Luxury Homes of the Upper Highway - Hillcrest, Kloof & Winston Park

Luxury Homes of the Upper Highway - Hillcrest, Kloof & Winston Park A current listing of luxury homes in Hillcrest, Kloof, & Winston Park KZN

This Roman Home Rules the Roost in KloofPrice: R11,5 milLike an architectural Michelangelo set amongst the brick & morta...
12/06/2026

This Roman Home Rules the Roost in Kloof
Price: R11,5 mil

Like an architectural Michelangelo set amongst the brick & mortar giants of exclusive Everton rd, this romanesque home of alabaster holds its own and stands yet still higher; elevated in both position and style. The beautifully modernised interior encased in a re-imagined classic exterior offers layer-upon-wallpapered-layer of luxurious living. From the welcoming entrance foyer flow the dining room (with easy-to-clean wood-look tiling) to the right, and the lounge (with hardwood flooring) and semi-open plan kitchen to the left. The kitchen romances with Casanova charm, offering Caesarstone countertops, a breakfast peninsula, a 5-plate gas hob, walk-in pantry, and a separate laundry area. The grand upstairs master-suite unapologetically occupies the entire second floor and comprises a spacious main, adjacent nursery & study, and private balcony, and the 3 downstairs bedrooms are all ensuite; one with stacking doors to the exterior, and another with French doors to a Juliet balcony; all framed with reinforced plantation shutters.

The property offers more than an entrée, but serves you a three-course meal of accommodation options with two additional cottages; one fancy two bed decked-to-the-nines with full open plan kitchen comprising sage cupboards & rose gold hardware, and the other, a warm one bed with cozy oak-coloured kitchenette.

When daytime turns to nighttime fun, why shout from the rooftops when you can party on the dancefloor of your very own clubhouse complete with undercover patio, enclosed pool area, gentlemen's bar, billiard room (with exposed ceiling beams), and adjacent gym.

A standalone greenhouse-style glass-walled office and 4-car doorless garage complete the picture.

This regal residence is so much more than a home, it’s a multi-tiered lifestyle escape offering resort-like living within Everton's secure & sought-after boomed-off area.

Contact Ryan Lategan to break the seal of this gift that keeps on giving and walk the future lawns of your happily ever after.

Disclaimer: the info contained herein is correct to the best of our knowledge, errors and omissions excepted. Buyers to conduct their own due diligence

House for sale in Everton. Luxury home for sale in the Upper Highway. House for sale in Kloof.

Like an architectural Michelangelo set amongst the brick & mortar giants of exclusive Everton rd, this romanesque home of alabaster holds its own and stands yet still higher; elevated in both position and style. The beautifully modernised interior encased in a re-imagined classic exterior offers lay...

Nestled within a friendly and family-loving enclave within the prestigious Cotswold Downs Golf & Country Estate is this ...
03/05/2026

Nestled within a friendly and family-loving enclave within the prestigious Cotswold Downs Golf & Country Estate is this stately new addition to our Luxury Portfolio. This approximately 638sqm residence is expertly designed to marry post-modern minimalist with farmhouse-chic. The interconnected entertaining spaces allow for seamless socialising and easy transition from intimate dining to laid back lounging with but a few steps, with their arrangement clearly carefully considered.

The kitchen with centre island, gas hob, breakfast nook and separate scullery offers enough prep area to cater for a multitude, and the separate dining room offers panoramic views of rolling greenery via floor to ceiling stacking doors. Two lounges, one sharing the views of the dining room and with a undercover built-in braai and the other with a feature fireplace and situated in the heart of the home, both boast breath-taking vaulted ceilings transparent glass doors. Off to the left are 3 of the 5 bedrooms; with the main comprising a walk-in dresser and a full ensuite and the other two oversized rooms sharing a central bathroom.

Downstairs is high flexible living space which can either function as a massive single guest suite, complete with studio-sized bedroom, walk-in dresser, ensuite bathroom, separate coffee station and separate lounge, or can be easily converted to two seriously-spacious bedrooms by simply adding built-in cupboards to the second room.
Attached to the home is an extra length double garage, above which is a platform offering additional guest parking reserved for this unit.

An outdoor pool on the upper balcony completes the picture.
Dogs allowed with approval by management.

With so much to offer this unit is priced-to-go and will obtained by the savvy buyer with an eye for value.

Contact Cotswold Downs accredited agent Ryan Lategan on 0763019952 for a private viewing of this meticulous masterpiece in Hillcrest’s favourite gated estate.

Equestrian Escape in Kirtlington Park Hillcrest - R7,4 mil*********Sometimes you’re not crunching the numbers. Sometimes...
18/01/2026

Equestrian Escape in Kirtlington Park Hillcrest - R7,4 mil
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Sometimes you’re not crunching the numbers. Sometimes it’s not about the ROI. Sometimes you don’t want people, you just want family and to forget the 9 to 5. Sometimes life comes first.

Get ready to get away and forget with this impeccably appointed Equestrian Estate escape.

Kirtlington Park, situated on the doorstep of the Camp Orchards farm and itself comprising acre upon acre of green pasture and hill after hill of horse-roaming paddocks, is anything but ordinary. This 24-hr guarded & gated estate epitomises exclusive & private living, and the home, set on a 1700sqm stand means you don’t need to know your neighbours.

Stretching its stately structure out over two sumptuous storeys this gentlemen’s residence exemplifies elegance. Wrought-iron chandeliers summon period pizzaz to both the double-volume entrance and the rear verandah. The home comprises two lower level dining areas, a lower and an upper level lounge, and lower & upper level offices (with the oversized upstairs office with its own exterior entrance making for easy flatlet conversion). From the indoor braai-adjacent bar to the chef’s kiss kitchen, caramel-toned timber accents warm in all the right places. Low maintenance porcelain tiles add an effortlessness to every corner and their flow over to the undercover entertaining area means spills don’t interrupt thrills with cleaning drills. The home’s sleeping sanctuary is set aloft, with a main ensuite with walk-in dresser, a secondary ensuite and a 3rd and 4th bedroom sharing a top-billing bathroom. Off the back patio and to complete the picture is a neat level garden and terracotta-framed pool for those sweltering summer months.

When buying’s such a breeze don’t be left with regret, contact Ryan Lategan to view the Haut Chateauette.

https://www.realestatecompany.co.za/kirtlington-park-house-for-sale-2462358

Fall in Love again - for investor or end userPrice R3,3 mil*Gated Estate house tenanted for the next 6 months with the o...
11/01/2026

Fall in Love again - for investor or end user
Price R3,3 mil

*Gated Estate house tenanted for the next 6 months with the option to extend the lease*

Like a Hallmark romance reminding you it’s never too late for love, this postcard property gently stokes the embers of a heart searching for home. The bricks and mortar of this family abode aren’t merely the materials which make up this well appointed residence, they are the pen and paper with which the architect has inscribed the story of his craft. Each meticulously placed bay window, and each right angle or soft curve like members of a choir sing together in perfect harmony. And once your breath has been taken away, the home, like any thoughtful host, offers you the space to get it back with a broad inhale of verdant garden.

The lower level comprises a central open concept kitchen extending in 3 directions towards a lounge (with French doors to the under-cover patio), dining room, and garage (which has been drywalled into 2 home office spaces, one pictured inset). Off the lounge is the stairwell, under-stair storage, and an ensuite guest bedroom. The upper level comprises a master ensuite and two other light-filled bedrooms sharing a bathroom.

Outside the magic continues with a set-back pool and a fire-pit with seating off the undercover entertainment verandah. The backyard offers more than enough room for a growing family to stretch its legs and get in their steps.

*Current rental income - R24,000 per month (but property has previously had long term tenants for R28,000 per month)

Life at Clifton Hill flows at a gentler pace. Start your mornings with a session at the fully equipped gym or a swim in the heated indoor pool at the Lifestyle Centre. Stroll along the nature trail, unwind in the sauna, or spend weekends enjoying the outdoor pools, tennis court, squash courts, and children’s play areas — all within the estate’s beautifully maintained grounds.

With 24-hour security, access control, and patrolling guards, peace of mind comes standard. The apartment includes one allocated parking bay, and a once-off Levy Stabilisation Fee of R25,000 is payable to the Homeowners Association.

Whether you’re a professional seeking a save investment in a secure estate, or a end user buyer ready to invest in quality and lifestyle, — this home offers an easy, refined living in one of the area’s most desirable estates.

Contact Ryan Lategan to arrange a private viewing of this special and flexible home.

The information contained herein is accurate to the best of our knowledge, errors and omissions excepted. Buyers to conduct there own due diligence prior to purchasing

Like a Hallmark romance reminding you it’s never too late for love, this postcard property gently stokes the embers of a heart searching for home. The bricks and mortar of this family abode aren’t merely the materials which make up this well appointed residence, they are the pen and paper with w...

A property for Yesterday, Today, and TomorrowR5,875 milRarely does a home so effortlessly balance the timeless beauty of...
07/01/2026

A property for Yesterday, Today, and Tomorrow
R5,875 mil

Rarely does a home so effortlessly balance the timeless beauty of a season passed with the eager anticipation of a season yet to come. The quiet beauty perched at 22 Pioneer rd does just this, it offers the remembrance of yesteryear with the potential of tomorrow. The primary residence, a historical AMAFA building, is situated in the centre of almost 3 acres of development-ready gently sloping garden. The home, offering 4 bedrooms, 3 bathrooms & a study, boasts a colonial wrap-around verandah, an open plan kitchen/dining/lounge, and an additional separate lounge with an ornate period fireplace and Origen pine flooring.

Separate from the main house is a large self-contained one-bedroom cottage (comprising open plan kitchen/lounge) and separate from this building is another freestanding one-bed bedsit (not photographed). Double staff quarters complete the picture.

For the Developer: The erf is sufficiently sized to comfortably accommodate up to six homes, and preliminary investigations into the establishment of a residential complex have yielded favourable feedback. The property further benefits from dual road frontage onto Pioneer Road and Greenacre Place. While the site offers immediate development potential under its current zoning, this potential may be significantly enhanced through rezoning, should increased allowable density be approved, making it well suited to a retirement or other higher-density residential village.

Contact Ryan Lategan to arrange a private viewing of this pluripotent property.

Disclaimer: The info presented herein is accurate to the best of our knowledge, errors and omission excepted. Buyers to conduct their own due diligence before submitting an offer.

Rarely does a home so effortlessly balance the timeless beauty of a season passed with the eager anticipation of a season yet to come. The quiet beauty perched at 22 Pioneer rd does just this, it offers the remembrance of yesteryear with the potential of tomorrow. The primary residence, a historical...

A Turnkey Hospitality PowerhousePrice: R15 millionSet amidst the verdant landscape of the Upper Highway, this extraordin...
26/06/2025

A Turnkey Hospitality Powerhouse
Price: R15 million

Set amidst the verdant landscape of the Upper Highway, this extraordinary wedding and events venue stands in a league of its own — boasting the largest events facility in the region and offering a fully equipped, ready-to-operate facility, with all furniture, equipment, and functional infrastructure. While not currently running at full capacity, all the groundwork is there for a seamless return to hosting weddings, corporate gatherings, retreats, and more. ready to continue its reputation for hosting top-tier weddings, conferences, and private functions.

At the heart of the property is a grand main events hall, with a capacity of 300 guests, fully air-conditioned and equipped with electric-start gas heating for year-round comfort. It is serviced by a commercial-grade kitchen, a fully fitted bar, and a flowing layout that makes hosting both seamless and impressive.

Additional on-site infrastructure includes:

- A luxurious 10-bedroom (20-sleeper) guest lodge with communal kitchen and dining hall

- A honeymoon suite, thoughtfully positioned for privacy

- A full staff commune, ensuring operational ease for live-in or rotational staff

A key highlight of the estate is the double-story private five-bedroom residence, where luxury and functionality meet. Lending itself easily to a boutique hotel, all five bedrooms are ensuite, and the home features multiple lounges, gas fireplaces, hardwood flooring, a swimming pool, elevated viewing decks, multiple braai areas, and a warm, inviting design perfect for both owners and VIP guests.

The property also features:

- A natural stream and electric waterfall

- A firepit and entertainment zone

- A gentleman's bar, wine cellar, and conference room with projector

- A gazebo for intimate ceremonies or outdoor dining

- A high-powered Voltex 1000kVA generator

- Ample parking to comfortably accommodate large-scale events

Every element of this property has been designed to deliver premium experiences with efficiency and style. Whether your vision is boutique weddings, high-end corporate functions, or exclusive wellness retreats, this versatile estate provides the perfect canvas.

If you believe in doing things without compromise, and you’re looking for a property that lets you operate at the very top of your game — this is your chance. Big canvas. Bigger potential.

Contact Ryan Lategan to arrange a private viewing of this landmark hospitality estate.

The information herein is correct to the best of our knowledge as provided by various parties, however errors and omissions excepted.

Wedding venue for sale near Hillcrest. Wedding and functions venue for sale near Kloof. Guesthouse for sale near Hillcrest. B&B for sale near Kloof. Hospitality property for sale in the Upper Highway KZN.

Set amidst the verdant landscape of the Upper Highway, this extraordinary wedding and events venue stands in a league of its own — boasting the largest events facility in the region and offering a fully equipped, ready-to-operate facility, with all furniture, equipment, and functional infrastructu...

Price: R11 million*****************A Home for King and Country – but in an Exclusive Gated Estate *****************Set a...
06/03/2025

Price: R11 million
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A Home for King and Country – but in an Exclusive Gated Estate
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Set amidst a backdrop of pristine pastures and eager equines this upmarket abode flaunts its gilded hoof with unabashed aplomb.

The homestead consists of a lavish primary residence, and 3 well-appointed adjoining flats, each with their own entrances, with a makeup as follows:

Primary Home – 3 bedrooms, 2.5 bathrooms, 1 study and gym room, walk-in closet, sewing room, 2 livingrooms and an open plan kitchen dining room, triple garage

Flat 1 - 2 beds, 1 kitchen, 1 lounge,1 bathroom

Flat 2 - 1 bed, 1 lounge with kitchenette, 1 bathroom

Flat 3 – 1 bath, 1 bedroom

The property is one of what will be a select handful of upmarket homes in the new Alverstone Equine Estate, a 6pm-6am guarded gated estate (with CCTV & perimeter electric fencing) with upmarket stables, paddocks, and other equestrian facilities.

If you feel normality is overrated, and luxury should never be apologised for, than this gated estate along Alverstone’s millionaires mile is right up your street.

Contact Ryan Lategan to tack up to a higher level of living with this robust residence.

The information herein is correct to the best of our knowledge as provided by various parties, however errors and omissions excepted.

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Expansive Living within a Sought-after Hillcrest ComplexPrice: R3,5 mil****************************Contact Ryan on 076 3...
21/02/2025

Expansive Living within a Sought-after Hillcrest Complex
Price: R3,5 mil
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Contact Ryan on 076 301 9952

When you approach this splendid 4-bedroom 4.5 bathroom, split-level duplex, the charm of the tree-lined street beckons with a serene invitation. The air is filled with the whispers of rustling leaves and the promise of community, offering a delightful backdrop for a life well-lived. Here, nestled within an esteemed neighbourhood walking distance to the malls and village , and just moments from prestigious schools like Highbury and Hillcrest Primary, you’ll find a sanctuary that strikes a harmonious balance between sophistication and comfort.

Upon entering, you’re greeted by an expansive open-plan kitchen, dining room, and lounge that create a warm embrace, inviting both laughter and quiet moments. The sunroom bathes in natural light, a perfect spot for morning coffee or evening conversations. Step outside to discover not one, but three charming covered entertainment areas: a braai zone for summer feasts, a pizza oven for culinary adventures, and a mancave that is more than a mere refuge—it’s a personal retreat where tales of glory and guffaws come to life. As dusk falls, gather around the bar area, where a whirlpool bath and fire pit await, ensuring every evening feels like a mini-vacation.

In the kitchen, the gas stove and undercounter oven stand ready for your culinary explorations, while the scullery offers practical space, ensuring your domain remains as immaculate as it is inviting. A double electric garage accommodates your vehicles with ease, and for those who require a little extra support, a separate staff ablution enhances the home’s convenience.

The lower level artfully blends function with flair, featuring a generously sized guest bedroom and half bathroom for visiting friends and a study that caters to both productivity and creativity. A thoughtfully placed guest toilet ensures your gatherings run smoothly, ready for the unexpected.

Ascend the striking wooden staircase to the upper level, where the master suite awaits—your personal oasis complete with an ensuite and ample built-in cupboards. A cozy pyjama lounge invites relaxation or separate TV lounge for the teenagers while two additional ensuite bedrooms provide luxurious privacy for family members or guests.

Outside, the beautifully landscaped garden offers a tranquil retreat from the bustle of daily life. Whether you're savouring the serenity with a book in hand or enjoying a peaceful afternoon, the enchanting surroundings will always delight. With easy access to the M13, commuting is as effortless as the life you’ll lead here.

And just to sweeten the deal: no transfer duties and levies under R2000. A rare combination of elegance and practicality? Indeed. Contact Ryan Lategan today to experience this exquisite haven—after all, your dream home awaits just beyond the door, and it’s a story waiting to be written.

NOTE: The property has been advertised at R3,5 mil as the total price of purchase (when transfer costs are added) is equivalent to the purchase of a standard R3,5 mil home as considered with the usual transfer duty of R183,000. But this is a developer unit so the transfer costs (of R183,000) are paid directly to the developer (who himself pays SARS their tariff), with no transfer duty being paid to SARS by the purchaser upon transfer. So any offer drafted would be the offer e.g R3,5 mil (were a full offer made) plus R183,000 = R3,683 mil and no further transfer duty would be paid to the conveyancers or SARS. So the amount ultimately spent by the purchaser (considering all transfer costs) is equivalent to them making a standard purchase of a home for R3,5 mil from a non-developer. Please contact agent for further clarification.

The information contained herein is correct to the best of our knowledge as provided by various parties, however errors and omissions excepted.

Home for sale in Kloof gated estate. Townhouse for sale in Kloof. Luxury mansion for sale near Hillcrest. House for sale in the Upper Highway KZN.

When you approach this splendid 4-bedroom 4.5 bathroom, split-level duplex, the charm of the tree-lined street beckons with a serene invitation. The air is filled with the whispers of rustling leaves and the promise of community, offering a delightful backdrop for a life well-lived. Here, nestled wi...

Address

Suite 12, The Yard Office, 71 Old Main Road
Hillcrest
3610

Opening Hours

Monday 08:00 - 16:00
Tuesday 08:00 - 16:00
Wednesday 08:00 - 16:00
Thursday 08:00 - 16:00
Friday 08:00 - 16:00

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