
Family-focused boutique Cockapoo breeder ~ Located in New England ~ Serving families East Coast to West Coast


Our Puppies
Cockapoo Puppies lovingly raised
by our family for your family
Thank you for your interest in our upcoming litters. We are dedicated to raising well-adjusted, healthy Cockapoos that thrive as lifelong companions. As we look ahead to our 2026 breeding plans, we invite you to learn more about our process, our health-tested parents, and how you can join our exclusive waitlist for future puppies.
Upcoming Cockapoo Litters

Maple x Moxie
Estimated Due Date: 1/25/26

Maple had her ultrasound and pregnancy has been confirmed!
We will be sure to update just as soon as we have 🐾 on the ground.

Charlotte Ann x Moxie
Estimated Due Date: March '26

Charlotte Ann has come into season and will soon be having dates with Moxie.
Details to follow, once pregnancy is confirmed.

Aria x Moxie
Estimated Due Date: March '26

Aria has come into season and has had dates with Moxie.
Details to follow, once pregnancy is confirmed.

Moon x Moxie
Estimated Arrival: Spring '26

Moon should be coming into season this spring. Based on previous litters, we estimate an arrival date between April -> June '26.
Stay tuned.
Current Cockapoo Litters
We have no pups at this time. We are eagerly awaiting the arrival of Maple's litter ~ Estimated Due Date, 1/25/26
Our Wait
If you'd like to be put on our waitlist for one of our upcoming Cockapoo puppy litters, the anticipated wait is approximately:
2 to >4 months for a black with white markings male or female
>4 to 6-/+ months for an apricot/red/buff/cream male
4-/+ to >6 months for an apricot/red/buff/cream female.


Please note: Wait time can vary (can be shorter or a little longer), as it depends on actual litter sizes, gender/color breakdown of the litter, and families preferences and availability to take pupy home when they are reached out to.
Our Standards
As a small family breeder we have limited litters per year and will not increase "production" at the expense of our breeding programs standards, which are:
To remain a small family breeder where all of our moms are beloved members of our family and home.
For our mothers to have litters as is healthy and safe for them with guidance from our wonderful veterinary practice,
To only pair and breed parents who have passed health testing so as to make sure we are bettering breed health in Cockapoos.
To love on and care for each and every puppy we are blessed to raise with all of our hearts.
Adopted
Cockapoo puppy litters we've placed - Current Moms
Our Cockapoo puppies have successfully transitioned into diverse forever homes, thriving everywhere from urban suites to rural neighborhoods. Known for their intuitive and highly social natures, they seamlessly integrate as the heart of any household. We take immense pride in our all grown up pups, who have evolved from their first playful steps into confident, well-adjusted companions and beloved members of their fur-ever family.
Click on the above link to see our "Cold Weather" F1 Cockapoo puppy litter.
Charlotte Ann x Moxie (F1b Pups)
Click on the above link to see our "Top Minecraft Players" F1b Cockapoo puppy litter.
Aria x Moxie (F1b Pups)
Click on the above link to see our "Playlist Faves" F1b Cockapoo puppy litter.
Click on the above link to see our "Flower Power" F1 Cockapoo puppy litter.
Charlotte Ann x Moxie (F1b Pups)
Click on the above link to see our "Mac & Cheese" F1b Cockapoo puppy litter
Click on the above link to see our "Spy School" F1b Cockapoo puppy litter.
Click on above link to see our "Tropical Fruits" F1 Cockapoo puppy litter.
Charlotte Ann x Moxie (F1b Pups)
Click on above link to see our "Greek Mythology" F1b Cockapoo puppy litter.
Click on above link to see our "Bob Marley" F1b Cockapoo puppy litter.
Click on above link to see our "Fast Food Fellas" F1 Cockapoo puppy litter.
Click on above link to see our "Birds of the World" F1b Cockapoo puppy litter.
Charlotte Ann x Moxie (F1b Pups)
Click on above link to see our "WOF - Sandwings" F1b Cockapoo puppy litter.
Click on above link to see our "I Can Read - Chicks" F1 Cockapoo puppy litter.
Click on above link to see our "Seeds and Grains" F1 Cockapoo puppy litter.
Click on above link to see our "Pokemon" F1b Cockapoo puppy litter.
Click on the above link to see our "Kung Fu Panda" F1 Cockapoo puppy litter.
Adopted
Cockapoo puppy itters we've placed - Retired Moms
Click above to see our "Faith, Hope & Charity" F1 Cockapoo puppy litter.
Click above to see our "Toby Mac & The Diverse City Band" F1 Cockapoo puppy litter.
Click above to see our "Elephant & Piggie" F1 Cockapoo puppy litter.
Click above to see our "Marvel Avengers" F1 Cockapoo puppy litter.
Click above to see our"Power Rangers, Dino C" F1 Cockapoo puppy litter.
Click above to see our "NATO Phonetic Alphabet" F1 Cockapoo puppy litter.
Click above to see our "Sugar Creek Gang" F1 Cockapoo puppy litter.
"Ewoks" F1 Cockapoo puppy litter
Click above to see our "Wings of Fire" F1 Cockapoo puppy litter.
What Our Families are saying
Read more testimonials on our Watch Me Grow Page
Read more testimonials on our Watch Me Grow Page
Destiny's entire family is instrumental in the raising of these pups; they are showered with love and positive training as they learn to navigate their new world. The qualtiy of our pup is a reflection on Destiny and her family and we feel utterly privileged to have found Chesley Hill Cockapoos.
~ Hazel S.
Once we came across Chesley Hill Cockapoos we instantly fell in love with the openness, caring and compassionate family that was raising, what seems like, the most adorable Cockapoo puppies in the world.
I believe it is so important to support responsible breeders, those who first start with health-tested parents and raise their pups within their home. Destiny has hand-crafted her entire program to set her pups up for success and I can say, it works! My pup handles new situations wonderfully, loves playing with other pups and people. Everyone we meet either comments on how cute he is or how well behaved he is.
~ Molly B.
Destiny is kind, professional, knowledgeable and a pleasure to work with.
Our pup is extremely smart, easy to train and just a love. I have absolute no doubt that those first 8 weeks with Destiny and her family made a huge impact on the kind of dog he is.
We couldn’t be happier!






































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