Caroline County, VA Real Estate | Caroline County, VA Waterfront Homes for Sale

Waterfront living doesn't get much better than this. Welcome to 280 Lake Caroline Drive—a beautifully updated lakefront retreat where every day feels like a vacation. Rare Deep-Water Lakefront Living—Turnkey, Updated, and Ready for Your Next Chapter at Lake Caroline.” Welcome to 280 Lake Caroline Drive, a private waterfront retreat where thoughtful updates, wide lake views, and true move-in readiness come together on one of Lake Caroline’s most desirable lots. Set on more than half an acre with breathtaking 180-degree lake views and deep-water access, this beautifully maintained home delivers the feel of a year-round resort with the comfort and practicality of everyday living. A long paved driveway leads to the attached two-car garage, with generous additional parking for guests, boats, and recreational vehicles. Professionally landscaped grounds, extensive irrigation, and a fully fenced backyard create a setting designed for privacy, ease, and outdoor enjoyment. Inside, the home has been extensively updated across both levels. Highlights include remodeled bathrooms, updated flooring, newer kitchen appliances, a 2024 HVAC system, 2022 water heater, and a whole-house water filtration system installed in 2025. Four large bay windows fill the home with natural light and frame spectacular water views from multiple rooms. The main level offers comfortable living spaces and direct access to an elevated three-season porch overlooking the lake. The primary suite includes its own private balcony, an ideal spot for morning coffee, sunrise views, and quiet evenings by the water. Two gas fireplaces add warmth and character on both levels. The finished lower level offers excellent flexibility for guests, extended stays, multigenerational living, remote work, hobbies, or entertaining. This level features a spacious family room, large bedroom, full bath, kitchenette, two bonus rooms, one currently used as a fourth bedroom, and additional storage space. Outdoor living is where this property truly shines. Enjoy an oversized lakeside deck, expansive lawn, attached storage shed, and private deep-water dock ready for boating, fishing, swimming, kayaking, paddleboarding, and quiet days on the water. Active lawn care and HVAC service contracts convey to the new owner, adding convenience from day one. Lake Caroline offers an outstanding waterfront lifestyle with a 277-acre full-service lake, two sandy beaches, swimming pool with lifeguards, clubhouse, playgrounds, tennis courts, pickleball courts, basketball courts, fishing, boating, water skiing, wakeboarding, jet skiing, kayaking, paddleboarding, and year-round community events. This is an exceptional fit for a full-time residence, relocation to the area, second home, weekend retreat, or move-up waterfront purchase. Located within a gated, amenity-rich community just minutes from I-95, shopping, dining, and schools, 280 Lake Caroline Drive is a rare opportunity to own one of Lake Caroline’s standout waterfront properties. Nothing left to do except move in and start enjoying lakefront living.

280 Lake Caroline Dr, Ruther Glen

Listing courtesy of Metro Premier Homes. Contact: 703606-4156

$779,000

5 Beds ⋅ 5 Baths

" Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier.

8821 Dorothy Ln, Denton

Listing courtesy of Wright Real Estate. Contact: (410) 924-3111

$390,000

3 Beds ⋅ 1 Baths

This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout. Step outside to find a welcoming porch and patio, ideal for relaxing or entertaining. The property includes a detached 40x24, 2 Car garage with workshop for ample storage. Nature enthusiasts will appreciate the wooded surroundings, stream access, and opportunities for fishing and hunting right at your doorstep. Located in a peaceful, rural setting, this home is just a short drive from local parks and community amenities. Embrace the tranquility and beauty of this unique property, where comfort meets nature.

4455 Smithville Rd, Federalsburg

Listing courtesy of RE/MAX Executive. Contact:

$569,000

4 Beds ⋅ 3 Baths

Your dream home has arrived! Nestled in the highly sought-after Pendleton community, this stunning home offers the perfect blend of modern living and peaceful countryside charm. Wake up each morning to breathtaking pond and golf course views, and end your day with spectacular sunrises and unforgettable sunsets from the comfort of your own backyard. Inside, you'll be welcomed by a bright, open-concept floor plan featuring luxury vinyl plank flooring, modern designer paint colors, and a spacious gourmet kitchen complete with quartz countertops, a large center island, and plenty of space for entertaining family and friends. Upstairs, you'll find generously sized bedrooms along with a versatile loft that makes the perfect second living area, media room, playroom, or home office. Step outside onto the custom-built, low-maintenance composite deck, beautifully accented with solar post lights that create the perfect evening ambiance. Additional storage is conveniently located beneath the deck, and the invisible pet fence conveys with the property, making it ideal for pet lovers. Perfectly situated just minutes from I-95, this home is only 10 minutes from Kings Dominion, 12 minutes from the highly anticipated Kalahari Resort & Indoor Waterpark, 25 minutes from Short Pump, and approximately 30 minutes from both Downtown Richmond and Fredericksburg, offering the perfect balance of tranquility and convenience. With incredible views, thoughtful upgrades, and an unbeatable location, this home truly has it all. Don't miss your opportunity to make this exceptional property your next home!

7040 Paine Pl, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$439,999

3 Beds ⋅ 2 Baths

Experience lakefront living at its finest with this beautifully maintained waterfront home on the main lake in Lake Land’Or! Offering 3 bedrooms, 2 bathrooms, and a full-size unfinished basement with endless potential, this home combines comfort, updates, and breathtaking views. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating the perfect space for everyday living and entertaining. Cozy up by the wood-burning fire place during the cooler months, or step outside to the expansive rear deck overlooking the lake, where you can enjoy your morning coffee, evening sunsets, and peaceful waterfront views. Major updates provide peace of mind, including new carpet (2023), a new HVAC system (2025), water heater (2017), a recently painted exterior, and a 30-year roof installed in 2010. A private dock offers convenient access to the main lake, making boating, fishing, kayaking, and paddleboarding just steps from your back door. Located within the gated Lake Land’Or community, residents enjoy an incredible selection of amenities, including multiple lakes and beaches, boat ramps and docks, community pools, picnic areas, pavilions, playgrounds, basketball courts, pickleball courts, tennis courts, an archery range, skeet shooting range, community gym, clubhouse, and 24-hour gated security with patrol. Whether you’re looking for a full-time residence or the perfect waterfront retreat, this exceptional home offers the ideal blend of comfort, recreation, and lakefront living.

8 Mahon Cir, Ruther Glen

Listing courtesy of EXP Realty, LLC. Contact: 8668257169

$1,200,000

4 Beds ⋅ 4 Baths

Bayfront living with exceptional waterfront amenities! This home offers a rare opportunity to enjoy water views, a boat dock with slip, and a private beach area. The sunroom/sun porch provides the perfect space to relax, entertain, or simply take in the peaceful waterfront setting. The home features a desirable first-floor primary suite with its own private exterior entrance and generous closet space. A separate suite over the garage, also with its own private entry, adds wonderful flexibility for guests, extended living, a home office, studio, or private retreat. With a spacious and versatile layout, multiple private-entry living areas, and direct access to the water, this property is full of potential and ready for its next chapter.

30019 Goose Point Ct, Port Royal

Listing courtesy of 1st Choice Better Homes & Land, LC. Contact: (540) 786-0088

$799,900

3 Beds ⋅ 2 Baths

Welcome to 322 Lake Caroline Drive, where every day feels like a vacation. Perfectly positioned on approximately 95 feet of protected shoreline with deep water, a rebuilt private dock complete with an expanded sun deck, and panoramic lake views, this exceptional waterfront home offers the lifestyle so many buyers dream about but rarely find. Located within the gated community of Lake Caroline, just minutes from I-95 and conveniently situated between Richmond and Washington, D.C., this beautifully maintained home combines peaceful waterfront living with an easy commute and outstanding community amenities. Completely reimagined in 2003, this home underwent an extensive renovation and expansion, transforming nearly every aspect of the property. Taken down to the studs, it was thoughtfully redesigned with a new floor plan, two additions, new drywall, insulation, electrical, plumbing, HVAC, and quality finishes throughout. The result is a home that offers the charm of an established waterfront setting with the features and functionality buyers expect today. Every improvement was thoughtfully designed to maximize natural light, capture stunning lake views, and create comfortable spaces for everyday living and entertaining. Rich hardwood floors, soaring ceilings, custom architectural columns, recessed lighting, and five skylights flood the home with natural light, creating a bright, open atmosphere that immediately welcomes you inside. Additional features include Andersen 400 Series windows and doors, a high-efficiency two-stage Trane HVAC system with an air cleaner installed in 2018, a new water heater in 2024, whole-house surge protection, surround sound throughout the home and rear deck, a separate laundry room, handicap accessibility, and a well-maintained crawlspace. Designed for both everyday living and entertaining, the custom kitchen is sure to impress. Featuring beautiful custom cabinetry, abundant countertop space, a center island with a prep sink, double ovens, a new cooktop, and thoughtful storage throughout, it's a space that will make even the most discerning home chef feel right at home. The spacious living room flows seamlessly to the screened porch, where you can enjoy your morning coffee while taking in peaceful lake views. The primary suite also offers direct access to the porch, allowing you to wake each morning to the beauty of the water. The primary bath features a relaxing soaking tub, separate walk-in shower, and generous space to unwind. Outdoor living is truly the centerpiece of this property. Spend evenings on the expansive rear deck overlooking the lake or head down on your golf cart to the private dock, completely rebuilt and expanded in 2012 to include a large sun deck. Whether you enjoy boating, fishing, kayaking, paddleboarding, swimming, or simply relaxing by the water, this property is ready to support every lakefront adventure. With approximately 95 feet of rip-rapped shoreline and deep water, you'll enjoy both beauty and peace of mind for years to come. Life at Lake Caroline extends well beyond your own backyard. Residents enjoy a 277-acre recreational lake, two sandy beaches, a swimming pool, a clubhouse, tennis, pickleball, and basketball courts, playgrounds, boating, fishing, and other water activities, and an active community with multiple events throughout the year. Whether you're searching for your forever home, a weekend escape, or the waterfront lifestyle you've always imagined, 322 Lake Caroline Drive offers a rare opportunity to own one of the community's finest lakefront properties. The setting is extraordinary. The lifestyle is waiting. Simply move in and start making memories on the lake.

322 Lake Caroline Dr, Ruther Glen

Listing courtesy of Coldwell Banker Elite. Contact: 5403730100

$399,000

4 Beds ⋅ 2 Baths

4 bedroom 2 bath rancher on 3.6 spacious acres on the headwaters of the Choptank.

13790 Drapers Mill Rd, Greensboro

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$1,500,000

4 Beds ⋅ 3 Baths

Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue marble countertops, handcrafted cabinetry, a Wolf gas cooktop, Sub-Zero refrigerator, beverage refrigerators, and a generous island create a space that's equally suited for everyday living and entertaining. Rich hardwood flooring, designer lighting, custom window treatments, and beautifully renovated baths continue throughout the home, while the primary suite offers a peaceful retreat complete with heated bathroom floors and access to a private Juliet balcony. The outdoor spaces are every bit as remarkable as the interior. Step outside to an expansive Balau hardwood deck overlooking the heated saltwater pool, surrounded by travertine, luxury stone, and professionally designed landscaping. Whether you're preparing dinner in the outdoor kitchen, relaxing beside the fire table, enjoying the tranquil fountain, or unwinding in the enclosed four-season sunroom, every space was designed to embrace the waterfront setting. A private pier is just steps away, making it easy to spend the day on the water before returning home to watch the sunset. The home was professionally redesigned with the help of Barclay Designs and interiors by Sanctuary Interiors. The home also features extensive upgrades throughout, including Everlast Advanced Composite Siding, updated HVAC 2023, modernized electrical, a custom bunk room, and countless custom finishes that simply must be seen in person. Located just minutes from Routes 50 and 404, you'll enjoy easy access to Annapolis, Easton, Delaware beaches, and the Chesapeake Bay region while still enjoying the privacy and tranquility of waterfront living. As an added bonus, the home is not located within the floodplain—a rare advantage for a property of this caliber.

23071 Tuckahoe Springs Dr, Denton

Listing courtesy of Sharon Real Estate P.C.. Contact:

$429,999

3 Beds ⋅ 3 Baths

WATERFRONT living awaits at 222 Sea Cliff Drive! This beautiful 1,800 square-foot Craftsman-style "Farmhouse floorplan" offers the perfect blend of charm, comfort, and modern conveniences. Featuring 3 bedrooms, 2.5 baths, and an open-concept design, this home is ideal for both everyday living and entertaining. The spacious eat-in kitchen showcases granite countertops, a breakfast bar, stainless steel appliances, and abundant cabinet and counter space. Luxury vinyl plank flooring extends throughout the main level, providing style and durability. A dedicated office space on the main level, beautifully enclosed with stylish barn doors, offers the perfect setting for working from home, studying, or pursuing hobbies while maintaining privacy from the main living areas. Upstairs, the primary suite features a walk-in closet and a private bath with a double vanity and shower. Two additional bedrooms and a conveniently located second-floor laundry room complete the upper level. The washer and dryer will convey, making this home truly move-in ready. Step outside and enjoy stunning waterfront views from the expansive backyard. Relax around the fire pit set within a beautifully landscaped pea-rock gathering area accented by solar lighting. The property offers the opportunity to add your own dock, creating the perfect setting for waterfront enjoyment. Additional smart-home features include coded smart locks on both the front and rear doors, Ring cameras and lighting at the front and rear of the home, wired smart lighting in the front, and solar-powered motion lights in the backyard. The inviting covered front porch is perfect for morning coffee or evening relaxation, and the two rocking chairs and porch swing will convey with the property. This exceptional waterfront home combines modern technology, flexible living spaces, outdoor enjoyment, and timeless Craftsman charm. Welcome home to 222 Sea Cliff Drive!

222 Sea Cliff Dr, Ruther Glen

Listing courtesy of Keller Williams Capital Properties. Contact: 5406598633

$625,000

2 Beds ⋅ 2 Baths

Always dreamed of living in a tree house on a Lake? Here's your opportunity....lovely A-frame home on Lake Caroline with Lake views from Living, dining room and Loft/Bedroom! This charming, updated home has a large, stone fireplace and large deck off the living room; for cozy nights and morning coffee. Well equipped kitchen with stove, microwave, dishwasher, stove top and refrigerator; open to expansive dining area. Main floor bedroom with ample closet space and adjacent bath; that has been updated w/large walk-in shower. Upstairs you find an open, loft/bedroom with vaulted, beamed ceiling and attached, updated bath w/walk-in shower; along with a mini-split to control your room temp. Covered lower patio leads into the basement & crawl space which is climate controlled; perfect for storing your Kayaks and water toys. Follow the paved steps/walkway down to the large yard and dock. Dock has diving platform and steps for ease into the water. The large garage (26 feet long) has room for cars, as well as a shop! Newer Roof. Come enjoy all the amenities that lovely, Lake Caroline has to offer! Close to Highways, shopping, restaurants and the new Kalahari Resort (12/26); making this perfect for a week-end getaway or a primary home!

206 Lake Caroline Dr, Ruther Glen

Listing courtesy of Hometown Realty Services, Inc.. Contact:

$1,550,000

5 Beds ⋅ 5 Baths

Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained — nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets — and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras — accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton — an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.

322 S 2nd St, Denton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$545,000

3 Beds ⋅ 3 Baths

Every once in a while, a property comes along that is so much more than just four walls—it is a place where stories are born, where friends become family, and where the hustle of the outside world just completely melts away. Welcome to your next great adventure, right here on Skinkers Neck Road. From the moment you step foot onto this charming 14-acre historic home, you are wrapped in a sense of genuine warmth and historic charm that you just can't replicate. It is the ultimate invitation to slow down, breathe in the fresh air, and start dreaming of the endless possibilities. Inside, every single room and every cozy corner tells a beautiful story. You’ll fall instantly in love with the timeless character that flows through the spaces, grounded by gorgeous, wide hand-milled wood floors that feel amazing underfoot. Imagine chilly Virginia evenings spent gathered together with your favorite people; with brick fireplaces in every room, there is always a cozy spot waiting to welcome you. It’s a home designed for connection, laughter, and making memories that last a lifetime. Step outside, and the magic continues. Nestled in 14 acres of complete wooded privacy, this property offers a beautiful, peaceful escape that is still just a quick 30-minute drive back to the heart of downtown Fredericksburg. Bask in panoramic views of rolling green pastures and your very own private pond. You'll find two perfectly cleared fields ready for whatever your heart desires. Use one cleared field for crops, sweet farm animals, or designated event parking, and the other cleared field as the ultimate outdoor event space. On hot summer days, you can take advantage of nearby river access to launch a kayak or just dip your toes in the water. Whether you are looking for a spectacular historic home to plant your own roots, a breathtaking wedding venue to host life's biggest celebrations, or a truly one-of-a-kind Airbnb that guests will rave about for years, this property is ready to be the backdrop for it all. Grab a warm drink, sit out by the water, and come see what makes this magical spot so incredibly special. Let's get started on your next chapter, friend!

2349 Skinkers Neck Rd, Rappahannock Academy

Listing courtesy of Nest Realty Fredericksburg. Contact:

$825,000

4 Beds ⋅ 3 Baths

WATERFRONT!! Stunning Lakefront home in Beautiful Lake Caroline! Nestled in a quiet cove, this gorgeous Waterfront Stucco comes with mature & natural landscapes leading down to your shoreline with a boat dock & patio deck. Ample room for boats, jet ski and lots of water sport toys. Inside you will find vaulted ceilings, skylights, architectural angles & lots of windows bringing the outside lighting in. Complete gourmet kitchen with island, gas cooking & nice pendant accent lighting. Nice open floorplan with dining area, ceramic tile surround fireplace family room and kitchen combination. This Custom-built Hamlet Home - The "Catalina Model" comes with unique rounded edging, bamboo, marble, stained concrete flooring and a double basement foundation. Main floor living has 3 bedrooms, 2 baths, Living, Dining, Kitchen and head to the basement to find game room, 2nd tile surround gas fireplace, even a humidor! Flex space for 4th bedroom or in-law suite. Walk out level to the patio deck with stainless steel outdoor kitchen and a full-size Hot Tub with extra deck support. Plus, we have the 2-car attached garage & workshop/storage too! This home has it all - Buy Now for Summertime FUN on the LAKE! Lake Caroline is a Full-Service Lake offering: 277-acre Lake, 2 sandy beaches, clubhouse, playgrounds, tennis, pickleball, basketball, water ski, wakeboard, jet ski, pontoon, kayak, paddleboard. Swimming & Fishing, Pool with lifeguards. Enjoy S'mores at your dock after Fun in the Sun! Lake Caroline is located just off I-95 between DC & Richmond, close to Shopping, Golf, Wineries, Kings Dominion Amusement Park, Dominion Raceway & the New Kalahari Waterpark opening later this year! Come Check it Out Today!

584 Lake Caroline Dr, Ruther Glen

Listing courtesy of Hometown Realty Services, Inc.. Contact:

$549,900

2 Beds ⋅ 2 Baths

Set along the widest stretch of Lake Caroline, this completely updated waterfront retreat offers sweeping views, easy outdoor living, and access to one of the region’s most amenity-rich private lake communities! 68 Saratoga Cove in Ruther Glen boasts a fully renovated home, resting on a .63-acre lot. The setting is a standout, folks! Positioned on the main body of the lake, the property enjoys open vistas across the water, with uninterrupted sightlines that shift throughout the day. The front yard is flat and grassy with a recently paved asphalt driveway offering generous parking, while the backyard extends seamlessly to the shoreline with a private dock, floating jet ski platform, and a dedicated launch for kayaks and canoes. A large waterfront patio creates a natural gathering space, complemented by a second lounging area at the dock for entertaining and room to host. The home’s exterior is classic, simple and functional, with a gray façade accented by black shutters. Inside, the home is all like-new, resulting in a clean, cohesive interior. The kitchen anchors the space with white cabinetry, stainless steel appliances, granite countertops, and luxury vinyl plank flooring that runs throughout the main areas. The open layout flows from the kitchen into a dining space and onward to a comfortable living area, with natural light and lake views drawing the eye outward. The primary bedroom is located just off the kitchen and features an updated ensuite bath with a walk-in shower outfitted with body jets, a bench, and handheld fixture, along with a double-door closet. A secondary bedroom and full hall bath offer additional accommodations, while a discreet laundry area with full-size washer and dryer is tucked behind pocket doors. The lakeside addition serves as a flexible lake room, with expansive windows, two closets, and direct access to the patio, making it well-suited as a family room, office, or entertaining space. The world is your oyster here – all with a lake view! Recent system updates include a new HVAC system, a separate split system for the lake room, and a tankless water heater, all completed in 2022. Residents of Lake Caroline enjoy access to a gated community with a private lake for boating, fishing, kayaking, and jet skis, along with a swimming pool, tennis and pickleball courts, basketball courts, parks, community docks, and year-round events. With this location, multiple parks, golf, shopping, dining, grocery, and I-95 access (Ladysmith and Ruther Glen exits) are within 10 minutes, and the hearts of Richmond and Fredericksburg are within 35 minutes. At 68 Saratoga Cove in Ruther Glen, the balance of waterfront living and everyday convenience comes into clear focus. We hope you will come enjoy your best summer yet here at this perfect lake home!

68 Saratoga Cv, Ruther Glen

Listing courtesy of Porch & Stable Realty, LLC. Contact:

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