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The Highlands Homes for Sale

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  • /38

    $632,000

    • 5 Beds
    • 3.5 Baths
    • 3,141 Sq Ft

    7530 Dunollie Dr, Chesterfield, VA 23838

    Have you ever dreamed of living in your own modern-day castle? Welcome to this stunning 5-bedroom, 3.5-bath retreat in the award-winning Highlands community. Nestled on a private 1.2-acre lot, this home offers a storybook setting with its turret-style roof, grand statement windows, and timeless architectural charm. Inside, you'll find luxurious finishes like crown molding, dark bamboo floors, and

    Agent Photo

    Nicole Diamond

    NextHome Signature Properties

    (804) 251-3073

    7530 Dunollie Dr, Chesterfield, VA 23838
  • /2

    $739,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 4,406 Sq Ft

    7324 Rosemead Ln, Chesterfield, VA 23838

    Welcome to your own private oasis in the highly desirable community of The Highlands. This elegant home offers over 4,400 square feet of thoughtfully designed living space, beautifully situated on a landscaped one-acre lot that backs to a peaceful creek.. From the moment you enter, you'll be impressed by the open floor plan, soaring 18-foot ceilings, and dramatic staircase. The formal dining

    Agent Photo

    Khaliyah Barakhyahu

    EXP Realty, LLC

    (804) 531-4726

    7324 Rosemead Ln, Chesterfield, VA 23838
  • /50

    $675,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 3,489 Sq Ft

    11221 Rabbit Ridge Rd, Chesterfield, VA 23838

    Welcome to the perfect blend of charm, comfort, and modern living. This beautifully renovated Cape Cod-style home offers five spacious bedrooms and three and a half baths, combining thoughtful design with high-end upgrades throughout. The first floor features gleaming hardwoods, anchored by a luxurious primary suite complete with a huge walk-in closet and a newly renovated spa-like bath with

    Thomas Rose Shaheen Ruth Martin & Fonville

    11221 Rabbit Ridge Rd, Chesterfield, VA 23838
  • /49

    $749,900

    • 5 Beds
    • 4.5 Baths
    • 4,194 Sq Ft

    8713 Mckibben Dr, Chesterfield, VA 23838

    Welcome to 8713 McKibben Dr! Inside, the striking floor-to-ceiling gas fireplace creates a warm and inviting ambiance, perfect for relaxing or entertaining. The heart of the home is the chef-inspired kitchen, thoughtfully designed with upgraded cabinetry, sleek stainless steel appliances, stunning countertops, and a spacious center island—combining both functionality and refinement. The main

    Jen Coppock Redfin Corporation

    8713 Mckibben Dr, Chesterfield, VA 23838
  • /50

    $699,000

    • 6 Beds
    • 4 Baths
    • 3,606 Sq Ft

    11137 Sterling Cove Dr, Chesterfield, VA 23838

    Welcome to this stunning 6-bedroom, 4-bathroom single-family home, offering 3,606 square feet of stylish, spacious, and light-filled living space. Situated on just over an acre, this property provides the perfect blend of privacy, space, & serenity. With recent updates, premium finishes, & resort-style community amenities, this home is truly move-in ready, thoughtfully designed for comfort,

    Cindy Allen Metro Premier Homes LLC

    11137 Sterling Cove Dr, Chesterfield, VA 23838
  • /50

    $824,000

    • 4 Beds
    • 4.5 Baths
    • 3,607 Sq Ft

    12618 Capernwray Terrace, Chesterfield, VA 23838

    Located in The Highlands community, this wonderful property sits on 2.7 private acres at the end of a cul-de-sac, with 1.5 acres fully landscaped. This house provides 5,065 total square feet, with 3,607 finished square-feet and an additional 1458 unfinished square-feet basement; this home features 4 bedrooms, each with a private bathroom and walk-in closet. Interior details include shiplap and

    Samuel Robertson Fathom Realty Virginia

    12618 Capernwray Terrace, Chesterfield, VA 23838
  • /40

    $700,000

    • 5 Beds
    • 3.5 Baths
    • 4,290 Sq Ft

    8214 Macandrew Ct, Chesterfield, VA 23838

    Exquisite Residence on a Premier 1.56-Acre Lot in The Highlands. This beautifully maintained home has been updated with numerous improvements. A new double oven and cooktop were added in 2025, along with updated lighting fixtures that bring a fresh, modern touch throughout. The HVAC systems for both the first and second floors were replaced in 2022 with a high-efficiency 18-SEER variable Lennox

    Jenny Maraghy Compass

    8214 Macandrew Ct, Chesterfield, VA 23838
  • /50

    $750,000

    • 5 Beds
    • 4.5 Baths
    • 4,875 Sq Ft

    9501 Gadwell Terrace, Chesterfield, VA 23838

    This beautiful Colonial offers the unique opportunity to have almost 4 acres of privacy while still having all the amenities of an established planned community! Upon entry, you're greeted by the two story foyer that leads to the formal living and dining rooms with hardwood floors & crown moulding on one side and the spacious family room complete with built-in shelving, beamed ceiling, and huge

    Terra Dantona Joyner Fine Properties

    9501 Gadwell Terrace, Chesterfield, VA 23838
  • /24

    $697,000

    • 5 Beds
    • 3.5 Baths
    • 3,806 Sq Ft

    11430 Avocet Dr, Chesterfield, VA 23838

    METICULOUSLY MAINTAINED + BEAUTIFULLY UPDATED IN WOODLAND POND! This classic, move-in ready home offers 3,800+ SQ FT of thoughtfully designed space, featuring 5 bedrooms, 3.5 baths, and a third-floor bonus room. All set on a professionally landscaped lot in one of Chesterfield’s most desirable custom-home communities. Curb appeal shines with custom-built shutters, handcrafted front railings, a

    Matt Cullather Real Broker LLC

    11430 Avocet Dr, Chesterfield, VA 23838
  • /44

    $745,000

    • 5 Beds
    • 4 Baths
    • 4,279 Sq Ft

    8106 Killbevan Dr, Chesterfield, VA 23838

    This spacious 4279 sq ft Hampshire floorplan home sits on 2.67 acre private lot, nestled in The Highlands Community; Lake Margaret section. Inclusive of a fully finished basement; offers a wet-bar for family & friends entertainment, this comfortable living space also includes a bedroom with walk-in closet & a full bath! The main level showcases a formal dining room, guest bedroom, full bath

    Michelle Johnson-Fisher United Real Estate Richmond

    8106 Killbevan Dr, Chesterfield, VA 23838
  • /11

    $719,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,130 Sq Ft

    8136 Clancy Ct, Chesterfield, VA 23838

    The Edgefield is a ranch home featuring four bedrooms, three-and-a-half baths, and a side-load garage. A dining area with hardwood flooring is located directly off the foyer. A spacious kitchen with granite counters, hardwood floors, an island, and a walk-in pantry is open to an adjoining dining area. The cozy family room features a gas fireplace and a home office with glass French doors and

    Kim Sebrell Keller Williams Realty

    8136 Clancy Ct, Chesterfield, VA 23838
  • /13

    $699,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,185 Sq Ft

    8124 Clancy Ct, Chesterfield, VA 23838

    The Asheboro by Eastwood Homes blends thoughtful design with timeless comfort—featuring 4 bedrooms, 3.5 baths, and a desirable side-load garage. From the moment you step inside, you'll notice the warmth of EVP floors flowing from the foyer into the elegant dining area and chef-inspired kitchen. Enjoy quartz countertops, a spacious island, a walk-in pantry, and seamless flow into the cozy family

    Kim Sebrell Keller Williams Realty

    8124 Clancy Ct, Chesterfield, VA 23838
  • /30

    $782,836 New Construction

    • 5 Beds
    • 4 Baths
    • 3,420 Sq Ft

    10013 Boschen Woods Place, Chesterfield, VA 23838

    The August II by Main Street Homes – Stunning 4-Bedroom Home on a large .81-Acre Lot!Welcome to The August II by Main Street Homes, situated on a rare .81-acre lot with incredible curb appeal! This beautifully designed home features a large brick front porch & welcoming double front doors that open into a spacious & light-filled interior.The main level boasts a two-story great room,

    Kim Tierney Virginia Colony Realty Inc

    10013 Boschen Woods Place, Chesterfield, VA 23838
  • /7

    $714,950 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,282 Sq Ft

    13030 Alsandair Dr, Chesterfield, VA 23838

    Welcome to the Windemere at Lake Margaret! Experience the ease of refined first-floor living in this beautifully designed 1-story home, offering both comfort and style in every detail. The open-concept chef’s kitchen is a true centerpiece, featuring a walk-in pantry, abundant counter space, and seamless access to the mudroom just off the attached two-car garage. The kitchen flows effortlessly

    Ariane Grabill Market Square Realty LLC

    13030 Alsandair Dr, Chesterfield, VA 23838
  • /48

    $849,000

    • 4 Beds
    • 2.5 Baths
    • 4,115 Sq Ft

    12830 Crathes Ln, Chesterfield, VA 23838

    Stunning one of a kind in The Highlands one owner custom built modern farmhouse located in a quiet cul-de-sac on a 2.6 acre private lot . Beautifully decorated 4 bedroom home loaded with upgrades. The main floor features a spacious foyer. To your left, a set of French doors welcome you the the office/study with beautiful wainscoting . Down the hall, the half bathroom and the stairs on your

    Rene Welvaert Fathom Realty Virginia

    12830 Crathes Ln, Chesterfield, VA 23838
  • /48

    $900,000

    • 4 Beds
    • 4 Baths
    • 4,242 Sq Ft

    10711 Old Squaws Ln, Chesterfield, VA 23838

    Prime waterfront property with a stunning classic-styled home that has been beautifully maintained from bow to stern! The first-floor primary suite features two walk-in closets, wood floors, a bay window, and a luxurious primary bath that includes an oversized tile shower and a towel warmer. The foyer displays a stunning Waterford Crystal Chandelier. Enjoy the relaxing waterfront views from the

    Wanda Huggins Shaheen Ruth Martin & Fonville

    10711 Old Squaws Ln, Chesterfield, VA 23838
  • /39

    $524,999

    • 5 Beds
    • 3 Baths
    • 2,708 Sq Ft

    8136 Fedora Dr, Chesterfield, VA 23838

    Sellers are offering $15000 towards buyers closing cost with an acceptable offer. Here's your chance to own your dream home in the highly sought-after Highlands! This well maintained property boasts a beautiful open floor plan with a full front porch and back deck, perfect for morning coffee or relaxing evenings. The home features five bedrooms, 3 full bathrooms and a large master suite with two

    Denise Jones United Real Estate Richmond

    8136 Fedora Dr, Chesterfield, VA 23838
  • /50

    $1,500,000

    • 4 Beds
    • 5.5 Baths
    • 8,394 Sq Ft

    9106 Avocet Ct, Chesterfield, VA 23838

    This amazing luxury estate on the lake in sought-after Woodland Pond features both a private dock and a salt-water swimming pool. Nestled on a large lot of over an acre, this beautiful property offers the perfect blend of privacy, space, and natural beauty. The Colonial-designed exterior with Hardiplank siding offers a transitional floor plan with oversized rooms across four levels. Several

    Ryan Sanford RE/MAX Commonwealth

    9106 Avocet Ct, Chesterfield, VA 23838
  • /49

    $938,900

    • 6 Beds
    • 5 Baths
    • 5,032 Sq Ft

    11600 Europa Dr, Chesterfield, VA 23838

    Luxury living awaits in this beautiful6-7 bedroom gorgeous home on 1.46 ACRES! CUSTOM FINISHES THROUGHOUT! The GOURMET KITCHEN is a chef's dream! Multi-generational design includes a FIRST FLOOR BEDROOM/IN LAW SUITE, MASSIVE FINISHED BASEMENT with bedroom/full bath, second floor bonus room and flex room offering endless possibilities. Unwind in the primary suite featuring a spa-like bath

    Lakisha Brown Shoreline Realty

    11600 Europa Dr, Chesterfield, VA 23838
  • /49

    $499,950 Open Sun 1PM - 3PM

    • 5 Beds
    • 2.5 Baths
    • 3,023 Sq Ft

    13813 Bluff Ridge Dr, Chesterfield, VA 23838

    Set on a peaceful 1-acre lot with mature trees & attractive curb appeal, this spacious 5-bedroom home offers over 3,000 sq ft of thoughtfully designed living space. Step inside to a welcoming 2-story foyer with hardwood floors, crown molding & an elegant chandelier. To the left, the formal dining room features three tall front-facing windows, picture frame molding, chair rail, & decorative trim

    James Strum Long & Foster REALTORS

    13813 Bluff Ridge Dr, Chesterfield, VA 23838
  • /50

    $999,950

    • 5 Beds
    • 4.5 Baths
    • 5,352 Sq Ft

    8300 Mckibben Dr, Chesterfield, VA 23838

    Nestled on nearly two acres in the picturesque neighborhood of Lake Margaret, this property is meticulously maintained inside and out, showcasing attractive curb appeal with a vibrant lawn & beautifully landscaped gardens! Step inside to a world of elegance with this stunning luxury property featuring 5-bedrooms and 4.1-bathrooms. As you enter through the front door, the foyer beautifully sets

    Kimberly Geddis Liz Moore & Associates

    8300 Mckibben Dr, Chesterfield, VA 23838
  • /35

    $619,950 Open Sun 2PM - 4PM

    • 5 Beds
    • 2.5 Baths
    • 3,191 Sq Ft

    11960 Nash Rd, Chesterfield, VA 23838

    MOTIVATED SELLER - OFFERING A $10K CLOSING COST INCENTIVE. Timeless elegance meets modern comfort in this stunning Victorian retreat in the heart of Chesterfield County. Located just minutes from I-95, Route 288, Pocahontas State Park, retail shopping, and top dining spots—this home offers the perfect balance of retreat and convenience.The long, private driveway leads to this beautifully

    Kelly Rivers United Real Estate Richmond

    11960 Nash Rd, Chesterfield, VA 23838
  • /48

    $585,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 3,346 Sq Ft

    12055 Hadden Hall Dr, Chesterfield, VA 23838

    Welcome to this meticulously maintained Charles Bailey semi-custom five-bedroom, 3.5-bath home nestled in the prestigious and highly sought-after community of The Highlands. Perfectly situated on the coveted and quiet street Hadden Hall, this beautiful residence combines timeless charm with modern comforts—and places you just a short stroll from the clubhouse and golf course.From the

    Dawn Wade Hometown Realty

    12055 Hadden Hall Dr, Chesterfield, VA 23838
  • /42

    $589,000

    • 4 Beds
    • 2.5 Baths
    • 2,712 Sq Ft

    8500 Brechin Ln, Chesterfield, VA 23838

    Come and see this STUNNING and meticulously maintained colonial in the lovely community of Chesterfield's "The Highlands"! This beautiful 4 bedroom / 2.5 bath home is well appointed throughout and glows with timeless charm and modern comfort. With a gorgeous brick front elevation, intentional landscaping and over 1.4 acres of mixed open/wooded land - it truly is a lovely home on a pristine lot.

    Cabell Childress Long & Foster REALTORS

    8500 Brechin Ln, Chesterfield, VA 23838
  • /41

    $575,000

    • 5 Beds
    • 3.5 Baths
    • 2,694 Sq Ft

    8413 Chandon Ct, Chesterfield, VA 23838

    Did you miss your opportunity for this gem? Buyer financing fell through. Nestled at the end of a quiet cul de sac, this striking colonial-style home offers the perfect blend of timeless charm & modern elegance. With a classic brick facade & transitional architectural details, the home boasts curb appeal & functionality. Step inside to find gleaming hardwood floors throughout the first & second

    Lisa Stone Long & Foster REALTORS

    8413 Chandon Ct, Chesterfield, VA 23838
  • /42

    $499,950

    • 4 Beds
    • 2.5 Baths
    • 2,581 Sq Ft

    11324 Regalia Dr, Chesterfield, VA 23838

    Welcome home to 11324 Regalia Drive, a beautifully maintained 4 bedroom 2.5 bathroom home tucked away on a private and wooded 1.78 acre lot in the sought after golf course community of The Highlands. Built in 2001, this 2,581 square foot colonial blends timeless charm with modern comfort in one of Chesterfield’s most desirable neighborhoods. Step inside to a bright light filled interior featuring

    Annie Nissen ERA Woody Hogg & Assoc

    11324 Regalia Dr, Chesterfield, VA 23838
  • /49

    $655,000

    • 4 Beds
    • 2.5 Baths
    • 4,148 Sq Ft

    9300 Owl Trace Ct, Chesterfield, VA 23838

    Spacious, Renovated Home on Nearly 3 Private Acres in Woodland Pond!! Looking for space, privacy, and style? This stunning home has it all—and then some. Tucked away on a peaceful cul-de-sac, this 4-bedroom, 2.5-bath beauty sits on a large 2.79-acre lot that feels like your own private park. Inside, you’ll find over 4,100 square feet of updated living space. The entryway greets you with gorgeous

    Ty Condrey Real Broker LLC

    9300 Owl Trace Ct, Chesterfield, VA 23838
  • /24

    $559,900

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    6920 Apamatica Ln, Chesterfield, VA 23838

    Quality Craftmanship in this spacious Parade of Homes Beauty, Nestled on a Lush, Landscaped 2/3 Acre lot with an 8-Zone Irrigation System. Features include hardiplank siding, and 2 zone heating and cooling.This property boasts countless upgrades -- The gourmet kitchen is the heart of this home, offering Quartz countertops, Custom cabinets with pull-out drawers, an Induction cooktop with a

    Pat Finney Long & Foster REALTORS

    6920 Apamatica Ln, Chesterfield, VA 23838
  • /14

    $610,000

    • 5 Beds
    • 3.5 Baths
    • 4,009 Sq Ft

    11401 Braidstone Ln, Chesterfield, VA 23838

    Spacious home featuring gorgeous landscaping, 2 fireplaces, a large corner lot in a subdivision with amenities galore! This 2003 Parade of Homes award-winning floor plan, recognized for Best Kitchen, Best Curb Appeal, Best Primary Suite, & Best Floor Plan, is located in The Highlands, a premier golf course community. Enjoy canoeing, kayaking, bike trails, nature walks, a pool, tennis, golf, and

    Bernice Sim RE/MAX Commonwealth

    11401 Braidstone Ln, Chesterfield, VA 23838
  • /17

    $579,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,010 Sq Ft

    7 Abercrombie Dr, Chesterfield, VA 23838

    Welcome to The Lehigh to be built on a wooded, private 1.5 acres in Lake Margaret in the Highlands! Enter the inviting foyer, where versatile flex space can be used as a playroom, living room or office. The gourmet kitchen boasts a large island and walk-in pantry and connects to the dining and family room. Off the 2-car garage, a family entry controls clutter and leads to an included first floor

    John Thiel Long & Foster REALTORS

    7 Abercrombie Dr, Chesterfield, VA 23838
  • /29

    $619,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,739 Sq Ft

    5 Abercrombie Dr, Chesterfield, VA 23838

    Get to know The Greenwood to be built on a wooded, private 1.5 acres in Lake Margaret at The Highlands. This 2- to 3-car garage single-family home spotlights style and convenience. Gather friends & family in the great room before enjoying a delicious meal cooked in your gourmet kitchen with a large island. The adjoining dining room overlooks an optional covered porch. Your luxury first-floor

    John Thiel Long & Foster REALTORS

    5 Abercrombie Dr, Chesterfield, VA 23838
  • /17

    $619,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,239 Sq Ft

    3 Abercrombie Dr, Chesterfield, VA 23838

    Get to know The Savannah, grand living on one level, to be built on a wooded, private 1.5 acres in Lake Margaret at The Highlands. A spacious great room is at the heart of this home and flows seamlessly into the gourmet kitchen and dining area. Three large bedrooms offer sanctuary and privacy. Nestled at the back of the house, the owner’s suite provides private access to the included covered

    John Thiel Long & Foster REALTORS

    3 Abercrombie Dr, Chesterfield, VA 23838
  • /3

    $959,990 New Construction

    • 7 Beds
    • 5.5 Baths
    • 5,082 Sq Ft

    13007 Alsandair Dr, Chesterfield, VA 23838

    This home is UNDER CONSTRUCTION. Estimated completion is mid-summer 2025. Other models and lots may be available. The Waverly is a stunning home featuring 7 bedrooms, 5.5 baths, and a walk-out basement all situated on an expansive 1.7+ acre lot! As you enter, you’ll find a large formal dining room just off the foyer, perfect for hosting. The open-concept design offers a well-appointed kitchen

    Kim Sebrell Keller Williams Realty

    13007 Alsandair Dr, Chesterfield, VA 23838

Why Live in The Highlands

The Highlands in Chesterfield is a master-planned community offering a blend of modern amenities and natural surroundings. Residents enjoy an 18-hole golf course, tennis courts, lakes, and proximity to Pocahontas State Park, Virginia’s largest state park, which is less than a 15-minute drive away. The neighborhood features newly built homes on spacious, tree-shaded lots, with many properties spanning an acre or more. Home styles include Colonial Revival, American Craftsman, and New Traditional designs, with prices ranging from $450,000 to $750,000. There is also a 55+ community near Lake Margaret. The Highlands is part of the Chesterfield County Public Schools system, with schools like O. B. Gates Elementary and Matoaca High offering various educational programs. The Golf Club at The Highlands offers practice facilities, a fitness center, and a restaurant and bar. Community events such as a Fourth of July parade, fall festival, and ChesterFest provide social opportunities for residents. For shopping and dining, Iron Bridge Road features stores like Kroger, ALDI, and Lidl, and restaurants such as El Patron Cantina Iron Bridge and Riptides Seafood. The area is car-centric, with Virginia State Route 288 about a mile north and Interstate 95 and US Route 1 approximately 5 miles east.

Frequently Asked Questions

Is The Highlands a good place to live?
The Highlands is a good place to live. The Highlands is considered very car-dependent and somewhat bikeable. The Highlands is a suburban neighborhood. The Highlands has 5 parks for recreational activities. It is sparse in population with 0.6 people per acre and a median age of 50. The average household income is $154,789 which is above the national average. College graduates make up 50.9% of residents. A majority of residents in The Highlands are home owners, with 8.9% of residents renting and 91.1% of residents owning their home. A local real estate agent serving The Highlands can help you decide if this neighborhood is the right one for you. Learn more on our The Highlands neighborhood guide.
How much do you need to make to afford a house in The Highlands?
The median home price in The Highlands is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,720 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K a year to afford the median home price in The Highlands. The average household income in The Highlands is $155K.
What are the best public schools in The Highlands?
The best public schools that serve The Highlands are:
What are the best private schools in The Highlands?
The best private schools that serve The Highlands are:
What are the most popular zip codes in The Highlands, Chesterfield, VA?
The most popular zip codes in The Highlands, Chesterfield, VA include 23838, 23831, 23832, 23237 and 23803.
What are the most popular neighborhoods near The Highlands, Chesterfield, VA?
The most popular neighborhoods near The Highlands, Chesterfield, VA are Chesterfield Courthouse, Centralia, Meadowbrook, South Chesterfield County and Windsor Hills.
Are home prices dropping in The Highlands?
Yes, home prices in The Highlands are down 5% in the last 12 months.

Home Trends in The Highlands, VA

Housing Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$500,000
Median 2 Bedroom Sale Price
$340,000
Average Price Per Sq Ft
$296
Number of Homes for Sale
2
Last 12 months Home Sales
51
Months of Supply
0.50
Median List Price
$525,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-7%
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