After 25 years on Manhattan’s Upper West Side, a couple sought a larger living space while remaining in their longtime neighborhood, navigating the competitive New York City real estate market to accommodate their growing family and evolving needs.

Laura Nupponen, 48, founder of a children’s group music classes company, and her husband, Kevin Kendall, 47, a mechanical engineer and consultant, originally owned a connected duplex in a historic brownstone where they raised their two children. The couple purchased the property in stages, initially acquiring the parlor-level studio from Mr. Kendall’s parents in 2000 and later adding the basement unit, linked by a spiral staircase. While the space had distinctive architectural features—original moldings and character—they eventually required more floor area as their family grew, noting challenges such as their children sharing a bedroom with differing temperature preferences, and accommodating a new dog.

Prioritizing proximity to their children’s school and family, the couple aimed to remain on the Upper West Side. Their list of essential features included three bedrooms, an office for Mr. Kendall’s home business, bike storage, a gym, and shared outdoor space. Their broker, Pat Lehman of Compass, highlighted prewar buildings with classic six-room layouts as optimal for their needs.

Their $1.5 million budget, funded by the sale of their prior apartment, led them to explore properties primarily in the West 80s to upper 90s, eventually extending north to the West 100s. Among the options considered were:

- A two-bedroom, two-bath co-op on West 94th Street featuring herringbone hardwood floors, original moldings, built-ins, and abundant light. Despite a somewhat awkward layout with separated living and dining rooms, the space included amenities such as a roof deck, gym, playroom, and storage. The asking price was $1.55 million, with maintenance fees near $2,900 monthly.

- A renovated three-bedroom, two-bath prewar unit on West 98th Street, on the market for over a year at asking prices initially from $1.6 million but later reduced to $1.499 million. The apartment offered updated kitchen and baths alongside original parquet floors, mahogany paneling, and French doors. Potentially, a fourth bedroom could be created from the dining area. Maintenance costs were about $2,300 per month. The building lacked a doorman and gym but included a roof deck.

- A larger four-bedroom, two-bath co-op on West 103rd Street in a 1924 elevator building with a doorman, gym, and playroom. The corner layout provided multiple exposures and proximity to Riverside Park; however, it lacked the charm of lower properties and was slightly farther from the children’s school. The listing price was $1.65 million with $2,900 monthly maintenance.

The couple’s preferred choice was the three-bedroom on West 98th Street, envisioning a conversion of the dining room into a primary bedroom. They made an initial offer of $1.375 million but were outbid by an all-cash purchaser at $1.4 million, despite a counteroffer at full price. Subsequently, a similar dynamic played out with the two-bedroom unit as well.

Ultimately, the couple purchased the larger West 103rd Street apartment for $1.635 million. Although the property required more renovation than anticipated, its amenities and layout suited their needs. The sale of their previous duplex took longer than planned, adding some stress, but after approximately a year, they felt secure in their new home.

Plans are underway to enhance the space further by adding picture-frame moldings, updating the main bathroom, and relocating the kitchen to expand their son’s bedroom. Despite a slightly longer commute to school, Ms. Nupponen emphasized the strong community atmosphere fostered by the neighborhood and co-op board. Their dog, Hazel, has also adjusted well, easily making new companions. The family is enjoying the additional space, with their 10-year-old daughter appreciating having her own room for the first time.