Chester Real Estate, Homes and Condos for sale

All Chester homes currently listed for sale in Chester as of 05/22/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Chester homes for sale or other Chester real estate, please contact us and one of our knowledgeable Chester REALTORS® would be pleased to assist you.


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$939,900
18 East Liberty Street, Chester CT 06412
5
BEDS
7
BATHS
6,054
SQFT
$155
$/SQFT
2.75
ACRES
1997
BUILT
"Luxury Home set high above the picturesque Village of Chester, CT with it's Upscale Restaurants and Country Shops. The approach down this driveway gives you the feeling of a country estate. The moment you enter this home you'll be in awe of the elegance, it's unique features and style. You'll be great by the view of an large Great Room with a barrel Style High Ceiling, A Drop Down Entertainment Center, a Center Stone Fireplace, a Theatre/Stage and even a Duckpin Bowling Alley! The open Dining area leads to a Gourmet Kitchen with High End Appliances, A Center Island with Seating and French Doors leading to a Wrap Around Deck overlooking Chester Village. The Master Bedroom with a high Barrel style Ceiling, Stone Gas Fireplace, Large Master Bath, Plenty of closets and French Doors that lead to a Patio and the In-Ground Pool. There are (4) Additional Bedrooms, a Den, Office and a Workout room. If you love to Entertain, Play Tennis or are a Thespian in search of a home with an Antique Theatre on site, this just might be the rare find you've been searching for!"
$899,900
134 Pinnacle Lane, Chester CT 06412
4
BEDS
7
BATHS
6,350
SQFT
$142
$/SQFT
5.86
ACRES
2007
BUILT
"Vermont in Connecticut! This timeless gem boosts a large first floor master-suite with private terrace and 4 additional bedrooms. Situated nicely on over 4 acres - the home is a 6200+ sq ft masterpiece built in 2007 with a focus on casual luxury living. Features include: Cedar shingle shake siding (treated), music room, large office, massive 1600+ sq ft walk-out lower level media/entertainment room, five full bathrooms & two half bathrooms, gym, wine cellar, and a 3 car garage . Minutes to the historic village of Chester which is vibrant with shopping, restaurants, local bazaars, and fairs. Close to Chester Airport, Cedar Lake and major commuting routes."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $924,900 TO $899,900 
$799,900
201 Pinnacle Lane, Chester CT 06412
4
BEDS
4
BATHS
3,307
SQFT
$242
$/SQFT
4.10
ACRES
2018
BUILT
"This beautiful two floor custom design home by ASW incorporates the attributes of a home built for entertaining with main floor master suite and laundry to suit an age-in-place lifestyle. The interior has nine foot ceilings atop an impressive open- concept great room and custom gourmet kitchen with granite throughout. Vaulted family room with fireplace. Separate formal dining room and study on main floor, 4 bedrooms, 3.5 baths, loft are all part of this design. Other plans & designs are available ! Call for builders spec's. Subject to change and availability. Agent related"
* LISTED OVER 120 DAYS 
$684,500
25 Gilbert Hill Road, Chester CT 06412
4
BEDS
5
BATHS
4,051
SQFT
$169
$/SQFT
1.01
ACRES
1987
BUILT
"One of Chester s finest homes is majestically sited with striking views of the CT River, the Hills of Lyme and expansive valley views. An absolutely immaculate home along with meticulously manicured grounds of lush lawns and gardens favor a peaceful feeling of serenity. Extraordinary quality throughout, custom designs and details have all been carefully selected, custom moldings and cabinetry throughout the kitchen, the baths and the closets. This home is flooded with natural light, facing Northeast allowing for the magical views of the morning sunrise. The master bedroom en-suite includes a gorgeous stone gas fireplace and access to a private deck, a perfect way to start and end the day. Dine in the chefs kitchen with all high-end appliances including Sub Zero, Bosch, Viking and Wolf, warming drawer, granite counters, tumbled marble back splash and a wine cooler. The third floor is adaptable in many ways from a guest suite with full bath and walk in closet with chandelier lighting to a game room or private get-away space. The first floor family room is perfect for Sunday football games and movie nights with surround sound, gas fireplace and large windows. Outdoor dining on the large wraparound Trex deck, the stone Paver patio or the gazebo while enjoying the impressive and breathtaking views is nothing short of stunning. And at the end of the day, take a leisurely stroll into town to dine at some of Connecticut Shoreline s best ranked restaurants."
$625,000
11 Sunset Avenue, Chester CT 06412
3
BEDS
3
BATHS
2,461
SQFT
$254
$/SQFT
6.00
ACRES
1987
BUILT
"The charming Colonial sits on a tranquil hillside with over six acres of open fields, a large wildflower meadow, and a pond. The property has been featured in local garden tours. Walk to the front of house, up the field stone steps that lead you to the stone patio with perennial flowers overlooking the beautiful property. The main floor is comprised of a Kitchen with Breakfast area, Corian countertops, sit-at-center-island, gas cook-top, custom cabinets, chestnut floors and was remodeled in 2017. French doors open out to a full length porch with views of the open field, flower meadow and pond. The Living room has a fireplace and a formal Dining room has custom built-ins. The mud room connects to the bright workshop/artist studio, which has three sides of windows. The Master Suite is on the second floor overlooking the pond, and includes a sitting room with a large size dressing room, full Bath, Laundry and a spacious Office with built-ins. The lower level includes two Bedrooms, a full Bath and a sitting room. There is French door access to the outside patio and gardens from this level. Solar panels installed by Aegis have supplied all of the electricity for this house. There is a 10 kW whole house automatic standby generator fueled by propane. A separate guesthouse is included on the property; with its current rent, it can pay 1/3 of your mortgage."
$599,000
42 Winthrop Road, Chester CT 06412
3
BEDS
3
BATHS
1,644
SQFT
$364
$/SQFT
25.60
ACRES
1976
BUILT
"Oakfield Farm, You'll first notice the beautiful stone walls and entry. Running horse sculptures adorn the first pasture as you head into the rest of this 25 acre horse farm. Sitting back off the road is a 1644 sf 3 bedroom 2.1 bath home with master bedrooms with en suite on first floor. The 9 -10 stall barn has 12x12 box stalls, tack room, grooming stall, hay storage and a 1/2 bath. There is a 190 x 140 foot sand ring for riding and training. Long views of pastures with mature oak trees gives this farm it's name. There is even a pond. If your looking for a well thought out horse farm in an idyllic setting, Oakfield Farm is for you. Additional features include a 15x15 sun room that overlooks the farm, 2 additional bedrooms and a full bath on the 2nd floor, 2 car detached garage that is attached to the horse barn, Run-in sheds in the large pastures, security system and possible subdivision potential if your looking for a second residence."
* PRICE LOWERED - $619,000 TO $599,000 
$599,000
33 Liberty Street, Chester CT 06412
0
BEDS
0
BATHS
2.93
ACRES
1848
BUILT
"This is a light industrial building that would be ideal for a residential conversion. The town is receptive to an adaptive reuse of the building as multifamily residential. Number of units will depend on septic system size. Poss subdivision to 3 lots."
* LISTED OVER 120 DAYS 
$529,900
22 Old County Road, Chester CT 06412
4
BEDS
4
BATHS
3,630
SQFT
$146
$/SQFT
3.62
ACRES
1986
BUILT
"Situated in the heart of the picturesque Lower Connecticut River Valley, this fascinating, Contemporary hilltop retreat boasts an open floorplan enhanced by soaring ceilings & expansive walls of windows. Flooded with natural light, the home is warm & inviting, creating the ideal space for comfortable, everyday living as well as a wonderful place to graciously entertain family & friends. The eat-in kitchen is newly renovated & features quartz countertops, tile backsplash & stainless appliances. The first-floor, master bedroom suite includes a gracious sitting room with French doors that provide access to the expansive, multi-faceted deck. The spacious family room & exercise area have a separate outdoor access & offers the potential for an in-law or au-pair suite. The property s professional landscaping incorporates a variety of perennial plantings with the mature trees that heightens the beauty of the home s natural surroundings. Chester is renowned for its quaint village featuring unique shops, numerous galleries & diverse restaurants. Multiple marinas & boat launches are found along Chester s river front offering boaters & water sports enthusiasts access to this recreational water course. Entrances to the Cockaponset State Forest provide hikers, bikers & horseback riders with miles of trails to explore. Chester offers an easy commute between Hartford, New Haven & New London and is located only two & one-half hours by automobile from both New York City & Boston."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $549,900 TO $529,900 
$529,000
45 Main Street, Chester CT 06412
5
BEDS
5
BATHS
3,531
SQFT
$150
$/SQFT
0.19
ACRES
1790
BUILT
"Chester Village cash cow! Annual rental potential of $60K gross. Beautifully restored 3 unit building with charm and character overlooking the beautiful Pattaconk river. Live for free in one unit and rent out the rest or rent all three. The middle unit is perfect for a business downstairs and live upstairs situation. The first two units are two bedroom, 1.5 bath, townhouse style with laundry on the second floor. The third unit is ranch style with one bedroom and one bath and is in pristine condition - currently used as an Air B&B with a strong rental history. The two bedroom units are adorned with stunning wide-plank hardwood floors and magnificent fireplaces, and all three have an added touch of character and history with beautiful wooden beams decorating the ceilings. All three units have separate utilities and basement storage, as well as their own private deck overlooking the peaceful and serene Pattaconk river. City water and city sewer. Unbeatable location with shopping, restaurants, and galleries just outside your front door. Convenient to Route 9 and I-95. The property is also zoned commercial."
$495,000
23 East Liberty Street, Chester CT 06412
3
BEDS
3
BATHS
2,189
SQFT
$226
$/SQFT
1.15
ACRES
2014
BUILT
"A short stroll from Chester Village this Craftsman style home is situated perfectly on a knoll. Enjoy one floor living at its best. The peaceful, tranquil setting has you living privately with nature. Lantern lit paved driveway guides you home. Upon entering this residence a generous foyer greets you with light from a clearstory & walls of glass. The keen sense of design & open floor plan continue to compliment this well planned home. The sun filled Living & Dining rooms are defined by natural lighting & open structure. The designer kitchen features custom cherry cabinets, granite & stainless. A walk in pantry off the kitchen is not to be overlooked. Eat at the breakfast nook or at the central high top bar. The dining room offers a larger eating space as well. The Master Bedroom En Suite is further testimony to both quality & design of this Craftsman style home. The Suite is spacious & carefully thought out. French doors from the Master bedroom lead to the patio. A dressing room/closet further compliment this suite. The full tile designer bath with freestanding tub complete the tour. Two additional bedrooms, 1.1 additional baths, plus full laundry room with utility sink are present. Gleaming hardwood flooring throughout. A bluestone patio & pergola unify the this home. 2 car heated garage with attached shop await a hobby or passion. Additional outbuilding with electricity. Outdoor shower is an additional treat. Whole house designed to be energy efficient."
$424,900
38 Railroad Avenue, Chester CT 06412
4
BEDS
3
BATHS
2,226
SQFT
$191
$/SQFT
1.18
ACRES
1918
BUILT
"Charming 1918 Colonial with curb appeal!! Situated on a park like setting with a beautiful deep backyard including a barn! Less than a mile walking distance to Chester Village! Walking distance to Chester Marina! The yard is a gardeners dream! Welcoming front porch! Spacious entry foyer opens up to the living room with a gas fireplace, built-ins & hardwood floors. Large formal dining room with built-ins & a gorgeous vintage lighting fixture! The kitchen was completely remodeled with white cabinetry, quartz counter tops, a farmhouse sink, stainless appliances & wonderful pull-out storage everywhere! The main floor master bedroom has a walk-in closet, full bath & french doors leading to the deck! Main floor laundry closet has full sized stack-able washer & dryer. Main floor den/family room is perfect for TV watching with a cozy gas fireplace & atrium doors to the expansive deck! The mudroom adjacent to the kitchen is the full length of the garage with storage galore! 2 car garage is attached to the mudroom/breezeway. 3 additional bedrooms on upper level with another full bath. There is a walk-up attic for easy storage access. The Trex deck & front porch are low maintenance. Charming barn out back has a gardeners potting area, great storage & a whimsical playroom for your pool table or hobbies! A grape arbor adds a nice touch in the garden. This home offers all the character you want with all the updates for your comfortable living!"
$415,000
5 School Lane, Chester CT 06412
3
BEDS
3
BATHS
1,474
SQFT
$282
$/SQFT
0.33
ACRES
1880
BUILT
"New new new!! Located just off Main Street in Chester Village, this meticulously maintained home is completely updated and move-in ready. Upon entering the front door, you feel as if you are stepping into a magazine. The living room spans the width of the house w/ an elegant gas fireplace w/ granite surround installed in 2017. The living room flows into the dining room complete w/ sliding doors which make the space even brighter and lead you out onto the new 784sqft wooden deck w/ pergola installed in 2018 for extra shade on warm summer days. The kitchen is a show stopper w/ a large marble island, granite countertops, a custom pantry w/ beverage fridge built in 2018 w/ beautiful barn doors, and sliding doors that leads onto the deck. All bedrooms on the second floor have brand new hardwood floors installed in 2019. The second and third bedrooms share a Jack & Jill bath and the private master bedroom has a custom closet built in 2016. The exterior of the home has had extensive landscaping and a new stone driveway in 2017. Other updates include a new roof in 2017, preventative basement waterproofing in 2019, and generator hookup 2018. Come live in Chester, located on the hillside of the CT River which boasts marinas, lakes, waterfalls, thousands of acres of state forest, and hiking trails! This vibrant community is known for its art, restaurants, history, music, theater, crafts, and year-round events. Just over 2 hours from both New York City and Boston, Chester is a true gem!"
* PRICE LOWERED - $425,000 TO $415,000 
$399,999
81-2 Turkey Hill Road, Chester CT 06412
3
BEDS
3
BATHS
2,032
SQFT
$197
$/SQFT
6.82
ACRES
1988
BUILT
"Nature lovers take notice! This private 6.82 acres abuts the Cockaponsett State Forest. Flat around the house, but rolling to the forest. Built in 1988, this contemporary home has been lovingly and meticulously cared for by the owners. It boasts a large three car garage, beautiful eat in kitchen, dining area, hot tub room, conversation pit, living room, three bedrooms, 2 1/2 baths and loads of storage. A rose garden, horseshoe pit and nature trails make this a spectacular paradise for nature lovers!"
* PRICE LOWERED - $415,000 TO $399,999 
$389,900
289 Middlesex Avenue, Chester CT 06412
2
BEDS
2
BATHS
1,040
SQFT
$375
$/SQFT
8.67
ACRES
1974
BUILT
"WATERVIEW OF CT. RIVER! Cozy Ranch with central air conditioning. Kitchen with slider to brick patio and hot tub. Large yard for gardening and fenced area. Views of Ct. River situated on 8.67 acres. This home can b expanded or BUILT YOUR DREAM HOME ON KNOLL and subdivide ranch on 2 acres. Area of fine homes. Living room/dining room with built-in bookcases, wood stove insert. Bay window with view of Ct. River. This charmer is close to quaint Chester Village for shopping, restaurants, Ct. River and marinas. Basement can be finished for family room/rec room. Over sized garage offers plenty of storage space. Convenient location for commuting. RARE OPPORTUNITY AWAITS YOU!"
$380,000
19 Hickory Hill Drive, Chester CT 06412
3
BEDS
3
BATHS
2,646
SQFT
$144
$/SQFT
1.02
ACRES
1984
BUILT
"Location, Location .This contemporary cape is located on a cul-de-sac, 1.02 acre wooded lot which is private and within walking distance to charming Chester! A roomy 2646 sq. ft., 3 Bedroom, 3 full bath house has a light filled open first floor living area and a first floor master bedroom with master bathroom and walk in closet. The house has been freshly painted and has extra room with a finished attic and vaulted ceilings that currently occupies space for a well known local artist, but could also be an office or playroom. Have your buyers come picture themselves in this potential gem."
* NEW LISTING 
$379,000
35 Bokum Road, Chester CT 06412
2
BEDS
2
BATHS
1,512
SQFT
$251
$/SQFT
7.24
ACRES
1983
BUILT
"Serene and secluded, this home and workshop offer privacy while being a stone's throw from Main St. With over seven acres on a hilltop in Chester, there is space fit for all of your needs and more. Feel the hilltop breeze, enjoy vast views from every angle.. Entertain on the large wraparound deck, which is partially covered. Inside, wood floors run throughout the home. The sizable kitchen opens to the dining room. Relax in the living room with wood stove and floor-to-ceiling stone wall or in the master suite with fireplace. The basement can easily be finished for more living space. Three hundred feet from the main house is an 1,872 sq ft custom-built insulated workshop. Metal siding & roof, 10 slab, 12 tall heavy duty insulated garage doors, with 13 6 and 10 widths. 200 amp service, with oversized conductors to handle pottery kiln, welders, and rotophase. This outbuilding lends the rare opportunity for your dream workshop, yoga/art studio, you name it! Only 2.1 miles (4 minutes) from Chester Center, famous for its galleries, shops and restaurants. Privacy, acreage, proximity and opportunity! Call today to view this property and all it has to offer."
$349,900
39 Wig Hill Road, Chester CT 06412
2
BEDS
3
BATHS
1,772
SQFT
$197
$/SQFT
8.32
ACRES
1970
BUILT
"Charming two bedroom Cape on over eight acres just outside of Chester Village. Unfinished second floor offers room for two or more additional bedrooms and another bath or two. Very private, but not secluded. The covered deck overlooks the private yard, patio, and inground pool. Large eat-in kitchen. 14 x 24' living room with fireplace. A Russel and Beach fireplace in the family room. Finished lower level with spacious 16 x 24' Rec. Room with fireplace, bar, half bath, and sliders out to the pool and patio. Central A/C. Two car oversized attached garage. Not far to town, Cedar Lake, the state forest or the CT River."
$349,900
192-2 Middlesex Avenue, Chester CT 06412
3
BEDS
3
BATHS
2,582
SQFT
$136
$/SQFT
2.39
ACRES
1996
BUILT
"More For Your Comfort, Convenience and Money! The home awaits someone who wants to fill its large porch with a swing or rocking chairs and a welcome mat that says something witty. The Colonial is move-in ready awaiting someone to fill its space with their own personal touches. Gleaming hardwood floors are throughout the house; kitchen boasts high top corian counters, cozy family room with gas fireplace and a master suite with bonus room. This home also features a new roof and new siding installed past two years. Off the back porch, you have an ideal level backyard, perhaps for the world s best backyard soccer field or for someone who loves to watch the deer prancing through. This home is near the river and close enough to the charming village of Chester. Never been to Chester? It s a perfect enclave of artists, cozy restaurants and a village stacked with cute nostalgic homes."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $364,000 TO $349,900 
$349,500
285 Middlesex Avenue, Chester CT 06412
3
BEDS
2
BATHS
3,368
SQFT
$104
$/SQFT
16.40
ACRES
1965
BUILT
"High above the Connecticut river you will find this true oasis which is anything but usual! This custom built contemporary offers terrific views of the Connecticut River, almost 17 acres of privacy & a post-modern design worthy of the term extraordinary! From the full glass family room to the look-out loft, you will be amazed with it's true contemporary charm! As you drive-up the long winding driveway your curiosity piques as the world fades away. The main level includes the kitchen & open dining room with strategically located built-ins, the full glass family room, main level bedroom & full bath. As you walk-up to the second level the dream begins to come-true as you enter the open & spacious living room with it's post-modern full length roof window with retractable shade, banks of sliders that open to a full length upper level wrap around deck overlooking the Connecticut River, fireplace with inserted wood stove, built-ins & look-out loft adding extra height to the view. The upper level also features the master bedroom that opens to the wrap around deck with that view via sliders, additional bedroom & full bath. The grounds offer open spaces with wonderful blooms, a patio & terrace, three car garage (two enclosed ports & an attached carport) with loft storage above & plenty of space to entertain or just roam freely! Conveniently located between NYC & Boston. Your special getaway awaits!"
$329,900
51 Straits Road, Chester CT 06412
3
BEDS
3
BATHS
1,953
SQFT
$169
$/SQFT
1.75
ACRES
1986
BUILT
"Welcome home to this Beautiful Cape in the Desireable Chester! This lovely home has over 1900 square feet of space and features 3 Bedrooms and 2.5 bathrooms! You will love taking advantage of your two-car attached garage, perfect for our New England Weather. Inside you will be greeted with beautiful hardwood floors, Spacious family room with a Fireplace and a Spacious eat-in kitchen with Stainless steel appliances and Gas cooking. Directly off of the Kitchen, you have access to your outdoor living area with a Slate patio and an invisible pet fence. Upstairs you will find your Master suite with an attached full bathroom featuring a radiant heat floor and walk-in closet. This home has everything you have been looking for. Schedule your Private tour today!"
$325,000
40 Turkey Hill Road, Chester CT 06412
3
BEDS
2
BATHS
1,800
SQFT
$181
$/SQFT
1.50
ACRES
1920
BUILT
"This quintessential 1920s Craftsman style cottage, complete with wrap around porch, sits on a quiet country road. Many custom features including soapstone counters in kitchen and bath, wood stove with tile fireplace, first floor bedroom, full bath with jetted tub and a stained glass transom window, and a den/family room on the main floor. The upper level hosts a master bedroom with large walk-in closet, full bath with claw foot tub, an additional bedroom and studio with skylight. Set on 1.5 acres of land just a short distance from downtown Chester, this home features an in ground pool, outdoor shower, one car garage and kayak rack. This property was built as a weekend home and was among the first homes in the area to have electricity (original generator housing is now root cellar) and legend say that a half-mile long hose pumped water from a nearby pond to fill the pool. Whether relaxing on the pool's deck, napping on the front porch or curled up by the fireplace, this home will become one's private sanctuary."
$325,000
74 Cedar Lake Road, Chester CT 06412
3
BEDS
2
BATHS
1,966
SQFT
$165
$/SQFT
1.90
ACRES
1972
BUILT
"On a lovely country road close to both Cedar Lake and Pattaconk Reservoir and contiguous to Cockaponset State Forest, this custom ranch style home will appeal to many Buyers. Built with superior materials and master craftsmanship, the three bedroom two full bath home with separate den and family room offers a flexible floor plan with space for everyone. Appointments include gleaming hardwood floors and natural trim, freshly painted walls and lots of windows that allow the home to be bathed in sunlight. A large wrap around deck accessed by sliders from the dining and family rooms can accommodate large parties and allows easy access to the back yard. The unfinished basement has high ceilings, and could easily be converted into additional living space if required but its present condition may be used for hobbies and woodworking. The grounds are landscaped and cleared to the small brook that feeds the Lake and borders Cockaponset, Connecticut s second largest park where hiking trails meander forever! Cedar Lake, a short stroll from the home is ideal for swimming with its two resident beaches and its boat launch is perfect for kayaks, canoes and small boats. In addition, riding stables are plentiful in the area. For those Buyers seeking an active, country life style or wanting to commune with nature, look no further. Chester is a sophisticated town with many fine dining restaurants, boutiques and art galleries and is close to Rte 9, it is an easy commute to Hartford."
$319,900
61-21 Goose Hill Road, Chester CT 06412
4
BEDS
3
BATHS
1,976
SQFT
$162
$/SQFT
4.00
ACRES
1995
BUILT
"Meticulously cared for, one owner cape located on private 4+ acres that abuts Water Co. land. First floor Master Bedroom has a walk-in closet, updated bath, separate entrance to wrap around porch. First floor open floor plan, Butler's pantry, sliders to large deck, office/bedroom, screened porch. Second floor has two spaces with ample built-in storage that have been used as bedrooms."
$315,000
89 Cedar Lake Road, Chester CT 06412
2
BEDS
2
BATHS
1,336
SQFT
$236
$/SQFT
4.00
ACRES
1806
BUILT
"A gentleman's farm on 4 picturesque acres of rolling countryside and meadow land with babbling brook and waterfall, this 6 room country Cape circa 1806, has been lovingly restored and updated. All rooms and ceilings have been freshly painted. The kitchen features new cabinets and granite counter tops. The spacious dining room and living room are accented with walls of reclaimed old barn board. The dining room and living room are separated by a sliding barn door authentically hand crafted by a local artisan. Hardwood floors through-out the first floor and carpet upstairs. Replacement windows. A short walk to Cockaponsett State Park with seemingly unending hiking trails and Cedar Lake with two resident beaches and boat launch ideal for small boats and canoes. A picture perfect country escape."
* NEW LISTING 
 
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