown Ashland, coffee shops , restaurants , shopping, & Southern Oregon University . Nice and bright natural light throughout with skylights in the living area. The kitchen has granite counters with stainless-steel appliances. Open floor plan flows into a spacious great room with 9ft ceilings and plenty of windows to take in the surrounding mountain views including Grizzly peak. Natural Fir doors and trim throughout. Ductless heating and air. Don't be fooled by the sq ft, this condo has a feel that it is much bigger. A modern and aesthetically pleasing living space in a small association. The furniture is included in the sale. Don't miss out on this rare opportunity to own a low maintenance home in Ashland. The unit is upstairs. Sellers are open to offers.

1249 Iowa, Ashland

Courtesy of RE/MAX Platinum

$690,000

Amazing opportunity with 5 legal lots per City of Ashland and phenomenal views. Amy Gunter of Rogue Planning & Development Services has extensively researched and received letter from City of Ashland Legal Lot Determination stating 5 lots. TID water rights. In addition there is a cute, sweet 2 bedroom, 2 bath home with detached garage. Orignal wood floors in bedroom and livingroom and maybe under the carpet in the hall. Living room has fireplace with built in bookcases on either side and you will love the unbelievable mountain views through the picture window. Home has been rented for many years and sits ''as is''. Cute unique kitchen with dining nook. Call listing agent for details and property package. Buyer to do their own due diligence for their own plans for the property.

2 Beds ⋅ 2 Baths ⋅ 220224672 MLS

Amazing opportunity with 5 legal lots per City of Ashland and phenomenal views. Amy Gunter of Rogue Planning & Development Services has extensively researched and received letter from City of Ashland Legal Lot Determination stating 5 lots. TID water rights. In addition there is a cute, sweet 2 bedroom, 2 bath home with detached garage. Orignal wood floors in bedroom and livingroom and maybe under the carpet in the hall. Living room has fireplace with built in bookcases on either side and you will love the unbelievable mountain views through the picture window. Home has been rented for many years and sits ''as is''. Cute unique kitchen with dining nook. Call listing agent for details and property package. Buyer to do their own due diligence for their own plans for the property.

595 Monroe Street, Ashland

Courtesy of Absolute Realty

$385,000

Move-in ready and professionally cleaned, this charming cottage features central heating and air conditioning, along with numerous updates throughout. Situated on a spacious 0.17-acre lot, the property offers a fully fenced backyard, automatic sprinklers, off-street parking, a garden shed, and a deer-protected garden enclosure--ready for someone to make it shine again. Recent improvements include exterior paint, siding repairs, rebuilt exterior stairs, new luxury vinal plank flooring in the main living area, new tankless water heater, new refrigerator and electric range. The detached bonus room with an efficient wall heat and air AC unit, and abundant light offers endless possibilities as a home office, guest retreat, or hobby room. Conveniently located near downtown Ashland, schools, Grange Co-op, and Ace Hardware.

2 Beds ⋅ 1 Baths ⋅ 220224333 MLS

Move-in ready and professionally cleaned, this charming cottage features central heating and air conditioning, along with numerous updates throughout. Situated on a spacious 0.17-acre lot, the property offers a fully fenced backyard, automatic sprinklers, off-street parking, a garden shed, and a deer-protected garden enclosure--ready for someone to make it shine again. Recent improvements include exterior paint, siding repairs, rebuilt exterior stairs, new luxury vinal plank flooring in the main living area, new tankless water heater, new refrigerator and electric range. The detached bonus room with an efficient wall heat and air AC unit, and abundant light offers endless possibilities as a home office, guest retreat, or hobby room. Conveniently located near downtown Ashland, schools, Grange Co-op, and Ace Hardware.

363 E Hersey Street, Ashland

Courtesy of John L. Scott Ashland

$455,000

Opportunity is knocking. This charming duplex in Ashland's beloved Railroad District has had extensive updating throughout. Both units offer 1 bed/1 bath layouts with a new foundation, plumbing, and electrical, plus fresh interior and exterior paint, new carpet, and laminate flooring. Currently tenant-occupied on both sides, this is a true turn-key addition to any investment portfolio. Walk to shops, restaurants, and the heart of Ashland from one of the most sought-after neighborhoods in town. Investors, this one's for you. Please do not disturb tenants. Showings are by appointment only.

220221378 MLS

Opportunity is knocking. This charming duplex in Ashland's beloved Railroad District has had extensive updating throughout. Both units offer 1 bed/1 bath layouts with a new foundation, plumbing, and electrical, plus fresh interior and exterior paint, new carpet, and laminate flooring. Currently tenant-occupied on both sides, this is a true turn-key addition to any investment portfolio. Walk to shops, restaurants, and the heart of Ashland from one of the most sought-after neighborhoods in town. Investors, this one's for you. Please do not disturb tenants. Showings are by appointment only.

457 C Street, Ashland

Courtesy of John L Scott Ashland

$759,000

71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

5 Beds ⋅ 6 Baths ⋅ 220221349 MLS

71, 73 and 75 Wimer. Gorgeous updated including plumbing and electric vintage home w/charm remaining a few blocks to downtown Ashland. The main home has 3 bedrooms (2 with ensuite baths) the 3rd bedroom has an ensuite 1/2 bath. Formal living and dining and eat in large kitchen w/breakfast bar & nook. Granite countertops. Wood floors on main level & carpet on stairs & bdrms. The woodwork door trim is beautiful & probably original. Newer deck & A/C unit. Detached building (71 and 73 Wimer) are one level studio units with kitchens & baths. 73 Wimer has private deck. Main house is rented for $2375.00 p/month & tenant pays utilities except water. Studios have been rented for $1250.00 & $1350.00 per month with utilities included & they have a separate shared laundry facility. Unique property for owner occupied or income producing. Circular driveway for main home & 2 parking spaces in front for studios. Has been traveler accomodations in the past. Buyer to do own due diligence on u

75 Wimer Street, Ashland

Courtesy of Absolute Realty

$350,000

Ashland Garden Cottages boast Earth Advantage Platinum Status with Owned Solar Panels. Energy Star appliances, efficient layout of 2 bedrooms, 1 bathroom, stackable washer/dryer, and a living area to include the kitchen, dining area, and living room. Covered front porch, no common walls, quartz countertops, tile shower, and designer lighting. All appliances shown are included in the sale.

2 Beds ⋅ 1 Baths ⋅ 220221178 MLS

Ashland Garden Cottages boast Earth Advantage Platinum Status with Owned Solar Panels. Energy Star appliances, efficient layout of 2 bedrooms, 1 bathroom, stackable washer/dryer, and a living area to include the kitchen, dining area, and living room. Covered front porch, no common walls, quartz countertops, tile shower, and designer lighting. All appliances shown are included in the sale.

162 Mountain View Drive, Ashland

Courtesy of Full Circle Real Estate

$365,000

Charming single-level cottage in one of Ashland's most desirable locations, with stunning views of Grizzly Peak. This clean, well-maintained home features new flooring throughout and an inviting, light-filled interior, with two bedrooms plus a detached bonus room (not included in sq. footage), perfect for home office or studio. Additional storage can be found in the spacious basement. Large undeveloped adjoining lot (not included in the sale) gives the property a feeling of openness and privacy. Among the cherry and apple trees, grapevines and herb garden, enjoy peaceful mornings on the porch, a perfect spot for coffee while taking in the quiet neighborhood. Ideally located close to downtown Ashland, Lithia Park, the Oregon Shakespeare Festival, Southern Oregon University, dining, and nearby hiking and biking trails.

2 Beds ⋅ 1 Baths ⋅ 220219842 MLS

Charming single-level cottage in one of Ashland's most desirable locations, with stunning views of Grizzly Peak. This clean, well-maintained home features new flooring throughout and an inviting, light-filled interior, with two bedrooms plus a detached bonus room (not included in sq. footage), perfect for home office or studio. Additional storage can be found in the spacious basement. Large undeveloped adjoining lot (not included in the sale) gives the property a feeling of openness and privacy. Among the cherry and apple trees, grapevines and herb garden, enjoy peaceful mornings on the porch, a perfect spot for coffee while taking in the quiet neighborhood. Ideally located close to downtown Ashland, Lithia Park, the Oregon Shakespeare Festival, Southern Oregon University, dining, and nearby hiking and biking trails.

480 Harrison Street, Ashland

Courtesy of Millen Property Group

$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

Courtesy of Full Circle Real Estate

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