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Winn C.

Star Sitter

Brookline, MA

5 out of 5.0 stars
31 reviews
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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

Rachel G.
Dog Boarding • Jul 28, 2025
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We were happy to have Winn's help taking care of our dog while we moved into our new condo. We needed a couple of days to get organized without having the dog underfoot, and he did great staying with Winn. Winn responds to messages immediately and was accommodating, keeping Jack for a few extra hours than originally scheduled.

Katie K.
Dog Boarding • Jul 15, 2025
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Winn was great with my golden retriever, Jackson. He facilitated a smooth drop-off, even when Jax was a little nervous. He also was flexible with is when our flight was delayed and kindly let us pick up Jax and hour later into the evening than expected. He was communicative and took great care of Jackson. Would recommend!

Melanie G.
Dog Boarding • Jul 06, 2025
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Winn is always attentive, flexible, communicates, and I know it takes a wonderful care of Millie. Star sitter!

Peter D.
Dog Boarding • Jun 19, 2025
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First time booking Winn, but very impressed! Easy and flexible communication, and I appreciated the chance for a meet and greet before the booking date to touch base in person. Will definitely be booking Winn again!

About Winn C.

Communication

6 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.

Services

Boarding
in the sitter's home
$88per night

Winn can host

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
Calendar last updated a day ago
Winn can host up to 1 pet per night
Boarding Cancellation Policy:

About Winn C.

Communication

6 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
All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.
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Winn C.

Star Sitter

Brookline, MA

5 out of 5.0 stars
31 reviews