OVERLOOK Homes with Trees/Woods View

Welcome to Overlook, a picturesque subdivision nestled in the heart of Portland, Oregon, within the vibrant Multnomah County. This charming community is renowned for its serene atmosphere and breathtaking views, where nature and urban living harmoniously intertwine. Overlook is a haven for those seeking a tranquil retreat without sacrificing the convenience of city life.

One of the standout features of homes in Overlook is the stunning vista of trees and woods that envelops the area. Imagine waking up each morning to the gentle rustle of leaves and the vibrant colors of nature just outside your window. Many homes in this subdivision are thoughtfully designed to maximize these views, offering expansive windows and outdoor spaces that invite the beauty of the surrounding landscape into your living space.

Overlook is not just about picturesque views; it's also a community that fosters connection and a sense of belonging. Residents enjoy easy access to local parks, walking trails, and recreational areas, making it an ideal place for families, outdoor enthusiasts, and anyone looking to embrace a lifestyle steeped in nature.

With its proximity to downtown Portland, Overlook residents can indulge in the city’s eclectic dining, shopping, and cultural attractions while still retreating to their peaceful sanctuary at the end of the day. Discover the charm of Overlook, where every home is a gateway to nature’s splendor, and experience the perfect blend of comfort, community, and breathtaking views. Your dream home awaits in this enchanting Portland subdivision!

Newest OVERLOOK Homes with Trees/Woods View

$199,900

295529707 MLS

Seize this rare chance to acquire two prime vacant lots with coveted CM3 zoning, situated on the corner of a dead-end street in the vibrant Overlook neighborhood. This location offers close proximity to the bustling N Mississippi Ave, the Vancouver/Williams Corridor, and the Legacy Emanuel Medical Center, all contributing to a phenomenal 91 BikeScore! Previously designed for a 14-unit apartment building, these lots are perfect for a multi-family dwelling or other lower-density residential developments. The CM3 zoning offers flexibility and high-density potential with reduced setbacks, making it ideal for maximizing your investment. Don’t miss out on this fantastic development opportunity in a sought-after area!

N Montana AVE, Portland

$749,900

593159608 MLS

Opportunity to acquire one side of a modern home with separate living quarters! This offering provides ~2,557 sq ft of well designed living space across three levels, delivering a functional and highly marketable layout for tenants or owner occupants seeking flexibility. Main level features a great room style design with seamless flow between kitchen, dining, and living areas, plus a convenient half bathroom for guests. Kitchen is equipped with a full size island with eat bar, stainless steel appliances, and extensive custom cabinetry, while large windows and sliding doors enhance natural light and connect to a covered deck and fully fenced yard, a key driver for livability and tenant retention. Upper level offers a 3 bedroom, 2 bathroom configuration including a primary ensuite with walk in closet and walk in shower, along with centrally located laundry for convenience. Ground level includes a highly sought after attached garage and separate living quarters with 1 bedroom, 1 full bathroom, and exterior access, currently rented and providing income from day one, creating flexibility for multigenerational use or continued supplemental rental income. Modern construction, efficient layout, and desirable features position this home for strong long term performance. Located near Arbor Lodge Park, New Seasons Market, and the dining, cafes, and retail along N Lombard St and St Johns, supporting consistent demand and long term value. [Home Energy Score = 10. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10182385]

5623 N GAY AVE, Portland

$749,900

4 Beds ⋅ 3 Baths ⋅ 797183613 MLS

Designed for modern living, I offer exceptional flexibility across three thoughtfully planned levels. Built by a multi-year Street of Dreams builder and Builder of the Year award winner by the Home Building Association, I pair elevated finishes with a layout created for connection, comfort, and versatility. My main level welcomes you with a bright, open great room where the kitchen, dining, and living spaces flow seamlessly together for everyday living and easy entertaining. A convenient half bath adds functionality for guests. My living room is anchored by a fireplace with striking floor to ceiling tilework, while expansive windows fill the space with natural light. My kitchen features a full size island with eat bar seating, stainless steel appliances, extensive custom cabinetry, and a window over the sink framing lush greenery. Stylish lighting and clean modern finishes continue throughout. From the dining area, a sliding door opens to a covered deck and fully fenced yard, extending the living space outdoors for relaxing, entertaining, or enjoying the peaceful surroundings. Upstairs, I offer three well proportioned bedrooms and two full bathrooms, including a spacious primary suite with a walk in closet and walk in shower. Laundry is conveniently located between the bedrooms. My ground level adds exceptional versatility with an attached garage and separate living quarters featuring one bedroom, one full bathroom, exterior access, and dedicated laundry. This flexible space is ideal for guests, multigenerational living, or potential rental income. Set in a well connected North Portland location near Arbor Lodge Park, New Seasons Market, the dining, cafes, and shopping along N Lombard Street, and convenient access to St. Johns, I offer modern comfort, functionality, and everyday convenience. [Home Energy Score = 10. HES Report at https://us.greenbuildingregistry.com/green-homes/OR10182385]

5623 N GAY AVE Unit #2, Portland

Start Your Search

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.