5 Bedroom homes for sale & real estate in Ashland, OR

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
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 lu

$845,000

5 beds5.5 baths3,647 sq ft

496 Beach St, Ashland, OR 97520

Private residence • R2 zoning • Detached annex

ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Beautiful 2018 Craftsman home in Ashland's Billings Ranch neighborhood with 5 bedrooms and 2.5 baths, backing to open space with Cascade mountain and valley views. A covered porch opens to a bright foyer and main-level office or fifth bedroom behind French doors. The vaulted great room has view windows and stacked-stone fireplace, open to dining and a kitchen with white shaker cabinetry, pantry, breakfast bar, and smart convection gas double oven plus a third oven. The main-level primary suite has patio access, dual copper sinks, soaking tub, walk-in shower, and walk-in closet. Upstairs: second living room with built-in desk, a bedroom with a second walk-in closet, additional bedrooms, and

$839,000

5 beds2.5 baths2,606 sq ft

425 W Nevada St, Ashland, OR 97520

Covered porch • Vaulted great room • Craftsman home

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Own a piece of Ashland's history with this incredible historical home, cherished by the same family for 100 years. Built in 1900, this 3,092 sq. ft. home offers 5 bedrooms and 3 full bathrooms and has been beautifully renovated for modern living while preserving its historic elegance. Original details include beautiful woodwork throughout, formal living and dining rooms, inglenook seating, wood flooring, original entry stairwell, and an original fireplace updated with a gas insert. The updated kitchen features custom cabinetry, granite countertops, a large island, and skylights. Updated bathrooms retain their vintage charm with claw-foot soaking tubs and gorgeous custom shower tile-work. Th

$1,250,000

5 beds3 baths3,092 sq ft

1068 E Main St, Ashland, OR 97520

Custom cabinetry • Historical home • Original details

ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This updated 5-bedroom, 3.5-bath home offers 3,270 sq ft on 22.05 acres. The gourmet kitchen features granite countertops and a stunning oversized island with 360-degree access for cooking and entertaining. Guest quarters and two separate laundry rooms provide flexibility. Updates include all-new doors and windows, a new roof, and new stucco with an imperfect smooth finish and upgraded cloth underneath designed to help reduce temperatures. A large garage with generous shop space accommodates vehicles, tools, and hobbies. The engineered greenhouse includes a concrete perimeter and separate power meter, with pot

$1,175,000

5 beds3.5 baths3,270 sq ft

1650 Neil Creek Rd, Ashland, OR 97520

Guest quarters • All-new doors • Gourmet kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Over 1/2 Acre lot near historic Ashland Plaza! This 5 bedroom 4 bath home offers 2,487 sqft of living space set in a highly sought after neighborhood just minutes from shopping, dining and entertainment such as the Oregon Shakespeare Festival. The spacious floor plan provides plenty of room for everyday living, hosting and creating dedicated spaces for work, hobbies or relaxation. Two fireplaces add warmth and character, while the multiple sliding doors allow natural light to flood the living areas. One bathroom features an ADA accessible shower with floor to ceiling tile and custom stone, delivering both style and functionality. Outside, the beautifully landscaped lot offers an ideal setti

$589,000

5 beds3.5 baths2,487 sq ft

485 Orchard St, Ashland, OR 97520

Multiple rv parking • Oversized lot • 0.55 acre lot

Property at 1058 Linda Ave, Ashland, OR 97520, 5 beds, 3 baths

$599,000

5 beds3 baths3,100 sq ft

1058 Linda Ave, Ashland, OR 97520

Property at 808 Pompadour Dr, Ashland, OR 97520, 5 beds, 5.5 baths

$1,299,000

5 beds5.5 baths4,935 sq ft

808 Pompadour Dr, Ashland, OR 97520

Property at 143 Granite St, Ashland, OR 97520, 5 beds, 2 baths

$789,000

5 beds2 baths1,935 sq ft

143 Granite St, Ashland, OR 97520

Property at 12300 Oregon 66, Ashland, OR 97520, 5 beds, 3 baths

$499,900

5 beds3 baths2,404 sq ft

12300 Oregon 66, Ashland, OR 97520

Property at 430 Ashland St, Ashland, OR 97520, 5 beds, 3 baths

$565,000

5 beds3 baths1,973 sq ft

430 Ashland St, Ashland, OR 97520

Property at 541 Fairview St, Ashland, OR 97520, 5 beds, 3 baths

$996,000

5 beds3 baths2,586 sq ft

541 Fairview St, Ashland, OR 97520

Property at 500 Ashland Loop Rd, Ashland, OR 97520, 5 beds, 6 baths

$2,500,000

5 beds6 baths6,033 sq ft

500 Ashland Loop Rd, Ashland, OR 97520

Property at 22494 Jefferson Rd, Ashland, OR 97520, 5 beds, 4.5 baths

$2,140,000

5 beds4.5 baths7,468 sq ft

22494 Jefferson Rd, Ashland, OR 97520

Property at 523 Strawberry Ln, Ashland, OR 97520, 5 beds, 3 baths

$995,000

5 beds3 baths3,105 sq ft

523 Strawberry Ln, Ashland, OR 97520

Property at 75 Wimer St, Ashland, OR 97520, 5 beds, 5 baths

$759,000

5 beds5 baths1,616 sq ft

75 Wimer St, Ashland, OR 97520

Property at 4567 Old Highway 99 S, Ashland, OR 97520, 5 beds, 3 baths

$1,175,000

5 beds3 baths4,918 sq ft

4567 Old Highway 99 S, Ashland, OR 97520

Property at 1440 E Nevada St, Ashland, OR 97520, 5 beds, 4.5 baths

$3,750,000

5 beds4.5 baths5,002 sq ft

1440 E Nevada St, Ashland, OR 97520

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Discover flexible living and income potential in this inviting home with an attached apartment. The 1,735-square-foot main residence features 2.5 bathrooms, a desirable main-floor primary bedroom, and two additional bedrooms upstairs. Distinctive leathered granite countertops elevate the kitchen, while a mini-split heating/cooling system and solar panels add year-round comfort and efficiency. The attached two-bedroom, one-bath apartment includes a compact kitchen--ideal for rental income, guests, or multigenerational living. Outside, enjoy a gazebo and garden beds, plus a city-maintained neighborhood playground nearby.

$600,000

5 beds3.5 baths2,517 sq ft

305 Davidson Way, Talent, OR 97540

Gazebo • Garden beds • Solar panels

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
A rare opportunity to own a distinctive Frank Clark-designed home in desirable East Medford! Built in 1936, this remarkable 4,283 sq ft residence offers 5 bedrooms, 3 bathrooms, and an impressive blend of timeless character and spacious living. Set on a beautifully established . 39-acre lot, the property features mature landscaping, inviting outdoor spaces, and a private gated swimming pool. Inside, you'll find generous living areas with exposed beams, wood floors, multiple fireplaces, unique architectural details, abundant natural light, and a spacious recreation room. The home's distinctive character is found throughout, creating spaces that feel both grand and welcoming. Ideally located

$850,000

5 beds3 baths4,283 sq ft

1906 E Main St, Medford, OR 97504

Wood floors • Exposed beams • Mature landscaping

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Exceptional East Medford luxury estate offering grand views & refined living! Beautiful entry with custom solid-wood doors, volume ceiling, hand-carved banister, Brazilian cherry floors & travertine/marble inlays. Chef's kitchen features commercial-grade Thermador appliances, 6-burner gas range/griddle, double ovens, Wolf induction cooktop, exquisite quartzite island, walk-in pantry, dry bar & wine fridge. New lighting, interior/exterior paint, HVAC, tankless water heater & slider doors. The fully renovated primary suite boasts panoramic view windows, double-sided fireplace, soaking tub, dual-head shower & walk-in closet. Multiple ensuite bedrooms + main-level

$1,399,000

5 beds4 baths5,250 sq ft

108 Monterey Dr, Medford, OR 97504

Hand-carved banister • Volume ceiling • 6-burner gas range

ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Country Setting & City Light Views! Beautifully updated home blends modern comfort without losing the charm of its era. Spacious rooms, wide hallways & an abundance of natural light. Bright entry, generous living & dining areas & multiple fireplaces. Main-level bedrooms include a primary featuring dual vanities separated by an enclosed shower & toilet area. Spacious kitchen w/ separate small deck, easy for evening bbqing & casual dining Functional layout w/ large pantry closet & half bath by attached garage entry. Downstairs, you'll find multiple bonus rooms for play, entertaining or study, 3 more beds, full bath w/ tub & shower, plus patio. A

$789,000

5 beds3.5 baths4,357 sq ft

783 S Stage Rd, Medford, OR 97501

Multiple fireplaces • City light views • Spacious kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Almost 2,300 square feet of space, a large yard and a long list of updates make this 5 bedroom, 2.5 bath home one to see! The main level offers an open floor plan with a separate living room and an oversized great room that serves as the centerpiece of the home. Surrounded by windows, the great room is filled with natural light with plenty of space for entertaining. Extensive updates include new interior paint, a recently painted exterior, new roof, windows, water heater, sewer line, skylights and stove. The home features split-zone heating and cooling with new upstairs A/C unit and smart thermostats. Updated bathrooms, new ceiling fans, lighting and fixtures and more modern touches through

$487,500

5 beds2.5 baths2,271 sq ft

1825 Hybiscus St, Medford, OR 97504

Open floor plan • Natural light • Extensive updates

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Ashland, OR
Welcome to 1459 Highcrest! Situated on a beautiful . 8-acre lot in a wonderful neighborhood, this spacious 5-bedroom, 4-bath home offers a peaceful, park-like setting. Step onto the large back deck and take in beautiful city views, incredible sunsets, and bright stars at night--a perfect setting for relaxing or entertaining. Inside, you'll find a spacious kitchen with a large pantry, along with both a living room and family room. The primary bedroom features a walk-in closet, while the private, partially fenced backyard adds to the sense of space and seclusion. Many trees, including apple trees and a large walnut tree, add even more charm. Additional usable land provides space to explore a

$574,999

5 beds4 baths3,204 sq ft

1459 Highcrest Dr, Medford, OR 97504

Large back deck • Private backyard • Apple trees

Property at 841 W 11th St, Medford, OR 97501, 5 beds, 2 baths

$320,000

5 beds2 baths1,400 sq ft

841 W 11th St, Medford, OR 97501

Property at Undisclosed address, Medford, OR 97501, 5 beds, 4 baths

$440,000

5 beds4 baths2,344 sq ft

Undisclosed address, Medford, OR 97501

Property at 1544 Satellite Dr, Medford, OR 97504, 5 beds, 3.5 baths

$1,100,000

5 beds3.5 baths4,452 sq ft

1544 Satellite Dr, Medford, OR 97504

Property at 402 Boardman St, Medford, OR 97501, 5 beds, 2.5 baths

$375,000

5 beds2.5 baths2,192 sq ft

402 Boardman St, Medford, OR 97501

Property at 2470 Herrington Way, Medford, OR 97504, 5 beds, 2.5 baths

$512,000

5 beds2.5 baths2,368 sq ft

2470 Herrington Way, Medford, OR 97504

Property at 6085 Adams Rd, Talent, OR 97540, 5 beds, 4.5 baths

$1,025,000

5 beds4.5 baths3,412 sq ft

6085 Adams Rd, Talent, OR 97540

Property at 1491 Montclair Ter, Medford, OR 97504, 5 beds, 4.5 baths

$2,000,000

5 beds4.5 baths6,231 sq ft

1491 Montclair Ter, Medford, OR 97504

Property at 2630 Kerrisdale Ridge Dr, Medford, OR 97504, 5 beds, 3.5 baths

$950,000

5 beds3.5 baths4,369 sq ft

2630 Kerrisdale Ridge Dr, Medford, OR 97504

Property at 24041 Highway 140, Eagle Point, OR 97524, 5 beds, 4 baths

$989,000

5 beds4 baths5,223 sq ft

24041 Highway 140, Eagle Point, OR 97524

Property at 502 S B St, Phoenix, OR 97535, 5 beds, 3 baths

$450,000

5 beds3 baths2,582 sq ft

502 S B St, Phoenix, OR 97535

Property at 50 Mariposa Ter, Medford, OR 97504, 5 beds, 3.5 baths

$1,395,000

5 beds3.5 baths4,353 sq ft

50 Mariposa Ter, Medford, OR 97504

Property at 2583 Oak View Cir, Medford, OR 97504, 5 beds, 3.5 baths

$1,285,000

5 beds3.5 baths4,189 sq ft

2583 Oak View Cir, Medford, OR 97504

Property at 2361 Kings Hwy, Medford, OR 97501, 5 beds, 2 baths

$895,000

5 beds2 baths2,565 sq ft

2361 Kings Hwy, Medford, OR 97501

Property at 214 N Peach St, Medford, OR 97501, 5 beds, 3 baths

$395,000

5 beds3 baths2,124 sq ft

214 N Peach St, Medford, OR 97501

5 Bedroom Homes for Sale in Ashland

There are currently 17 5 bedroom homes in Ashland. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Ashland stay on the market for 79 days and receive 1 offers. Popular neighborhoods include East Ashland, Central Ashland, South Ashland, Mountain Meadows, and Lithia Park. This map is refreshed with the newest listings in Ashland every 15 minutes.

In the past month, 38 homes have been sold in Ashland. In addition to houses in Ashland, there were also 23 condos, 15 townhouses, and 9 multi-family units for sale in Ashland last month. Ashland is a moderately walkable city in Jackson County with a Walk Score of 55. Ashland is home to approximately 19,600 people and 9,047 jobs. Find your dream home in Ashland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Ashland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Ashland. Our Ashland real estate stats and trends will give you more information about home buying and selling trends in Ashland. If you're looking to sell your home in the Ashland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Ashland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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