Ryan Bollard

Ryan Bollard

Licensed Real Estate Salesperson

Washington Depot Brokerage

6 Green Hill Road
PO Box 329
Washington Depot, CT 06794
  • Born In:
    Bridgewater, CT
  • Live In:
    Woodbury, CT
  • Interests:
    Hiking,, Boating, Camping, Cooking, Traveling
  • Can’t Live Without:
    Litchfield County Nature

Ryan Bollard started his career in real estate as a photographer.  He has enjoyed working with several agencies to create beautiful photos of their real estate listings.  It was then Ryan fell in love with helping agents and homeowners list and sell their homes.  To this day, Ryan still enjoys creating top-quality photos and videos of his clients’ homes.  In a time when so many homes are bought and sold based on their online profile, it is paramount to show each home’s features and amenities with the best quality possible.  

Loyalty and thoughtfulness are the most important attributes to Ryan when representing his clients. Acknowledging that a home is most likely the biggest purchase people will make in their lifetime, it is his top priority to be the guide that they can trust and depend on. 

Raised in Bridgewater Connecticut, Ryan has been an active part of the Southern Litchfield County community ever since childhood. Ryan attended Shepaug Valley Middle & High School and to this day attests to the quality of education and sense of community that accompanies the region. He attended Champlain College in Vermont and earned a degree in Digital Cinematography through Full Sail University in Florida. 

When Ryan isn’t busy helping his clients with buying and selling their homes, he can most likely be found out enjoying the pristine trails in Litchfield County and greater New England. Whether it’s hiking or out hunting for landscape photos, Ryan loves exploring all of the nature that Litchfield County has to offer. On hot summer days when hiking isn’t quite as appealing, Ryan can be found beating the heat in the cool waters of Lakes Lillinonah & Candlewood.

Ryan Bollard started his career in real estate as a photographer.  He has enjoyed working with several agencies to create beautiful photos of their real estate listings.  It was then Ryan fell in love with helping agents and homeowners list and sell their homes.  To this day, Ryan still enjoys creating top-quality photos and videos of his clients’ homes.  In a time when so many homes are bought and sold based on their online profile, it is paramount to show each home’s features and amenities with the best quality possible.  

Loyalty and thoughtfulness are the most important attributes to Ryan when representing his clients. Acknowledging that a home is most likely the biggest purchase people will make in their lifetime, it is his top priority to be the guide that they can trust and depend on. 

Raised in Bridgewater Connecticut, Ryan has been an active part of the Southern Litchfield County community ever since childhood. Ryan attended Shepaug Valley Middle & High School and to this day attests to the quality of education and sense of community that accompanies the region. He attended Champlain College in Vermont and earned a degree in Digital Cinematography through Full Sail University in Florida. 

When Ryan isn’t busy helping his clients with buying and selling their homes, he can most likely be found out enjoying the pristine trails in Litchfield County and greater New England. Whether it’s hiking or out hunting for landscape photos, Ryan loves exploring all of the nature that Litchfield County has to offer. On hot summer days when hiking isn’t quite as appealing, Ryan can be found beating the heat in the cool waters of Lakes Lillinonah & Candlewood.

Ryan Bollard started his career in real estate as a photographer.  He has enjoyed working with several agencies to create beautiful photos of their real estate listings.  It was then Ryan fell in love with helping agents and homeowners list and sell their homes.  To this day, Ryan still enjoys creating top-quality photos and videos of his clients’ homes.  In a time when so many homes are bought and sold based on their online profile, it is paramount to show each home’s features and amenities with the best quality possible.  

Loyalty and thoughtfulness are the most important attributes to Ryan when representing his clients. Acknowledging that a home is most likely the biggest purchase people will make in their lifetime, it is his top priority to be the guide that they can trust and depend on. 

Raised in Bridgewater Connecticut, Ryan has been an active part of the Southern Litchfield County community ever since childhood. Ryan attended Shepaug Valley Middle & High School and to this day attests to the quality of education and sense of community that accompanies the region. He attended Champlain College in Vermont and earned a degree in Digital Cinematography through Full Sail University in Florida. 

When Ryan isn’t busy helping his clients with buying and selling their homes, he can most likely be found out enjoying the pristine trails in Litchfield County and greater New England. Whether it’s hiking or out hunting for landscape photos, Ryan loves exploring all of the nature that Litchfield County has to offer. On hot summer days when hiking isn’t quite as appealing, Ryan can be found beating the heat in the cool waters of Lakes Lillinonah & Candlewood.

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Testimonials

Ryan, is absolutely amazing, we met Ryan through a mutual friend who recommended him. We have worked with many other realtors in the past but Ryan is definitely a cut above the rest. Ryan is definitely stuck with us with all things real estate.

Jason Smith

Ryan Bollard is amazing. He was always available when we called - even at the last minute to book a showing the same day. Very knowledgable of the area. Upbeat, informed, easy going - one our best experiences with an agent we have had. During this tough real estate market (2024) he remained positive that we would find our new home and we did with his help. We highly recommend him!

Daniel Lauter & Donna Soszynski

Ryan did a great job.

Patrick & Michele Sweeny

Ryan Bollard is genuine and very professional. He went above and beyond to make sure the purchase of our home went smoothly. He obviously loves being a real estate agent and is grateful to be affiliated with your agency. Thank you!

Gregory & Joy Bollard

Ryan is awesome. I would work with him again in a heartbeat.

Patrick McCormack

My Listings

Lot 8 Willow Brook Drive $544,900 link

Lot 8 Willow Brook Drive

Roxbury, CT 06783 | Litchfield County
$544,900
10 Acres

Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill"...

10.00
acre
Lot 7 Willow Brook Drive $524,900 link

Lot 7 Willow Brook Drive

Roxbury, CT 06783 | Litchfield County
$524,900
10.13 Acres

Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill"...

10.13
acre

My Sales

101 South Street $951,000 link

101 South Street

Roxbury, CT 06783 | Litchfield County
$951,000
6 Beds 4/2 Baths 5,439 Sqft 38.05 Acres

Look no more! With over 38 acres of land and over 5000sqft of living space, this home will allow you to create your very own oasis! Perfectly configured for multi-generation living,...

6
bed
4/2
bath
5,439
sqft
208 Sawyer Hill Road $800,000 link

208 Sawyer Hill Road

New Milford, CT 06776 | Litchfield County
$800,000
3 Beds 2/1 Baths 2,257 Sqft 5.58 Acres

Set at the top of an open meadow bordered by stone walls, this Habitat Post & Beam Saltbox has beautiful sunset views. The house was custom built in 1998 with an open floor plan....

3
bed
2/1
bath
2,257
sqft
110 Washington Ridge Road $750,000 link

110 Washington Ridge Road

New Milford, CT 06776 | Litchfield County
$750,000
4 Beds 4/1 Baths 3,124 Sqft 17.42 Acres

A Classic four bedroom cape style home in one of New Milford’s most prestigious residential neighborhoods. The open concept main level features a gracious two-story entry foyer,...

4
bed
4/1
bath
3,124
sqft
95 Transylvania Road $735,000 link

95 Transylvania Road

Roxbury, CT 06783 | Litchfield County
$735,000
3 Beds 2/1 Baths 3,540 Sqft 4.78 Acres

Welcome to the one of a kind, 95 Transylvania Rd! This timber frame, constructed in 1998, sits on ~4.78 manicured acres nestled amongst the forests of Fawn Woods. A two leveled...

3
bed
2/1
bath
3,540
sqft
306 Woodbury Road $700,000 link

306 Woodbury Road

Washington, CT 06793 | Litchfield County
$700,000
3 Beds 2/1 Baths 2,369 Sqft 3 Acres

Discover this stately & sought-after one-level home, expertly crafted & nestled back on a peaceful country road just outside the heart of Washington. Set atop a desirable three-acre...

3
bed
2/1
bath
2,369
sqft
110 Yale Avenue $500,000 link

110 Yale Avenue

Middlebury, CT 06762 | New Haven County
$500,000
3 Beds 2 Baths 1,800 Sqft 0.47 Acres

Welcome to your dream colonial! This charming 3-bedroom, 2-bathroom home boasts a timeless appeal, complete with modern updates and classic features. Step onto the inviting front...

3
bed
2
bath
1,800
sqft
Lot 1 Willow Brook Dr Drive $480,000 link

Lot 1 Willow Brook Dr Drive

Roxbury, CT 06783 | Litchfield County
$480,000
10.79 Acres

Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill"...

10.79
acre
Lot 3 Willow Brook Drive $450,000 link

Lot 3 Willow Brook Drive

Roxbury, CT 06783 | Litchfield County
$450,000
14.99 Acres

Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill"...

14.99
acre
Lot 6 Willow Brook Drive $450,000 link

Lot 6 Willow Brook Drive

Roxbury, CT 06783 | Litchfield County
$450,000
10 Acres

Welcome to your new private paradise, Willow Brook Dr! Enjoy the pristine meadows, woodlands, and breathtaking westerly views atop this private road. Situated in the "Good Hill"...

10.00
acre
40 Warren Way $426,000 link

40 Warren Way

Watertown, CT 06795 | Litchfield County
$426,000
3 Beds 3/1 Baths 4,150 Sqft 0.23 Acres

Your search ends here! This incredibly accommodating, move-in ready 3 bed/ 3.5 bath Colonial has been meticulously maintained since its purchase in 2020. Recent improvements offer:...

3
bed
3/1
bath
4,150
sqft
15 Ridgewood Road $394,000 link

15 Ridgewood Road

Woodbury, CT 06798 | Litchfield County
$394,000
3 Beds 2 Baths 1,819 Sqft 0.6 Acres

Terrific location- quiet neighborhood and only minutes to town centers of Woodbury, Southbury & Middlebury. So much potential and versatile space with this floor plan. Originally...

3
bed
2
bath
1,819
sqft
20 Scuppo Road $390,000 link

20 Scuppo Road

Woodbury, CT 06798 | Litchfield County
$390,000
3 Beds 1 Baths 1,160 Sqft 1.21 Acres

Welcome home to this charming 3-bedroom, 1-bath house on a private lot! This property features newly refinished hardwood floors and recessed lighting throughout. The main level...

3
bed
1
bath
1,160
sqft