This beautifully maintained home in the vineyards offers timeless style and easy florida living on a southwest-facing lakefront lot with lush landscaping, great curb appeal, and a brand-new roof completed in 2023. A double-door entry with glass accents and a palladian window opens to soaring 12’ ceilings, hardwood floors through the main living areas include: living room, dining room, family room, breakfast nook and hallways. Sunny and brightly lit home sparkles with natural light. The formal dining room shows off decorative millwork, a dramatic picture window with custom draperies, and tall ceilings, while the living room features hardwood floors, sliders that fully pocket to the lanai, and a welcoming flow. The kitchen blend’s function and charm with white cabinetry, cork flooring, granite counters, stone backsplash, stainless appliances, and an oversized sink overlooking a pass-through window to the lanai. A bay-window breakfast nook with pendant lighting opens to the bright family room with plantation shutters, sliders to the lanai, and a wet bar perfect for entertaining. The owner’s suite is a true retreat with its own vestibule, three closets, french door access to the pool, and a spa-inspired bath with oversized vanity, separate makeup space, floating soaking tub, walk-in seamless shower, and enclosed water closet. Two guest suites offer comfort and privacy, and a separate den with vaulted ceilings, built-ins, and a large picture window that works as a home office or optional fourth bedroom. Outdoor living is easy with an expansive covered and screened lanai featuring paver decking, recessed lighting, a ceiling fan, and electric shutters, all overlooking sparkling lake views. Additional highlights include an oversized paver driveway and walkways, a 2-car garage with attic access, and a laundry room with utility sink. With southwest exposure filling the home with light, you’ll love the relaxed vibe, and while vineyards doesn’t require club membership, options are available to enjoy two 18-hole golf courses, a racquet center with 12 har-tru tennis courts (six lit for night play) and eight gel-cushioned pickleball courts with led lighting, multiple dining venues, plus a world-class wellness center offering a gym, spa, barber shop, salt cave, and more.

Valley Oak At Vineyards, 226 Monterey Dr, Naples, Florida 34119, image 1

Sold - Mar 11, 2026

$1,995,000 $70K

3 Beds
3 Baths
2,702 SqFt
$738/SqFt

House sold in Valley Oak At Vineyards226 Monterey Dr, Naples, FL 34119

Experience refined living in this completely reimagined residence offering over 2, 700 square feet with 3 bedrooms plus a private den/office and 3 full bathrooms. No detail was overlooked in this full top-to-bottom renovation, featuring all new electrical and plumbing systems and a brand new high-efficiency hvac system. Wide plank oak flooring sets a sophisticated tone throughout the entire home and the chef’s kitchen is a true showpiece, appointed with premium appliances including a viking range and microwave drawer, fisher & paykel built-in refrigerator and dishwasher, all complemented by taj mahal natural quartzite countertops. Integrated sonos audio enhances the ambiance throughout the home. The primary suite is a serene retreat with a custom built-in closet and a spa-inspired bathroom showcasing marble flooring, a walk-in shower, soaking tub, toto washlet, and linen storage. Two private guest suites each enjoy their own beautifully appointed full bathrooms, offering comfort and privacy for all. Outdoor living is enhanced with a refinished pool, spa, and sun deck, all complemented by a stunning shellstone deck. Additional improvements include new pgt impact resistant windows and doors, a storm rated garage door, a newly paved driveway, new landscaping and sod, new irrigation system, 500-gallon propane tank, solid core doors, and a bespoke fireplace with integrated shelving. Residents of valley oak enjoy low quarterly fees which include fiber-optic cable and wi-fi. Membership at the prestigious vineyards country club is optional and offers access to 36 holes of championship golf, 12 har-tru tennis courts, 8 pickleball courts, bocce, a world-class wellness center & spa, a resort-style pool with food and beverage service, multiple dining venues, and so much more!

Valley Oak At Vineyards, 232 Silverado Dr, Naples, Florida 34119, image 1

Sold - Jan 05, 2026

$885,000 $10K

3 Beds
2¹/₂ Baths
2,667 SqFt
$332/SqFt

House sold in Valley Oak At Vineyards232 Silverado Dr, Naples, FL 34119

Welcome to 232 silverado drive, a bright and inviting home in the highly sought-after valley oak enclave of the vineyards—one of naples’ premier master-planned communities. Offering 3 bedrooms, 2.5 baths, plus a dedicated flex space, this 2, 667 sq. Ft. Residence delivers both functionality and comfort in an exceptional location. Step inside and immediately feel the openness created by soaring cathedral ceilings, multiple skylights, and expansive windows that flood the home with natural light throughout the day. The thoughtful layout includes generous living and dining areas, along with a relaxing florida room perfect for morning coffee, reading, or quiet conversation—all while taking in serene golf course views. Recent upgrades add tremendous peace of mind, including a 2020 roof, 2024 a/c, and hurricane protection on all windows. Outdoor living shines with a screened-in swimming pool, ideal for year-round enjoyment and entertaining in true florida fashion. Valley oak is known for its family- and pet-friendly atmosphere, peaceful streets, and access to a-rated schools, making it a top choice for buyers seeking comfort and community. Residents of the vineyards enjoy an optional membership offering a luxury lifestyle with access to two 18-hole championship golf courses, a racquet center featuring tennis and pickleball, multiple dining venues, and a state-of-the-art wellness center complete with gym, spa, barber shop, salt cave, and more. This home blends natural light, space, views, and amenities—an exceptional opportunity in one of naples’ most desirable neighborhoods.

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Valley Oak At Vineyards, 222 Monterey Dr, Naples, Florida 34119, image 1

Sold - Dec 30, 2025

$1,118,000 $132K

3 Beds
3 Baths
2,451 SqFt
$456/SqFt

House sold in Valley Oak At Vineyards222 Monterey Dr, Naples, FL 34119

Experience the perfect blend of elegance, privacy, and florida lifestyle at 222 monterey dr, a distinctive courtyard single-family home with private casita in the prestigious vineyards country club. The main residence boasts a split-bedroom layout with 2 bedrooms, formal dining, and 2 bathrooms, including a remodeled primary suite bathroom featuring dual sinks, a separate shower, and a luxurious stand-alone soaking tub. The kitchen offers a bar, sleek stainless-steel appliances, soft-close cabinetry, a walk-in pantry, and an inviting eat-in space with a great view of the courtyard. Big windows throughout the home flood the space with natural light, highlighting the formal dining area and the airy ambiance created by soaring 14-ft ceilings and crown molding. The floors in the main house are a warm wood-tone plank laminate for a stylish and modern finish. The separate casita features a bedroom, bath, and kitchenette—perfect for hosting guests, accommodating in-laws, or creating a private home office. At the heart of the property, the expansive brick-paver courtyard features a sparkling pool and raised spa with southern exposure—perfect for basking in all-day sunlight. A covered area in the courtyard elevates outdoor living with a bar featuring lights at night, a mini fridge, and a cozy sitting area, ideal for relaxing or entertaining. Lush landscaping surrounds the property, including a serene, landscaped backyard behind the main house. A two-car garage with a paved circular driveway provides convenience and spacious parking. Optional membership of the vineyards country club unlocks a world of luxury amenities, including 36 holes of championship golf, 12 har-tru tennis courts, 8 pickleball courts, a new wellness center & spa, and a newly renovated clubhouse. Ideally located in north naples with easy access to i-75, and just minutes away from pristine beaches, shopping at waterside shops, and the vibrant dining and cultural scene of mercato and downtown naples.

Valley Oak At Vineyards, 265 Silverado Dr, Naples, Florida 34119, image 1

Sold - Sep 04, 2025

$1,750,000 $150K

3 Beds
2¹/₂ Baths
2,356 SqFt
$743/SqFt

House sold in Valley Oak At Vineyards265 Silverado Dr, Naples, FL 34119

Tucked away on a quiet cul-de-sac in valley oak at the vineyards, this renovated single-story home offers refined living with timeless style. Wide plank wood-look ceramic floors, solid core doors, and custom millwork showcase the quality throughout. The open kitchen features white cabinetry, stainless steel appliances, and a large quartz island ideal for entertaining. Enjoy a cozy den with a wood-burning fireplace and built-ins. The spacious primary suite includes dual custom walk-in closets, a soaking tub, and peaceful garden views. Set on an oversized lot in the x flood zone, the fully fenced backyard features artificial turf and a striking phoenix sylvestris date palm. Additional highlights: brand-new hvac, all-new impact windows and doors (2024), and optional vineyards club memberships with access to a renovated clubhouse, fitness center, spa, and social activities.

Valley Oak At Vineyards, 5831 Cinzano Ct, Naples, Florida 34119, image 1

Sold - Aug 13, 2025

$1,765,000 $235K

5 Beds
4¹/₂ Baths
3,822 SqFt
$462/SqFt

House sold in Valley Oak At Vineyards5831 Cinzano Ct, Naples, FL 34119

Sensational remodel on quiet cul-de-sac in highly desired valley oak in the vineyards! Wide open floor plan with 12’ ceilings and soaring 22’ entry. The gourmet kitchen of your dreams! Complete with endless quartz counters, premium stainless steel appliances including induction cooktop, side-by-side refrigerator, double ovens, giant island with tons of additional cabinets for storage, farmhouse sink and reverse osmosis water system. Separate breakfast nook and wet bar area with sink and permanent ice maker. Cozy living room with concrete finish electric fireplace. Large formal dining room, and home office facing the front of the house. Main floor master bedroom is its own wing with his and her walk-in closets. Master bath features dual sinks and large walk-in shower. Bonus room and guest bath off the entry. Large second story loft area, bringing you to 4 bedrooms upstairs including a jack n’ jill suite. French windows and warm oak hardwood floors throughout the whole house provide a light and bright feel with great, natural light all day. All new, solid-core 8’ foot interior doors. Perfect your cannonball in the backyard pool!! 3 to 6 ft gradual descent pool, large paver lanai and coastal pool bath. Storage galore with multiple attics and hidden space under the stairs! 2 car garage with epoxy floors and additional bump out. Round-about paver driveway. Mature landscaping and storm drainage system around the property. Pond and golf course views from the cul-de-sac. 24-hour manned security gate. Centrally located between pine ridge and vanderbilt beach roads. Easy access to i-75. Close to shopping, parks and naples' world-famous beaches. Recognized as one of best developments in all of naples, the vineyards recently underwent a $20-million-dollar renovation and offers a state-of-the-art wellness center with spa, indoor/outdoor gym and lap pool. Two 18-hole championship golf courses, tennis and pickleball. Membership is optional and sold separately.

Valley Oak At Vineyards, 204 Monterey Dr, Naples, Florida 34119, image 1

Sold - Jun 25, 2025

$1,875,000 $20K

3 Beds
2¹/₂ Baths
2,282 SqFt
$822/SqFt

House sold in Valley Oak At Vineyards204 Monterey Dr, Naples, FL 34119

Introducing this tastefully renovated residence in one of the vineyard’s most desired subdivisions, valley oak. This modern ranch-style estate home has been designed and decorated, ready for immediate move-in. The spacious 2275+ sq ft under-air, 3 bed + den, 2.5 bath home on a very private lot has privacy and exclusivity in one of naples premier locations. Meticulously finished, this elegant estate boasts an open floor plan with soaring ceilings, a coveted northeastern exposure, filling the rooms with vibrant natural light. As you enter your exquisite chef’s kitchen, it commands attention, boasting contemporary lines w/ natural quartzite countertops and coming complete with a stainless-steel appliance package. Each of the two guest bedrooms are spacious retreats, offering ample closet space and warm finishes. Not to be outdone, the master suite includes a walk-in closet, and the master bathroom comes complete with dual vanities, a glass-wall shower, and a free-standing soaker tub. Your outdoor oasis awaits with a covered seating area and plenty of space to entertain with an immaculate pool/spa, all completed by private preserve views. The vineyards underwent a 20-million-dollar renovation in 2019 and offers a state-of-the-art wellness center w/spa, gym, lap pool, two championship golf courses, tennis, and pickleball. Multiple memberships are optional, with golf memberships available. The vineyards is highly regarded as a top community in naples, boasting a new wellness center with spa, gym and lap pool. Two 18-hole championship golf courses, tennis and pickleball all while being centrally located close to shopping, i-75, the beach and vineyards elementary school. Membership is optional. -renovation by keystone custom homes-

Valley Oak At Vineyards, 258 Monterey Dr, Naples, Florida 34119, image 1

Sold - Jun 13, 2025

$760,000 $190K

3 Beds
2 Baths
2,428 SqFt
$313/SqFt

House sold in Valley Oak At Vineyards258 Monterey Dr, Naples, FL 34119

Welcome to your dream home at 258 monterey dr, in the prestigious community of the vineyards in naples, florida. This meticulously maintained single-family home features 3 spacious bedrooms, a versatile den, and a warm, inviting living and dining area with high ceilings. The kitchen is partially separated by a wall, offering a breakfast corner with views of the stunning pool area. Enjoy your mornings with a cup of coffee, gazing out over the sparkling waters and lush greenery. The beautifully designed pool area provides ultimate privacy and serenity, surrounded by nature's splendor. Unwind in the hot tub while listening to birds serenade you under the floridian sun. The home features wood and tile flooring, with well-maintained carpet in the bedrooms. The large attached garage offers space for 2 cars and additional storage. The house is surrounded by a wonderful floridian landscape. The vineyards community offers a luxurious lifestyle with access to the vineyards country club, which features world-class amenities including two 18-hole championship golf courses, a state-of-the-art fitness center, elegant dining options, and a lavish spa. Residents can choose from various golf and social memberships to suit their preferences, providing opportunities for leisure, recreation, and socializing.

Valley Oak At Vineyards, 231 Monterey Dr, Naples, Florida 34119, image 1

Sold - Apr 14, 2025

$1,800,000

3 Beds
3 Baths
3,262 SqFt
$552/SqFt

House sold in Valley Oak At Vineyards231 Monterey Dr, Naples, FL 34119

Welcome to 231 monterey drive in the prestigious gated community of valley oak at the vineyards. This well-appointed residence offers three bedrooms and three newly remodeled baths with over 3, 200 square feet of comfortable living space. Enter and be greeted by the panoramic lake view observed from the lanai. Step outside and discover your private oasis with pool, and a custom-designed fireplace for relaxation and entertainment. The floor plan includes living, dining, family room, den/study, and modern kitchen with sub-zero refrigerator. The primary suite includes sliders that access the pool and covered lanai. The primary bath features double sinks, separate tub and shower, and two walk-in closets. The guest bedrooms are away from the primary suite. The two-car garage is air-conditioned and includes a workshop. This home has been well cared for with many upgrades including a new picture screen lanai cage, storm smart storm screens, new garage doors, new air-conditioner, new epoxy garage floor, generac whole-house generator and more. Experience the ideal blend of comfort and convenience in this beautiful home. Vineyards country club is private and offers two 18-hole golf courses, pickleball, a resort pool, racquet center, wellness center and spa, fitness center, massage and salon services, and dining. Membership is optional. Vineyards is convenient to beaches, restaurants, shopping and all naples has to offer.

Valley Oak At Vineyards, 207 Monterey Dr, Naples, Florida 34119, image 1

Sold - Apr 02, 2025

$1,300,000

4 Beds
3¹/₂ Baths
3,145 SqFt
$413/SqFt

House sold in Valley Oak At Vineyards207 Monterey Dr, Naples, FL 34119

Tucked within the prestigious vineyards country club located within valley oak, this custom-built divco home offers a rare combination of space, elegance, and privacy. With 4 bedrooms, a den, and 3.5 baths, this residence is designed for a lifestyle of exceptional comfort. Elegant living & outdoor escape: upon entering, you're greeted by a bright and spacious living and dining area, bathed in natural light from large sliding glass doors that lead to the pool deck. At the heart of the home, the kitchen and family room create a welcoming environment, perfect for everyday living or entertaining. Featuring ample cabinetry, a breakfast bar, and a cozy dining nook, the kitchen seamlessly blends style and functionality. Step outside to the screened lanai, where you'll find a private, sparkling pool—ideal for relaxation or hosting guests in your own personal oasis. Spacious lot & prime location: one of the standout features of living in the vineyards is the generous lot sizes, offering an abundance of space for privacy and outdoor enjoyment. The location is second to none—close to top-rated schools, shopping, fine dining, and naples’ world-famous beaches. With easy access to i-75 and downtown naples, you're never far from everything this vibrant area has to offer. The vineyards country club lifestyle: ownership here offers more than just a home—it’s an invitation to an extraordinary lifestyle. Optional private memberships to the exclusive vineyards country club grant access to two 18-hole pga championship golf courses, as well as tennis, pickleball, bocce courts, a state-of-the-art fitness center, and a luxurious spa with a lap pool. Whether you're an active golfer, fitness enthusiast, or simply seeking relaxation, the vineyards offers a wealth of options to suit every interest. Begin your next chapter here: this isn’t just a house—it’s a chance to embrace the luxurious naples lifestyle, all while enjoying the peace and serenity of a gated, golf-course community. The vineyards offers a perfect balance of elegance, convenience, and recreation, making it an ideal place to call home.

Valley Oak At Vineyards, 263 Silverado Dr, Naples, Florida 34119, image 1

Pending

$1,425,000 $75K

4 Beds
3 Baths
2,942 SqFt
$484/SqFt

House for sale in Valley Oak At Vineyards263 Silverado Dr, Naples, FL 34119

Welcome to this beautiful home in valley oak, located within the highly sought-after vineyards community. This spacious property offers four bedrooms, three full baths, detached bonus room, and a dedicated office with elegant french doors. Inside, you’ll also find a cozy tv room featuring blackout curtains, a stunning chandelier, and detailed wall trim. The semi-open floor plan allows for optimal entertaining with a large kitchen and step in pantry. The family room includes a custom built-in wall with plenty of storage and a warm, wood-burning fireplace. Each bedroom layout is well thought out and offers great closet space. Step outside to a generous outdoor oasis boasting a large heated pool, an expansive covered patio with both sitting and dining areas, and a pool house/casita. The casita/bonus room is currently set up as a movie room complete with a projector and screen, but it can easily serve as an additional office, game room, or home gym! The property also includes a detached third-car garage perfect for car enthusiasts, woodworkers, or more storage. Enjoy numerous upgrades throughout the home, including a brand-new ac system, a new wine fridge, a newer roof (2018), fresh landscaping, and more!

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Yorktown At Kensington, 5242 Kensington High St, Naples, Florida 34105, image 1

$1,799,000 $101K

4 Beds
3¹/₂ Baths
3,482 SqFt
$517/SqFt

House for sale in Yorktown At Kensington5242 Kensington High St, Naples, FL 34105

This masterpiece of elegance and comfort, perched on the 9th hole of kensington, is move-in ready and designed to maximize its 3, 482 sq ft of well-appointed living space. Brand-new updates further elevate this residence with the addition of a sparkling new pool and panoramic picture-frame cage, transforming the lanai into a resort-style retreat that perfectly frames sweeping views of the 9th fairway. Soaring 18-foot ceilings and expansive windows fill the home with natural light, illuminating the exquisite european oak hardwood flooring throughout. Designed for both grand entertaining and effortless everyday living, this 4-bed + den, 4-bath arthur rutenberg residence features an expansive great room with a wet bar and cozy wood-burning fireplace, ideal for hosting guests. The formal dining room and eat-in gourmet kitchen provide multiple dining options, while the generous-sized loft offers additional space for relaxation or recreation. The renovated kitchen is a showstopper, boasting custom cabinetry, high-end appliances, and a spacious center island perfect for entertaining. The dedicated office/flex space impresses with custom built-in shelving and its own bath. The sprawling primary suite on the ground floor is a serene retreat, offering breathtaking golf course views, while the remodeled en-suite bath features a jacuzzi tub, quartz double vanity, and a walk-in shower. Upstairs, the vip bedroom with an en-suite bath and private balcony offers stunning golf course views—a perfect spot for sunbathing. Two additional spacious bedrooms and another full bathroom with towel warmers complete the second floor. A versatile den/5th bedroom on the ground floor is ideal for a home office, an au pair, or multigenerational living. Additional highlights include an oversized 3-car garage, hurricane shutters on all windows and doors, and recent upgrades, such as a new roof (2021), high- efficiency a/c, new water heater, and freshly painted interior and exterior. The optional kensington golf & country club offers an 18-hole championship golf course, a restaurant, a cutting-edge fitness center, tennis & pickleball courts, a new resort-style pool & more. This home offers an exceptional living experience in one of naples’ most desirable communities, just minutes from vibrant entertainment, shopping, and dining at mercato and waterside, and pristine gulf beaches!

2 to 4 BR

Bedrooms

N/A

Price Tier

N/A

SqFt Range

1993

Year Build

Total Floors

N/A

Total Units

N/A

Total Sales

Subdivision Amenities

Basketball

Barbecue

Beauty Salon

Bike And Jog Path

Bocce Court

Business Center

Clubhouse

Community Room

Fitness Center

Full Service Spa

Golf Course

Hobby Room

Internet Access

Park

Pickleball

Play Area

Pool

Private Membership

Putting Green

Restaurant

Sauna

See Remarks

Shuffleboard Court

Sidewalk

Spa/Hot Tub

Streetlight

Tennis Court(s)

Underground Utility

Volleyball

Barbecue

Bike And Jog Path

Golf Course

Park

Sidewalk

Frequently Asked Questions

How much are the maintenance fees (HOA) in Valley Oak At Vineyards?

The current monthly maintenance fee at Valley Oak At Vineyards is ~0.07 per unit SqFt.

What is included in the Valley Oak At Vineyards monthly association dues?

The single_family_home dues at Valley Oak At Vineyards cover: Cable, Internet/Wi Fi Access, Legal/Accounting, Manager, Master Assn. Fee Included, Reserve, Security, Street Maintenance, Street Lights, Sewer, Trash Removal, , Insurance, Lawn/Land Maintenance, Irrigation Water, Master Antenna/Satellite, Repairs.

What are Valley Oak At Vineyards Pet Policies & Restrictions?

Valley Oak At Vineyards Valley Oak At Vineyards is a pet-friendly “Dogs and Cats OK” subdivision for both owners and tenants. Please note that pet policies may change at the discretion of management and/or the Homeowners' Association (HOA) and may not apply to renters. Restrictions may apply to certain breeds, and size and weight limits may be in place.

What are the interior features of the residences?

Valley Oak At Vineyards Interior features include: Bar, Built-In Cabinets, Fire Sprinkler, Fireplace, Pantry, Smoke Detectors, Volume Ceiling, Walk-In Closet(s), Built-In Cabinets, French Doors, Laundry Tub, Vaulted Ceiling(s), Window Coverings, Laundry Tub, Closet Cabinets, Custom Mirrors, Wet Bar, Fire Sprinkler, Cathedral Ceiling(s), Foyer, Pull Down Stairs, Tray Ceiling(s), Foyer, Fireplace, Wired for Sound, Cathedral Ceiling(s), Pantry

What are the available unit views from Valley Oak At Vineyards?

Valley Oak At Vineyards unit views: Landscaped Area, Privacy Wall, Golf Course, Pool/Club, Lake, Landscaped Area, Water, Lake

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