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Horses grazing in neighboring pastures. Elk wandering through the valley. Summer afternoons spent beside the pool. In the heart of May Valley, a gated entrance and circular drive introduce this beautifully renewed 4-bedroom home, set amid manicured grounds with a detached 2-bedroom, 2-bath ADU offering possibilities for extended living or rental income. Inside the main home, warm hardwoods lead through gracious formal rooms adorned with elegant columns and intricate millwork, where expansive windows draw the surrounding greenery into view. A fireside living room opens to the formal dining room, while beyond, a granite-appointed kitchen with 6-burner cooktop connects to an inviting family room beneath richly detailed coffered ceilings. Upstairs, the spacious primary suite offers a retreat of its own, with a fireplace and marble-clad bath featuring a jetted soaking tub. Outside, mature evergreens frame expansive lawns and the sparkling in-ground pool, where long summer days give way to evenings spent entertaining beneath the open sky. Extensive 2026 updates, a 3-car garage and RV parking complete this fully fenced acre, with Squak Mountain trails and downtown Issaquah just moments away.

4 Beds ⋅ 3 Baths ⋅ 2597930 MLS ⋅ FIRST LOOK Status

Horses grazing in neighboring pastures. Elk wandering through the valley. Summer afternoons spent beside the pool. In the heart of May Valley, a gated entrance and circular drive introduce this beautifully renewed 4-bedroom home, set amid manicured grounds with a detached 2-bedroom, 2-bath ADU offering possibilities for extended living or rental income. Inside the main home, warm hardwoods lead through gracious formal rooms adorned with elegant columns and intricate millwork, where expansive windows draw the surrounding greenery into view. A fireside living room opens to the formal dining room, while beyond, a granite-appointed kitchen with 6-burner cooktop connects to an inviting family room beneath richly detailed coffered ceilings. Upstairs, the spacious primary suite offers a retreat of its own, with a fireplace and marble-clad bath featuring a jetted soaking tub. Outside, mature evergreens frame expansive lawns and the sparkling in-ground pool, where long summer days give way to evenings spent entertaining beneath the open sky. Extensive 2026 updates, a 3-car garage and RV parking complete this fully fenced acre, with Squak Mountain trails and downtown Issaquah just moments away.

21620 SE May Valley Road, Issaquah

Listing Broker: Windermere Real Estate/East; Karl Lindor; 206-890-8227; karl@windermere.com

$1,100,000

An expression of tranquility, this captivating Issaquah retreat on nearly 2 acres delivers the goods. Thoughtful design and quality craftsmanship come alive beneath soaring ceilings, while natural light moves throughout and nature joins the conversation from almost every view. Living, dining and kitchen spaces unfold with an easy flow that invites gatherings, dinners that linger or simply a little room to breathe. Owners completely rebuilt in 2010 and created and amazing sanctuary that speaks to the senses with 2,200 square feet of living space offering 3 bedrooms, 1.75 baths, an interior loft and a small finished lower-level area for hobbies, fitness or storage. Recent updates include new roof, fresh exterior paint and updated bathrooms. Home is also wired for a generator. Tastefully presented and impeccably cared for, this amazing oasis will inspire those seeking a turn-key solution. A garden to tend, the trickle of a seasonal creek and occasional visits from passing deer are all part of the escape. This is a home with soul, grounded in its surroundings. Gather, unwind and escape. Find calm. Feel at home.

3 Beds ⋅ 2 Baths ⋅ 2591856 MLS ⋅ PENDING Status

An expression of tranquility, this captivating Issaquah retreat on nearly 2 acres delivers the goods. Thoughtful design and quality craftsmanship come alive beneath soaring ceilings, while natural light moves throughout and nature joins the conversation from almost every view. Living, dining and kitchen spaces unfold with an easy flow that invites gatherings, dinners that linger or simply a little room to breathe. Owners completely rebuilt in 2010 and created and amazing sanctuary that speaks to the senses with 2,200 square feet of living space offering 3 bedrooms, 1.75 baths, an interior loft and a small finished lower-level area for hobbies, fitness or storage. Recent updates include new roof, fresh exterior paint and updated bathrooms. Home is also wired for a generator. Tastefully presented and impeccably cared for, this amazing oasis will inspire those seeking a turn-key solution. A garden to tend, the trickle of a seasonal creek and occasional visits from passing deer are all part of the escape. This is a home with soul, grounded in its surroundings. Gather, unwind and escape. Find calm. Feel at home.

19150 SE May Valley Road, Issaquah

Listing Broker: Windermere Real Estate/East; Jess Beyers; 206-612-7868; thebeyersteam@windermere.com

$925,000

A RARE OFFERING IN MAY VALLEY! This bucolic estate is ready to begin a new story. Located on 1.65 acres in a private, gated community in the coveted Issaquah School District. Move-in ready, the home has been thoughtfully updated with new lighting, kitchen appliances and countertops, bathroom vanities, toilets, mirrors, closet doors, and beautiful, durable LVP flooring throughout. A new roof and exterior paint add peace of mind and complete the exterior transformation. The versatile property is flat, cleared & useable. At the heart of the estate is a remarkable 60' x 80' barn that has a history longer than most of us. It is solid & ready to be put back into work whether it be for horses, livestock, cars, wood shop, studio or memorable grand events. The pasture can be cross-fenced for the horses & the garden is already fenced & waiting to be planted. Walk or ride to Squak Mtn trailhead ACROSS THE STREET & access 13 miles of hiking trails & six miles of horse trails! This home offers the best of both worlds—the serenity of country living with the convenience of being just minutes from historic Old Town Issaquah. Whether you envision an equestrian retreat, hobby farm, creative compound, or simply a private estate with room to grow, this is a truly exceptional opportunity to begin the next story of an extraordinary property.

3 Beds ⋅ 2 Baths ⋅ 2583691 MLS ⋅ PENDING Status

A RARE OFFERING IN MAY VALLEY! This bucolic estate is ready to begin a new story. Located on 1.65 acres in a private, gated community in the coveted Issaquah School District. Move-in ready, the home has been thoughtfully updated with new lighting, kitchen appliances and countertops, bathroom vanities, toilets, mirrors, closet doors, and beautiful, durable LVP flooring throughout. A new roof and exterior paint add peace of mind and complete the exterior transformation. The versatile property is flat, cleared & useable. At the heart of the estate is a remarkable 60' x 80' barn that has a history longer than most of us. It is solid & ready to be put back into work whether it be for horses, livestock, cars, wood shop, studio or memorable grand events. The pasture can be cross-fenced for the horses & the garden is already fenced & waiting to be planted. Walk or ride to Squak Mtn trailhead ACROSS THE STREET & access 13 miles of hiking trails & six miles of horse trails! This home offers the best of both worlds—the serenity of country living with the convenience of being just minutes from historic Old Town Issaquah. Whether you envision an equestrian retreat, hobby farm, creative compound, or simply a private estate with room to grow, this is a truly exceptional opportunity to begin the next story of an extraordinary property.

13714 217th Avenue SE, Issaquah

Listing Broker: John L. Scott, Inc.; Angela Nebeker; 425-269-9550; angelanebeker@johnlscott.com

$980,000

Nestled in a peaceful forest setting within the highly regarded Issaquah School District, this one-of-a-kind Tudor castle retreat blends timeless character with modern comfort. Stone-and-brick inspired exterior, built-in bookshelves, and distinctive architectural details create a warm, storybook atmosphere throughout. Inside, you'll find new carpets, a hidden powder room behind a bookshelf in the Craftsman library, a cozy fireplace, a spa-like clawfoot tub perfect for relaxing and a new electric heat pump which provides efficient heating and cooling. Outside, enjoy your own private woodland escape with an outdoor fire pit, sauna, and plenty of space to unwind. The spacious garage offers room for vehicles, outdoor gear, hobbies, and storage, while nearby trails provide easy access to the Pacific Northwest lifestyle. A standout feature is the tower deck, where you can take in forest views, watch meteor showers, and on clear nights, even catch the northern lights. Drift off to the sounds of nature, from distant coyotes to evening frogs, and experience the tranquility of this unique setting. Offering the charm of a private woodland castle with convenient access to Eastside amenities, this exceptional home is truly unlike anything else

2 Beds ⋅ 3 Baths ⋅ 2531653 MLS ⋅ SOLD Status

Nestled in a peaceful forest setting within the highly regarded Issaquah School District, this one-of-a-kind Tudor castle retreat blends timeless character with modern comfort. Stone-and-brick inspired exterior, built-in bookshelves, and distinctive architectural details create a warm, storybook atmosphere throughout. Inside, you'll find new carpets, a hidden powder room behind a bookshelf in the Craftsman library, a cozy fireplace, a spa-like clawfoot tub perfect for relaxing and a new electric heat pump which provides efficient heating and cooling. Outside, enjoy your own private woodland escape with an outdoor fire pit, sauna, and plenty of space to unwind. The spacious garage offers room for vehicles, outdoor gear, hobbies, and storage, while nearby trails provide easy access to the Pacific Northwest lifestyle. A standout feature is the tower deck, where you can take in forest views, watch meteor showers, and on clear nights, even catch the northern lights. Drift off to the sounds of nature, from distant coyotes to evening frogs, and experience the tranquility of this unique setting. Offering the charm of a private woodland castle with convenient access to Eastside amenities, this exceptional home is truly unlike anything else

19027 SE May Valley Road, Issaquah

Listing Broker: Windermere Bellevue Commons; Igor Pechkovskyi; ; Selling Office: Keller Williams Eastside.

$775,000

Discover a rare retreat in Issaquah where privacy, space & modern comfort come together on over half an acre. Thoughtfully updated, this home showcases a chef-inspired open kitchen, spa-like bathrooms & a light-filled open layout perfect for both everyday living & entertaining. Enjoy seamless indoor-outdoor living w/expansive patios & a covered BBQ area designed for memorable gatherings. An attached garage plus a detached shop provide exceptional storage and workspace, while the finished studio above the shop offers flexible options for a home office, gym, or creative escape. Recent upgrades include a newer heat pump & HVAC system for efficient, year-round comfort. Ideally located just minutes from hiking trails, parks, shopping, & dining.

4 Beds ⋅ 3 Baths ⋅ 2461511 MLS ⋅ SOLD Status

Discover a rare retreat in Issaquah where privacy, space & modern comfort come together on over half an acre. Thoughtfully updated, this home showcases a chef-inspired open kitchen, spa-like bathrooms & a light-filled open layout perfect for both everyday living & entertaining. Enjoy seamless indoor-outdoor living w/expansive patios & a covered BBQ area designed for memorable gatherings. An attached garage plus a detached shop provide exceptional storage and workspace, while the finished studio above the shop offers flexible options for a home office, gym, or creative escape. Recent upgrades include a newer heat pump & HVAC system for efficient, year-round comfort. Ideally located just minutes from hiking trails, parks, shopping, & dining.

19134 SE May Valley Road, Issaquah

Listing Broker: KW Lake Washington So; Melissa Hudson; ; Selling Office: John L. Scott Orting.

$2,505,000

Rare 11.8-Acre Hobby Farm in Scenic Issaquah! A truly one-of-a-kind property offering the perfect setup for a home business, equestrian lifestyle, or full hobby farm living. The beautifully updated home features a sun-drenched great room, chef’s kitchen with 48inch range, granite counters, and an elegant marble 5-piece primary suite. Outside, enjoy a 2,592 sq ft multi-use outbuilding (once used as a winery), 6-stall barn, fenced pastures, sport court, shop, and 3-car garage with EV charging. Complete with water filtration system, automatic generator, and endless possibilities. Located just 1 mile from Squak Mt trail access and minutes to downtown Issaquah, this is a rare opportunity to live, work, and play surrounded by nature.

3 Beds ⋅ 3 Baths ⋅ 2391341 MLS ⋅ SOLD Status

Rare 11.8-Acre Hobby Farm in Scenic Issaquah! A truly one-of-a-kind property offering the perfect setup for a home business, equestrian lifestyle, or full hobby farm living. The beautifully updated home features a sun-drenched great room, chef’s kitchen with 48inch range, granite counters, and an elegant marble 5-piece primary suite. Outside, enjoy a 2,592 sq ft multi-use outbuilding (once used as a winery), 6-stall barn, fenced pastures, sport court, shop, and 3-car garage with EV charging. Complete with water filtration system, automatic generator, and endless possibilities. Located just 1 mile from Squak Mt trail access and minutes to downtown Issaquah, this is a rare opportunity to live, work, and play surrounded by nature.

13228 202nd Avenue SE, Issaquah

Listing Broker: RE/MAX Northwest; Laura M. Ford; ; Selling Office: Realogics Sotheby's Int'l Rlty.

$1,350,000

Three dwellings offering an endless possibility of uses. Primary home is ranch-style with three beds + den/office, two inviting living spaces, vaulted ceiling & striking fireplace, primary suite with walk-in closet & en-suite, charming courtyard, & two-car garage. New kitchen, flooring, & roof. Upper unit in guest home features two-beds, two-baths, laundry, & attached garage + carport. Lower unit includes impressive library with one-bed, kitchenette, French doors, high ceilings, & custom built-ins perfect for book lovers. 1.6 acre property offers exceptional privacy, sitting high off the street, gated, & accessed via a private road. Located in May Valley moments to hiking trails & Issaquah amenities. Award winning Issaquah schools!

5 Beds ⋅ 6 Baths ⋅ 2305492 MLS ⋅ SOLD Status

Three dwellings offering an endless possibility of uses. Primary home is ranch-style with three beds + den/office, two inviting living spaces, vaulted ceiling & striking fireplace, primary suite with walk-in closet & en-suite, charming courtyard, & two-car garage. New kitchen, flooring, & roof. Upper unit in guest home features two-beds, two-baths, laundry, & attached garage + carport. Lower unit includes impressive library with one-bed, kitchenette, French doors, high ceilings, & custom built-ins perfect for book lovers. 1.6 acre property offers exceptional privacy, sitting high off the street, gated, & accessed via a private road. Located in May Valley moments to hiking trails & Issaquah amenities. Award winning Issaquah schools!

11109 Renton Issaquah Road SE, Issaquah

Listing Broker: Ensemble; Chris Conroy; ; Selling Office: Skyline Properties, Inc..

$1,450,000

Extremely sought after, 4 BDRM one-level living in South Issaquah. Situated in the HIGHLY desirable Sunset Valley Farms Community. This pristine gem provides tranquility in a peaceful and picturesque environment. You’ll notice it’s stately elegance as soon as you pull up the beautiful tree lined S curve driveway! Lives like a desired rambler w/a 3-car garage below, EV ready! Updated tastefully throughout with gleaming hardwoods, newer bathrooms and a gorgeous new kitchen featuring a quartz waterfall island. 3 fireplaces, a lovely bonus room & unique layout provide a great space for gatherings and guests. Enjoy relaxing evenings in your hot tub located just off the primary suite, you will LOVE this home! Newer HVAC+AC & an 85" OLED TV!!!

4 Beds ⋅ 2 Baths ⋅ 2303425 MLS ⋅ SOLD Status

Extremely sought after, 4 BDRM one-level living in South Issaquah. Situated in the HIGHLY desirable Sunset Valley Farms Community. This pristine gem provides tranquility in a peaceful and picturesque environment. You’ll notice it’s stately elegance as soon as you pull up the beautiful tree lined S curve driveway! Lives like a desired rambler w/a 3-car garage below, EV ready! Updated tastefully throughout with gleaming hardwoods, newer bathrooms and a gorgeous new kitchen featuring a quartz waterfall island. 3 fireplaces, a lovely bonus room & unique layout provide a great space for gatherings and guests. Enjoy relaxing evenings in your hot tub located just off the primary suite, you will LOVE this home! Newer HVAC+AC & an 85" OLED TV!!!

21003 SE 138th Place, Issaquah

Listing Broker: COMPASS; Cindy Kelly; ; Selling Office: COMPASS.

$575,000

Charming 2BD 1BA cottage in a private country setting but close to downtown Issaquah and Renton (10 minutes to either). Extra large 693 Sq Ft double tandem garage/workshop. Home has a fully fenced back yard, sits back off the country road and surrounded with trees and flowers. The adorable cottage has hardwood floors throughout, a full bath with shower and tub and a stack washer and dryer. Large detached 2 car garage and workshop with several outbuildings for storage. Issaquah School District. Centrally located to I-90 and 405 and close to an abundance of hiking and biking trails.

2 Beds ⋅ 1 Baths ⋅ 2280917 MLS ⋅ SOLD Status

Charming 2BD 1BA cottage in a private country setting but close to downtown Issaquah and Renton (10 minutes to either). Extra large 693 Sq Ft double tandem garage/workshop. Home has a fully fenced back yard, sits back off the country road and surrounded with trees and flowers. The adorable cottage has hardwood floors throughout, a full bath with shower and tub and a stack washer and dryer. Large detached 2 car garage and workshop with several outbuildings for storage. Issaquah School District. Centrally located to I-90 and 405 and close to an abundance of hiking and biking trails.

18423 SE May Valley Road, Issaquah

Listing Broker: North Pacific Properties; Chris Toppen; ; Selling Office: Windermere RE/Capitol Hill,Inc.

$1,999,950

Luxurious & rare one-level-living on a grand scale! Experience the ultimate peaceful, private lifestyle in this spectacular estate setting. The expansive patio is truly exceptional - perfect for hosting gatherings & soirées under the stars. A sports court with night lighting & sprawling, level, manicured yard provide endless opportunities for recreation & entertainment. This nearly 5 acre oasis offers an abundance of space for gardening, pets, RV's, nature walks & everyday play. Thoughtfully designed interior with chef's kitchen, grand dining & living rooms, large family room, multiple flex rooms, office, 5 bds, picturesque walls of windows, 3 car garage & so much more! Award winning Issaquah Schools and easy drive to amenities & freeways.

5 Beds ⋅ 4 Baths ⋅ 2241187 MLS ⋅ SOLD Status

Luxurious & rare one-level-living on a grand scale! Experience the ultimate peaceful, private lifestyle in this spectacular estate setting. The expansive patio is truly exceptional - perfect for hosting gatherings & soirées under the stars. A sports court with night lighting & sprawling, level, manicured yard provide endless opportunities for recreation & entertainment. This nearly 5 acre oasis offers an abundance of space for gardening, pets, RV's, nature walks & everyday play. Thoughtfully designed interior with chef's kitchen, grand dining & living rooms, large family room, multiple flex rooms, office, 5 bds, picturesque walls of windows, 3 car garage & so much more! Award winning Issaquah Schools and easy drive to amenities & freeways.

13353 202nd Avenue SE, Issaquah

Listing Broker: Berkshire Hathaway HS NW; Tami Miller; ; Selling Office: Windermere Real Estate/PSR Inc.

$1,800,000

Creekside Estate in a serene setting. Down a private drive set far off the main road is a magnificent 1.65 acre property w/175 ft on Issaquah Creek. Featuring picturesque, covered porches in the front & back, the elegantly designed yet comfortable home offers an open layout. Impressive 2 story great room w/formal dining, grand office & chef’s kitchen w/slab granite & custom cabinets. Open fields & outdoor entertaining spaces are perfect for lavish entertaining or quiet relaxation. Sumptuous main floor primary suite w/spa-inspired bath & tranquil views. All upper guest bedrooms have Jack/Jill bath access. Car lovers will delight in the oversized 4-car garage! Just minutes south of everything Downtown Issaquah has to offer. Issaquah Schools

5 Beds ⋅ 4 Baths ⋅ 2239356 MLS ⋅ SOLD Status

Creekside Estate in a serene setting. Down a private drive set far off the main road is a magnificent 1.65 acre property w/175 ft on Issaquah Creek. Featuring picturesque, covered porches in the front & back, the elegantly designed yet comfortable home offers an open layout. Impressive 2 story great room w/formal dining, grand office & chef’s kitchen w/slab granite & custom cabinets. Open fields & outdoor entertaining spaces are perfect for lavish entertaining or quiet relaxation. Sumptuous main floor primary suite w/spa-inspired bath & tranquil views. All upper guest bedrooms have Jack/Jill bath access. Car lovers will delight in the oversized 4-car garage! Just minutes south of everything Downtown Issaquah has to offer. Issaquah Schools

15639 Issaquah Hobart Road SE, Issaquah

Listing Broker: Windermere Real Estate/East; Julie Taylor; ; Selling Office: Skyline Properties, Inc..

$810,000

Welcome to this great rambler in Issaquah on shy ¼ acre lot with fenced backyard. Home boasts 3 bedrooms bath, living room, family room, spacious kitchen with access to patio and fenced backyard. Kitchen has granite countertops and all appliances stay. New roof and hot water tank. Home is heated with forced air propane. Separate laundry room with room for storage. Fenced backyard with garden areas to relax in. Close to shopping, entertainment, outdoor activities, Renton, & I-90. Yet in a quiet area off May Valley Road. Located in the desirable Issaquah School District.

3 Beds ⋅ 2 Baths ⋅ 2222556 MLS ⋅ SOLD Status

Welcome to this great rambler in Issaquah on shy ¼ acre lot with fenced backyard. Home boasts 3 bedrooms bath, living room, family room, spacious kitchen with access to patio and fenced backyard. Kitchen has granite countertops and all appliances stay. New roof and hot water tank. Home is heated with forced air propane. Separate laundry room with room for storage. Fenced backyard with garden areas to relax in. Close to shopping, entertainment, outdoor activities, Renton, & I-90. Yet in a quiet area off May Valley Road. Located in the desirable Issaquah School District.

11736 188th Avenue SE, Issaquah

Listing Broker: KW North Sound; Todd D. Duitsman; ; Selling Office: Aqua.

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