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Winn C.

Star Sitter

Brookline, MA

5.0 out of 5 stars
42 reviews
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Services

These prices are for 1 dog.

Prices include all fees.

Winn can host

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
Dogs over 1 year old
Spayed and neutered dogs only
No females in heat
Takes only 1 client at a time

Availability

I lead a fairly predictable schedule during the week and keep my calendar updated. For any more details, please inquire within! I work full-time and in-office, however I do have flexibility to work a few days from home each week and will do so if I'm looking after your pet. Most evenings are spent at home or nearby. I have some degree of flexibility to accommodate special needs if necessary. Full honesty: my greatest differentiating feature is probably that I seldom travel on weekends when most people like to travel (holiday weekends, Thanksgiving, the December holidays).

Available
Not available
SMTWTFS
Boarding Cancellation Policy:

About Winn C.

Communication

10 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates

Skills

8 years of experience
Oral medication administration
Senior dog experience
Can provide daily exercise

Safety, trust & environment

I live in a large, well-maintained and dog-safe apartment in a very safe neighborhood. Dogs will be leashed and supervised while outside. If I am taking care of your dog during a workday and unable to be at home, my next-door neighbor is an avid dog lover who will pull spot-duty if needed.

Home

Lives in an apartment
Does not have a yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 2-4 hours

Information Winn C. would like to know about your pet

All the typical things: anxieties, likes/dislikes, health-related issues, how much they shed, other idiosyncrasies. I'm adaptable and will do my best to accommodate! Note that food, food/water bowls, treats, leashes, and toys are to be provided by owner.

A typical day

Standard routine involves a walk first thing in the morning and again in the late afternoon (if your dog prefers to go out more, please let me know). There are a number of park spaces nearby that I frequent with the dogs I care for. I generally try to match the dog's vibe while we hang--content to play with toys around the house or simply chill/cuddle in proximity. Please let me know how your doggo enjoys spending their time and I will do my best to emulate their typical environment.

Location

Brookline, MA

Winn C.'s Neighborhood

Winn C. has Star Sitter status

The Star Sitter program highlights responsive sitters who deliver highly rated care and have a history of listing accurate availability and preferences, making it easier for pet parents to find the best care for their pets.

World's Best Dog Funcle

Pet care experience

I've been dog-adjacent for most of my life, lived with a roommate's dog for 4+ years, and have been a go-to dogsitter for various friends since moving to Boston in 2019. Your doggo would be staying with me (just me!) in a large, well-maintained 1 bedroom apartment in the middle of Coolidge Corner (within walking distance of plenty of excellent park spaces).

Reviews

Nate W.
Boarding • may. 25, 2026
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Winn is like a professional! He's great with our dog and very flexible.

Susan K.
Boarding • abr. 27, 2026
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Winn is someone that I trusted instinctively partly because he’s so organized. He seems very knowledgeable about dogs.

Melanie G.
Boarding • abr. 07, 2026
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Winn is so great with Millie and easy to communicate with. Always know Millie is in great care!

Brian K.
Boarding • feb. 24, 2026
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Winn was great with my semi-senior dog, i highly recommend.

About Winn C.

Communication

10 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates

Skills

8 years of experience
Oral medication administration
Senior dog experience
Can provide daily exercise

Safety, trust & environment

I live in a large, well-maintained and dog-safe apartment in a very safe neighborhood. Dogs will be leashed and supervised while outside. If I am taking care of your dog during a workday and unable to be at home, my next-door neighbor is an avid dog lover who will pull spot-duty if needed.

Home

Lives in an apartment
Does not have a yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 2-4 hours

Information Winn C. would like to know about your pet

All the typical things: anxieties, likes/dislikes, health-related issues, how much they shed, other idiosyncrasies. I'm adaptable and will do my best to accommodate! Note that food, food/water bowls, treats, leashes, and toys are to be provided by owner.

A typical day

Standard routine involves a walk first thing in the morning and again in the late afternoon (if your dog prefers to go out more, please let me know). There are a number of park spaces nearby that I frequent with the dogs I care for. I generally try to match the dog's vibe while we hang--content to play with toys around the house or simply chill/cuddle in proximity. Please let me know how your doggo enjoys spending their time and I will do my best to emulate their typical environment.

Each sitter joining Rover needs to pass a background check. And by booking on Rover, you can get photo & message updates, 24/7 support, and reimbursement for eligible vet care.
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Winn C.

Star Sitter

Brookline, MA

5.0 out of 5 stars
42 reviews