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$3,975,000

This one-of-a-kind estate is tucked away behind a gated drive featuring a 2-sided infinity pool & spa. With a nod to its mid-century modern heritage, the home is updated throughout with vaulted ceilings, skylights and bold beams setting the tone. The kitchen is the heart of the home with marble countertops, a giant island, full-sized Sub-Zero refrigerator & separate freezer and a French La Cornue range. Eat inside in the casual dining area or directly outdoors with the view of the valley and pool. Enjoy the fireplace or TV from the adjacent family room. There's a formal dining room, living room and extra den plus office. Don't miss the 350sf primary ensuite with two sinks, free-standing tub and walk-in closets. There are 3 more bedrooms near the primary, and the 5th bedroom is on the opposite side of the home with ensuite bathroom. The 2-sided infinity pool is custom designed to show off the view. The gated front yard also provides a large flat play area along with a 3-car garage and parking for 4+ add'l cars. Originally designed by Henry Hill, the legendary co-founder of the Second Bay Tradition, this estate stands as a testament to a movement that sought to harmonize modern design with the rugged beauty of Northern California.

5 Beds ⋅ 5 Baths ⋅ 41126231 MLS

This one-of-a-kind estate is tucked away behind a gated drive featuring a 2-sided infinity pool & spa. With a nod to its mid-century modern heritage, the home is updated throughout with vaulted ceilings, skylights and bold beams setting the tone. The kitchen is the heart of the home with marble countertops, a giant island, full-sized Sub-Zero refrigerator & separate freezer and a French La Cornue range. Eat inside in the casual dining area or directly outdoors with the view of the valley and pool. Enjoy the fireplace or TV from the adjacent family room. There's a formal dining room, living room and extra den plus office. Don't miss the 350sf primary ensuite with two sinks, free-standing tub and walk-in closets. There are 3 more bedrooms near the primary, and the 5th bedroom is on the opposite side of the home with ensuite bathroom. The 2-sided infinity pool is custom designed to show off the view. The gated front yard also provides a large flat play area along with a 3-car garage and parking for 4+ add'l cars. Originally designed by Henry Hill, the legendary co-founder of the Second Bay Tradition, this estate stands as a testament to a movement that sought to harmonize modern design with the rugged beauty of Northern California.

8 Oak Arbor, Orinda

Listing courtesy of Diane Dwyer from Compass. 925-997-7555

Selling Office: Compass.

$3,875,000

104 Van Ripper Lane rests on an idyllic lane in the beloved Sleepy Hollow neighborhood; a place where charm, elegance, & comfort come together. Recently remodeled, this home beautifully balances modern sophistication with timeless appeal. Coffered ceilings welcome you with a sense of airiness & light, setting the tone for the warmth that fills every corner. With 5 bedrooms, 4.5 baths, & a well-appointed office (or 6th bedroom), this expansive 4,225± sqft home offers space for everything & everyone that matters most. The chef’s kitchen is a dream, featuring top-of-the-line appliances, a built-in wine fridge & bar, & a generous walk-in pantry. It’s ideal for everyday living & effortless entertaining. French doors bathe the home in natural light & open to a lush backyard retreat; complete with an expansive patio, large lawn, & an outdoor BBQ & living area designed for gatherings under the stars. Here, mornings begin with coffee in the sun-drenched breakfast nook, evenings unfold with dinner in the formal dining room, and nights are spent fireside. Located close to award-winning Sleepy Hollow Elementary, Sleepy Hollow Tennis and Swim, town, and commute routes; 104 Van Ripper Lane is more than a home. It’s a lifestyle, a feeling, and a place to belong.

6 Beds ⋅ 5 Baths ⋅ 41119488 MLS

104 Van Ripper Lane rests on an idyllic lane in the beloved Sleepy Hollow neighborhood; a place where charm, elegance, & comfort come together. Recently remodeled, this home beautifully balances modern sophistication with timeless appeal. Coffered ceilings welcome you with a sense of airiness & light, setting the tone for the warmth that fills every corner. With 5 bedrooms, 4.5 baths, & a well-appointed office (or 6th bedroom), this expansive 4,225± sqft home offers space for everything & everyone that matters most. The chef’s kitchen is a dream, featuring top-of-the-line appliances, a built-in wine fridge & bar, & a generous walk-in pantry. It’s ideal for everyday living & effortless entertaining. French doors bathe the home in natural light & open to a lush backyard retreat; complete with an expansive patio, large lawn, & an outdoor BBQ & living area designed for gatherings under the stars. Here, mornings begin with coffee in the sun-drenched breakfast nook, evenings unfold with dinner in the formal dining room, and nights are spent fireside. Located close to award-winning Sleepy Hollow Elementary, Sleepy Hollow Tennis and Swim, town, and commute routes; 104 Van Ripper Lane is more than a home. It’s a lifestyle, a feeling, and a place to belong.

104 Van Ripper Ln, Orinda

Listing courtesy of Tina Frechman from Dudum Real Estate Group. 925-915-0851

Selling Office: Corcoran Icon Properties.

$3,450,000

For comp purposes only. House sold of market per seller request. Fabulous rancher on one of Orinda's favorite streets. Rare expansive lot with pool, gardens, and large grassy area.

5 Beds ⋅ 4 Baths ⋅ 41128329 MLS

For comp purposes only. House sold of market per seller request. Fabulous rancher on one of Orinda's favorite streets. Rare expansive lot with pool, gardens, and large grassy area.

65 Van Ripper Ln, Orinda

Listing courtesy of Emily Estrada from Village Associates Real Estate. 925-708-8116

Selling Office: Golden Gate Sotheby's Int'l Re.

$3,195,000

Sleepy Hollow Summit - This is the one! Location, location, location - this exceptional property at the end of a cul de sac offers a perfect “10” setting with breathtaking views . Finding a setting like this with a "New" home is next to impossible to find. The original home was mostly taken down to the foundation and completely reimagined and rebuilt by local builder MF3 Construction. From the moment you arrive, the curb appeal is undeniable — featuring a new paver driveway, inviting entry, and a stunning 250+ year-old oak tree framing the home. Step into your new home with wide plank oak floors throughout. Open concept great room features vaulted ceilings. The living area offers a warm and inviting space centered around a linear gas fireplace, while the dining area is perfectly positioned to capture sweeping Sleepy Hollow Valley views. The kitchen is a showpiece, featuring Miele Marble countertops and backsplash, premium Dacor appliances including a 48” range and 42” refrigerator, white oak island cabinetry, and designer pendant lighting. A spacious walk-in pantry serves as a seamless extension of the kitchen, complete with abundant cabinetry and a prep sink. Just off the great room is a separate family/media room enclosed by double pocket doors. A thoughtfully designed mudroom is conveniently located off the garage and driveway entry. The primary suite was designed as a true retreat. Vaulted ceilings elevate the sleeping quarters, while expansive valley views and direct access to a private paver patio create a serene setting. The generous walk-in closet offers ample space and functionality. The spa-inspired primary bathroom features marble flooring, a freestanding soaking tub with Roman filler framed by picture windows, a glass-enclosed shower with bench seating, dual vanities, and a full-height linen cabinet. Last — and certainly not least — is the property itself. The rear paver patio is designed for entertaining and taking in the unparalleled views. Watch the morning fog roll over the hills. The grounds feature all-new landscaping, paver patios, porches, and walkways, along with a beautiful lower entertaining area centered around a magnificent oak tree. The setting evokes the feeling of Carmel Valley. As you make your way down the expansive property, you’ll find an additional level with planting beds and an existing greenhouse.

4 Beds ⋅ 5 Baths ⋅ 41136714 MLS

Sleepy Hollow Summit - This is the one! Location, location, location - this exceptional property at the end of a cul de sac offers a perfect “10” setting with breathtaking views . Finding a setting like this with a "New" home is next to impossible to find. The original home was mostly taken down to the foundation and completely reimagined and rebuilt by local builder MF3 Construction. From the moment you arrive, the curb appeal is undeniable — featuring a new paver driveway, inviting entry, and a stunning 250+ year-old oak tree framing the home. Step into your new home with wide plank oak floors throughout. Open concept great room features vaulted ceilings. The living area offers a warm and inviting space centered around a linear gas fireplace, while the dining area is perfectly positioned to capture sweeping Sleepy Hollow Valley views. The kitchen is a showpiece, featuring Miele Marble countertops and backsplash, premium Dacor appliances including a 48” range and 42” refrigerator, white oak island cabinetry, and designer pendant lighting. A spacious walk-in pantry serves as a seamless extension of the kitchen, complete with abundant cabinetry and a prep sink. Just off the great room is a separate family/media room enclosed by double pocket doors. A thoughtfully designed mudroom is conveniently located off the garage and driveway entry. The primary suite was designed as a true retreat. Vaulted ceilings elevate the sleeping quarters, while expansive valley views and direct access to a private paver patio create a serene setting. The generous walk-in closet offers ample space and functionality. The spa-inspired primary bathroom features marble flooring, a freestanding soaking tub with Roman filler framed by picture windows, a glass-enclosed shower with bench seating, dual vanities, and a full-height linen cabinet. Last — and certainly not least — is the property itself. The rear paver patio is designed for entertaining and taking in the unparalleled views. Watch the morning fog roll over the hills. The grounds feature all-new landscaping, paver patios, porches, and walkways, along with a beautiful lower entertaining area centered around a magnificent oak tree. The setting evokes the feeling of Carmel Valley. As you make your way down the expansive property, you’ll find an additional level with planting beds and an existing greenhouse.

18 Saint James Ct, Orinda

Listing courtesy of Mario Feusier, III from Dudum Real Estate Group. 925-212-4514

Selling Office: Compass.

$3,000,000

4 Beds ⋅ 4 Baths ⋅ 41141551 MLS

66 Van Ripper Ln, Orinda

Listing courtesy of Ann Sharf from Village Associates Real Estate. 925-200-0222

Selling Office: Compass.

$2,764,312

Luxury Oasis in Orinda’s exclusive Sandhill enclave of Sleepy Hollow, this remodeled single-level Mid Century Modern retreat blends privacy, luxury, and seamless indoor/outdoor living with sweeping views, dramatic floor-to-ceiling windows, and nine skylights that bathe the home in warm natural light. The chef is never left out of the action with this open floor which includes a gourmet kitchen featuring a Sub-Zero refrigerator, 6-burner Wolf range, quartz countertops, and an oversized island designed for entertaining. Spa-inspired bathrooms include programmable radiant heated floors with Phylrich and Grohe fixtures, while a 7-zone HVAC mini split system provides personalized comfort throughout. The manicured backyard offers a true private haven with an outdoor BBQ, firepit, and peaceful spaces to relax, entertain, with pastoral views as if from an eagle's nest. Close to the Sleepy Hollow Swim and Tennis club, scenic trails, downtown Orinda, BART, and award-winning Orinda schools. Experience life in one of Orinda’s most coveted neighborhoods, where privacy, beauty, and luxury living come together.

4 Beds ⋅ 3 Baths ⋅ 41138118 MLS

Luxury Oasis in Orinda’s exclusive Sandhill enclave of Sleepy Hollow, this remodeled single-level Mid Century Modern retreat blends privacy, luxury, and seamless indoor/outdoor living with sweeping views, dramatic floor-to-ceiling windows, and nine skylights that bathe the home in warm natural light. The chef is never left out of the action with this open floor which includes a gourmet kitchen featuring a Sub-Zero refrigerator, 6-burner Wolf range, quartz countertops, and an oversized island designed for entertaining. Spa-inspired bathrooms include programmable radiant heated floors with Phylrich and Grohe fixtures, while a 7-zone HVAC mini split system provides personalized comfort throughout. The manicured backyard offers a true private haven with an outdoor BBQ, firepit, and peaceful spaces to relax, entertain, with pastoral views as if from an eagle's nest. Close to the Sleepy Hollow Swim and Tennis club, scenic trails, downtown Orinda, BART, and award-winning Orinda schools. Experience life in one of Orinda’s most coveted neighborhoods, where privacy, beauty, and luxury living come together.

233 Melody Ln, Orinda

Listing courtesy of Vlatka Bathgate from Coldwell Banker. 925-597-1573

Selling Office: KW Advisors East Bay.

$2,050,000

A magical 4-bedroom, 2 bath, 2058 sq ft, north Orinda beauty on a picturesque .26 ac setting of lush lawns and exquisite landscaping. Freshly painted inside and out, gorgeous wood floors, with a spectacular flat backyard lawn ready for entertaining and playtime. Take the modern concrete stepping stones over to the new 150-sf modular “Shed” with heating and A/C, ready and perfect for your home office! A newly renovated kitchen and bathrooms have the design elements you have been looking for! The new kitchen has all the amenities: Viking stovetop, ovens and dishwasher, brass fixtures, a white porcelain farm sink, quartz countertops and back splash, a stool bar to grab a quick bite to eat, and a pass-through window to the outside dining area and patio. A lovely large and winding outdoor tile patio is perfect for dining and casual seating. Overlook views of the newly sodded lawn and stunning fully fenced in private backyard. Three bedrooms and one bath upstairs with a hall storage cubby. Downstairs an exquisite and dramatic primary bedroom looks out to the lush backyard. A fireplace keeps things cozy, with an ample walk-in closet, and an extra hobby room (another office?). The new bathrooms with the latest design elements have tasteful decorative tile floors, gold tone fixtures, and quartz countertops. Sleepy Hollow and Miramonte schools, minutes to the Freeway and bus lines.

4 Beds ⋅ 2 Baths ⋅ 41134209 MLS

A magical 4-bedroom, 2 bath, 2058 sq ft, north Orinda beauty on a picturesque .26 ac setting of lush lawns and exquisite landscaping. Freshly painted inside and out, gorgeous wood floors, with a spectacular flat backyard lawn ready for entertaining and playtime. Take the modern concrete stepping stones over to the new 150-sf modular “Shed” with heating and A/C, ready and perfect for your home office! A newly renovated kitchen and bathrooms have the design elements you have been looking for! The new kitchen has all the amenities: Viking stovetop, ovens and dishwasher, brass fixtures, a white porcelain farm sink, quartz countertops and back splash, a stool bar to grab a quick bite to eat, and a pass-through window to the outside dining area and patio. A lovely large and winding outdoor tile patio is perfect for dining and casual seating. Overlook views of the newly sodded lawn and stunning fully fenced in private backyard. Three bedrooms and one bath upstairs with a hall storage cubby. Downstairs an exquisite and dramatic primary bedroom looks out to the lush backyard. A fireplace keeps things cozy, with an ample walk-in closet, and an extra hobby room (another office?). The new bathrooms with the latest design elements have tasteful decorative tile floors, gold tone fixtures, and quartz countertops. Sleepy Hollow and Miramonte schools, minutes to the Freeway and bus lines.

32 Las Vegas Road, Orinda

Listing courtesy of Melanie Snow from Coldwell Banker. 925-360-0344

Selling Office: Compass.

$2,050,000

Timeless contemporary design, sweeping views, and exceptional indoor/outdoor living are all here in this sophisticated 4+BD/2++BA Sleepy Hollow estate. Set in coveted Bear Ridge, this contemporary 4451 SQFT home offers serenity, privacy and exquisite vistas on 1.5 acres of oak woodlands. The home opens dramatically to soaring beamed ceilings, sunny skylights, and floor-to-ceiling windows and glass doors, making beautiful Briones and Mt. Diablo views its ever-present backdrop. In the elegant living and dining areas, entertain and relax with family and friends or open the doors to the expansive wraparound deck for al fresco dinners and conversation. The adjoining eat-in kitchen and great room open seamlessly to the deck. The secluded primary suite enjoys a walk-in closet, huge ensuite bath, deck access, and private patio. Upstairs, find three bright bedrooms with full bath and powder room; downstairs are two large flexible rooms with exterior doors, ready for your needs as a playroom, studio, office, or family room. The lower level also provides access to the back yard, another powder room, and an ample bonus storage space. Your commute is easy with a two-car garage and nearby BART and HWY 24. Sought-after K-12 schools, shopping, dining, and entertainment are just down the hill.

4 Beds ⋅ 4 Baths ⋅ 41128669 MLS

Timeless contemporary design, sweeping views, and exceptional indoor/outdoor living are all here in this sophisticated 4+BD/2++BA Sleepy Hollow estate. Set in coveted Bear Ridge, this contemporary 4451 SQFT home offers serenity, privacy and exquisite vistas on 1.5 acres of oak woodlands. The home opens dramatically to soaring beamed ceilings, sunny skylights, and floor-to-ceiling windows and glass doors, making beautiful Briones and Mt. Diablo views its ever-present backdrop. In the elegant living and dining areas, entertain and relax with family and friends or open the doors to the expansive wraparound deck for al fresco dinners and conversation. The adjoining eat-in kitchen and great room open seamlessly to the deck. The secluded primary suite enjoys a walk-in closet, huge ensuite bath, deck access, and private patio. Upstairs, find three bright bedrooms with full bath and powder room; downstairs are two large flexible rooms with exterior doors, ready for your needs as a playroom, studio, office, or family room. The lower level also provides access to the back yard, another powder room, and an ample bonus storage space. Your commute is easy with a two-car garage and nearby BART and HWY 24. Sought-after K-12 schools, shopping, dining, and entertainment are just down the hill.

116 Tappan Lane, Orinda

Listing courtesy of David Gunderman from KW Advisors East Bay. 510-205-4369

Selling Office: KW Advisors East Bay.

$1,800,000

For comp purposes.

5 Beds ⋅ 3 Baths ⋅ 41128487 MLS

For comp purposes.

530 Miner Rd, Orinda

Listing courtesy of Sharon Ho from Compass. 415-680-6852

Selling Office: Coldwell Banker.

$1,598,000

24 Las Vegas Road offers the Orinda lifestyle buyers dream about: beautifully updated living space, generous indoor-outdoor flow, and a backyard full of possibilities. This recently remodeled home features a fresh, modern kitchen, updated bathrooms, new lighting, stylish flooring, and sunlit living spaces throughout. Huge living room windows fill the home with natural light, while the spacious bedrooms offer extra closet space and flexibility. The primary suite opens to an expansive, private, elevated deck, creating a peaceful retreat overlooking the property. A large bonus room with vaulted ceilings and oversized windows adds even more room to gather, work, play, or relax. Outside, the large backyard is ready for your imagination: add a pool, patio, sports court, garden, play area, or your dream outdoor entertaining space. Additional highlights include an outdoor elevator, two-car garage, side patio area, extra storage, and a terraced front yard. Just minutes to highly ranked public schools, parks, restaurants, Orinda Library, Lafayette Reservoir, Highway 24, downtown Orinda, and BART, this close-in location is hard to beat. A rare opportunity in one of Orinda’s most desirable communities.

3 Beds ⋅ 2 Baths ⋅ 41135119 MLS

24 Las Vegas Road offers the Orinda lifestyle buyers dream about: beautifully updated living space, generous indoor-outdoor flow, and a backyard full of possibilities. This recently remodeled home features a fresh, modern kitchen, updated bathrooms, new lighting, stylish flooring, and sunlit living spaces throughout. Huge living room windows fill the home with natural light, while the spacious bedrooms offer extra closet space and flexibility. The primary suite opens to an expansive, private, elevated deck, creating a peaceful retreat overlooking the property. A large bonus room with vaulted ceilings and oversized windows adds even more room to gather, work, play, or relax. Outside, the large backyard is ready for your imagination: add a pool, patio, sports court, garden, play area, or your dream outdoor entertaining space. Additional highlights include an outdoor elevator, two-car garage, side patio area, extra storage, and a terraced front yard. Just minutes to highly ranked public schools, parks, restaurants, Orinda Library, Lafayette Reservoir, Highway 24, downtown Orinda, and BART, this close-in location is hard to beat. A rare opportunity in one of Orinda’s most desirable communities.

24 Las Vegas Rd, Orinda

Listing courtesy of Brendan Moran from 5 Star Real Estate. 925-464-1025

Selling Office: California 24.

$1,200,000

A rare opportunity on one of Orinda's most coveted streets, just minutes from Sleepy Hollow Elementary. This modern home offers 2,234 square feet of light filled living space, with all three bedrooms and two and a half bathrooms conveniently located on the main level, plus a versatile fourth bedroom or office on the lower level, ideal for a home office, guest suite, or media room. An open dining and living area sets the tone, with a few steps down leading to the living room, where vaulted ceilings, clerestory windows, and a built-in window seat overlooking the trees create a peaceful spot to unwind. The kitchen opens to a casual gathering space with a sitting area anchored by a fireplace, along with a breakfast nook where French doors lead out to the back patio, perfect for everyday living. A powder room rounds out the main living spaces for easy entertaining. The primary bedroom offers a wall of windows overlooking the trees, its own fireplace, and an en suite bath. One of the additional bedrooms has real character of its own, with an angled corrugated metal ceiling and a clever built-in platform bed with shelving below, while the third bedroom rounds out the main level. The two secondary bedrooms share a well appointed hall bath. Downstairs, the bonus room offers flexibility for today's lifestyle, whether that means a home gym, playroom, or private office with its own access. A two car garage adds everyday convenience. This hidden gem sits in one of Orinda's favorite neighborhoods, offering privacy, character, and a true sense of place. A wonderful opportunity for the next owner to bring their own vision and make it their own. Don't miss this rare chance to own a piece of one of Orinda's most beloved streets.

4 Beds ⋅ 3 Baths ⋅ 41139827 MLS

A rare opportunity on one of Orinda's most coveted streets, just minutes from Sleepy Hollow Elementary. This modern home offers 2,234 square feet of light filled living space, with all three bedrooms and two and a half bathrooms conveniently located on the main level, plus a versatile fourth bedroom or office on the lower level, ideal for a home office, guest suite, or media room. An open dining and living area sets the tone, with a few steps down leading to the living room, where vaulted ceilings, clerestory windows, and a built-in window seat overlooking the trees create a peaceful spot to unwind. The kitchen opens to a casual gathering space with a sitting area anchored by a fireplace, along with a breakfast nook where French doors lead out to the back patio, perfect for everyday living. A powder room rounds out the main living spaces for easy entertaining. The primary bedroom offers a wall of windows overlooking the trees, its own fireplace, and an en suite bath. One of the additional bedrooms has real character of its own, with an angled corrugated metal ceiling and a clever built-in platform bed with shelving below, while the third bedroom rounds out the main level. The two secondary bedrooms share a well appointed hall bath. Downstairs, the bonus room offers flexibility for today's lifestyle, whether that means a home gym, playroom, or private office with its own access. A two car garage adds everyday convenience. This hidden gem sits in one of Orinda's favorite neighborhoods, offering privacy, character, and a true sense of place. A wonderful opportunity for the next owner to bring their own vision and make it their own. Don't miss this rare chance to own a piece of one of Orinda's most beloved streets.

53 Sleepy Hollow Ln, Orinda

Listing courtesy of Shannon Conner from Village Associates Real Estate. 925-980-3829

Selling Office: Coldwell Banker.