Refine Search
Map
Sort by
$1,250,000
3 Beds ⋅ 4 Baths ⋅ 25-306 MLS
THIS POND BAY CLUB UNIT is set in a prime location next to the beach in Estate Chocolate Hole. Just listed, ''Castaways Villa'' is a beautiful contemporary 3 bedroom and 3.5 bath unit offering views of Chocolate Hole Bay and just steps from the beach. Featuring a spacious gourmet kitchen, tasteful furnishings, outdoor living area, and air-conditioning through-out, this is also a successful short term rental property. A RARE waterfront condominium offering on St. John. Buyers agree to honor all confirmed rental reservations to the date of closing and to split the tax stamps equally at closing. The adjacent Unit J4 is a mirror image and also listed for sale.

126 Rem Chocolate Hole Unit J3, St John

Listing courtesy of American Paradise Real Estate, Inc..

$1,250,000
2 Beds ⋅ 3 Baths ⋅ 25-299 MLS
Discover your dream come true at 'View Come True' at The Hills! This exquisite two-bedroom, two-and-a-half-bathroom condo boasts a spacious living area and a custom kitchen, making it the ideal investment property for a St. John vacation rental. Prepare to be captivated by the breathtaking views that greeting you from every room and the balcony including the views of St. Thomas, Pillsbury Sound and a multitude of surrounding islands. The sunsets and sparkling lights of St. Thomas are the real show in the panorama vista. Nestled within the secure confines of The Hills, a private gated community, you'll enjoy access to an onsite gym, a clubhouse featuring a delightful restaurant, and meticulously manicured landscaping.

11 Enighed Unit 1B 201, St John

Listing courtesy of Holiday Homes of St. John.

$1,230,250
2 Beds ⋅ 2 Baths ⋅ 24-355 MLS
Moonglow Cottage is an octagonal Deltec home with spectacular views of Coral Bay, East End , Haulover ,Hurricane Hole and the British Virgin Islands beyond. Vistas abound from every part of this spacious Caribbean home... there are gentle breezes and an ocean view from every room! The screened outdoor dining veranda is only steps away from a well-appointed gourmet kitchen with owner-created ceramic tiles complementing the stainless steel and granite and custom cypress cabinetry. An air conditioned bedroom with a king size four-poster bed awaits after star gazing in the spa. Every attention to detail was made from floor (nonslip tiles) to ceiling (custom cypress ceiling). Down a flight of stairs takes you to a beautiful 1 bedroom / 1 bath apartment with the same gorgeous views.

29f-G Calabash Boom, St John

Listing courtesy of 340 Real Estate Company LLC..

$1,999,000
3 Beds ⋅ 3 Baths ⋅ 25-291 MLS
Welcome to Ocean's Song, a beautifully built masonry villa named for the soothing sounds of the rocky shoreline below. This thoughtfully designed property features two separate units that create a flexible floor plan for guest space or immediate rental potential. Island stonework details add warmth and character to the living room, while the coral stone pool deck provides an elegant outdoor space to soak in the turquoise water views. With abundant storage throughout and solid construction, this home has never been rented but is well-suited to become an income producer. Residents enjoy a private neighborhood beach where kayaks and paddle boards are often left ready for afternoon adventures. Ocean's Song is solid, serene, and full of possibility for its next owner.

15a-7-17 Rendezvous & Ditleff, St John

Listing courtesy of Cruz Bay Realty.

$1,600,000
3 Beds ⋅ 3 Baths ⋅ 25-272 MLS
Experience timeless Caribbean charm on the tranquil East End of St John. This 3 bedroom, 3 bath home sits on 2-4 Haulover, the purchase includes 2-3, 2-5, 2-7 and 5-R Haulover parcels. This Caribbean style architecture features an expansive great room and dining area that open to a stunning stone patio - perfect for entertaining or soaking in the serene surrounds. Lush tropical landscaping embraces the property, complemented by thoughtful upgrades including solar power and a triple water filtration system. A rare opportunity to own a classic island retreat with incredible views

2-3,4,5,7 Haulover, St John

Listing courtesy of Islandia | Christie's International Real Estate.

$1,595,000
3 Beds ⋅ 3 Baths ⋅ 25-279 MLS
Ballena Blue is a beautiful 3-bedroom, 3-bath villa featuring a new pool surrounded by a spacious sun deck & a shaded cabana area perfect for lounging, dining, & grilling. From both the villa & the pool-conveniently situated side by side-you'll enjoy sweeping panoramic views of Rendezvous Bay & beyond to St. Croix.Fully air-conditioned and thoughtfully designed for comfort, Ballena Blue offers a warm & inviting atmosphere. Both main-level bedrooms are accessible from the great room, w) the primary suite offering extra space and privacy. The wraparound deck provides ample seating to relax & take in the breathtaking vistas.A short set of stairs leads down to the third bedroom & bath on the lower level. The villa features an all-paved drive from town with generous parking &turnaround.

15d-3 Rendezvous & Ditleff, St John

Listing courtesy of 340 Real Estate Company LLC..

$395,000
1 Beds ⋅ 1 Baths ⋅ 25-234 MLS
Charming Carolina Cottage with Expansion Potential! Nestled in the lush greenery of Carolina, this unique one-bedroom, one- bathroom home offers island living with room to grow. The two-level layout provides functionality and charm: the lower floor includes laundry and storage space, while the upper floor features an open living area, kitchen, bedroom, and a loft that can serve as a guest sleeping area, office, or creative nook. Enjoy serene valley views from the property's wide driveway, which accommodates up to six vehicles, perfect for entertaining or future expansion. A 20-foot storage container is included on site. This property is a versatile investment for both homeowners and builders alike.

1-32a Carolina, St John

Listing courtesy of Holiday Homes of St. John.

$3,500,000
3 Beds ⋅ 3 Baths ⋅ 25-71 MLS
Beachfront Beauty - Newly Renovated 3-Bedroom, 3-Bathroom Oasis.Nestled along the serene coastline of Johnson's Bay, this newly renovated 3-bedroom, 3-bathroom beach house offers a rare opportunity to own a stylish and modern retreat just steps from the shore. With sleek, contemporary finishes throughout, this home is the perfect blend of comfort and luxury.The open-concept living area boasts breathtaking ocean views, seamlessly connecting the living, dining, and kitchen spaces. The chef-inspired kitchen is equipped with state-of-the-art appliances, chic countertops, and ample storage. Every bathroom has been beautifully updated with high-end fixtures and designer touches, creating a spa-like atmosphere.

6c-3 St. Quaco & Zimmerman, St John

Listing courtesy of Cruz Bay Realty.

$3,500,000
4 Beds ⋅ 4 Baths ⋅ 25-253 MLS
Tennis Villa is a classic Chocolate Hole estate offering an exceptional blend of space, privacy, and recreation. This single-level home features a gourmet kitchen, vaulted-ceiling living areas, and a sunny south-facing courtyard with a 43-foot pool. A detached pool house provides the 4th bedroom and bath. The regulation-sized tennis court was resurfaced in 2023 and includes pickleball markings. Solar panels with Tesla battery backup ensure year-round comfort and safety with a concrete roof. Enjoy lush landscaping setting, harbor views, and a prime location just minutes from Cruz Bay and walking distance to boating access in Great Cruz Bay.

66 Chocolate Hole, St John

Listing courtesy of Holiday Homes of St. John.

$7,500,000
6 Beds ⋅ 5 Baths ⋅ 24-336 MLS
Breathtaking views from this ultimate tropical paradise situated on a spacious 1.03 acre parcel on the water with over 120' of shoreline where you can enjoy water activities right at your doorstep! ''Lime In De Coconut'' is a successful rental villa with a large great room and gourmet kitchen that enjoys beautiful water and sunset views. The main villa consists of 5 bdrms and 4 baths and can accommodate up to 12 guests. ''Coconut Cottage'' is a cozy wood frame studio cottage with bath, deck & hot tub that is also a successful short-term rental and is a perfect getaway for a couple or can be rented together with the main villa. This property is complete with solar and an all house automatic generator. Buyer & Seller to equally split the costs of the transfer stamp tax.

132 Chocolate Hole, St John

Listing courtesy of Islandia | Christie's International Real Estate.

$2,900,000
4 Beds ⋅ 5 Baths ⋅ 24-293 MLS
Villa Romance is an elegant, custom built, stone & masonry home with lush tropical landscaping situated on a spacious .50 acre parcel in popular Estate Chocolate Hole, only minutes to restaurants, shops and north shore beaches. This tastefully furnished villa consists of 4 bdrms with en-suite baths, gourmet kitchen, spacious great room and a relaxing pool & entertainment area with stunning harbor and ocean views. Truly a ''must see'' to appreciate the attention to details. Previously used as a private family retreat, this villa is new to the short term rental market. Buyer shall honor future bookings. Buyer & Seller shall equally split the costs of the transfer tax. Buyer to confirm square footage, cistern capacity and all information.

164a Chocolate Hole, St John

Listing courtesy of Islandia Real Estate.

$4,995,000
4 Beds ⋅ 4 Baths ⋅ 25-235 MLS
Blue View Villa, a stunning new property built in 2019, exuding a classic soft modern Caribbean style. This exceptional home is perched on a spacious plot, offering panoramic views from sunrise over the serene Ram's Head to sunset over the majestic St. Thomas. With three oversized bedrooms and en-suite bathrooms, each designed with ample space and the flexibility to convert to a 4 bedroom villa. Blue View Villa caters to both comfort and functionality, equipped with solar panels and Tesla Batteries. Located just minutes from Cruz Bay and with private neighborhood beach access within walking distance. Blue View Villa is ideally set up to operate as a vacation rental, though it is tempting to move right in!

15a-3-24 Rendezvous & Ditleff, St John

Listing courtesy of Holiday Homes of St. John.

$565,000
2 Beds ⋅ 1 Baths ⋅ 24-92 MLS
$25,000 Price drop! This sweet island cottage, just a few minutes walk to Gifft Hill school, is nestled at end of road in the valley of Gift Hill. This Charming Caribean style home, with partial wrap around decking and lush gardens, is your perfect starter home.Enjoy the fruit trees and ample space for vegetable garden and more. This home is in immaculate condition, featuring new kitchen counters and cabinets, new flooring and a lovely living room with vaulted ceiling and large sliding doors to the outdoor covered decking. The bedroom has a new AC unit with large windows overlooking the lush exterior.The second bedroom, currently used as an art room/office could also be the perfect guest bedroom with private deck outside.

9-17-G Glucksberg, St John

Listing courtesy of 340 Real Estate Company LLC..

$749,000
2 Beds ⋅ 2 Baths ⋅ 25-35 MLS
Wind Diva is a great Caribbean Cottage close to Coral Bay with Coral Harbor & Hurricane Hole water views. Wrap around deck with covered porch. Upstairs enjoys an open floor plan with kitchen, dining, living room with primary bedroom / bath and laundry room. Beautiful stone walls and pathways for the entrance and down to the lower level where there is a room with a queen bed platform and a desk that could be finished into another bedroom.Off the paved driveway is a small deck with one bedroom / one bath. Ample flat parking area. This cottage is a must see to appreciate! Meticulously maintained.

1-37a Carolina, St John

Listing courtesy of 340 Real Estate Company LLC..

$930,000
3 Beds ⋅ 2 Baths ⋅ 25-29 MLS
Well maintained home in Coral Bay. Upper level is a 2 bedroom / 1 bath kitchen dining living room and deck. The lower level is a spacious short term rental with kitchen, dining & living area. Beautifully landscaped with fruit trees, 2 tesla power walls & solar net metering. Must see to appreciate

1-29 Rem Carolina, St John

Listing courtesy of 340 Real Estate Company LLC..

$638,000
2 Beds ⋅ 2 Baths ⋅ 25-173 MLS
Bay Tree Cottages is a secluded, private end of the road property surrounded by lush large bay rum trees and the natural beauty of Bordeaux Mountain. The main house has a large upstairs kitchen, dining, living area with laundry and the downstairs has one large bedroom with ample closets and ensuite bathroom. Both levels have covered porches. The smaller cottage has kitchen, dining and living area as well with a sleeping loft, shower and separate bathroom with composting toilet. At the entry is a small shop / garage. This gardeners dream property has a lot of potential. Property has certificate of occupancy and permanent power. Buyers to verify cistern size and square foot of buildings.

10-49 Carolina, St John

Listing courtesy of 340 Real Estate Company LLC..

$2,800,000
5 Beds ⋅ 5 Baths ⋅ 22-234 MLS
The name Beach Walk sums up the allure of this unique 5 bedroom - 5.5 bath home. Swim, paddle, kayak, snorkel & explore a magnificent tropical reef in the aquamarine waters of pristine Chocolate Hole Bay right from your door. The seaward facing wall of picture windows highlights extraordinary bay and Caribbean Sea views and with full AC; pool; easy, paved access; minutes to Cruz Bay restaurants & shopping, this home has it all. Guests absolutely love this property. A magical island home to share with family and friends; Beach Walk will not disappoint.

130 Chocolate Hole, St John

Listing courtesy of Holiday Homes of St. John.

$2,690,000
5 Beds ⋅ 5 Baths ⋅ 25-194 MLS
Perched between Great Cruz Bay and Chocolate Hole, Blue Dolphin Villa blends modern updates with island charm. Expanded by over 1,000 sq ft, it now features a new primary suite, gym, and playroom, adding flexibility for owners or rentals. The pool deck with glass railings captures sweeping bay views, while lush gardens and a covered pavilion create a private, resort-like setting. Inside offers an updated kitchen, beautiful stonework, and comfortable bedrooms. A major upgrade includes a 26kW Generac generator with automatic transfer switch, ensuring reliable power. Turnkey with strong rental appeal. Seller financing available.

300-9 Chocolate Hole, St John

Listing courtesy of Holiday Homes of St. John.

$595,000
1 Beds ⋅ 1 Baths ⋅ 22-132 MLS
Private, second floor corner unit with lovely westward sunset views framed by lush landscaping. Serendip has a loyal following of visitors that seek the ''in-town'' experience on an oversized wooded site with a welcoming pool, expansive parking, private storage and laundry facilities and on-site management. New tile throughout the unit makes this place shine.

9-7 Enighed Hibiscus Unit Hibiscus, St John

Listing courtesy of Holiday Homes of St. John.

$1,385,000
2 Beds ⋅ 2 Baths ⋅ 25-34 MLS
Welcome to Caneel Trailside Cottage - a fully-furnished, turnkey gem box of a villa perched above Cruz Bay providing direct access to the vast Virgin Islands National Park trail system. This two-bedroom, two-bathroom masonry home is a haven for outdoor enthusiasts providing convenient proximity to dining, shopping and postcard perfect white sand beaches all within a short drive. Well established as one of St John's most beloved vacation rentals, the villa is equally suitable as a private island retreat.

5fa-2 Pastory, St John

Listing courtesy of US Virgin Islands Sotheby's International.

$2,250,000
4 Beds ⋅ 4 Baths ⋅ 24-244 MLS
'Sunset Serenade Suites'' are the definition of opportunity. This property sits on 2 adjacent parcels & is a true turnkey business that runs itself with a management team, housekeepers, landscapers, & booking system in place for you. Understated luxury, comfortable accommodations & incredible views all close to the shops & restaurants in Cruz Bay keep this property booked with a steady stream of repeat guests. Each suite offers a parking space & private entrance, ample outdoor space, A/C, wifi, W/D, & 2 with full kitchens. The grounds boast with lush, professional landscaping offering a variety of palms in addition to many tropical fruits (mango, lime, avocado, banana, papaya, plantain, passionfruit, cherry).

10-5 & Enighed, St John

Listing courtesy of Cruz Bay Realty.

$12,000,000
4 Beds ⋅ 5 Baths ⋅ 22-51 MLS
Discover Indo House, an exquisite waterfront masterpiece boasting unparalleled modern craftsmanship. Every detail of this home exudes opulence, from the bespoke kitchen to the expansive floor-to-ceiling glass windows and meticulously crafted bamboo ceilings. Each of the four bedroom suites offers a lavish private bathroom, generous walk-in closets, and breathtaking vistas of Great Cruz Bay. Embrace a lifestyle of luxury waterfront living, whether you're lounging in the infinity-edge pool or hosting lavish gatherings in the vast outdoor living area.

300-64 Chocolate Hole, St John

Listing courtesy of Islandia | Christie's International Real Estate.

$1,095,000
4 Beds ⋅ 4 Baths ⋅ 25-161 MLS
MAJOR PRICE REDUCTION! Blue Vista Duplex is a rare investment gem perched just above Cruz Bay with breathtaking sunset views and cooling island breezes. This charming property offers two income producing units: a spacious 3 bedroom upper residence and a private 1 bedroom lower unit. Live in one and rent the other or maximize rental potential with both. Located in a peaceful neighborhood just minutes from town, you'll enjoy easy access to dining, shopping, and the ferry dock without sacrificing tranquility. With its unbeatable location, stunning views, and flexible layout, Blue Vista Duplex is the perfect blend of island living and smart investing. Don't miss your chance to own a piece of paradise on St. John.

8a Rem Enighed, St John

Listing courtesy of Cruz Bay Realty.

$2,499,000
3 Beds ⋅ 3 Baths ⋅ 25-52 MLS
Villa De Vida is a stunning hilltop showplace in the serene enclave of Chocolate Hole which combines luxury with privacy and offers enchanting ocean views and lush tropical landscaping on 1.21 acres of property. The spacious kitchen and Great Room open on to an expansive Ipe wood deck perfect for entertaining and an inviting swimming pool where you can enjoy colorful sunsets and the twinkling lights of St. Thomas at night. The three charming bedroom suites are housed in separate buildings, each linked to the Great Room by covered walkways and arched entrances. Elegantly furnished with thoughtful touches, this villa captures the spirit of relaxed luxury. Whether as a vacation rental or private residence, this is an idyllic island retreat and the former home of a famous country music star!

13 Chocolate Hole, St John

Listing courtesy of American Paradise Real Estate, Inc..

$530,000
1 Beds ⋅ 2 Baths ⋅ 25-128 MLS
Discover the enchanting blend of gentle breezes and stunning sunrises year-round in this idyllic neighborhood. This delightful Caribbean cottage boasts magnificent views of St. John's East End, Johnsons Reef, the Caribbean Sea, and the British Virgin Islands. With one bedroom and two bathrooms, it serves as an ideal starter home. Set on nearly an acre, the current layout offers ample opportunities for future expansion, complete with approved plans for a single-family home available with the purchase.

23 Freemans Ground, St John

Listing courtesy of Cruz Bay Realty.

$1,150,000
2 Beds ⋅ 2 Baths ⋅ 25-65 MLS
Unparalleled Views & Endless Potential! Perched on over half an acre across two parcels, this solid masonry and native stone 2-bed, 2-bath home offers privacy, easy paved access, and breathtaking views. Owners buried power lines for unobstructed sunrises, moonrises, and stargazing--visible from every room. The upper level features a great room, kitchen, full bath (outdoor shower), and custom mahogany Murphy bed. The mid-level has two bedrooms, a full bath (outdoor shower), and can convert into a separate apartment. Freshly resealed cisterns March 2025. Enjoy plentiful flat parking, single car garage and storage, plus room to add bedrooms, a pool, or a second home. First time on the Market! MUST SEE.

2-7 & 2-4 2-7 2-4 Concordia St, St John

Listing courtesy of 340 Real Estate Company LLC..

$1,250,000
2 Beds ⋅ 3 Baths ⋅ 25-66 MLS
Windwardside Cottages, a turnkey rental opportunity, offers classic Caribbean charm with three masonry pods perfectly intertwined amongst bricked pathways and lush gardens. Each of the two bedroom pods offer ensuite baths and outdoor showers. The guest bedroom pod also offers a small kitchenette. The main pod comprises the living room, kitchen with newer appliances, the third full bath and two porches to choose from -both of which capture the expansive and easterly post card views of Coral Bay to the BVI. Two hot tubs on property-one in guest cottage and one off the main pod. New hardwood screen doors and decorative shutters, new ceiling fans, updated landscaping and two Tesla power walls with nineteen panels. This property has been meticulously maintained, and it shows!

28-13 Calabash Boom, St John

Listing courtesy of American Paradise Real Estate, Inc..

$2,499,000
3 Beds ⋅ 3 Baths ⋅ 25-378 MLS
Perched in the serene enclave of Chocolate Hole on 1.21 acres, Villa De Vida is more than just a home—it's a sanctuary of inspiration, privacy, and breathtaking beauty. The property's design complements its inspirational aura. A spacious kitchen and living area open effortlessly to an expansive Ipe wood deck, where sunsets paint the sky in brilliant hues. The large multi leveled deck overlooks St. Thomas with Hart Bay below. Every aspect of Villa De Vida celebrates both individuality and connection. The three private bedroom suites are housed in separate buildings, each linked to the great room by covered walkways and arched entrances. The feeling of island living is elevated by the outdoor showers. Professional, lush landscaping and the secluded, yet convenient, location add to the relaxed luxury feel of this amazing property! It's no wonder a well known country star felt inspired to write some of his greatest hits from this beautiful retreat. Varnished mahogany wood and cathedral ceilings throughout. Covered storage area below would make a great workshop and there's an additional enclosed room that can also be a utilized for something besides storage.

13 Chocolate Hole, St. John

Listing courtesy of Calypso Realty PC.