Homes for Sale in Chesapeake, VA Between $250,000 to $300,000

Welcome to your dedicated resource for Homes for Sale Between $250,000 to $300,000 in Chesapeake, VA. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesapeake, VA agent, Barn Door Homes specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $250,000 to $300,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Chesapeake, VA Homes for Sale Between $250,000 to $300,000

$320,000

3 Beds ⋅ 2.1 Baths ⋅ 10643459 MLS

Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this property offers easy access to everything Chesapeake has to offer. Whether you're a first-time homebuyer, downsizing, or seeking an investment opportunity, this townhome presents n excellent opportunity. Quarterly HOA fees help mINTin the community, providing added convenience nd peace of mind. Don't miss your chance to make this Chesapeake property your next home!

709 Montrose Court, South Chesapeake

$1,104,938

4 Beds ⋅ 3.1 Baths ⋅ 10643126 MLS

Warning: You may never want to leave home! Welcome to the Buena Vista by Kirbor Homes, where every room is designed to make everyday life feel a little more extraordinary. Whether you're hosting the holidays, cheering on your favorite team, or simply enjoying a quiet evening in, this home is ready for it all. The show-stopping kitchen is sure to become everyone's favorite gathering spot, featuring our upgraded Chef's Appliance Package, an oversized island, and plenty of room for everything from charcuterie boards to cookie decorating marathons. The open-concept layout keeps the conversation flowing from the kitchen to the dining area and great room, so no one ever misses out on the fun. When it's time to recharge, the luxurious first-floor primary suite offers the perfect escape, while the additional bedrooms and flexible living spaces provide endless possibilities for guests, hobbies, a home office, or that home gym you've been promising yourself. Step outside to the covered rear porch and imagine slow mornings with coffee, backyard cookouts, or winding down with a glass of wine as the sun sets. Located in the desirable Sanderson Estates, the Buena Vista pairs spacious homesites with the quality craftsmanship and thoughtful details Kirbor Homes is known for. This isn't just another new construction home—it's the kind of place where memories are made, traditions begin, and you'll happily volunteer to host every family gathering. Schedule your tour or Design Center appointment today and see why the Buena Vista might just ruin every other floor plan for you. Builder contract. Ask about available lender incentives!

2801 Raccoon Trail, South Chesapeake

$630,000

5 Beds ⋅ 3 Baths ⋅ 10643153 MLS

Home is being sold AS-IS.Come home to the beautiful 5bdrm, 3 bth with 3000 sqft of living space to enjoy. Freshly painted. Centrally located in the heart Great Bridge near shopping, dining, and the interstate.

1202 Copper Knoll Lane, South Chesapeake

$415,000

5 Beds ⋅ 3.1 Baths ⋅ 10643431 MLS

Welcome to 1706 Martin Ave in Chesapeake! Solar panel is paid off, and average monthly electrical bill is minimal to none. This charming home offers 5 spacious bedrooms and 3.5 bathrooms, great for comfortable living. The kitchen has been beautifully updated with granite countertops, a stylish backsplash, modern light fixtures, and stainless-steel appliances.Fresh paint throughout the home and new carpet upstairs add a clean, move-in-ready feel. Two HVAC units ensure year-round comfort and efficiency.Out back, you’ll find a large detached unit featuring new flooring, lighting, and paint—great for a home office, studio, guest space, or endless other possibilities.Don’t miss this incredible opportunity!

1706 Martin Avenue Avenue, Central Chesapeake

$585,000

4 Beds ⋅ 2.1 Baths ⋅ 10643196 MLS

Welcome to this one of a kind custom all brick home designed for buyers who appreciate true craftmanship, architectural character, and timeless traditional design. Offering nearly 3000 sqft, 4 bedrooms and 2.5 baths, this home showcases features rarely found in newer construction, including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and 3 fireplaces that bring warmth and character throughout. This is not a builder grade flip or cookie cutter renovation, but a home built with quality, detail, and lasting charm. Outside, enjoy a private backyard retreat with a saltwater inground pool. Ideally located near local bases, shopping, dining, and major interstates, this is a rare opportunity to own a home with true character and lasting value.

913 Montebello Circle, South Chesapeake

$605,000

4 Beds ⋅ 2.1 Baths ⋅ 10642996 MLS

Welcome to luxury, low-maintenance living in the highly sought-after Westfield at Hickory Manor! This beautifully upgraded Galloway Model, built in 2018, offers 2,059 sq ft of stylish, thoughtfully designed living space with quality finishes throughout. The open-concept layout is superb for everyday living and entertaining, featuring spacious, light-filled rooms, an upgraded kitchen, a private primary suite, and flexible additional bedrooms. Enjoy resort-style amenities including a pool, 24-hr fitness center, clubhouse/community center, and playgrounds. Located in the sought-after Hickory School District with easy access to shopping, dining, military bases, major interstates, and more, this move-in ready home offers comfort, convenience, and lifestyle. Schedule your private showing today!

508 Cavendish Way, South Chesapeake

$775,000

4 Beds ⋅ 3 Baths ⋅ 10643343 MLS

Live the fresh life! Rarely does something this special come to market. Come see one of Western Branch's loveliest riverfront properties in an established neighborhood with no HOA. Designed for a lifetime of family fun and multigenerational living, this beautifully crafted 2-story on the Elizabeth River combines timeless elegance with all modern comforts. Through the soaring two-story foyer, you'll discover thoughtful details around every corner...signature hardwood floors, spa-like bathrooms, custom kitchen cabinetry, and more. A luxurious primary suite awaits you upstairs with its own balcony overlooking the pool. This lot has deep water access with beautiful views of the water. Relax in the saltwater pool during the hot summer days or relax in the hot tub for those cooler winter evenings. New roof (2025), water heater (2022), pool pump (2024), and salt cell (2026). A truly rare waterfront retreat.

3808 Stonebridge Landing, West Chesapeake

$410,000

3 Beds ⋅ 2.1 Baths ⋅ 10643082 MLS

Welcome to this spacious 3-bedroom, 2.5-bath home offering over 1,900 square feet of comfortable living in the heart of Chesapeake's desirable Greenbrier area. The thoughtfully designed floor plan features generous living spaces, a welcoming great room with a fireplace, and an updated kitchen with beautiful quartz countertops that continue into the bathrooms for a cohesive, modern look. Step outside to enjoy the stamped concrete patio, added in 2021, providing the perfect space for relaxing or entertaining. Additional updates include a new HVAC system (2018), refrigerator (2024), and dryer (2026), offering peace of mind for years to come. Conveniently located within driving distance of shopping, dining, parks, Greenbrier's business district, major interstates, and military bases, this well-maintained home is ready for its next owner.

640 Sweet Leaf Place, South Chesapeake

$330,000

3 Beds ⋅ 2.1 Baths ⋅ 10643331 MLS

Seller is offering $5,000 toward the buyer’s closing costs with an acceptable offer! Welcome to this beautifully maintained 3-bed, 2.5-bath townhome built in 2020, offering the perfect blend of style, comfort, and low-maintenance living. The open-concept floor plan features a spacious kitchen with granite countertops, a walk-in pantry, and plenty of cabinet space, flowing seamlessly into the living and dining areas—can be used for everyday living and entertaining. Upstairs, you’ll find a generous primary suite with a private bath, along with two additional bedrooms and a full bath. Come outside to enjoy the private rear deck, designed for relaxing after a long day. Condo fees include water, sewer, trash, grounds maintenance, and playground access, making homeownership even more convenient. Ideally located near military bases, shopping, dining, and major highways, this move-in ready home offers exceptional value in the heart of Chesapeake. Take advantage of the $5,000 seller concession and schedule your private showing today!

2833 Estella Way, Central Chesapeake

$524,900

3 Beds ⋅ 2.1 Baths ⋅ 10643243 MLS

Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing Landing, South Chesapeake

$699,000

5 Beds ⋅ 2.1 Baths ⋅ 10642890 MLS

This property is a gardener's dream. It has a variety of flowering plants that provide blossoms throughout the growing season. Blooms are sequenced for near year round color. There are 10 field-stone edged garden beds add stunning features to the landscape. One garden bed in the back has a goldfish pond. One in the front features an unique natural stone bench. Back yard includes vegetable garden plot that faces the sun for garden fresh produce. Back yard oasis includes a hot tub and six foot privacy fence. Two patios are connected by a master-crafted pave walk-way. Oversized garden shed helps keep garage clutter free. Two lockable gates one on each side of the property. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well and two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized primary bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk in closet is medium sized with plenty of storage space. Washer and dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake

$499,500

4 Beds ⋅ 2 Baths ⋅ 10643133 MLS

This beautifully renovated 4-bedroom, 2-bath home featuring 2,117 sq. ft. of bright and open living space is ready for you! The updated kitchen features custom cabinetry, quartz countertops, custom tile backsplash, large island, and stainless steel appliances. Perfect for cooking and entertaining. Tastefully finished bathrooms include custom tile, updated vanities, newer toilets, flooring and fixtures. Major recent updates include newer roof, ductwork, vapor barrier. Interior updates include recently replaced LVP, carpets, electrical fixtures, plumbing fixtures and paint. Centrally located near by to shopping, schools, beaches and bases. Schedule your showing today!

257 Coachman Drive, Central Chesapeake

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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.