248 Pinewood Trail, Trumbull

Live. Work. Float…

This Craftsman-style compound overlooks its own pond and waterfall, across the brook from deeded open space and a leisure stroll away from Pinewood Lake.  An oasis.  Designed to sit in harmony with the natural surroundings, it feels like a “home away from home,” but you never have to leave. With a detached 576 sqft office and a one-bedroom guest cottage, this residence provides all the space needed to be separate but together while still leaving room for solitude.


4 Bedrooms


3 Full, 2 Half Baths


3,745 Sq/Ft


1.74 Acres

Work/Life balance actualized in the prettiest of ways

Part of what makes an investment smart is the way it supports your life. The property at Pinewood Trail has been carefully crafted over the past 30 years to create just the right amount of separation between the main house, office, and cottage to preserve privacy without compromising anyone’s views.  Suffice it to say the results are stunning.

How do you explain good design? It’s in the thoughtful details

The stunning setting here was integral to the building design. The master suite is on the side of the house facing the waterfall for its soothing sounds and natural cooling. The kitchen windows extend all-the-way to the ceiling for viewing the gardens and birdlife over morning coffee. And walls of glass across the back of the house take advantage of the southern exposure and open to the expansive deck. Even the laundry room is prime for nature-gazing with oversized windows, because shouldn’t all work be enjoyable?

Nurture your nature

Hand laid stone walls and a massive deck form multiple levels of outdoor space for dining, cooking, Hot Tubbing, or just whiling away the days and taking in all that nature-y goodness.

“Water takes you away from distractions and simplifies the visual landscape…Being near it can calm and connect us, increase innovation and insight, and even heal what’s broken.”
Wallace J. Nichols

Blue Mind: How Water Makes You Happier, Healthier, and Better at What You Do

I wish you water

Soaking in the hot tub or sitting on the master suite balcony, immerse yourself in the quiet joy.

4 Car Garage

Electric vehicle charging and heat included in the main two-car garage – along with ample parking for six additional cars. The second two-car garage on the upper level is easy for guests of the cottage or ideal for an auto enthusiast. 

Zen & the Art of Landscape Design


Guest Cottage Details & Gallery


Full Kitchen

Living/Dining Room
– Sliding glass doors to patio

Full Bathroom
– Glass Shower
– Stacked Washer/Dryer

Bluestone Patio
– Garden and BBQ


– Built-in custom closets
– Built-in dresser


Separate Utilities
– Propane and Electricity

Central A/C

Laundry Hookup


Metal roof and gutters


Garden Shed & Potting Table

All the Nuts & Bolts

– Four car garage
– Guest parking for six cars
– Custom designed garden shed
– Breezeway connecting garage to the house
– Architectural shingles (3 layers)
– Copper gutters and downspouts
– Custom designed Western Red Cedar Trusses and brackets
– Solid 1 ¾” interior doors
– Rocky Mountain hardware on all doors
– Monitored security system with cameras inside and out

– Central air conditioning in house, office, and guest cottage
– Radiant heated floors and European-style steam radiators in main house
– Ground-mounted array of 45 solar panels
– 400 amp electric service
– Cannondale House Generator
– City sewer
– 2″ city water line
– Instant hot water heater in main house
– 500 gallon buried propane tank
– 320-gallon oil tank in garage

– Automatic irrigation system
– Outdoor landscape accent lighting
– 20′ wide X 30′ drop waterfall and pond
– 650 SF bluestone walkways, retaining wall, and steps
– Stone walls along both sides of driveway
– Stone curbing throughout
– Illuminated stone pier at the street with house number
– Perennial gardens throughout designed and cared for by professional landscape architect owner

The Location


A Quaint Community Lake

Pinewood Lake Association is a private community organization located on over 60 acres in Trumbull, Connecticut. Originally developed as a resort to rival the Catskills in the 1930s, it offered lake-side cabins, recreation, and an auditorium boasting a revolving stage with leading-edge theatre productions. Today the association still maintains the historic theater as a clubhouse for programs and gatherings, and members continue to enjoy the resort-like amenities. The beach on the south side of the lake has a designated swimming area, floating dock, and boat rentals. And, the lake’s abundant supply of bass, pickerel, common carp, northern pike, and trout promise great fishing.

The lake also borders both Beach Park and Twin Brooks Park, providing easy access to the town swimming pool and miles of walking, hiking, and biking trails.


Pequonnock River Valley / Rails to Trails

“The State of Connecticut designates “corridors of open space” as official greenways. These corridors protect natural resources, preserve scenic landscapes and historical resources, offer opportunities for recreation, connect existing protected areas and provide access to the outdoors.

The Pequonnock (Housatonic) Railbed Greenway was designated in 2001 and is located along the path of the abandoned Housatonic Railroad line. The greenway extends from Bridgeport through Trumbull and Monroe and into Newtown. 

Trails run the gamut from a flat 2.5 mile former railroad bed to steeper trails that claim the ridges on either side of the river. 

Suitable for children, walking with dogs, and mountain biking. 




“Trumbull is right in the heart of cultural activities, such as museums, theaters, concerts and major sporting events; educational activities at all levels.

The Trumbull Public School System, in partnership with the community, strives to meet the educational needs of all students within a challenging and supportive academic environment that empowers each student to become a life-long learner and to live and participate in a democratic, diverse and global society.

Trumbull is also the home of the 1989 Little League World Champions.”




Tashua Knolls Golf Course

Two beautiful courses (18 & 9 hole) situated on picturesque farmland originally inhabited by the Tamtashua Indians. Tashua is a community park, open to the public with a clubhouse and restaurant. Additional features include a kiddy pool, lighted basketball and tennis courts, regulation size swimming pool and a tot lot playgroud. 






Luxury Specialist & Accredited Buyers Agent 

(203) 258-4171

Email Carrie
SPACES CT is Affiliated with RE/MAX Heritage Real Estate
20 Saugatuck Avenue
Westport, CT 06880
Listing info is sourced from 3rd parties. We don’t represent it’s accuracy. Info shown is subject to change, errors and omissions including price. We only display select listings from Fairfield County. We update every 72 hours. In that time a house may not be available. Licensed real estate sales person in the State of Connecticut, #0800286.