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$850,000
4 Beds 3 Baths 10653178 MLS
All brick ranch in the sought-after Hickory school district, set back from the road on almost 4 acres offering exceptional privacy, great curb appeal and mature plantings. This spacious home offers an open floor plan, 4 bedrooms, 3 full baths and an oversized 3 car attached garage. The kitchen features hardwood floors, walk-in pantry and a bay window in the breakfast area. Spacious family room with fireplace, plus formal living and dining rooms and a separate study/office. The primary suite features a jetted tub with skylights above, separate shower, double sinks and its own water heater. Enjoy the screened porch overlooking the expansive property. Additional features include a high crawl space, replacement windows and architectural roof replaced in 2015. A rare combination of acreage, privacy and space in Hickory!

2329 Centerville Turnpike S, South Chesapeake

$998,895
5 Beds 3.1 Baths 10652907 MLS
Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem.

1910 Hallmark Way, South Chesapeake

$650,000
5 Beds 2.1 Baths 10652716 MLS
Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

$989,900
4 Beds 3.1 Baths 10652733 MLS
Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac) , only 10 lots on clear land bordered by mature trees as a backdrop. The primary opulent primary bath including an extra large closet and another large en suite are on the first floor along with a flex room. Our newest option is a "butlers kitchen" complete with full sink tucked just behind the well equipped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semicustom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be approved within the city. No main road lots here! If you are looking for new construction it a definite 'MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, come see! Preferred lender incentives be sure to ask for details. We have 1 acre 3 acre and a 20 acre lot

4020 Tucker Lane, South Chesapeake

$385,000
4 Beds 2.1 Baths 10652567 MLS
This all-brick ranch is just waiting for you to call it home! Featuring 4 bedrooms & 2.5 baths, this spacious home has been thoughtfully updated throughout the years. Major improvements include a roof and water heater updated in 2020, HVAC replaced in 2022 & windows approximately 12 years old. Inside, you’ll find a large kitchen with expansive countertops, stainless steel appliances, a formal dining room, and a generously sized living room complete with a cozy gas fireplace. Primary bedroom has a walk-in in closet while the other bedrooms are generous in size. The outdoor space is just as impressive! The back deck overlooks the large, fully fenced backyard. 2 concrete driveways offer plenty of parking & the 2nd driveway extends to a double gate into the backyard, providing convenient access for trailers, boats, recreational vehicles, or additional parking. Come see everything this home has to offer and make it yours! Some photos have been virtually staged.

909 Portland Street, Central Chesapeake

$885,000
4 Beds 3.1 Baths 10651664 MLS
Enjoy peaceful country living on 3 beautiful acres, just 5 miles from all your city favorites. This immaculate light-filled 4-bedroom, 3.5-bath home offers 9ft ceilings, detailed crown molding, custom built-ins, a main-level primary suite with a full bath, plus a convenient first-floor laundry room and mudroom. The chef's kitchen features leathered granite countertops, custom tile backsplash, SS appliances, and a center island. Upstairs offers 3 additional bedrooms, a large loft, and a second primary suite with a full bath, standalone tub, dual vanity, and 2 large walk-in closets. Outdoors, enjoy a resort-style backyard with a fenced inground saltwater pool surrounded by stamped concrete and a gazebo. The property also features solar panels, 2 barns, raised garden beds, a playset, a fire pit, and an extended driveway with ample space for an RV or boat. A rare blend of privacy, upgrades, and convenience!

2517 Number Ten Lane, South Chesapeake

$1,519,000
5 Beds 4.1 Baths 10651679 MLS
Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath, new paint and new flooring! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

$610,000
4 Beds 2.1 Baths 10651226 MLS
This well-maintained home features hardwood floors throughout the main living areas. The kitchen includes stainless steel appliances, 42-inch cabinets, quartz countertops, a large deep sink, two pantries, and a spacious island with bar seating. The family-room offers a fireplace, and the dining room features French doors. Upstairs, the primary suite includes a vaulted ceiling and private bath with dual sinks, a custom tiled shower, and a jetted tub. Three additional bedrooms, a full bath with dual vanities, and a laundry room complete the second floor. The sunroom overlooks the fenced backyard and extended patio, providing additional space for outdoor living and entertaining. Exterior recently repainted. Located in the Grassfield school district with convenient access to the expressway, shopping, and dining.

1853 Rockwood Drive, South Chesapeake

$1,500,000
5 Beds 3.1 Baths 10650552 MLS
A builder's own estate — private, impeccable, and set on approximately eight wooded acres at the end of a quiet Chesapeake cul-de-sac. Custom-built by the builder for his own family, this brick-and-stone home reflects a level of care you rarely find. Nothing here has been left untouched; it lives like new construction. A long gravel drive winds past mature trees to the home, where a sweeping front porch offers multiple entries and room to linger. Deer, turkey, and other wildlife are frequent visitors. Inside, a grand open floor plan rises to cathedral ceilings, finished with updated tile flooring, crown molding, and Hunter ceiling fans. The living area anchors around a dramatic stone fireplace and flows into an eat-in kitchen with rustic cabinetry, updated KitchenAid appliances, an electric cooktop, and a large center island with bar seating. The first floor holds a spacious primary suite, generously sized baths, and a well-placed Jack-and-Jill. Upstairs, brand-new carpet runs through bedrooms of exceptional size, and the primary closet is fitted with extensive custom built-ins. The two-story garage apartment is a standout, two bedrooms, 1.5 baths, multiple living areas, and a full eat-in kitchen, great for guests, multigenerational living, or income potential. The garages themselves have been freshly painted white, bright and spotless. Recent improvements include fresh paint throughout, LED lighting, updated kitchen and bath fixtures, two new HVAC units, a mini-split serving the room over the garage, smoke detectors, smart locks, and an on-demand propane water heater. Estate infrastructure is equally serious: 600-amp electrical service, a four-inch private well with pump house, a new water-softening system, hard-ducted HVAC, an illuminated crawl space, and a septic system serviced in 2026. A concrete parking pad completes the property. Privacy, craftsmanship, and acreage — a genuinely distinctive Chesapeake estate.

1120 Kathleen Lane, South Chesapeake

$879,000
4 Beds 3 Baths 10650413 MLS
Nestled on a quiet cul-de-sac lot on 3 private acres in one of South Chesapeake's most coveted neighborhoods, this 4-bedroom, 3-bath home offers timeless luxury and exceptional craftsmanship. The main level features a 2-story foyer, formal dining room, dedicated office, fully renovated full bath with flex room for a possible 1st-floor bedroom or in-law suite. A beautiful new kitchen with amazing quartzite countertops, Viking appliances , and a handmade Shaws fireclay sink opens to a large sunlit living room & sunroom. Upstairs, the primary suite features a walk-in closet and a stunning Carrara marble bath. Three additional bedrooms, a fully renovated hall bath, and a massive bonus room over the garage offer flexible room for a possible 5th bedroom or media space. Notable upgrades include new carpet up/new wide plank oak floor down, all bath & kitchen fixtures by Lefroy Brooks/Perrin & Rowe, custom blinds, geothermal HVAC 2023. Full update list in photos & uploaded to MLS.

517 New Zealand Reach, South Chesapeake

$839,900
5 Beds 4.1 Baths 10649639 MLS
Discover luxury, space, and versatility all in one remarkable Chesapeake address. 3504 Riverwood Crescent delivers an extraordinary living experience, offering a total of 5 bedrooms and 5 bathrooms thoughtfully tailored for comfort and style. Every detail has been considered to provide an elevated lifestyle for you and your family.Designed with ultimate flexibility in mind, the layout includes a completely private 1-bedroom, 1-bathroom in-law suite—complete with its own dedicated amenities—making it ideal for multi-generational living, extended family, or visiting guests while ensuring complete privacy for everyone under your roof.Nestled in a peaceful neighborhood while remaining close to top-tier dining, shopping, and major commuter routes, this home truly has it all. Don't miss the opportunity to make this incredible property your own!

3504 Riverwood Crescent, South Chesapeake

$565,000
4 Beds 2.1 Baths 10649467 MLS
Located in the highly sought-after Grassfield School District, this spacious home offers over 2,400 square feet of comfortable living space with 4 bedrooms, a dedicated study, and 2.5 bathrooms. The thoughtfully designed floor plan features a bright and inviting sunroom sitting area just off the kitchen. Continue outside to enjoy the large backyard, offering plenty of room for gardening, pets, or future entertaining. Recent updates provide added value and peace of mind, including a new hot water heater (2026), new air conditioner condenser (2025), new living room carpet (2026), updated downstairs toilet (2026), and new primary bathroom faucets (2026). Outdoor improvements include a back patio (2020), new back porch (2023), and new front porch/deck stairs (2024), creating welcoming spaces to enjoy both the front and backyard.

1916 Orangewood Road, South Chesapeake

$825,000
4 Beds 4 Baths 10647485 MLS
Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, South Chesapeake

$500,000
5 Beds 3 Baths 10646864 MLS
Charming & lovingly updated farmhouse in heart of Deep Creek on 1.2 acres includes all modern conveniences while respecting historic heritage w/features like original hardwood floors, crown molding, chair railing w/both welcoming front porch & screen porch. Beautiful kitchen w/SS appliances, granite counters, peninsula w/gas range, prep sink, SS wine fridge, oversized breakfast bar & pendent lighting. Bright & airy upstairs w/3 beds 2 w/walk-in closets, linen closet & updated hall bath w/beaded board wainscoting. 4th bed downstairs w/ensuite bath. Fantastic laundry room w/cabinetry, counter space, shelving & utility sink. Updates include: newer HVAC, ductwork & insulation, hardy plank siding & vinyl replacement windows. Spacious backyard 2 sheds & irrigation. Detached garage boasts almost 1500 sq feet split between the 2 levels. Upstairs living area has a full bedroom, bathroom and bonus closet/storage area. Great for your guests!

3248 Galberry Road, South Chesapeake

$659,900
5 Beds 3.1 Baths 10646835 MLS
If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, South Chesapeake

$550,000
5 Beds 2 Baths 10646017 MLS
Embrace the off-the-grid lifestyle on 0.96 acres in Chesapeake's desirable Blackwater area, zoned for highly sought Hickory schools! This property maximizes self-sufficiency with pure water from a premium 600+ ft Certified Artesian well, a double tank water softener, and a tankless electric water heater. To drive utility costs down further, consider adding a maintenance-free solar panel program at no cost for instant savings without equipment hassles. Inside, the layout features a versatile room off the living room (perfect for an office or homeschool/playroom) plus a FROG, creating up to 6 bedroom-like spaces. The oversized septic system easily supports an ADU, multi-generational living, or rental income. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens. Best of all, sellers are open to negotiating improvements with an acceptable offer to help customize this homestead exactly to your liking!

1336 Blackwater Road, South Chesapeake

$609,900
4 Beds 3.1 Baths 10644569 MLS
100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

$916,000
3 Beds 2.1 Baths 10643968 MLS
HURRY; THIS HOME WON’T LAST!!! If you are looking for privacy this single family home situated on a spacious 1-acre lot with “no” HOA fee & convenient interstate access is for you!!! The attention to detail & custom upgrades are simply “impeccable”! Home features double door front entrance, 3 bedrooms including that much sought after “first floor primary” with a luxurious spa inspired bath, custom closet, 2 & 1/2 baths, family room with gas fireplace, gourmet kitchen with upgraded “GE Cafe” appliances, loads of custom cabinetry, huge kitchen island, custom trim work though-out, upgraded flooring, enhanced lighting & plumbing fixtures, mudroom with customized storage, large loft with window nook, extra large rear “screened” in covered porch & 2 car side load garage! This amazing home on this incredible lot is a true must see!!!

109 Ballahack Road, South Chesapeake

$1,069,417
5 Beds 4 Baths 10643118 MLS
The Rivermont is where everyday living feels just a little more special. Designed with comfort, style, and connection in mind, this thoughtfully crafted home offers the perfect spaces to gather, relax, and make lasting memories. At the heart of the home, the chef-inspired kitchen flows effortlessly into the spacious dining area and inviting great room, creating the ideal setting for everything from Sunday brunches to holiday celebrations. Just beyond, step onto the covered rear porch—your new favorite spot for morning coffee, evening cocktails, or cheering on a summer thunderstorm from the comfort of home. The vaulted first-floor primary suite provides a peaceful retreat, while generously sized secondary bedrooms and flexible living spaces offer room for family, guests, hobbies, or a home office. Every detail reflects the quality craftsmanship and thoughtful design Kirbor Homes is known for. Located in the desirable Sanderson Estates, you'll enjoy spacious homesites and the perfect blend of peaceful surroundings with convenient access to shopping, dining, recreation, and major commuting routes. Whether you're hosting family dinners, relaxing on the porch, or simply enjoying the comfort of a brand-new home, the Rivermont is designed for the moments that matter most. Come see why this could be the perfect place to call home! Contact LA to schedule an appointment at our design center today! Builder Contract. Ask about our current incentives!

2861 Raccoon Trail, South Chesapeake

$988,613
4 Beds 3.1 Baths 10643550 MLS
CURRENTLY IN FOUNDATION! STILL TIME TO PERSONALIZE THE FINISHES IN YOUR DREAM HOME! Meet the Holden by Kirbor Homes! A home that checks all the boxes and then a few you didn't even know you wanted! From the moment you step inside, you'll love the bright, open layout that's designed for everything from holiday gatherings to cozy movie nights. The chef-inspired kitchen is the true heart of the home, featuring a spacious island where everyone naturally gather, plenty of cabinet space, and an easy flow into the dining area and Great Room. Whether you're hosting friends or enjoying a quiet morning with coffee, this home is designed to make every day feel a little more special. When it's time to unwind, head on over to the first-floor primary suite, complete with a spa-like bath and generous walk-in closet. Need a home office, playroom, or hobby space? You've got that, too! Upstairs, you'll find spacious secondary bedrooms and a versatile loft that's ready to become your game room, media room, fitness space, or whatever best fits your lifestyle. If you've been searching for a home that's equal parts stylish, functional, and welcoming, you've just found it. Come see why the Holden feels like home the moment you walk through the door. Builder contract required. Reach out today to schedule an appointment at our Design Center and experience the beautiful finishes and thoughtful selections that have been chosen for this home. Ask about current builder incentives and available opportunities to make this dream home yours!

2116 Sanderson Road, South Chesapeake

$235,000
2 Beds 2.1 Baths 10643204 MLS
Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and a great position tucked toward the backside of the building. Enjoy a quiet serene lifestyle. The functional floor plan provides comfortable everyday living. 2 Bedrooms on the 2nd floor along with 2 Full-Baths with a convenient powder room on the 1st floor. Generous closet space and plenty of storage throughout. A private, new fully fenced patio provides a great space to relax or unwind. Additional highlights include an HVAC system replacement (2025), stove and microwave (2025) and two reserved parking spaces right out front. Just minutes from major interstates, shopping, dining, hospitals and everyday conveniences. Vacant and move-in ready,

1002 Willow Green Court, South Chesapeake

$1,750,000
4 Beds 4 Baths 10642797 MLS
Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, South Chesapeake

$524,900
3 Beds 2 Baths 10642197 MLS
Recently appraised at $600k, opportunities for instant equity like this are rare. Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake

$649,900
4 Beds 2.1 Baths 10641240 MLS
Welcome Home! A Stephen Alexander build where timeless design meets the comfort of everyday living. Tucked away on nearly half an acre in sought-after Grassfield, this beautifully cared-for home has been lovingly maintained by its original owners since day one. 4 spacious bedrooms, 2.5 baths, and nearly 3,200 sqft of inviting space with room for both quiet mornings and lively gatherings. The screened-in porch creates the perfect spot for coffee, conversations, and slow summer evenings. Outside, the backyard feels like a private escape, backing to peaceful woods with space to play, relax, and enjoy nature right at home. Homes this well cared for, in this setting, and with so much character are hard to find. Come see all that 2008 Burson Drive has to offer— a place designed not just to live, but to make memories!

2008 Burson Drive, South Chesapeake

$609,900
6 Beds 3 Baths 10641027 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

2223 Hampton Roads Parkway, West Chesapeake

$1,257,400
5 Beds 4 Baths 10640535 MLS
Proposed To Be Built- Waterfront Custom Home Community Located on the Western Branch of the Elizabeth River! Beautiful Creek Front Large Lot. Home Features Hardie Plank Exterior w/ Stone Accents. A Large Covered Rear Porch/ Dining Area w/ Stamped Concrete. Open Airy Floor Plan w/ Gourmet Kitchen, a Large Center Island, 36" Gas Cooktop, 9' Ceilings First and Second Floors. First Floor Features Eng. Hardwood. First Floor Primary Bedroom w/ Luxury Bath and Freestanding Tub. Additional first floor Study/Bed Room w/ Full Bath, Spacious second floor with Two Bedrooms, Two Baths ( One En-Suite, One Hall Bath). Large Bonus Room, Step-up Game/Recreation Room over the Family Room features a Second Floor Balcony with a Beautiful Creek View! Yard Fully Sodded and Irrigated. Many Special Features Included. Sasser has been a member of the Southern Living Custom Builder Program for 30+ years and awarded SL Custom Builder of the Year. * If Financing Buyer to obtain a Custom to Permanent Loan.

2832 Martins Point Way, West Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.