255 Redstart Dr, Chester, MD 21619
Property image
Property image
SOLD
MAY 29, 2026

$789,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,791 sqft

255 Redstart Dr, Chester, MD 21619

Refinance Your Home
Currently Off Market - Sold May 29, 2026 for $780,000 (6% below list price)

Home Value

Trulia Estimate
$789K
Since last month
Increased$5K (+0.6%)
Since last year
Decreased$36K (-4.3%)
Since last sale
Increased$11K (+1.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -4% in the last 10 years
MonthEstimated value
2026
August 2026$791K
July 2026$787K
June 2026$783K
May 2026$826K
April 2026$828K
March 2026$828K
February 2026$827K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
259 Redstart Dr, Chester, MD
0.01
Single-Family Home
$799,990
05/12/26
4
3
2,791
711 Warbler Way, Chester, MD
0.06
Single-Family Home
$739,990
09/01/26
4
3
2,791
629 Warbler Way, Chester, MD
0.06
Single-Family Home
$694,900
12/10/25
4
3
2,791
539 Warbler Way, Chester, MD
0.14
Single-Family Home
$769,990
05/15/26
3
3
2,789
527 Warbler Way, Chester, MD
0.16
Single-Family Home
$784,990
01/27/26
3
3
2,789
528 Warbler Way, Chester, MD
0.18
Single-Family Home
$799,500
06/05/26
4
3
2,791
519 Warbler Way, Chester, MD
0.18
Single-Family Home
$799,990
01/29/26
3
3
2,789
141 Redstart Dr, Chester, MD
0.18
Single-Family Home
$879,990
03/31/26
3
3
2,789
164 Redstart Dr, Chester, MD
0.20
Single-Family Home
$844,900
10/28/25
3
3
2,789

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
259 Redstart Dr, Chester, MD 21619
0.01
$799,990
4
3
2,791
Recently Sold
629 Warbler Way, Chester, MD 21619
0.06
$694,900
4
3
2,791
Recently Sold
247 Redstart Dr, Chester, MD 21619
0.02
$899,990
3
3
2,772
For Sale
711 Warbler Way, Chester, MD 21619
0.06
$739,990
4
3
2,791
Recently Sold
715 Warbler Way, Chester, MD 21619
0.07
$779,990
4
3
2,791
For Sale
621 Warbler Way, Chester, MD 21619
0.07
$691,900
2
2
1,993
Recently Sold
719 Warbler Way, Chester, MD 21619
0.07
$793,000
4
3
2,807
Off Market
630 Warbler Way #2211, Chester, MD 21619
0.09
$524,900
2
2.5
2,003
Recently Sold
630 Warbler Way #2212, Chester, MD 21619
0.09
$499,990
2
2.5
2,003
Recently Sold
630 Warbler Way #2221, Chester, MD 21619
0.09
$706,900
2
2.5
2,602
Recently Sold
630 Warbler Way #2222, Chester, MD 21619
0.09
$514,990
2
2.5
1,900
Recently Sold

Local Information

  • Map ViewExplore the area around 255 Redstart Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2026
2,791 sqft
$279/sqft
2 Car Garage
HOA $263/mo

About this House

The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and a 2-car garage, this home balances everyday comfort with thoughtful design details. A dedicated home office provides the perfect space for remote work or study, while the great room is anchored by a striking two-story shiplap fireplace with a granite surround, creating a warm and inviting focal point. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French-door refrigerator, and pendant lighting, complemented by a tile backsplash and quartz countertops that continue into the owner’s bath. LVP flooring flows through the foyer, kitchen, dining area, great room, owner’s suite, and bedroom two, while tile finishes the full baths and laundry room. Plush carpeted spaces in the loft, second floor, and additional bedrooms add comfort where it counts. The owner’s bath features a spa-like shower with seating, a handheld wand, and double sinks for added convenience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.
255 Redstart Dr, Chester, MD 21619 is a 4 bedroom, 3 bathroom, 2,791 sqft single-family home built in 2026. It last sold for $780,000 on May 29, 2026 (6% below the $829,990 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $789,400, with a rent estimate of $3,815/month.
Last check for updates: about 12 hours ago
Listed by Mary Anne Kowalewski, (240) 375-5074
KOVO Realty
Bought with: Unrepresented, (844) 552-7444, Unrepresented
Source: Bright MLS, MLS#MDQA2016024

Home Details for 255 Redstart Dr

Interior Features

Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2791 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Roof: Architectural ShingleOther Structures: Above GradeFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Garage Faces Front,Attached,Driveway
Pool
Pool: Community
Frontage
Waterfront: RiverNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Chester River
Finished Area
Finished Area (above surface): 2791 Square Feet

Property Information

Year Built
Year Built: 2026
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Raised Ranch/Rambler
Building
Construction Materials: Advanced FramingIs a New Construction
Property Information
Condition: ExcellentParcel Number: 1804126583

Price & Status

Price
List Price: $829,990Price Per Sqft: $279/sqft
Status Change & Dates
Off Market Date: Fri May 29 2026Possession Timing: 120-180 Days

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERCommunity: Four Seasons At Kent Island
School Information
Elementary School District: Queen Anne's County Public SchoolsJr High / Middle School District: Queen Anne's County Public SchoolsHigh School District: Queen Anne's County Public Schools

Building

Building Details
Builder Model: SimoneBuilder Name: K. Hovnanian Homes
Building Area
Building Area: 2791 Square Feet

Community

Is a Senior Community

HOA

Has an HOAHOA Fee: $263/Monthly

Lot Information

Lot Area: 7000 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDQA2016024Above Grade Unfinished Area: 2791

Additional Information

HOA Amenities: Billiard Room,Clubhouse,Fitness Center,Game Room,PoolSource Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
May 29, 2026
Source: Bright MLS #MDQA2016024
Sold
$780,000
Feb 2, 2026
Source: Bright MLS #MDQA2016024
Pending
$829,990
Jan 28, 2026
Source: Bright MLS #MDQA2016024
Listed For Sale
$829,990

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
70
5MoM

Around this home

What Locals Say about Chester

At least 36 Trulia users voted on each feature.

  • 88 % Say parking is easy

  • 88 % Say car is needed

  • 86 % Say people would walk alone at night

  • 83 % Say it's dog friendly

  • 83 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 65 % Say neighbors are friendly

  • 64 % Say kids play outside

  • 64 % Say there's wildlife

  • 57 % Say yards are well-kept

  • 53 % Say there are sidewalks

  • 49 % Say they plan to stay for at least 5 years

  • 48 % Say there are community events

  • 44 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 17 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Dlmaheux
    "I’ve been here 20 years and don’t even lock my doors the majority of the time. Super safe. Wonderful sense of community all around "
    0
    Flag
  • Colinjgallagher525
    "Tucked away million dollar homes with great down-to-earth people living in them. It’s a warm community and bay living at its finest. "
    0
    Flag
  • Peggy Young
    "Board meetings, water aerobics, pickle ball, tennis, a gym, kayaking, paddle boarding. Mah jongg, bingo, games day, social committee,walking club "
    0
    Flag
  • Trulia User
    "Water aerobics, happy hours, cardboard boat races, kayaking, mah jongg, game day dog walking. Boating "
    0
    Flag
  • Peggy.young
    "Lots of spaces to walk dogs, lots of people who love dogs. Great way to meet neighbors. Just about everyone on the shore has a dog. Also a number of good kennels for when you travel. "
    3
    Flag
  • Taylor T.
    "Lots of dogs everyone walks them all hours of the night and their is little stops with bags to pick up Feeses "
    0
    Flag
  • kara
    "I've lived here for three years and the neighbors are very friendly mostly. They look out for each other..."
    0
    Flag
  • Robert M Heyn
    "Its always so pleasant here in Chester. Its like Everyone says HI and knows one another. The school systems are great and Chester is central located to all surrounding areas of shopping, dining, water, Annapolis and Easton. Some of tue most beautiful views in the MD pertaining to water and nature."
    1
    Flag
  • J0J0s4X4
    "They are required to clean up after them. The HOA used to pay a pooper scooper company which provided pooper containers, scoops, and bags after used to be deposited in the container. The Board decided that the dog owners should pick up the cost of picking up after their dogs and quit paying the $26,000 per year for the company."
    0
    Flag
  • Wilson
    "Not very many families, but within a great school district. Good community for people who don’t really have children. "
    0
    Flag
  • J0J0s4X4
    "it is a child friendly development and very safe. also, most homeowners have video security systems."
    0
    Flag
  • Peggy y.
    "Chester is a real community, where you know just about everyone. I live in a condo, so life is as easy as it gets. There are lots of walking trails, and you are always a stone’s throw from the Chesapeake Bay or the Chester River."
    3
    Flag
  • Eric D.
    "I live in this area. Great place to raise a family. Access to beaches, parks, cross island trail."
    0
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 255 Redstart Dr

  • What is 255 Redstart Dr estimated to be worth?
    Trulia's estimated value for 255 Redstart Dr in Chester, MD is $789,400.
  • What is the price history for 255 Redstart Dr?
    255 Redstart Dr in Chester, MD last sold for $780,000 in May 2026.
  • Is Chester a buyer's or seller's market?
    Chester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Chester?
    Residents describe Chester, MD as easy to park in, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Chester, MD.
  • Does 255 Redstart Dr have air conditioning?
    Yes, 255 Redstart Dr in Chester, MD has air conditioning.
  • Does 255 Redstart Dr have a pool?
    Yes, 255 Redstart Dr in Chester, MD has a pool.

Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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