Winchester bay Real Estate Search

Winchester bay Historical Properties for Sale

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Newest Winchester bay Historical Properties for Sale

$515,000
3 Beds 2 Baths 636798502 MLS
Originally built in 1904, this timeless multi-level home blends classic character with tasteful modern updates, offering 3 bedrooms and 2 bathroom. Rich in charm and thoughtfully enhanced, the home features a beautifully remodeled kitchen with striking black cabinetry, stainless steel appliances, a copper farmhouse sink with coordinating copper accents, and stunning live-edge granite countertops. The spacious interior offers abundant storage throughout, a beautiful brick fireplace that serves as the centerpiece of the living area, and a ductless mini-split for efficient year-round comfort. An attached tandem garage provides additional space for parking, storage, or a workshop. Positioned on three tax lots totaling approximately 0.54 acres, this elevated, estate-like property enjoys breathtaking bay views from both levels. The backyard provides plenty of space to relax, garden, or entertain and is home to mature apple and plum trees, along with wild blackberries that add to the property's charm. Outside, the versatile three-bay shop offers endless possibilities for hobbies, storage, or workspace, while ample RV and boat parking provides room for all your recreational equipment. With commercial zoning, this property presents potential to operate a business from home, or simply enjoy the flexibility this unique zoning provides. As an added bonus, the seller is including a beautiful teakwood king-size bed, as well as a set of custom wrought iron entry gates that have not yet been installed, allowing the new owner the opportunity to incorporate them into the property as they choose. Offering historic charm, modern updates, incredible views, and exceptional versatility, this is a truly one-of-a-kind property ready for its next chapter.

228 S EMPIRE BLVD, Coos Bay

$464,999
3 Beds 1 Baths 201840165 MLS
OPEN HOUSE 8/15 & 8/16 11AM-1PMThis 3-bedroom, 1-bath Craftsman bungalow has undergone a down-to-the-studs renovation, pairing charm and comfort. Classic Portland character, completely reimagined for modern living. Step inside to 1,254 square feet of bright, inviting living space where warm wood tones, abundant natural light and a clean, contemporary palette create a home that feels modern without losing its character. An open, easy-flowing layout connects the main living spaces, while carefully selected finishes—including rich wood details, matte black accents and distinctive green tile—bring warmth and personality throughout. A refreshed laundry room, along with cleverly integrated storage throughout the home, makes efficient use of every square foot. The renovation extends well beyond what you can see. New electrical, plumbing, HVAC, insulation, framing, windows, doors and flooring provide the peace of mind of a thoroughly updated home, while a new roof adds another major improvement for years to come. Additional lower-level space provides even more flexibility for storage and everyday use. Outside, the home maintains its classic bungalow presence with a gabled roofline and welcoming covered entry, and a large tool shed offering valuable space for tools, projects, bikes and outdoor equipment. Set in an established SE Portland neighborhood with convenient access to parks, neighborhood shops and the rest of the city, this home offers something increasingly difficult to find: the character of a Portland bungalow, the thoughtful details of a custom renovation, and the confidence of knowing the work went far deeper than the finishes.Yard in photos is not an exact depiction of finished landscaping.

4930 SE 59th AVE, Portland

$899,000
4 Beds 3 Baths 686240177 MLS
An extraordinary opportunity to own a meticulously restored luxury residence on the National Register of Historic Places, where timeless architecture meets modern sophistication. Showcasing over $300,000 in high-quality renovations, this turnkey home has been thoughtfully reimagined with exceptional craftsmanship while preserving the character and charm that make historic homes so desirable. Every improvement was carefully designed to enhance today's lifestyle without compromising the home's architectural integrity. The elegant main residence offers beautifully updated living spaces filled with natural light, refined finishes, & a seamless blend of historic details & contemporary comfort. From the restored craftsmanship to the carefully selected materials & designer touches throughout, every inch reflects pride of ownership & attention to detail. Adding tremendous value is the fully permitted ADU, creating exceptional flexibility for income-producing rental opportunities, multigenerational living, extended guest accommodations, or a private executive office or creative studio. Whether you're seeking supplemental income or versatile living options, this space significantly enhances the property's long-term value. Step outside to an entertainer's backyard, offering space for outdoor dining, relaxing, & gathering with family & friends. Thoughtfully landscaped & designed for year-round enjoyment, this private retreat is ideal for hosting everything from intimate evenings to large celebrations. Perfectly situated in Portland's coveted Alphabet District, just moments from the vibrant energy of NW 23rd Avenue, you'll enjoy award-winning restaurants, boutique shopping, neighborhood cafés, parks, galleries, & convenient access to some of the city's most beloved destinations. This walkable location combines urban convenience with classic neighborhood charm. It's a must see! [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10207093]

224 NW 20TH AVE, Portland

$2,900,000
5 Beds 3 Baths 508062474 MLS
Built in 1929 and offered for only the second time in more than 80 years, 4061 SW Greenleaf Drive is a rare English-style residence whose history has been preserved while every element has been thoughtfully reimagined for modern life. Set on one-third of an acre in Portland’s coveted Greenleaf Hills, the 5,151-square-foot home underwent a comprehensive 15-month transformation led by GEN Architects, Amanda Klash Interiors, and Mooney Construction. A new primary wing and garage were added, while the interiors, plumbing, electrical, and mechanical systems were completely renewed. The vision was exacting: to open and modernize the home without compromising the warmth, craftsmanship, or integrity of its original architecture. That attention to detail is beautifully woven throughout. Custom inset cabinetry, Waterworks fixtures, a La Cornue range with a custom metal hood, and Carrara marble create a refined yet welcoming kitchen. Two interior wood-burning fireplaces, integrated Sonos audio, dual-zone climate systems, and carefully selected finishes bring comfort and ease to every room. Outside, the grounds were fully redesigned with layered landscaping, irrigation, a fountain, outdoor lighting, and a private rear patio anchored by a third wood-burning fireplace. Greenleaf is known for its peaceful, low-traffic streets and long-term homeowners, offering exceptional privacy just minutes from downtown and Northwest 23rd. From the front door, walk toward the zoo, accessed by nearby trailheads, or set out for a run along the beloved Fairmount Loop. This is more than a beautifully renovated home. The English-style residence possesses the character that can only be acquired over time: a gracious silhouette, enduring craftsmanship, substantial rooms, and an unmistakable sense of permanence. It is a storied Portland residence, thoughtfully transformed for its next generation!

4061 SW GREENLEAF DR, Portland

$299,000
5 Beds 3 Baths 362917768 MLS
Opportunities like this don't come around often. This unique property features a spacious 2,490-square-foot main home offering 4 bedrooms and 2 bathrooms, plus a detached 486-square-foot cottage complete with its own bedroom, bathroom, kitchen, and living area. Whether you're looking for multi-generational living, space for guests, or the opportunity to generate passive rental income, this property offers exceptional versatility. Built in 1900, the main home blends timeless character with thoughtful updates. Step through the front door into a freshly painted entry and admire the soaring ceilings, elegant crown molding, updated flooring, and bright living spaces. The main level offers a comfortable living room, dining room, kitchen, laundry, full bathroom, and primary bedroom for convenient main-level living. Upstairs, an elegant staircase leads to three additional bedrooms and a second full bathroom. Hardwood floors are ready for your personal touch, while the spacious bedrooms offer flexibility for family, guests, or a home office. Downstairs, the basement provides abundant space for storage, utilities, or future possibilities. The detached cottage provides a complete second living space with its own kitchen, living room, bedroom, and bathroom, while the detached garage adds covered parking and even more storage. Whether you're drawn to the historic charm, thoughtful updates, or the flexibility of two separate living spaces totaling nearly 3,000 square feet, this property is ready for its next chapter.

130 SW 2ND ST, Pilot Rock

$515,000
4 Beds 3 Baths 317414313 MLS
Outstanding development opportunity or make it your own! The property is zoned RM1 and is primed for row housing or low density multi family units. Nestled in the heart of the sought-after Montavilla neighborhood in SE Portland, this large and inviting Craftsman bungalow is brimming with character and original charm. Sitting on a generous corner lot, the home offers a spacious yard perfect for outdoor enjoyment, complete with a detached 2-car garage and a cozy fire pit. Step inside to discover the timeless beauty of oak hardwood floors that flow throughout the main level. Original wood double-hung windows allow natural light to pour in, highlighting the rich details of the home. The formal entryway welcomes you with a large coat closet, and the spacious living room offers a cozy spot to unwind. The heart of the home is the elegant dining room, featuring stunning box beam ceilings, built-in bar and storage, and classic crown molding that adds warmth and sophistication.The kitchen is well-appointed with granite countertops, stainless steel appliances, and a charming breakfast nook. A bathroom on each floor adds convenience, and the main floor is home to two generous bedrooms with fir wood floors.Upstairs, the massive primary bedroom offers plenty of space and privacy, with a full bathroom just down the hallway. The full basement provides even more living space, including a large family room, a utility room with laundry, a bathroom, and a kitchenette—ideal for multi-generational living or a flexible living setup.Though the home is in need of some rehab and upgrades, the potential here is endless. Located just minutes from Montavilla's vibrant shops, cafes, and parks, this charming Craftsman is the perfect blend of old-world character and modern potential. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10013126]

8921 SE WASHINGTON ST, Portland

$259,000
237231838 MLS
Rare Commercial Business Opportunity, Ruth Lane Farms in Historic Downtown Joseph is looking for its next owner!Step into a flourishing commercial boutique where historic architectural elegance meets curated retail enchantment. Located directly on high-foot-traffic Main Street in the heart of Joseph, Oregon,a premier Pacific Northwest destination framed by the Wallowa Mountains. Ruth Lane Farms is now available as a turnkey business opportunity.From the moment customers cross the threshold of this stunning historic building, they leave the everyday behind and experience the magic of Ruth Lane Farm, Known for its immersive visual displays, whimsical atmosphere, and artfully staged home decor, this beloved boutique has cultivated a devoted following of locals, seasonal tourists, and design enthusiasts alike. Situated in a historic building featuring rich architectural character, high ceilings, expansive street-facing display windows, and prominent signage visibility. Impeccably branded identity with established inventory, loyal customer base, and strong repeat customers. Driven by Joseph's thriving arts, tourism, and outdoor recreation. Thoughtfully designed space that creates a multi-sensory shopping experience maximizing space efficiency, visual storytelling, and retail display opportunities. Ample space for expanding product lines, hosting private boutique events and seasonal workshops. Whether you are looking to step into an established, turnkey business or bring your own creative retail dream to an historic downtown setting, Ruth Lane Farms offers an extraordinary foundation in one of Eastern Oregon's most vibrant communities.Inquire today for full financial details, lease structure, inventory inclusion options, and private walkthrough.

10 S MAIN ST, Joseph

$349,000
633551557 MLS
Great opportunity to own 2 house on nearly a half acre in North Bend on separate yet adjacent tax lots. The zoning is RM and R5, so many possibilities to add more units. Tiny homes are allowed in North Bend and with a lot this big there are plenty of rooms to add tiny homes and increase your income. Talk to the city planner with your ideas and plans. Square footage of both homes equal 2,218 Sq. Ft and are 3 bedroom & 3 bathrooms. 2521 Everett is a 1940's Cottage, very private, set back with trees in front and back. 900 Sq. Ft. plus a full basement with separate access. 2 Large porches on the front and back. One bedroom with walk-in closet, spiral staircase leads you to a bonus loft area. A large bathroom with a closet. This one is tenant occupied and currently renter for $1,200 per month and tenant pays their own utilities. The lower level is a huge concrete basement that can be used for additional living spaces or converted back into a large garage/work area. 2519 Everett is a well maintained 1973 manufactured home with a great rental history. 1,368 Sq. Ft., originally a 3 bed/2 bath. It has been conveniently separated by a privacy wall and now the front is a 1 bed/1 bath with a large living room, bar area, kitchen, laundry and a bonus area that makes a great dining room or office area. This section of the manufactured home rented for $1,200 per month. The Seller decided not to rent it out to leave more options for a prospective Buyer. The back has a separate entrance (sliding door), private patio, living room, 1 bedroom, 1 bath and makes a great mother-in-law unit, care-giver space or guest space. This unit and the attached unit share the same water/sewer and electric meter and is paid by the owner. This is a great neighborhood and is in desirable Hillcrest Elementary school district. Shopping & Restaurants just a few blocks away. Room for the Big Boy toys, RV's, ATV's and everything else.

2519 Everett AVE, North Bend

$820,000
3 Beds 2 Baths 320717502 MLS
Welcome to Broadmoor's Historic Farmhouse. Timeless excellence restored and reimagined. Poised atop the gentle slope of the manicured .23-acre lot, the vision of the home takes you back in time. The covered front porch invites you to take a seat, slow down and gaze across the lawn. Each finish in this home was carefully curated and is elegantly showcased by sunlight. Original and reclaimed Red Oak and Douglas Fir floors have been preserved on each level. Walking through the home you will encounter wainscoting, hidden built-ins, comprehensive millwork and no lack of character. A 2024 redesign focused on the kitchen installing new quartz counters and high end Smeg and Fisher & Paykel appliances. Sophisticated craftsmanship is showcased in each of the remodeled bathrooms. Upstairs the primary suite truly is a retreat. With the dual wardrobes, a Fleurco soaking tub, and heated marble floors, the ensuite bath leaves nothing to be desired. Two other spacious bedrooms can be found on the second level. Each light fixture, each doorknob, each cabinet pull, and every touch point was handpicked to create an immersive experience. The home has been extensively updated over the past 10 years including a 2015 re-pipe, 2015/2019 foundation rejuvenation, a 2019 re-wire, a 2019/2023 re-roof, 2023 Pella architectural windows and much more. Well over $300k has been invested to elevate the home. Beyond the cosmetics there are modern conveniences like the Nest thermostat, heated tile floors, and central AC. Offering an unmatched location near Raleigh Park, adjacent to Jesuit High School and close by New Seasons and the latest La Provence. Calling this property "Home" you can enjoy the harmony of the past and the present, every day.

7985 SW MAPLE DR, Portland

$599,000
3 Beds 3 Baths 422417786 MLS
This is what it looks like when a home is updated with quality and care without losing what made it special in the first place! Perched on Telegraph Hill with beautiful bay views, this 1912 home offers 3,456 square feet, two primary suites and the kind of craftsmanship and character that is increasingly hard to find.From the street, classic architecture, a beautifully fenced front yard and incredible curb appeal immediately set it apart. Inside, substantial improvements were made with quality in mind while preserving the character of the home. The kitchen was rebuilt from the studs with new cabinetry, granite countertops, hardwood floors, tile backsplash, stainless steel appliances and a large eat-in island. Bathrooms have been refreshed with updated vanities and fixtures, while new lighting, refinished walls and fresh paint brighten the home throughout.And there is A LOT of house here! Beyond the oversized living areas and two primary suites, you'll find a sunroom, separate den/office, large laundry room and additional lower-level space. The den/office offers potential for another bedroom with an adjoining walk-in closet, while the lower level creates possibilities for guests, hobbies, extended living or a future ADU configuration, subject to buyer verification and applicable approvals. The laundry room also offers potential for a second kitchen.Outside, enjoy a fully fenced yard, deck off the kitchen and patio above the garage with bay views. Finding this much space is one thing. Finding it with bay views, quality improvements, flexible living options and more than a century of preserved craftsmanship is another! This isn't a cookie-cutter remodel or a house you'll find another version of down the street. If you've been waiting for something truly different, don't overlook this one!

380 N 2ND CT, Coos Bay

$289,000
2 Beds 1 Baths 765620078 MLS
Welcome home to the perfect collision of timeless Craftsman character and unbeatable curb appeal. Nestled on a beautifully landscaped oversized lot, this charming home immediately draws you in with its mature greenery, inviting front sitting porch, brand-new roof, and classic architectural details that never go out of style. Step inside to discover a spacious living room filled with natural light streaming through updated vinyl windows, flowing seamlessly into the adjoining dining area to create a warm and welcoming space for everyday living or entertaining. Just beyond, you'll find a functional kitchen featuring a newly installed farmhouse sink, range, and plenty of space to make your own. The thoughtfully designed floor plan offers two generously sized bedrooms on the main level. The primary suite is a standout, complete with beautiful bay windows, a large walk-in closet, and private access to the oversized Jack-and-Jill bathroom. The second bedroom offers plenty of space for family, guests, or a home office, while the bathroom's dual access provides convenience from both the primary suite and the main living area. Need more room? The attached walk-in pantry and storage area adds incredible flexibility, while the basement offers abundant storage and exciting potential for future expansion. A large framed room is already in place and only needs an egress window to become a true third bedroom. The basement laundry area, shelving, and storage spaces have all been thoughtfully refreshed and are ready for their next owners. Outside, you'll find even more to love. Enjoy ample off-street parking, a detached garage, chicken coop, raised garden beds, and an expansive backyard filled with mature landscaping that creates a peaceful, park-like retreat—all while remaining conveniently located in town. If you've been searching for a home that perfectly blends historic charm, functional living, and room to grow, this is one you won't want to miss.

344 S 3RD ST, Athena

$560,500
3 Beds 2 Baths 646825280 MLS
3840 SW Patton Rd. | Southwest Portland Opportunity with Character, Cash Flow and Plenty of Deck Space-Tucked into the coveted Southwest hills, this 1921 home blends old Portland charm with real upside. To clarify, this is 2 separate living units. No interior stairwell. Originally a classic 2 bedroom, 1 bath main-level home, the property later added a separate lower-level living space with its own exterior access, creating a flexible setup that works well for owner-occupants, investors and multi-generational living.The main level offers approximately 1,150 square feet of living space, along with massive decks stretching across the entire backside of the home, about 600 square feet of outdoor living space perfect for morning coffee, evening wine, entertaining or just taking in the setting. The home’s NW cabin vibe and early-1900s farmhouse roots give it warmth, personality and a lot of possibilities.The lower level unit is approximately 950 square feet and is currently rented, providing a nice income stream that helps offset ownership costs. The current owner has also rented out the main level in the past, so the entire home has functioned as two separate rental units. That creates flexibility whether you are looking for a home with income potential, a setup for extended family, or an investment property with strong versatility.Priced well below much of what the Southwest hills has to offer, this is the kind of property that rewards vision. Set nicely amongst the tree's in a wonderfully natural setting within the city... just bring your inner English gardener goals and this home will fulfill your needs! Come & get it.

3840 SW PATTON RD, Portland

$1,395,000
4 Beds 3 Baths 371095164 MLS
Storybook English Cottage in Portland Heights. Beautifully restored & thoughtfully updated, this residence was designed by renowned architect Roscoe Hemenway & expertly built by Allison Dean. The home has been meticulously renovated between 2022 & 2025 with uncompromising attention to detail, seamlessly blending timeless character with today's modern luxuries. Privately sited on a beautifully landscaped .62-acre parcel, the home offers 3,833 SF of elegant living spaces, designer finishes, & exceptional indoor-outdoor living. The gracious main level features refinished hardwood floors, an elegant formal dining room, & a stunning designer kitchen with custom cabinetry, soapstone countertops, & Wolf, Thermador, Sub-Zero, & Asko appliances. The spacious living room is wrapped in French-paned windows overlooking enchanting gardens, while French doors open to an expansive entertaining deck & covered outdoor dining area with skylights & a dedicated gas line for year-round enjoyment. Flexible living includes four bedrooms, beautifully renovated baths, a media room, lower-level family room, game room, greenhouse, & abundant storage. The luxurious primary suite enjoys windows on three sides, multiple closets, & a spa-inspired ensuite bath. Meandering garden paths, lush mature landscaping, stone patios, & towering evergreens create the feeling of an English countryside estate just minutes from NW 23rd, Hillsdale, downtown Portland, & Portland Heights Park. Additional highlights include central A/C, designer lighting & fixtures throughout, extensive custom millwork, a newer roof, seismic upgrades with the home professionally strapped to its foundation, & countless high-end improvements. A true once-in-a-generation opportunity to purchase your very own storybook home. [Home Energy Score = 1. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10073592]

2700 SW ENGLISH LN, Portland

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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.