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$1,737,500
5 Beds ⋅ 4 Baths ⋅ 2133406 MLS
Located in the heart of Vilano Beach, 152 Sherwood Ave offers the perfect blend of luxury, space, and coastal lifestyle. Just a short walk to both the Atlantic Ocean and the Intracoastal Waterway, and minutes from historic downtown St. Augustine, this beautifully designed home is ideally positioned to enjoy everything the area has to offer. Situated on a 75' x 125' lot, the home features 4,402 sqft under air (5,367 total) with 5 bedrooms, 3.5 bathrooms, a private office, flex room, and a dedicated theater room with projector and screen. The kitchen is equipped with a gas stove, and the home is enhanced by a Control4 whole-home sound system. The outdoor living space is designed for relaxation and entertaining with a heated pool, gas poolside fireplace, paver lanai, and low-maintenance turf yard. Additional features include a 24' x 25' garage, security system, and perimeter security cameras. A rare opportunity to own a spacious home just steps from both the ocean and Intracoastal.

152 Sherwood Avenue, St. Augustine
$1,710,000
5 Beds ⋅ 7 Baths ⋅ 2133655 MLS
Stunning English Country Manor estate pool home boasting 5 bedrooms, 6.5 bathrooms, & 3 car garage in exclusive gated King & Bear community of World Golf Village...steps from amenities, overlooking scenic pond and King & Bear Golf Course. Thoughtfully designed home with striking combination of brick and stone creates timeless charm with a grand 30-ft foyer & open staircase make dramatic first impression. Private family entry foyer plus an adjacent paneled library. Gourmet chef's kitchen with gas stove opens to spacious living areas perfect for entertaining. Lovely brick side porch off kitchen. Large private main-floor primary retreat offers a peaceful escape. Guest suite with ensuite bath on main floor. Upstairs features three bedrooms, each with its own ensuite plus game room. Outdoor living is a dream with heated pool & spa, stunning rock waterfall, fire pit, hockey rink and spacious yard. Perfect for entertaining. Steps away to golf club & communities amenities. No CDD.

1170 Registry Boulevard, St. Augustine
$1,694,466
7 Beds ⋅ 7 Baths ⋅ 2133148 MLS
The Aspen floor plan has a stunning 4,972-sq ft design that marries elegance with functionality. With six bedrooms, four & a half bathrooms & a three-car garage, this two-story layout is crafted to accommodate every family member's needs. Step through the grand entry to the open, two-story living room. This space serves as the heart of the home, flooded with natural light & perfect for cozy evenings. The kitchen, equipped with an extended island & a hidden pantry, flows seamlessly into a charming nook & the main living area, creating a warm & inviting hub. The master suite is a true retreat, complete with a luxurious master bath, oversized walk-in closet & private access to the covered lanai. An additional flex room on the main floor provides space for an office, gym, or guest suite. Upstairs, the Aspen boasts a spacious game room overlooking the living area below & five generously sized bedrooms, each designed with ample closet space.

613 Chestnut Oak Road, St. Augustine
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 2159612 MLS
Just one house off the sand, this professionally designed beach house on Broward Street is a masterclass in relaxed coastal luxury. Newly built in 2024 and fully move-in ready, this 5-bedroom, 4-bathroom home spans over 2,700 square feet across three levels, offering a thoughtful blend of livability, style, and craftsmanship. An elevator connects all three floors, making everyday living and guest access both seamless and convenient—whether you're hauling beach gear or hosting friends and family. The main living area is perched on the third floor, where an open-concept kitchen, dining, and living space flows effortlessly onto a spacious deck—perfect for catching the ocean breeze and enjoying the coastal lifestyle. The kitchen features honed Taj Mahal countertops, custom white oak tongue-and-groove paneling on the island, and panel-ready Fisher & Paykel and Bosch appliances, anchored by a Thor range.

6435 Broward Street, St. Augustine
$1,650,000
5 Beds ⋅ 6 Baths ⋅ 2125941 MLS
1105 Registry Boulevard is a statement of refined living. 1 of only 10 exclusive homes in ''The Estates'' section of the coveted King & Bear community. Sitting on half an acre and boasting 5600 square feet of living space, this home has been updated and elevated to reflect modern luxury living at its very best. Recently refreshed exterior and interior paint with new engineered hardwood flooring throughout give a blend of warmth and elegance. Complete comfort is a given with upgrades like whole house water-softener, RO water filtration, UV light filter and dehumidifier system installed together with three separate AC Systems, two tankless hot water heaters and a laundry room for each level. Relaxing is easy in the grand living room space with vaulted ceilings and custom curio cabinets, gas fireplace and views out to the heated pool area. Step outside to a full summer kitchen complete with its own fireplace and screened in lanai. From the front of the home enjoy westerly views and sunsets over hole number 10 on the prestigious King & Bear Golf Course. First floor master suite with luxurious spa-style master bathroom featuring floor to ceiling marble tile, spacious jetted tub and impressive double shower with multi body jets. There is so much to love about this home! Custom his & hers walk in closets, plantation shutters throughout, spacious heated and cooled gym or theater room, formal dining area and office that could double as 5th bedroom... The list goes on. New roof installed in 2022. This magnificent property truly needs to be seen in person so make sure to schedule your showing today!

1105 Registry Boulevard, St. Augustine
$1,645,000
4 Beds ⋅ 4 Baths ⋅ 2129072 MLS
Experience historic luxury at 290 St. George St, the former personal residence of famed architect Fred Henderich. Masterfully reimagined by John Benoit of BEHST Builders, this estate seamlessly fuses 1900s ''Old World'' soul with 21st-century sophistication. Positioned on a rare 62.5x200 lot stretching from St. George to Cordova St, the property offers stunning Lake Maria Sanchez views and parking for 10+ cars. The main home radiates light, showcasing original woodwork, coffered ceilings, and a gourmet kitchen with custom cabinetry and a butler's door. The primary downstairs suite features floor to ceiling tile work, a tub and a walk-in shower, flowing into a sunlit morning room. Upstairs, find a nautical suite complete with a steam shower. Beyond a private sanctuary, this estate is a lucrative asset. The detached cottage is a designer showstopper with a vaulted living area and private lakefront verandas. Perfectly positioned as a high-end luxury rental in the heart of St. Augustine.

290 St. George Street, St. Augustine
$1,640,293
4 Beds ⋅ 5 Baths ⋅ 2133367 MLS
The Monica floor plan is a masterclass in modern luxury, blending expansive spaces with thoughtful details that make daily living a pleasure. Spanning an impressive 3,488 square feet, this one-story home offers four bedrooms, four and a half baths, and a four-car garage. Every corner of this home is designed for both comfort and sophistication, making it ideal for families who appreciate the finer things.

447 Chestnut Oak Road, St. Augustine
$1,635,247
5 Beds ⋅ 6 Baths ⋅ 2133987 MLS
Experience luxury living in Iron Branch by Toll Brothers on an expansive 1.49 acre homesite with our stunning Flint Cottage Model, thoughtfully designed with an open-concept floorplan perfect for both everyday living and entertaining. This beautifully appointed home offers 5 bedrooms and 5.5 bathrooms providing comfort and privacy for family and guests alike. We will be holding this home at drywall stage so a customer would have the luxury of choice for their interior finishes. Price listed is prior to interior design selections.

464 Richland Manor Road, St. Augustine
$1,630,000
2096359 MLS
A special Commercial property is now available just north of the Historic District, and south of the Municipal Airport . With a colorful history as the iconic Harley Davidson Dealership, there is 7198 Sq Ft of total space under roof that has 3730 SF of finished retail space (under HVAC) and 3468 of warehouse space all The current zoning is City of St Augustine CM-2 (Commercial Medium Intensity) , which provides for multiple uses and shows a traffic count of approximately 36,500 daily. additional parking space can be provided by contiguous property to the rear. Aerial Map location in ''Documents''

3956 N Ponce De Leon Boulevard, St. Augustine
$1,600,000
5 Beds ⋅ 5 Baths ⋅ 2128008 MLS
This former Cornerstone model home is situated on a private lot overlooking the water and the 13th fairway in Palencia. This sought-after multi-generational floor plan includes a 700-square-foot generation suite with a separate entrance, a spacious living room, a kitchenette, and a bedroom with an ensuite bath. Complete with a pool, spa & outdoor summer kitchen, this home is ideal for year-round indoor outdoor living & entertaining. Inside, you'll find a bright and open floor plan with five bedrooms, a study, a loft bonus room, and over 4,700 square feet of living space. The family room showcases 20' coffered ceilings, second-story transom windows, built-in bookcases, and a linear fireplace. 12' slider doors open out to a covered screened lanai with a heated saltwater pool & spa. The spacious kitchen boasts crisp white shaker cabinetry, a two-toned island breakfast bar, quartz countertops, a gas cooktop, and a walk-in pantry with custom shelving. (Continued) The generation suite has its own entrance off the split one-car garage, offering both convenience and privacy. Complete with a living room, a kitchenette, an ensuite bedroom & 700 sqft of living space, this floor plan is ideal for multi-generational living. An eye-catching stairway leads up to a second-floor open loft w/ additional living space & a walk-in closet. Upstairs finds three additional bedrooms & two full baths. A spacious, covered upstairs balcony offers sweeping views of the water and the golf course. You'll find upgraded finishes throughout, like continuous engineered hardwood flooring downstairs, LVP flooring upstairs, custom closets, 8' doors, wainscoting & shiplap & plantation shutters. A hallway leads back to a built-in stop-and-drop and a walk-in laundry room, complete with a dog-washing station, a soaking sink & upper and lower cabinetry. The attractive coastal exterior features low-maintenance Hardie siding & shakes, Bahama shutters & a split 3-car garage. There's a well for irrigation & landscape Lighting Located in the sought-after gated community of Palencia, home to world-class amenities, an A-rated Elementary school & a championship Arthur Hills-designed golf course. Residents enjoy a fitness center, three community pools, lighted clay tennis courts, pickleball, sports fields, pocket parks, fitness trails, and a boardwalk leading to the Intracoastal.

224 Vale Drive, St. Augustine
$1,580,000
6 Beds ⋅ 5 Baths ⋅ 2134295 MLS
Refined Luxury in Palencia. From the moment you walk through the door, the intention behind this home is unmistakable. Spanning 4233 square feet, the residence offers 6 bedrooms, 4.5 baths, a dedicated office, a spacious loft, a versatile flex/dining room, and beautifully connected living areas designed for both everyday living and elegant entertaining. Custom designs and thoughtfully selected finishes define each space, while the outdoor setting with a heated saltwater pool and spa captures the essence of the Florida lifestyle. Custom built by Cornerstone Homes, this residence features one of the builder's most sought-after floorplans, designed to balance comfort, functionality, and sophisticated living. Positioned on a preserve homesite, the home enjoys a natural backdrop and peaceful views from both the main living spaces and outdoor areas. Inside, engineered hardwood floors extend throughout the main living areas, complemented by soft neutral tones and refined coastal-inspired that feel both timeless and welcoming. The dramatic 2-story family room serves as the centerpiece of the home, highlighted by custom coffered ceilings, a striking fireplace, and abundant natural light, creating a space that feels both grand and comfortable. The gourmet kitchen blends elegance with everyday functionality. A large quartz island anchors the room, surrounded by stainless steel appliances, custom cabinetry, a dedicated coffee bar, a generous walk-in pantry, a sun-filled breakfast area, and an integrated workspace. The main-level primary suite offers a private retreat with tray ceilings and a spa-inspired bath featuring a freestanding soaking tub, oversized shower, and dual vanities. A second bedroom suite on the main level, currently used as an exercise room, can easily serve as a private guest suite. Upstairs, 4 additional bedrooms, 2 full bathrooms, and a spacious loft with a built-in bar provide flexible space for relaxing, entertaining, or gathering. The backyard creates a beautiful outdoor setting designed for Florida living. A heated saltwater pool and oversized spa are surrounded by elegant travertine decking and outdoor living space overlooking the preserve. The extended covered lanai features a summer kitchen with quartz bar seating and a custom outdoor fireplace, creating a space ideal for both entertaining and quiet evenings at home. Additional highlights include smart home controls for lighting and fireplaces, a well-appointed laundry room with a drop zone, and a 3-car garage. Palencia offers an exceptional lifestyle with an Arthur Hills-designed golf course, resort-style pools, tennis and pickleball courts, basketball courts, a clubhouse and fitness center, scenic walking trails, parks, and a boardwalk leading to the Intracoastal Waterway. Historic St. Augustine, nearby beaches, and Jacksonville are all within convenient reach. Homes with this level of design, outdoor living, and location rarely become available. Schedule a private showing to experience what makes this home truly special. Seller is a licensed real estate agent but not related to the listing agent.

247 Vale Drive, St. Augustine
$1,576,500
4 Beds ⋅ 5 Baths ⋅ 2153761 MLS
Perfectly positioned on a private preserve lot, this stunning custom-built pool home is a rare find in Palencia. Surrounded by towering oaks and tropical palms, the nearly half-acre lot offers exceptional privacy on a quiet street of just sixteen homes. Built by Cottage Home Company as a model home, this thoughtfully designed floor plan offers an open-concept layout with four bedrooms, a study, a bonus room, and over 3,800 square feet of living space. Designed for year-round indoor/outdoor living, a pocketing sliding glass wall opens to a covered lanai. The backyard is a private oasis featuring a heated saltwater pool and spa with water and fire features. A detached cabana includes a full outdoor summer kitchen with a wraparound bar, a fireplace, ambient lighting, surround sound and an automated sunshade. Fully fenced and lushly landscaped, the backyard is a true sanctuary complete with a barrel sauna & landscape lighting Inside, a stunning barrel foyer with intricate floor-to-ceiling paneling leads into the family room anchored by a gas fireplace & built-in bookcases. The chef's kitchen features stacked cabinetry with slow-close drawer banks, roll-out shelving, marble countertops and a 9-foot island breakfast bar. Top-of-the-line Thermador appliances - including a six-burner gas cooktop and built-in refrigerator - make this space as functional as it is beautiful. Elevated finishes are found throughout, including cased windows, 8-foot doors, crown molding, wainscoting, tongue-and-groove ceilings, automated window shades, plantation shutters and custom closets. A hidden stairwell leads to a double bonus room with a full bath, walk-in closet, and covered balcony overlooking the private backyard. A hallway with a built-in drop zone leads to a split 3-car garage complete with an EV charging plug, epoxy flooring, and overhead storage. Exterior upgrades include a well for irrigation, a mosquito misting system, a whole-house generator, phantom screens, automated screens, security cameras, a paver driveway, and travertine pool decking - to name a few. The exterior of the home is freshly painted, and a new roof is scheduled to be installed before closing. Located inside the gates of Palencia, residents enjoy access to world-class amenities: an A-rated elementary school, a championship Arthur Hills-designed golf course, a fitness center, three community pools, lighted clay tennis courts, pickleball, sports fields, fitness trails, pocket parks, and a boardwalk leading to the Intracoastal. This is the home you've been waiting for.

122 Senora Court, St. Augustine
$1,533,555
5 Beds ⋅ 5 Baths ⋅ 2132944 MLS
Luxury new construction on just over an acre in an intimate gated community. This thoughtfully designed home features 12' ceilings, wood floors, and cove crown molding throughout the main living areas, along with a private office at the front of the home. The gourmet kitchen is the centerpiece, offering an expansive quartz island, double-stacked cabinetry, custom range hood, Thermador refrigerator, and double ovens. A spacious butler's pantry with abundant cabinetry and beverage cooler adds both style and function. The dining area is surrounded by windows, filling the home with natural light. The well-planned layout offers private bedroom wings and flexible living spaces ideal for guests, a home gym, or multi-generational living. The primary suite features a bay window and spa-inspired bath with dual sinks and a large walk-in shower with floor-to-ceiling tile and frameless glass. Upstairs includes a loft, private bedroom and full bath. Covered patio overlooks the expansive backyard.

108 Canopy Hall Drive, St. Augustine
$1,501,326
5 Beds ⋅ 6 Baths ⋅ 2119422 MLS
The Monica floor plan is a masterclass in modern luxury, blending expansive spaces with thoughtful details that make daily living a pleasure. Spanning an impressive 3,488 square feet, this one-story home offers four bedrooms, four and a half baths, and a four-car garage. Every corner of this home is designed for both comfort and sophistication, making it ideal for families who appreciate the finer things.

589 Chestnut Oak Road, St. Augustine
$1,501,138
5 Beds ⋅ 6 Baths ⋅ 2133361 MLS
The Monica floor plan is a masterclass in modern luxury, blending expansive spaces with thoughtful details that make daily living a pleasure. Spanning an impressive 3,488 square feet, this one-story home offers four bedrooms, four and a half baths, and a four-car garage. Every corner of this home is designed for both comfort and sophistication, making it ideal for families who appreciate the finer things.

273 Brook Ridge Way, St. Augustine
$1,500,000
3 Beds ⋅ 4 Baths ⋅ 2121257 MLS
Wake up to panoramic Atlantic Ocean views from this direct oceanfront home at 3264 Coastal Highway in St. Augustine, where coastal elegance meets effortless beach living just minutes from historic downtown. Designed for relaxation and entertaining, this spacious three bedroom, three and a half bath residence features vaulted ceilings, expansive windows, and a versatile bonus game room with additional sleeping space ideal for hosting guests or maximizing rental potential. Wrap around Trex decking and a generous sand level patio create seamless indoor outdoor living, perfect for sunrise mornings, ocean breezes, and unforgettable coastal gatherings. A protective seawall, updated living spaces, and a layout tailored for both personal enjoyment and investment opportunity make this property a rare find along Northeast Florida's sought after shoreline. Whether used as a second home, vacation retreat, or income producing property, this residence delivers the lifestyle and location buyers are actively searching for. Buyer to verify square footage, rental regulations, and all property details. Direct oceanfront home in St Augustine FL 32084 with Atlantic views, immediate beach access, and close proximity to historic downtown St Augustine and Northeast Florida coastal attractions.

3264 Coastal Highway, St. Augustine
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 2136778 MLS
Some properties check a box or two. This one checks every single one. Set on a rare street to street lot running from Rudolph to Gloria on Anastasia Island, this solid concrete block home sits at a high elevation with exceptional dune protection and unobstructed Atlantic views that stop you in your tracks. Two fully independent units, each with two bedrooms and two bathrooms and their own private entrance, make this property equally compelling as a primary residence, a multigenerational compound, a vacation retreat, or a proven income producing investment. The upper level is the crown jewel. An open concept great room flows seamlessly from the gourmet kitchen through the dining and living areas and out to a rear deck where the Atlantic becomes your backdrop. The kitchen is anchored by a large granite island, custom tile work, and premium appliances. Outside, a hot tub, grilling station, and panoramic ocean vistas make the deck an extension of the living space rather than an afterthought. The ocean facing primary bedroom paired with its spa caliber en suite, soaking tub, and double glass enclosed shower is in a category of its own. The current owners use this level as their personal retreat and have rented only one bedroom while keeping the primary bedroom locked off entirely. The upside for a new owner willing to put both bedrooms into rotation is significant. The ground floor unit stands beautifully on its own. Polished concrete floors, an open kitchen and living layout, two well appointed bedrooms, and stylish bathrooms create a space that feels both modern and inviting. It has been a consistent and reliable performer as a short term rental. Beyond the two units, the property includes a regulation bocce ball court, a spacious garage with ample room for vehicles and all your beach gear, and a detached storage unit with its own mini split system that works perfectly as a private home office or climate controlled storage.Two outdoor showers, two private entrances, one extraordinary location. This is Anastasia Island living at its finest. Schedule your private showing today.

5730 Rudolph Avenue, St. Augustine
$1,485,000
4 Beds ⋅ 4 Baths ⋅ 2140460 MLS
Experience luxury living in this exceptional 2021 custom built pool home, set on an estate lot over ½ acre. Located in the gated community of Markland, this 4-bedroom, 3.5-bathroom, 4,349 square foot home blends timeless craftsmanship, advanced smart home technology, and resort style outdoor living. Inside you'll find soaring 12-foot ceilings, 8-foot doors, wide plank wood look tile, plantation shutters, crown molding, coffered ceilings, and craftsman style trim throughout. Architectural details include board & batten trim, picture frame molding, custom built-ins, cathedral ceiling with beams and custom designs by Inspired Closets. The gourmet kitchen is a showpiece with soft close cabinetry, stacked uppers, Cambria countertops, a double thick oversized Cambria quartz island with extra cabinetry for storage, custom wood hood, Electrolux range, double oven, dishwasher, Frigidaire tower refrigerator/freezer, clay fire farmhouse sink, and a walk-in pantry with custom shelving. The luxurious primary suite offers a spa inspired bath with dual vanities, Cambria quartz, freestanding tub, glass tile wall, rain head, body sprays, handheld shower, niche, and built-in bench. The family room opens to an extraordinary outdoor retreat featuring an expanded covered lanai, travertine flooring, screen enclosure, custom gas fireplace, outdoor kitchen, and a heated saltwater pool with raised spa, all controlled by the Pentair app. A fully PVC fenced backyard and preserve views create privacy and space to enjoy the large yard behind the pool. Bedrooms 2 and 3 are private ensuites with extended vanities and large showers with dual shower heads and walk-in closets with custom shelving and drawers. The oversized laundry room offers abundant cabinetry, sink, backsplash, and a walk in storage closet. This true smart home includes a Control4 system, wireless access points, exterior surveillance cameras, video doorbell, smart lock, motion sensors, full security alarm, smart lighting, HVAC, irrigation, garage doors, and built in speakers in the flex room and lanai. The flex room also features a 7.1 Marantz surround sound system for an immersive media experience. Additional spaces include a 4th bedroom/flex room, dedicated office, dining room, café, coffee bar with cabinets and beverage fridge and powder room. The oversized garage includes an epoxy floor, custom shelving, and a finished single bay with mini split--used as a gym. Exterior features include a large paver circle driveway with tons of parking, Hardie board siding, stone accents, architectural shingle roof, whole home Generac generator, water softener and gutters. Markland is a 314-acre master planned gated residential community home to 355 single family residences. This St. Johns County enclave offers the amenities of a larger community while maintaining an intimate, connected feel. Residents enjoy the Manor House, resort style pool, lakeside fire pit, fitness center, tennis, pickleball, basketball, kayak launch & boat dock, playground, and dog park. Markland is also in the heart of golf country, surrounded by several premier courses -- including the world-renowned World Golf Village just minutes away. Located in the top-rated St. Johns County school district, close to shopping, restaurants, historic downtown St. Augustine, major highways, and less than 15 miles from the Atlantic Ocean, Markland offers an unmatched blend of convenience, recreation, and coastal living. Don't let this be the one that got away!

60 Westcott Parkway, St. Augustine
$1,480,000
4 Beds ⋅ 3 Baths ⋅ 2135778 MLS
Reintroduced to the market at an exceptional new value, this extraordinary oceanfront residence within the gated enclave of Ocean Gate I offers a level of privacy and refinement rarely found along St. Augustine's coastline. With only 12 residences behind its beautifully appointed, secured entrance, this is coastal living reserved for the few. Offering four bedrooms and designed to live like a private seaside retreat, the home is constructed of solid concrete block and includes a spacious two-car garage--an uncommon luxury in oceanfront condominium living. A gracious foyer welcomes you inside, where a dramatic spiral staircase creates an architectural focal point and an immediate sense of elegance. The interiors are both sophisticated and inviting, with a thoughtfully updated kitchen that blends style and function for effortless entertaining. The primary suite, privately positioned on the lower level, opens to its own porch and captures beautiful ocean views, creating a serene and restorative retreat. Upstairs, the main living area extends to an open balcony where sweeping ocean views provide a stunning backdrop for everyday living and entertaining. Beyond the residence, Ocean Gate I offers an elevated lifestyle--featuring a private pool exclusively for its residents, tennis courts, and access to a boardwalk leading to a wide, sandy stretch of pristine beach. Recent association-led improvements further enhance the property, providing peace of mind and a truly turnkey experience. A rare opportunity to own within one of the area's most intimate and distinguished oceanfront communities--now offered at a compelling new price point where privacy, architecture, and the rhythm of the sea converge.

616 Mediterranean Way, St. Augustine
$1,458,064
4 Beds ⋅ 5 Baths ⋅ 2140022 MLS
Live luxuriously in the Monica! Single-story, 3,969 sq ft with 4 bedrooms, 4.5 baths, and 4-car garage. Open-concept kitchen, dining, and living areas extend to the lanai. Master suite with spa bath, walk-in closet, and French doors. Flexible layouts, optional game room.

141 Chestnut Oak Road, St. Augustine
$1,457,500
5 Beds ⋅ 5 Baths ⋅ 2148803 MLS
Tucked behind lush landscaping and designed for both privacy and connection, this exceptional John Kenny Custom Home offers a living experience unlike any other. From the moment you arrive, you're welcomed into a stunning courtyard centered around a sparkling pool--the heart of the home. The main residence is thoughtfully positioned on one side, while a private ''Casita'' sits on the other, creating a retreat-style setting ideal for guests, extended family, a home office, or multigenerational living. A whole-house Generac generator delivers reliable backup power, allowing you to enjoy your home year-round without interruption. Offered for the very first time by its original owners, this meticulously maintained property features a total of 5 bedrooms, 4.5 bathrooms, and a 3 car garage. The main home includes a first-floor bedroom and full bath, with two additional bedrooms and two baths upstairs. Across the courtyard, the detached casita offers a first-floor bedroom and full bath, while the oversized upper-level suite features its own full bath and built-in kitchenette, providing ample space to be used as a guest suite, office or entertaining flex space. Inside, wood flooring flows throughout the main living areas, where a gas fireplace serves as the centerpiece of the family room. The thoughtfully designed floor plan includes an eat-in kitchen for casual dining as well as a separate dining room for special occasions. Beautiful exposed wood beam ceilings showcase the craftsmanship and character expected in a John Kenny custom home. This truly is a rare opportunity to own a one-of-a-kind property offering flexibility, privacy, and timeless design.

286 Vale Drive, St. Augustine
$1,455,330
6 Beds ⋅ 7 Baths ⋅ 2142667 MLS
comp purposes

82 Maple Creek Lane, St. Augustine
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 2125588 MLS
143 Washington Street is more than a home -- it is a rare opportunity to experience luxury coastal living in the heart of historic downtown St. Augustine. Perfectly positioned overlooking the tranquil waters of Lake Maria Sanchez, this exceptional newer-construction residence offers the charm and walkability of the nation's oldest city without the compromises often found in historic homes. Built in 2021 and being offered fully furnished, this turnkey retreat blends sophisticated modern design with effortless waterfront living. Expansive windows flood the home with natural light while framing breathtaking water views from multiple levels. Designed for both relaxation and entertaining, the open-concept layout flows seamlessly to private outdoor living spaces where sunrise coffees and sunset evenings become part of everyday life. Step outside to your resort-style pool overlooking the lake, creating a setting that feels more like a private luxury getaway than a downtown residence. Whether enjoying wine by the water, entertaining guests, or taking a short stroll to St. George Street, acclaimed restaurants, boutiques, galleries, and marinas, every detail of this property is centered around lifestyle. Unlike many homes in the historic district, this elevated modern residence offers the peace of mind of newer construction, contemporary systems, spacious parking, and low-maintenance living -- all while preserving the timeless character and atmosphere that make St. Augustine so special. Ideal as a primary residence, luxury second home, or high-end vacation retreat, this fully furnished property delivers a rare combination of modern luxury, walkability, water views, and turnkey convenience in one of Florida's most iconic coastal destinations. Experience historic downtown living reimagined at 143 Washington Street.

143 Washington Street, St. Augustine
$1,445,000
4 Beds ⋅ 3 Baths ⋅ 2148297 MLS
Walk or bike to the beach from this beautifully designed 4-bedroom, 3-bath coastal residence in the highly sought-after Ocean Ridge community of St. Augustine Beach. Built by Riverside Homes in 2020, this thoughtfully designed home offers 2,727 square feet of living space with timeless coastal style and modern comfort. A welcoming front porch leads into an open-concept floor plan featuring soaring vaulted and beamed ceilings, luxury vinyl plank flooring, and abundant natural light throughout. The gourmet kitchen showcases floor-to-ceiling white shaker cabinetry, granite countertops, a herringbone tile backsplash, built-in Bosch appliances, a large center island, and a butler's pantry. The flexible layout includes a private study, first-floor guest suite, spacious owner's retreat, and an upstairs loft opening to a covered balcony. French doors lead to the covered lanai and backyard with room for a future pool beneath beautiful mature live oaks. Additional features include an outdoor shower and pre-plumbing for a future outdoor kitchen. A rear gate provides convenient access through the neighborhood, making beach walks and bike rides even easier. Ideally located just moments from the beach, restaurants, shops, and local favorites, this exceptional Ocean Ridge home captures the very best of St. Augustine Beach living.

472 Ridgeway Road, St. Augustine
$1,445,000
4 Beds ⋅ 3 Baths ⋅ 2135734 MLS
Experience the perfect fusion of mid-century charm and coastal modern luxury in this exceptional home, where timeless design meets contemporary elegance. Offering over 3,600 square feet of thoughtfully designed living space and positioned on a quarter-acre lot, this residence boasts sweeping views of a tidal creek and the river beyond, visible from nearly every room. The third-floor sunroom and wraparound deck provide front-row seats to stunning sunsets and the downtown skyline. Step inside to find a spacious living area, where original terrazzo floors pay homage to the home's mid-century roots. The open living and dining rooms are ideal for entertaining, while the family room offers a cozy retreat. A gas fireplace adds warmth and ambiance, perfect for relaxing evenings. At the heart of the home, the expansive kitchen opens to every common area, making it a hub for both daily living and special gatherings. Abundant cabinets, a butler's pantry, and a micro workstation provide ample storage and workspace. The south wing features three bedrooms, including a primary suite with water views and an en-suite bathroom. A vintage-inspired bathroom serves the additional bedrooms and guests, maintaining the home's unique character. The Florida room is a standout, with walls of windows offering panoramic views of the creek and its abundant wildlife. This versatile space is perfect for relaxation or recreation, complete with a wet bar and custom shelving. Ascend the beautiful hickory stairs to the second-floor studio, a light-filled space perfect for creative pursuits or intimate gatherings. The owner's suite on this level is a tranquil retreat, offering breathtaking views and a luxurious bathroom with a soaking tub and spacious shower. The third-floor sunroom is the crowning jewel, with 360-degree views of the creek, river, and city skyline. Whether you're enjoying morning coffee or evening cocktails, this space is a serene haven. Outdoor living includes a covered lanai off the Florida room, a 275-square-foot patio for alfresco dining, and a private dock for Creekside relaxation, stand up paddle, fishing, kayaking. The meticulously landscaped garden, sheltered patio, and secluded screened room offer complete privacy and a serene outdoor oasis. The garage is generous in size for cars and toys, while the generator and impact glass windows throughout ensure peace of mind. This home is a magical blend of elegance and comfort, offering a lifestyle that feels like a retreat every day. Book your private tour today!!

205 Coquina Avenue, St. Augustine
$1,440,000
4 Beds ⋅ 3 Baths ⋅ 2159181 MLS
Located on a quiet cul-de-sac within the prestigious community of Anastasia Dunes, this welcoming home is just steps to the beach. Custom built on 1/3acre, this home offers both privacy and an ideal island location. Majestic Oaks and dappled sunlight open to a picturesque front porch. Inside, vaulted ceilings adorned with wood beams and wide open spaces create an elegant coastal retreat. The warm sophisticated kitchen, showcasing solid maple cabinetry, a sandy taupe glass backsplash and understated Fantasy Brown countertops, seamlessly transitions to the outdoors. Expansive windows frame peaceful preserve views and glass doors open directly to the paver patio and fire pit for easy indoor/outdoor living. The spacious downstairs master feels like a resort with views of lush tropical landscaping and a truly luxurious en-suite complete with a deep soaking tub. A custom solid wood barn door opens toa separate wing of the home featuring a light-filled office and a 2nd downstairs guest suite. With French doors opening to the outdoor patio, this additional downstairs suite offers both privacy and comfort for guests and extended family. Upstairs, a large bonus room works perfectly as a media room, while two more spacious bedrooms share a thoughtfully designed Jack-and-Jill bath. Nearby, the upstairs loft with a shiplap accent wall serves as an ideal hobby space or fitness room. Rarely does a home offer such an exceptional balance of luxury, privacy, and convenience. Family living is perfected at this beachside sanctuary in beautiful Anastasia Dunes! Situated on a private third-acre lot just steps from the ocean, this home allows you to easily walk or bike to local restaurants, coffee shops, ice cream parlors, the pier, and the amphitheater--all the special places that make St. Augustine Beach the perfect place to call home.

912 Sandy Beach Circle, St. Augustine
$1,416,500
4 Beds ⋅ 3 Baths ⋅ 2145643 MLS
Just steps from the ocean, this fully furnished, turn-key property offers a rare opportunity to own an income-producing vacation rental in one of St. Augustine's most sought-after neighborhoods, Anastasia Hills. Whether you're looking for a proven investment, second home, or primary residence, 5483 Pelican Way has endless possibilities. The layout features three stories in total with four bedrooms plus a large den space. On the first level, you'll find a private guest/in-law suite with its own bedroom, bathroom, living room and kitchenette, plus an oversized two garage and large storage room space. The main living level includes a remodeled kitchen, open living area with vaulted ceilings, two bedrooms, and a large den currently used as a bunk room for guests. Upstairs, the primary suite offers sweeping ocean views, a large walk-in closet, and an additional flex room ideal for a nursery, office, yoga room, or extra closet space. Outside, choose between two spacious balconies, a hot tub, fire pit, and a backyard with plenty of room to add a pool. Improvements include a new roof (2022), HVAC systems (2020 & 2021), impact windows and French doors (2018), fiber cement siding (2018), epoxy garage floors (2023), and more. Located at one of the highest elevations of Anastasia Island, no flood insurance is required. It also benefits from county zoning, meaning lower taxes and fewer restrictions. Call today to schedule a tour!

5483 Pelican Way Way, St. Augustine
$1,402,500
4 Beds ⋅ 4 Baths ⋅ 2137773 MLS
Welcome to ''SERENITY NOW'' IN BEAUTIFUL VILANO BEACH. This is the beach home you have been waiting for your whole life. Built in 2006 on concrete pilings with hurricane proof windows looking out at the ocean, St Augustine Inlet leading to the ICW. The kind of beach home that guests book without hesitation. The 4 bedrooms, 4 bath layout keeps bedrooms tucked away while the main living space stays open and flooded with natural light. The open layout of the elevated main floor keeps the family room and kitchen connected, so everyone stays part of the conversation while enjoying views of the ocean. Gas powered tankless heating; electric HVAC with two remote controlled zones; the new electric fireplace in 2025 is a beauty; house covered over by a hurricane proof new roof in 2025. Step out onto the wrap around decks facing the ocean to the north/around to the southeast exposure with your morning coffee or the afternoon cocktail. You will never want to leave; neither will guests/friends Steps to the beach and the ocean with a full body enclosed outdoor shower to get the sand off and be ready for the evening activities. Located in Flood Zone X, (no need for flood insurance) LOMA FEMA Letter of Map Amendment documents supporting Flood Zone X designation offers added peace of mind. Recent DBPR Certificate of Balcony and Stairs Home Inspection as well. Maple wood floors throughout the interior of the property. Full water purificaion system throughout the home. Weather/rust proof outdoor deck furniture and iodized aluminum patio table with 8 chairs on the deck make for terrific late evening summer dinners to the sound of the crashing waves. Combined with solid construction; hardiboard exterior siding freshly painted 2025 and a practical layout, the home feels easy to own and live in. See list of upgrades and improvements in documents section of the listing.

510 Porpoise Point Drive, St. Augustine
$1,400,000
7 Beds ⋅ 5 Baths ⋅ 2159371 MLS
Luxury Coastal Retreat with Heated Pool & Spa | Walk to Vilano Beach | Proven Vacation Rental Opportunity Just a short 6-minute walk from the sand, this beautifully renovated 7-bedroom, 4.5-bath coastal retreat offers over 4,000 square feet of living space in one of St. Augustine's most sought-after beachside communities. Whether you're searching for a primary residence, second home, or high-performing vacation rental investment, this exceptional property delivers the ideal blend of luxury, location, and lifestyle. Designed to accommodate large gatherings, the home comfortably sleeps up to 18 guests and features expansive living spaces, soaring ceilings, and a dramatic two-story great room highlighted by wood coffered ceilings and a stunning statement chandelier. The open-concept layout flows seamlessly from the spacious living areas to the private outdoor oasis. Step outside to enjoy your own heated saltwater pool, spa, and covered summer kitchen with built-in grill--perfect for entertaining after a day at the beach. The backyard provides the resort-style experience today's buyers and vacation guests seek. A dedicated game and bunk room creates the ultimate hangout space for guests, complete with arcade games, shuffleboard, and flexible sleeping arrangements, making this property especially attractive for multi-generational vacations and group rentals. Located in the heart of Vilano Beach, you'll enjoy easy access to Surfside Park Beach, the Tolomato River, neighborhood parks, and scenic coastal trails. The property is also just minutes from Historic Downtown St. Augustine, where residents and visitors can explore St. George Street, Castillo de San Marcos, award-winning restaurants, boutique shopping, museums, and year-round attractions. Property Highlights: 7 Bedrooms | 4.5 Bathrooms Over 4,100 SF of renovated living space Heated saltwater pool and spa Covered outdoor entertaining area with built-in grill Spacious game room/bunk room Sleeps up to 18 guests Walkable to Vilano Beach and Surfside Park Minutes to Historic Downtown St. Augustine Excellent opportunity for vacation rental income Ideal primary residence, second home, or investment property 2 minute walk to tennis court and dog park. Rarely does a property combine beach access, luxury amenities, large-group accommodations, and proximity to Historic St. Augustine in one exceptional offering. Experience the best of Florida coastal living while enjoying the flexibility and income potential of a premier beach destination property. Call today for a private showing.

157 Lawn Avenue, St. Augustine
$1,400,000
5 Beds ⋅ 5 Baths ⋅ 2150169 MLS
Situated on an 80-foot-wide lot in the gated Hidden Creek community of SilverLeaf, this beautifully appointed MasterCraft ''Harper'' floor plan offers the perfect blend of luxury, comfort, and resort-style outdoor living with no CDD fees. Designed for both everyday enjoyment and entertaining, the property features a first floor owner's suite plus additional first floor guest suite, screen-enclosed pool and spa, outdoor kitchen, fire pit gathering area, and professionally landscaped backyard with privacy fencing. Inside, thoughtfully designed living spaces are complemented by custom storage solutions and luxury finishes throughout. Just minutes from neighborhood amenity center, St. Augustine's beaches, shopping, dining, and historic attractions, this home presents an exceptional opportunity in one of the area's most desirable neighborhoods. Notable Upgrades & Features Outdoor kitchen including gas grill and XL Green Egg Commercial-grade gas fire pit with electric starter Professional landscape design Fully fenced backyard backing up to expansive preserve Custom family room built-in bookshelf wall Alta natural woven window shades Custom primary closet organization system Custom pantry organization system with additional refrigerator Custom laundry room storage and cabinetry Whole-home water softener Leaf-protection gutter system 80 ft wide lot Screen-enclosed heated and cooled pool and spa

73 Arbor Creek Drive, St. Augustine
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