House Sitting Kenwood

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Over 125
pet parents in Kenwood have booked house sitting

Kenwood, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
47 reviews
17 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$35
per night
4.9 out of 5 stars
18 reviews
3 repeat clients
5 years of experience
Hyde Park, Chicago, IL, 60615

Lucille was a fantastic sitter and our dog had a blast. She was so thoughtful about making sure our dog Lea felt comfortable, and she kept us updated with great photos and videos.

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Karlos B.
Sitter Profile Image: Zoe R.
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Zoe R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
14 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60615

Zoe watched our sweet pup and her cousin for an evening. She was on time (early), friendly, and sweet.

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Colleen S.
Sitter Profile Image: Victoria G.
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Victoria G.
from
$85
per night
5.0 out of 5 stars
29 reviews
4 repeat clients
21 years of experience
Hyde Park, Chicago, IL, 60615

Victoria housesat and cared for our two cats for a short trip. She was attentive and communicative, bringing up concerns as they came up and offering suggestions, like thinking of whisker fatigue and being mindful of litter box behavior. Appreciate you taking good care of our kitties!

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Quinn Q.
Sitter Profile Image: Maia S.
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Maia S.
from
$35
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60637

Maia is the best sitter we’ve ever had. I can’t say enough good things about her. She’s kind and communicative and undoubtedly great with animals. We find our dog and 🐱 to be noticeably more content when she’s stayed with them than with any other sitter. She’s even seemed to win over my shy little cat who normally takes so long to warm up to people. It’s the biggest relief to leave them in her care and Maia will always be our first choice for a sitter.

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Talisa B.
Sitter Profile Image: Alexis W.
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Alexis W.
Star Sitter
from
$73
per night
5.0 out of 5 stars
29 reviews
8 repeat clients
5 years of experience
Chicago, IL, 60637

Alexis took wonderful care of our dog and home while house sitting. Great communication before and during our time away. I’d recommend Alexis to anyone and will look to rebook in the future.

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Lauren S.
Sitter Profile Image: Jasmine P.
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Jasmine P.
from
$175
per night
5.0 out of 5 stars
98 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

Jasmine is fantastic. She is unfailingly kind, calm and easygoing. She leaves our dogs calm and our house spotless - both of which leave us feeling stress-free for our travel and return.

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Cynthia H.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$45
per night
5.0 out of 5 stars
31 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

Elizabeth took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.

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Jenny L.
Sitter Profile Image: Nicole R.
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Nicole R.
from
$50
per night
4.9 out of 5 stars
56 reviews
21 repeat clients
3 years of experience
Bridgeport, Chicago, IL, 60616

Nicole was the absolute best with your boy Chico. He need alot of specialized attention and is reactive with other dogs and she navigated everything like a pro. She left our home spotless and was so respectful while staying. We got so many pictures and updates - it was the first trip I had where I didn’t have anxiety about how Chico was doing. She even trimmed his nails and got him a bandana - can’t say enough great things. Will 1000% book with Nicole again

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Hayley B.
Sitter Profile Image: Danielle K.
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Danielle K.
from
$50
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
8 years of experience
Woodlawn, Chicago, IL, 60637

About: I have pet sit all kinds of loving dogs. Since I was 15 My family, friends and neighbors have trusted me to walk, feed, play with and care for their pets. I work full time virtually, so I am flexible and can care for your beloved pups while at home. I only have availability to do overnight boarding on weekends. I have a spacious place for your dog to have plenty of room to play and be comfortable. In addition, I have a dog park and a spacious park/field a walk away from my home. There also is a trail for us to walk as well. I am equipped to feed, walk and sing to your pup.

Sitter Profile Image: Ava M.
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Ava M.
from
$55
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
11 years of experience
Chicago, IL, 60621

Ava was wonderful with our 3 pups. She knew how to manage their chaos and treated them so sweetly. She left the place looking great and really just went above and beyond. We will definitely be using her services again.

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Gail S.
Sitter Profile Image: Dominique F.
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Dominique F.
from
$40
per night
4.6 out of 5 stars
73 reviews
39 repeat clients
16 years of experience
South Shore, Chicago, IL, 60637

Dominique did a great job with my 2 cats and 1 dog. She also took good care of my apartment. She sent me numerous of pictures and videos and also followed my instructions well especially pertaining to one of my cats who needs a little extra supervision. Thank you and I would book again.

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Cornelius D.
Sitter Profile Image: Emmaline H.
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Emmaline H.
from
$31
per night
1 repeat client
10 years of experience
Chicago, IL, 60615

About: What sets me apart is my focus on individualized care for each pet. I take time to understand their routine, personality, and comfort needs so they feel safe and relaxed while you're away. I’m reliable, attentive, and make communication a priority by providing regular updates with photos and messages. Pet care fits easily into my daily routine because I have a flexible and organized schedule that allows me to prioritize visits, feedings, and check-ins consistently. I’m able to plan my day around morning, afternoon, and evening care as needed, making sure pets receive attention on time and without rush. I’m also good at managing responsibilities, so I can balance pet care with other commitments while still being reliable and responsive. Whether it’s drop-ins, feeding, playtime, or house sitting, I can adapt my routine to meet each pet’s needs and ensure they stay comfortable and well cared for throughout the day. I provide care for pets in their own home to help keep them comfortable in their familiar environment. I offer house sitting, where I stay in the home as needed to provide companionship, maintain routines, and make sure pets are fed, walked, and well cared for. I also offer dog walking and daily walks to ensure pets get regular exercise, bathroom breaks, and attention throughout the day. In addition, I can handle scheduled feedings and basic care routines exactly as instructed by the owner. I do want to note that I do not offer boarding or training services. My focus is on in-home care and walking services, making sure pets stay safe, relaxed, and well looked after while their owners are away or busy.

Sitter Profile Image: Olivia H.
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Olivia H.
from
$50
per night
15 years of experience
Hyde Park, Chicago, IL, 60615

About: I have had 4 small dogs my whole life, but have also been a neighborhood pet sitter for dogs of all sizes for many years! I love all pups! I have Tuesdays and weekends off so I can spend the entire day with your pup while you’re away! We will go on walks and hang out outside :) I live in a dog friendly apartment. My apartment has a patio with access to a whole outdoor area where your pup can go potty and run around and sun bathe!

Sitter Profile Image: Niayla B.
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Niayla B.
from
$30
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
12 years of experience
Hyde Park, Chicago, IL, 60613

Niayla was amazing! She was so communicative throughout the day while watching our dogs, sending updates and photos. I will definitely be using her services again and couldn’t recommend her enough! Thank you Niayla!

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Chandler J.
Sitter Profile Image: Bella B.
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Bella B.
from
$40
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60615

Bella did a great job with our pups. Great communication and she was very flexible working with our pack. I'd gladly have her back to watch them any time.

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Andrew M.
Sitter Profile Image: Julia G.
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Julia G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
6 years of experience
Hyde Park, Chicago, IL, 60614

About: Hello!! My name is Julia I’m 23 and I love animals. Ever since I was little I’ve always had a special interest in nature and animas especially cats! One of my favorite childhood memories is rescuing feral kittens in my neighborhood and finding homes for them. In my teens years I started dog and cat sitting for friends and family and ever cared for horses and rabbits in my high schools FFA. As of now I’m a painter and artist with a lot of time on my hands and would love to spend some quality time with your pets! When staying with a pet I like to follow a schedule for potty and feeding times since familiar routines can calm pets that might be anxious around new people :)

Sitter Profile Image: Claire P.
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Claire P.
from
$70
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
Sitter Profile Image: Jessica G.
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Jessica G.
Star Sitter
from
$75
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
10 years of experience
New City, chicago, IL, 60609

About: I have always owned a variety of pets and enjoy their company. I also enjoy long walks on trails in my free time, I would say it's one of my hobbies apart from exploring the city. I have always been very fond of animals and hope to work with them someday. For now i would be happy doing any sort of work that involves animals. I'm currently available to work as either a sitter or walker and am hoping to try it out soon. I actually have a very flexible schedule! Please just message me and I will respond promptly. Thank you for reading, have a great day today! I have experience petsitting at other peoples homes so no need to worry about me! If housed at my home I have a cat running around so no cat biters!

Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$88
per night
4.7 out of 5 stars
12 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60653

About: Welcome to my care profile! Thanks so much for your consideration. My name is Jasmine 🌻 I am a plantbased artist from Chicago whose main focus is about reconnecting and interweaving ourselves with nature to cultivate vitality and a cohesive social eco environment in which every being thrives in harmony. I am an enthusiastic world traveler, animal and nature lover committed to sharing joy and my authentic glow everywhere I go. As a seasoned holistic wellness consultant, caregiver, empowerment content creator, and community herbalist I work from home and close to the earth because I love to be outside and nurturing all living creatures. My main personal values center integrity with my inner wisdom, and connecting deeply with all that there is in my environment by sharing love & compassion to every being I encounter. I believe that everyone’s presence is a gift so I take the time to be in gratitude with all living beings I encounter moment by moment. When I was younger I always had a big heart and would care deeply for everyone and everything. I grew up with a guiñea pig, a fish, making friends with trees and babysitting my younger siblings and neighborhood children. I often visited my grandmama’s house to help her play with and care for her German Shepard. As a teenager I attended a rural farming school in Vermont and volunteered on many farms near Boston where I learned how to grow produce and raise livestock namely, cows, ducks, chickens, turkeys, and goats. While In Claremont California, I obtained my BA in Environmental Analysis Africana Studies and a Minor in Studio Art, studying the intrinsic interdependence and the ultimate beauty and creative web connections that support and maintain life. Additionally, I often took care of many of my friends' dogs (chihuahua and other medium mix breeds) while away on extended trips, namely playing with pets, walks, bathing, and poop time. In my 20’s I have had various house sitting opportunities to collect packages and tend for pets, cats, fish and gardens. Currently as a full time dog walker, herbalist and land steward, I feed the local wildlife, tend to an abundant native species garden and perform other domestic duties to maintain the beauty of the home. I believe that we are one with nature so connecting with nature is how we connect with ourselves. Also as an avid world traveler, I look forward to connecting with local animals and plants of any environment. My offering: Providing Premium Care Service Diverse care experiences and utmost dedication to quality care make me the perfect candidate to care for your love one(s) and home. My goal with clients is for us to build a genuine rapport of honesty, trust, and open communication. I am attentive, loving, responsible, nurturing and flexible to fit the needs of everyone I care for. Thanks for your consideration in trusting me in such a sacred opportunity to care for your home, plants, and pets while you're away. I will provide you with the peace of mind and consistent updates to assure you everything is going well at home so you can continue to enjoy your present. What I provide: Safety trust and peace of mind while your away Caring for your all pet needs(play groom, walk, feed) 3 checkin with photos each day Emotional connection with pets Positive Energy I look forward to chatting with you. Messages is the best form of communication for me. Peace ~Goddess Jasmine I currently work virtually as an entrepreneur on part time bases generally less then 10 hrs a week. This give me flexibility and able to sure your needs with the upmost attention. Via consistent messaging, clear communication, reviewing responsibilities and providing updates, I hope to build a genuine rapport of honesty, trust, and open communication with your family 🐶

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The median cost per night for house sitting in Kenwood is $50

Pet parents share their Rover experiences - Kenwood

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5.0 out of 5 stars

Alexis is wonderful! She had quite the introduction to my sassy rescue pup. She had to deal with his being very snippy and clean up a few messes. Through all of it, she was loving and patient. By the end of her stay, even my "spirited" dog was smitten. An excellent hooman!

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Carly A.
House Sitting
5.0 out of 5 stars

Kristine was great with taking care of my anxious pup- especially during the fourth of july holiday when the fireworks can make him more nervous than normal. I could tell he had been well cared for!

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Laura F.
House Sitting
5.0 out of 5 stars

Allison has helped us with over night stays twice now and she is SO great! Very responsive and Peyton loves her!

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Katie D.
House Sitting
5.0 out of 5 stars

Dominique did a great job with my 2 cats and 1 dog. She also took good care of my apartment. She sent me numerous of pictures and videos and also followed my instructions well especially pertaining to one of my cats who needs a little extra supervision. Thank you and I would book again.

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Cornelius D.
House Sitting
5.0 out of 5 stars

maia was wonderful, very communicative and respectful. peanutis an anxious dog and she was nice and calm when we got home. will definitely be booking her to hang out with peanut again

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Audrey T.
House Sitting
5.0 out of 5 stars

Grace took exceptional care of our dog, Coco! She was incredibly kind, patient, and attentive, and it was clear that she genuinely cares about the pets she works with. Coco was comfortable and happy with her, which gave us so much peace of mind. Grace went above and beyond to make sure Coco was well taken care of, and her professionalism and warm personality made the entire experience wonderful. We’re so grateful for her excellent service and will definitely be requesting Grace again. Thank you for treating Coco like family!

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ketki P.
House Sitting
5.0 out of 5 stars

Ahriel was communicative, kind, and took great care of my 3 animals on short notice - including a large senior dog and a toothless cat! She asked thorough questions when interviewing her which was reassuring. Since the stay was short notice, she was unable to meet the animals before hand or get a lay of the land (confusing apartment building), but did an incredible job with everything no less. Would recommend her and will hopefully get to use her in the future!

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Madison A.
House Sitting
5.0 out of 5 stars

Mia took good care of Doby while I was away. She kept me updated with photos and she left my house clean and tidy. Knowing Doby was in such good hands made my vacation so much more relaxing. I would absolutely book Mia again for my next trip and highly recommend her to anyone looking for a caring and reliable dog sitter!

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Edie c.
House Sitting
5.0 out of 5 stars

Ava shared pictures and accurately followed all our instructions, we are very grateful for the boarding service provided =)

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Gabriel T.
House Sitting
5.0 out of 5 stars

Niayla was wonderful. It was my first time leaving my cat, Camille, at home by herself for two weeks and Niayla clearly gave her so much love, attention, and cuddles while I was gone. It really put my mind at ease to have someone in my home who so obviously truly cared for Camille. I could tell in all the photos and from the updates that they really enjoyed each other’s company and could not be more grateful to have found Niayla on this app!

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Sabrina M.
House Sitting
5.0 out of 5 stars

Elizabeth was amazing with my cat. This was my first time using a sitter I didnt know personally and she eased all of my fears. Multiple updates with pictures. Not to mention being great to work with- with a calming personality. Would definitely book her again.

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Joy M.
House Sitting
5.0 out of 5 stars

As usual, Staci was amazing with our cats and dog on our 10 day vacation. Zero complaints, great service, she goes above and beyond.

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Eleanor F.
House Sitting
5.0 out of 5 stars

Emily was an excellent dog sitter and I would hire her again. She was communicative and sent updates throughout the day which gave me great peace of mind. I never had to reach out and ask how my dog was doing because she proactively kept me informed. She was also accommodating with my dog’s feeding routine and mindful of his reactivity to bikes/scooters which I really appreciate. When I returned home everything was exactly as I had left it. I highly recommend Emily.

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Daritza H.
House Sitting
5.0 out of 5 stars

Jozelin took great care of our dog, Derby. She was communicative and responsive and sent us great photos of Derby while we were on vacation. I would recommend booking Jozelin to care for your pets!

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Kaylyn T.
House Sitting
5.0 out of 5 stars

Rahmya was amazing! She was very flexible in setting up a meet and greet and instantly prioritized befriend Stormie. I got lots of updates and update pictures daily of stormie which made the whole process of being out of town much easier. I never felt like Stormie wasn't in good hands. The home was clean and perfectly tidy when we arrived back, which was so appreciated when returning from our trip. I would 100% recommend Rahmya for anyone looking for a pet sitter 💙

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Lillian W.
House Sitting
5.0 out of 5 stars

Bri does an absolutely incredible job! My dogs are obsessed with her and she send the best pics. She has also taken care of several issues w my house while she was house sitting. She is responsible and trustworthy, 100% recommend!

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Kate B.
House Sitting
5.0 out of 5 stars

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
House Sitting
5.0 out of 5 stars

Annie was amazing! I am so thankful for her kindness to my three animals (two cats and a dog). She was so attentive, communicative, and caring, following all of their care routines by the book! Her love of animals is very apparent. I highly recommend her and will definitely be using her again. Thank you Annie!

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Veronica M.
House Sitting
5.0 out of 5 stars

Lucille is an incredibly kind and attentive cat sitter. She made him feel loved and played with him so much. She even took him for a stroll on his backpack. Would highly recommend. Felt like our baby was in wonderful hands!

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Joanna A.
House Sitting
5.0 out of 5 stars

Phenomenal. Anais took great care of our doges and home. She was extremely responsive to our messages and sent update pictures every day.

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Gabriel L.
House Sitting
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Sitters in Kenwood average 4
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