2025 HOBI for “Outstanding Not So Big Remodeled Home” 

2024 HOBI for Authors Way as “Best Pocket Community” in CT

HOBI Award Winning Builder for "Best Spec House CT" and "Best Large Commercial Rehab" in 2023


Authors Way

Westport CT








                                                                          EXAMPLE OF BUILDER'S PRIOR PROJECTS

Rick Benson’s most recent prior HOBI Awards in 2021 include *Best Spec Home of the Year, *Best Spec Home $3M-$4M, *Best Not So Big Spec Home

Nearly 40 years in real estate development & construction, specializing in residential homes & condominiums.  Energy Star Builder since 2005.  Successful completion of numerous single family homes and subdivisions in Westport, Weston & Fairfield (ranging in price from $300,000 to $7,000,000), condominium projects in Westport, Milford, Trumbull & Greenwich, and renovation projects in Westport. 

R.B. Benson & Company, Inc., Westport, CT 

Recent projects

List of Prior Projects (click to expand)


New Construction              6 Brookside Park, Westport..............................1800 SF2 Brookside Park, Westport..............................1896 SF14 Canal Rd, Westport (Custom)......................2000 SF301 Main St., Westport.....................................2660 SF * 12 Sterling Dr., Westport  ..................................2800 SF5 Sandhopper Trail, Westport...........................3000 SF19 Sterling Dr., Westport..................................3200 SF6 Court of Oaks, Westport................................3200 SF8 Court of Oaks, Westport................................3533 SF10 Court of Oaks, Westport..............................3540 SF1 Hickory Dr., Westport...................................3700 SF1 Windrush Lane, Westport..............................3880 SF2 Windrush Lane, Westport..............................4547 SF3 Windrush Lane, Westport..............................3660 SF4 Windrush Lane, Westport..............................4500 SF5 Windrush Lane, Westport..............................3700 SF8 Windrush Lane, Westport..............................4000 SF16 Spriteview Ave., Westport...........................3600 SF4 Sandpiper Rd, Saugatuck Shores, Westport...4205 SF10 Pond Edge Rd. Westport ............................4250 SF *107 Clapboard Hill Rd, Westport......................4319 SF28 Calumet Dr., Westport.................................4500 SF *77 Fanton Hill Rd. Weston...............................4800 SF420 Fence Row, The Ridge, Fairfield...............5200 SF1 Country Rd., Westport...................................5341 SF *7 Redcoat Road, Westport................................5568 SF76 Steward Hill Circle, The Ridge, Fairfield....5800 SF2 Buttonwood Lane, Westport..........................5675 SF *4 Buttonwood Lane, Westport..........................5900 SF5 Buttonwood Lane, Westport..........................5589 SF *6 Buttonwood Lane, Westport..........................6000 SF24 Valley Rd., Wilson Point, Norwalk.............6200 SF 8 Wakeman Rd, Westport.................................6280 SF *4 Wakeman Acres, Westport............................6306 SF *17 Salem Rd, Westport.....................................6400 SF *2 Tiffany Lane, Westport..................................8200 SF *25 Flower Farm Circle, Westport.......................6280 SF *18 Sturges Commons, Westport.......................8,700 SF 1 Flower Farm Lane, Westport.........................9550 SF *3 Flower Farm Lane, Westport........................10,184 SF *Flower Farm Lane, Westport...........................10, 400 SF *359 Greens Farms Rd, Westport......................7,200 SF*15 Green Acre Lane, Westport........................13,000 SF ** includes finished attic and/or cellar 
  Custom Homes/Major Addition/Renovation Projects for Clients (1999-Present) 245 Post Rd. E. – Saugatuck Church kitchen, baths, steeple repairs, fireproofing245 Post Rd E. – Parsonage at Saugatuck Church, new HV/AC, bath renovations, new windows5 Church Lane (former Chamber of Commerce Building) – complete renovation5 Buttonwood Lane – add 3 season screen porch17 Buena Vista, Westport – kitchen, baths, addition, foundation, deck, roof15 Green Acre, Westport – added 3 car garage with 3 car lifts & BR suite above, home theater, wine cellar, tennis court, sport court, 2 golf greens, spa tub.1 Country Road, Westport – completed a partially renovated house started by others14 Salem Rd, Westport – new HV/AC, repair serious storm/tree damage, new deck7 Brookside Park, Westport – Kitchen, bath, new HV/AV, plumbing, wiring, trim18 Rocky Ridge, Westport – new kitchen, bath, convert garage to family room, MBR addition, structural repairs, new septic, new windows & skylights, new deck24 Valley Rd., Norwalk – major repairs to FR, 4 BRS, 3 Baths after severe water damage.7 North Ave., Westport – replace 1898 barn, completely renovate and expand 1850’s farm house7 Fieldcrest Rd., Westport – Expanded family room, added new 3 season room, new windows, new deck, partial new roof105 North Compo – Complete interior renovation + addition15 High Point Rd., Westport – interior and exterior renovations12 Sterling Dr., Westport – interior renovations26 Sterling Dr., Westport – retaining wall replacement, new deck, new garage129 Harbor Rd., Westport - lift home for FEMA compliance, add elevator10 Allen Raymond Lane – adjacent to new Y – major renovation8 Allen Raymond Lane – adjacent to new Y – major renovationYMCA Camp Mahackeno – built 2 new open sided Camp Pavilion buildings14 Canal Road – new custom home 5 Marsh Rd, Westport - lift home for FEMA compliance43 Spriteview, Westport –Renovate for FEMA compliance, 100% new19 Edgemarth Hill – Addition, major renovation34 Marine Ave., Westport – lift home for FEMA compliance6 Sea Spray Rd., Westport – Phase I-lift home for FEMA compliance, phase 2 addition17 Marine Ave., Westport – lift home for FEMA compliance, rebuild entire first floor14 Spriteview Ave., Westport – lift home for FEMA compliance, major renovation71 Hillandale Ave., Westport – Greens Farms Church – numerous capital improvements
Multi Family Properties Developed (1981-1990) Edgewater Commons, Westport..............25 unitsEdgewood Green, Greenwich.................22 units, sold land with approvalsMariners Walk, Milford...........................33 unitsKendall Green, Milford...........................34 unitsBay Pointe Village, Milford....................39 unitsGovernors Ridge, Trumbull..................151 units

Testimonials

Our experience with Rick Benson and team has been extremely professional. The home we purchase 12 Sterling Drive caught our eye while looking for an opportunity to move closer to Compo beach and Mill Pond. The home is a modern contemporary design making the most of the water views which are absolutely amazing. The home gives us everything we were looking for in a community that is extremely welcoming. The house truly felt like home as soon as we moved in. Moving closer to the beach is a lifestyle change. Easy access to the Beach, Water and Longshore facilities promotes an active lifestyle. After owning the home for a year, we can truly say that Rick and team have been great to deal with.

Simon Whittington, Westport


Our family purchased a home in Westport and we planned to make some modifications and upgrades to the home prior to moving. Living in Los Angeles at the time, we realized that doing a significant remodel from almost three thousand miles away was not ideal but we planned on making numerous visits during the process which would hopefully allow us to keep a close eye on the project and progress. Unfortunately, within a month of closing on the home, the world found itself in a global pandemic and our plans of oversight were shut down. We spoke with a number of capable and well know contractors and after much review, decided to put our new home and it’s renovations in the hands of Rick Benson. The process was not easy given the distance; samples, colors and designs were all handled remotely, via email, telephone or zoom. Decisions that were usually simple became more like leaps of faith but Rick, his project manager Kevin Remson and their team of skilled contractors handle our renovation with care. Our project was completed on time for our scheduled arrival and we couldn’t be more thrilled with the final results.

77 Bayberry Ln., Westport, CT


We are extremely pleased with the custom home that RB Benson and Company built for us in Westport CT in 2019. From the moment we met Rick to discuss a potential purchase of a tear down, we knew we would get a quality home with attention to every detail. Rick's vast knowledge of Westport's planning, zoning and conservation helped us navigate the process and keep us on track. His building team, led by Kevin Remson, was highly professional, reliable and incredibly hardworking. Kevin was by our side through the entire process, helping us solve problems and streamline the numerous decisions along the way. We couldn't have picked a better team to build our dream house and highly recommend Rick and Kevin for any project.

Rick and Karen Leever 111 Harbor Road, Westport CT


When investigating a project to lift my house after the impacts of Hurricane Sandy, Rick Benson had the most experience in the area and was successfully able to navigate the complicated approvals from the local, State & Federal authorities. For me, he made the entire process seamless, dramatically improving my home’s exterior & interior, while balancing the restrictions of being on the water. When questions arose during construction, he was always available, even going so far as to answer a mobile call while he was climbing in Africa! He’s a pillar in the community, giving time, energy and money to great causes. I admire his work by the shore and am sure the project on Author’s Way will pay homage to the author and create a new community of neighbors that can aspire to follow in the legacy of AE Hotchner.

Jeff Manchester, Westport, CT


We retained Rick Benson and his team to knock down and build new on our property in the Saugatuck Shores area of Westport in 2012. As is common in the neighborhood, it is a cottage size and construction, taking advantage of wonderful views. The house features many environmentally advanced systems such as geothermal heating, radiant floor system, and a metal roof. Permits and variances were necessary, and Rick worked well with our engineer and architects to successfully see everything through. Rick was able to complete the project on time and on budget, and we are most pleased with the house, which is often complemented by guests and neighbors. We are very pleased with our completed house and working with Rick.

John & Cindy Fitzgerald, Westport, CT


We are extremely pleased with the custom home that RB Benson and Company built for us in Westport CT in 2019. From the moment we met Rick to discuss a potential purchase of a tear down, we knew we would get a quality home with attention to every detail.  Rick's vast knowledge of Westport's planning, zoning and conservation helped us navigate the process and keep us on track. His building team, led by Kevin Remson, was highly professional, reliable and incredibly hardworking.  Kevin was by our side through the entire process, helping us solve problems and streamline the numerous decisions along the way. We couldn't have picked a better team to build our dream house and highly recommend Rick and Kevin for any project. 

Rick and Karen Leever 111 Harbor Road, Westport CT


We have known Rick Benson for many decades and his wonderful reputation in Westport as a person, and for his very high quality construction works. It has been our good fortune to experience his meticulous planning and subsequently timely execution of complex construction projects, including a lift of our entire home. He is someone who brings unique energy to everyone involved in his projects. Rick is a true professional...always on a quest for excellence...he delivers on what he commits to. Especially in today's world, it is really refreshing to interact with such a person as Rick Benson!

Tom and Betty Lou Cummings, Westport, CT