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$850,000
5 Beds ⋅ 9 Baths ⋅ 193951 MLS
Located at the base of Red Mountain on one of Aspen's most coveted and iconic streets known as Willoughby Way. This legendary estate underwent an extensive, luxurious remodel making it one of Aspen's most sought-after properties. Located in a private, gated sanctuary this is your majestic escape with direct views of Aspen Mountain, stunning mature trees surrounding a large pond with fountain and close downtown proximity. Considered one of Aspen's legacy properties, this grand, completely rebuilt home is almost 12,000 sq ft on 2.45 acres and invites you with substantial glass windows and a stunning juxtaposition of stone, wood and metal exterior detail. There are few Aspen rentals offering such close proximity to Aspen's downtown with a private gated entrance, level of detail, and amenities which include pool, hot tub, spa room, exercise room, state of the art theatre, library, elevator, ski and mudroom with dog grooming bath, indoor and outdoor dining, private living throughout and spectacular direct views of Aspen Mountain to name a few. This timeless Estate within a summer walk or bike ride to Aspen is a rare rental opportunity. Flexible rental terms. Contact listing brokers with all inquiries

Aspen
$220,000
6 Beds ⋅ 8 Baths ⋅ 192984 MLS
An iconic Red Mountain estate offering the rare combination of architectural elegance and genuine warmth. Meticulously maintained and move-in ready, this residence delivers a seamless, resort-caliber experience across every season. Soaring ceilings and walls of glass frame unparalleled views of Aspen Mountain and the entire Elk Mountain Range -- a breathtaking backdrop enjoyed from the expansive living spaces, the main-floor master suite, and a series of beautifully appointed terraces anchored by a private hot tub perfectly positioned to soak in every peak on the horizon. The main floor features a luminous master suite, formal dining room, private office, and a chef's kitchen with butler's pantry. The lower level offers five additional bedrooms, a family room, game room, home theater, and gallery. The home sleeps 14 across two king suites, two queen suites, and two bunk rooms -- each with full-over-twin and twin-over-twin configurations -- perfect for families and multi-generational groups.

Aspen
$200,000
6 Beds ⋅ 9 Baths ⋅ 192838 MLS
This masterfully designed lower Red Mountain estate features 6 expansive bedrooms with spa-inspired en-suite bathrooms, offering an unparalleled level of scale and sophistication. The residence is anchored by dual primary suites, two incomparable sanctuaries providing equal measures of privacy, luxury, and panoramic views. From the grand entrance, the silhouette of the Elk Range takes center stage, framing an artfully appointed living area and den. The open-concept kitchen, dining, and living areas are well-balanced, creating intentional spaces for both intimate gatherings and more formal events. The professional-grade kitchen is both a powerful tool in the hands of a culinary master and the epicenter of family gatherings. The lower level is the ultimate space for entertaining, featuring a bespoke bar and a sprawling lounge designed for hosting at any scale. This floor seamlessly integrates a private cinema, a sculptural glass elevator, and a sophisticated wine room. Even from this level, dramatic mountain views follow you around every corner. The living areas extend effortlessly outdoors to expansive terraces, where a custom spa is perfectly positioned to capture the romance of Red Mountain. Offering a front-row seat to the alpenglow and panoramic vistas, this space is the ultimate vantage point. The property effortlessly folds into the natural setting of salvation ditch and the surrounding natural cooridor. Complete with a spacious garage and a premier ADU perfect for guests or staff, this estate is a zen retreat that balances high-octane entertaining with serene mountain beauty.

294 Draw Drive, Aspen
$150,000
7 Beds ⋅ 9 Baths ⋅ 192638 MLS
Experience one of Aspen's most coveted settings at 99 Shady Lane. This exceptional riverfront property is ideally situated at the confluence of Hunter Creek and the Roaring Fork River, offering a rare combination of natural beauty, privacy, and immediate access to downtown Aspen and the Rio Grande Trail. The main residence features six beautifully appointed bedrooms and multiple inviting living areas providing ample space for both relaxation and entertaining. Expansive windows frame breathtaking views of the river and surrounding landscape, while the interiors strike a perfect balance between warmth and sophistication. Complementing the main home is a separate, historic cabin with loft, perfect for guests or extended family. The outdoor living is extraordinary, with a a private hot tub overlooking the river, an in-ground trampoline and thoughtfully designed lounge and dining areas. A unique dining wagon and expansive lawn and playground create an unmatched setting for both entertaining and family enjoyment. This is truly an iconic Aspen retreat.

99 Shady Lane, Aspen
$175,000
5 Beds ⋅ 6 Baths ⋅ 192434 MLS
Newly completed in Spring 2026, this contemporary Red Mountain residence is available for rent for the first time. The home features five en-suite bedrooms, including a bunk room, generous natural-light filled living spaces and expansive Aspen Mountain views. Set on a private ¾-acre lot with a flat lawn surrounded by mature aspen trees, the property offers multiple decks, front and rear patios, outdoor kitchen and fire pit, along with a jacuzzi and two-car garage. All just minutes from downtown and nearby trails.

323 E Reds Road, Aspen
$950,000
6 Beds ⋅ 10 Baths ⋅ 190380 MLS
Perched gracefully on the hillside, this stunning 9,641-square-foot estate captures breathtaking views of Aspen Mountain and the surrounding peaks. Designed for both comfort and grandeur, the open-concept kitchen and dining area provide the perfect setting for entertaining, while the striking fireplace serves as a dramatic focal point in the spacious living room. The home features six luxurious en-suite bedrooms, an elevator for seamless access to all levels, and a lower-level retreat complete with a lounge, full bar, card table, theater, and yoga room—ideal for relaxation or entertaining guests. Step outside to experience the pinnacle of indoor-outdoor living: an outdoor kitchen and dining area, meticulously landscaped grounds, a built-in stone hot tub, and an impressive 80-foot pool offer resort-style living at its finest. From its elevated design to its exceptional amenities, this property delivers the ultimate Aspen luxury experience.

979 Red Mountain Road, Aspen
$100,000
4 Beds ⋅ 6 Baths ⋅ 189906 MLS
4 bedroom, 6 bathroom sanctuary on Red Mountain offering comfort, style, and expansive views. Designed with an open-living concept ideal for families and entertaining, this home encapsulates the Aspen lifestyle at its finest. Amenities include a chef's kitchen with dining for 10, wet bar, fireplace, Sonos sound system, and designer furnishings with top-of-the-line appliances. A private office off the primary suite can serve as an additional bedroom or nursery, and all guest bedrooms feature en suite baths for comfort and privacy. Additional highlights include radiant heat, AC, elevator, expansive deck off the main living area, hot tub, garage, snow-melted driveway, and thoughtful attention to detail throughout. The elegant outdoor dining area captures endless sunshine and sweeping views of Aspen Mountain, Aspen Highlands, the Maroon Bells, Independence Pass, Sopris Mountain, and beyond—creating a true mountain retreat.

349 Draw Drive, Aspen
$100,000
4 Beds ⋅ 6 Baths ⋅ 184427 MLS
This stunning new property is located in Aspen's coveted Red Mountain area just 1 mile to down town Aspen. Guests can relax and enjoy breathtaking mountain views. The grand living room boasts high ceilings, and the gourmet kitchen flows into a dining area, all featuring luxurious finishes. The outdoor space includes a patio with seating, a water feature, custom grill, hot tub, and landscaped lawn for seamless indoor-outdoor living. The spacious primary suite offers privacy on its own level and leads to a private seating area with Aspen Mountain views. Each bedroom suite is elegantly designed for comfort. Enjoy additional entertainment in the lower-level room with a bar or the home theater. The property also features a one-car garage and air conditioning in the primary suite, main living area, and guest suite

27 Nighthawk Drive, Aspen
$120,000
5 Beds ⋅ 4 Baths ⋅ 183031 MLS
Known as the ''5th Avenue'' of Aspen, the homes in the Willoughby Way neighborhood have the best address and views in Aspen. This wonderful home has all of the amenities to create a perfect vacation in Aspen. Easily accessible to town and situated on lower red mountain, the location enables guests to walk or bike to town without having to climb the steep hill to upper red mountain, while still enjoying the best views in Aspen. Each bedroom offers king size beds, white oak floors, marble bathrooms, and spectacular views to make each resident feel comfortable. Master suite includes gas fireplace in the seating area, steam shower, soaking tub with heated floors. The home has 2 kitchens (upstairs and downstairs), bikes, air conditioning throughout, hot tub, gym, heated patios, cable/wifi, and everything else you could desire while in residence. This home is exactly what a discerning guest expects when visiting Aspen. Just a short walk to the Rio Grande Trail or Sunnyside trail. This home has it all.

59 Herron Hollow Road, Aspen
$300,000
6 Beds ⋅ 9 Baths ⋅ 177596 MLS
There are few properties in Aspen offering this level of sophistication and luxury. Awake to breathtaking views of downtown Aspen, Aspen Highlands, and Buttermilk ski areas from this extraordinary contemporary home. The gourmet kitchen and beautiful living and dining spaces are unparalleled. Experience the main floor primary suite, a serene private oasis, along with four ensuite bedrooms on the lower level with access to the patio, infinity pool, and hot tub. Privacy and proximity to everything Aspen has to offer. STR.0069.2024

257 Ridge Road, Aspen
$250,000
6 Beds ⋅ 7 Baths ⋅ 170079 MLS
A rare opportunity to rent an expansive mountain estate on Aspen's prestigious Willoughby Way, now offered for monthly and weekly rental. Situated on just under two acres, this 8,350 SF home is the ideal Aspen vacation spot for you and your friends and family. The estate includes six en-suite bedrooms including a guest apartment, full fitness room, billiards room with full bar, extensive deck space for outdoor entertaining and an inviting outdoor gazebo with hot tub nearby and lots of yard space. Recent updates in 2021 include new kitchen appliances, new gym equipment, new large screen TV's, high-speed internet, outdoor gas grill, RadPower E-bikes and High Society Paddleboards. Willoughby Way offers beautiful Aspen Mountain views with easy access to the downtown core.

411 Willoughby Way, Aspen
$125,000
5 Beds ⋅ 7 Baths ⋅ 172427 MLS
Experience the natural beauty of Aspen from the expansive decking of Red Mountain Rise, all the way to Aspen Mountain, Independence Pass and Maroon Bells. Located on Red Mountain, Aspen's premier residential terrain, this all-season sanctuary is aglow with modern mountain style with snow and stone hues and whimsical Nordic décor. Bask in the open air on uber-private terraces with the utmost privacy, epitomizing the coveted Colorado mountain lifestyle, which draws global travelers to this luxury Aspen home rental on Red Mountain.

476 Wrights Road, Aspen
$100,000
3 Beds ⋅ 5 Baths ⋅ 163229 MLS
World-renowned architect Chad Oppenheim created this mountain chalet to be the perfect family enclave. The modern interiors feature reclaimed barnwood accents with floor-to-ceiling windows showcasing dramatic views of Aspen's ski hills. The gourmet kitchen is a cook's dream with Staub cookware, Viking range, dual ovens and a coal or wood-fired grill. Enjoy a dip in the infinity-edge hot tub from the privacy of the backyard complete with mountain stream running through it. There are three bedroom suites and a bonus loft with its own bathroom. A rare design gem on Red Mountain within minutes of town and all outdoor recreation.

178 Bennett Bench, Aspen
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