306 E Chester Street, Kingston, NY 12401
Property image
Property image
SOLD
DEC 11, 2025

306 E Chester Street
Kingston, NY 12401

  • 3 Beds
  • 1 Bath
  • 1,234 sqft

$410,000

Last Sold: Dec 11, 2025
17% over list $350K
$332/sqft
Est. Refi. Payment $2,664/mo*
Refinance Your Home

$410,000

Last Sold: Dec 11, 2025
17% over list $350K
$332/sqft
Est. Refi. Payment $2,664/mo*
Refinance Your Home
3 Beds
1 Bath
1,234 sqft

Local Information

  • Map ViewExplore the area around 306 E Chester Street.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome to Chester Oak Cottage, a circa 1935 move-in ready cottage charmer in the heart of Kingston, with original details, thoughtful modern updates, and a private backyard retreat. The inviting, freshly rebuilt front porch sets the tone, opening into a sun-filled living area with custom built-in bookcases and decorative moldings. A separate dining room flows into the updated kitchen, where patio doors lead out to a pea-gravel landscaped terrace, perfect for morning coffee. Stone steps ascend to a quaint yard framed by mature trees with a cozy fire pit area, creating a surprisingly private setting just minutes from town.

Upstairs you'll find three bright bedrooms and a fully renovated bathroom featuring new tile, vanity, and fixtures. Original hardwood floors, freshly sanded and sealed, run through every room, and high-end paint and wallpaper from Farrow & Ball and Warner House bring warmth and personality. A walk-up attic offers excellent storage, while the partially finished basement with laundry can flex as a home office, gym, or creative space. A private driveway fits two cars comfortably, providing easy access and peace of mind.

Recent enhancements include: a new furnace, exterior repainting, new shutters and windows, added fencing, custom built-ins, a gut-renovated bathroom, updated light fixtures, and new kitchen and laundry appliances.

Located just minutes from Kingston's Uptown and Downtown districts, this home offers easy access to local favorites including Chleo, Camp Kingston, Sorry Charlie, and Village Grocery & Refillery. Outdoor destinations like Sojourner Truth State Park and the Rondout Creek Trail are nearby, as are beloved neighborhood spots like Mickey's Igloo ice cream stand.
306 E Chester Street, Kingston, NY 12401 is a 3 bedroom, 1 bathroom, 1,234 sqft single-family home built in 1935. It last sold for $410,000 on Dec 11, 2025 (17% above the $350,000 asking price). It is currently off market. The Trulia Estimate is $425,100, with a rent estimate of $2,750/month.

Home Highlights

Parking
2 Open Spaces
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
$332/sqft
Listed
180+ days ago

Home Details for 306 E Chester Street

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior Entry,Partial,Storage Space,UnfinishedNumber of Rooms: 8Types of Rooms: Bedroom, Bathroom, Dining Room, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1234 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Washer, Refrigerator, Range, Dryer, DishwasherDishwasherDryerLaundry: In BasementRefrigeratorWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Wall/Window Unit(s)Has HeatingHeating Fuel: Forced Air
Gas & Electric
Electric: 200+ Amp ServiceHas Electric on Property
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Ceramic Tile, Hardwood
View
Has a ViewView: Neighborhood

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Front Porch, PorchFencing: Fenced, GateExterior: LightingFoundation: Block
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Paved,Off Street,Driveway
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1234 Square FeetFinished Area (below surface): 360 Square Feet

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Cottage
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 080004808300020180000000

Price & Status

Price
List Price: $350,000Price Per Sqft: $332/sqft
Status Change & Dates
Off Market Date: Fri Oct 31 2025

Location

Direction & Address
City: Kingston
School Information
High School District: Kingston Consolidated

Building

Building Area
Building Area: 1234 Square Feet

Lot Information

Lot Area: 6969.6 sqft

Miscellaneous

BasementMls Number: 20254909Above Grade Unfinished Area: 1234
Last check for updates: about 14 hours ago
Listed by Anthony Dargenzio, (518) 821-0826
Houlihan Lawrence Inc.
Jessica Brasseur, (850) 714-3045
Houlihan Lawrence Millbrook Of
Bought with: Mary Orapello, (845) 590-0386, Howard Hanna Rand Realty
Source: HVCRMLS, MLS#20254909

Price History for 306 E Chester Street

DatePriceEventSource
12/11/2025$410,000Sold
HVCRMLS #20254909
11/01/2025$350,000PendingHVCRMLS #20254909
10/22/2025$350,000PendingToActiveGlobal MLS #202528243
10/17/2025$350,000ContingentHVCRMLS #20254909
10/08/2025$350,000Listed For SaleHVCRMLS #20254909
11/17/2020$210,000Sold
N/A
09/09/2020$209,900PendingAgent Provided
08/13/2020$209,900PriceChange
Agent Provided
07/23/2020$224,900PriceChange
Agent Provided
07/16/2020$249,000Listed For SaleAgent Provided
04/11/2005$142,000Sold
N/A
09/16/2004$128,522Sold
N/A

Market trends in Kingston

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
79
4MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$282,979
Home facts updated by county records

Comparable Sales for 306 E Chester Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
272 E Chester Street, Kingston, NY
0.09
Single-Family Home
$309,000
07/06/26
3
1
1,078
377 E Chester Street, Kingston, NY
0.18
Single-Family Home
$320,000
07/02/26
3
1
1,271
135 Stephan Street, Kingston, NY
0.30
Single-Family Home
$400,000
06/17/26
3
1
1,421
44 Wood Street, Kingston, NY
0.35
Single-Family Home
$360,000
03/26/26
3
1
1,580
36 Hayes Street, Kingston, NY
0.26
Single-Family Home
$330,000
07/16/26
2
1
869
199 2nd Avenue, Kingston, NY
0.29
Single-Family Home
$415,000
08/22/25
3
2
1,933
106 Florence Street, Kingston, NY
0.26
Single-Family Home
$341,146
05/20/26
3
2
1,399

Nearby homes

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Assigned Schools

These are the assigned schools for 306 E Chester Street.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Kingston

At least 351 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 83 % Say it's dog friendly

  • 76 % Say parking is easy

  • 76 % Say yards are well-kept

  • 69 % Say there are sidewalks

  • 68 % Say there's holiday spirit

  • 67 % Say it's walkable to restaurants

  • 66 % Say kids play outside

  • 65 % Say people would walk alone at night

  • 58 % Say there's wildlife

  • 55 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 50 % Say it's quiet

  • 50 % Say streets are well-lit

  • 45 % Say it's walkable to grocery stores

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Dragonslayer 316
    "No parks for to walk dogs and might be a pain in some situations just not good for dogs period so that’s about it"
    0
    Flag
  • Desiree Salomone
    "unique architecture, country but all the best things that a city has to offer, beautiful, near the water, mix of people "
    1
    Flag
  • Justingray57
    "Years ago they had fireworks in the plaza, a carnival, then they would have Santa in the Plaza, Santa was actually my uncle incidentally I was conflicted even into my teenage years as to the validity of Santa as he seemed to know way too much about me personally, anyway it felt very family oriented 30 years ago, not so much now"
    0
    Flag
  • Carlyhull13
    "Best in kingston - a lot of kids live here. Clean and crime free. Great neighborhood to raise a family."
    0
    Flag
  • Julee Molina
    "You can’t get around without a car. There are No sidewalks or pedestrian bridges. Not pedestrian friendly. Roads littered with potholes. "
    0
    Flag
  • Lab
    "The neighborhood is awesome. Has a small town feel with all the amenities of a small city. I absolutely LOVE living here. "
    0
    Flag
  • Bernabei.erika
    "No commute - I work from home or use the Albany or Newark airport. Most people here work from home or in local businesses"
    0
    Flag
  • Trulia User
    "Mix of historical architecture and nature, open lots, limited light pollution. The beautiful waterfront."
    0
    Flag
  • Julee Molina
    "Lack of sidewalks and isn’t pedestrian friendly 😔. Town should prioritize people over cars by building footbridges and adding sidewalks. "
    0
    Flag
  • M2eshorti169
    "If they like to take walks the road is very busy and no sidewalk. They would like that there are other dog owners to make playdates with. "
    1
    Flag
  • Moparman67
    "I’ve lived in the area my whole life. People are friendly and nice. Traffic has picked up in the years. "
    0
    Flag
  • Arnaldo N
    "Easy access to a number nature trails and vehicle free paths. Currently only 1 dog park located at Kingston Point. Would love to see a few more added throughout the rest of Kingston. "
    2
    Flag
  • Trulia User
    "It’s alright some odd stuff with sidewalks and park for sure. Hidden gems and near the trails are a plus. "
    0
    Flag
  • Trulia User
    "Is a very quiet neighborhood very kind of neighborhood for the most part people say to ourselves but at the same time I am very friendly and outgoing when we cross paths"
    0
    Flag
  • Trulia User
    "I’ve lived here most of my life. A mix of local and people from the city which makes for a nice blend of differences. Lots of cute local spots to eat and quiet area."
    2
    Flag
  • Beez T.
    "It’s a great place for families and to raise kiddos. We have the best neighbors and our road is quiet. There’s a Stewart’s only a half mile away. "
    1
    Flag
  • Jbhsr1939
    "Dog friendly. Areas to walk with medium to low traffic. Parks within walking distance. Walking, biking, dog-walking trails 1/2 mile from neighborhood. "
    1
    Flag
  • Mmeubauer
    "Everyone knows almost everyone and are friendly. Little league field and park which have lots of events."
    0
    Flag
  • Ey-hav Noname
    "It’s walkable depending on which area you live in. If not, you can always drive to one of the many parks or trails in and around the surrounding area."
    1
    Flag
  • Huy B.
    "The proximity to farmers markets, local hardware stores and the Catskills nature is amazing. Only 1.5 - 2hrs From NYC "
    0
    Flag
  • Gueneviere W.
    "Great waterfront dining and farmer’s market on the weekend. Lovely walkway on the Rondout. Kids play outdoors and families eat at picnic tables. "
    0
    Flag
  • Julie L. A.
    "friendly neighbors make this a great neighborhood. "
    0
    Flag
  • Heidi G.
    "Lots of family and single happenings, best Farmer’s Market around, nice parks, lovely homes, friendly community "
    0
    Flag
  • Maria I.
    "My commute is usually to Poughkeepsie for work. I find that traffic is light around the city of Kingston"
    0
    Flag
  • Cortneyajefferson
    "I love how diverse it is here. There is always something fun going on and the city is loaded with delicious restaurants "
    0
    Flag
  • Leanna H
    "We have the quick stop deli that is at the head of the neighborhood and it is very convenient because u can run there real quick if u need milk bread eggs anything really. Also it’s right next to an airport my son loves watching the planes overhead . The streets are very wide and low traffic so it is a nice neighborhood to take long walks with the kids or animals "
    0
    Flag
  • Loveydove7766
    "Lots of room to walk dogs. Not a lot of through traffic. Every house has a big yard that would be good for dogs "
    1
    Flag
  • Stacey A. M.
    "Social & Public Events in each District, farmers market, festivals, parades, public library book clubs, & many events such as Business mixers"
    0
    Flag
  • Amylynnjacobsen02
    "They would like it . Plenty of people walk their dogs on a regular basis. A great neighborhood and they even clean up after the dogs!"
    0
    Flag
  • Sigmathews
    "I've lived here a little over a year. many of my neighbors seem to be house bound or very elderly. I have met a few neighbors, while they are friendly enought most do not seem interested in socializing. I miss that about my old neighborhood. everyone knew each other!!"
    0
    Flag
  • Jennifer B.
    "Lots of road work and construction. Too many detours. Kids in the road. Have to really watch where you drive. Pretty safe for the most part. Right by local school "
    0
    Flag
  • Edwin Choc
    "Beautiful city I just came here to visit my friends and family. One day I’ll move here. Also i came here every sunday for church "
    0
    Flag
  • Katina
    "Schools aren't bad here but there is a high drug use rate. Certain areas of Midtown are not safe. Railroad tracks run straight through town. "
    0
    Flag
  • TJL
    "Lots of dogs in our neighborhood play together! It’s a very dog friendly town. Tons of trails and riverfront."
    0
    Flag
  • Katina
    "Kingston has Movies in the Park over the summer. We also have free farmers markets every Tuesday in the summer. Local rail trails are easily accessible. "
    0
    Flag
  • Aleesmithphd
    "Cars are the main mode of transportation but there is a public transit system. I do not know much about it since I drive. "
    19
    Flag
  • AndrewH
    "Close proximity to all malls and shopping. Restaurants are within 1 mile. Quiet neighborhood yet within 5 minutes to all the shopping and restaurants in the area. Only 5 miles to NYS thruway."
    1
    Flag
  • Dan
    "Farmers market on Saturday on Wall St. Events literally every day of the year. Events are for the youngest to the oldest. "
    0
    Flag
  • Dan G.
    "Multicultural, multi-income, multi-age; all things children should learn about and be a part of. Very accessible community leaders. "
    0
    Flag
  • Hsafier
    "Great energy and new life coming into Kingston. It’s a fun small city with easy living and great amenities. Proximity to NYC adds to its appeal. Great outdoor opportunities with rail trails, Hudson River and lots of open space nearby. We love living in Kingston. "
    0
    Flag

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Homes for sale near 306 E Chester Street

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Off Market Homes Near 306 E Chester Street

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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
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