Having languished on the market for nearly a year since its last listing, it seems that, once again, Donald Trump’s Connecticut mansion, which he shared with the late Ivana, has failed to secure a buyer. While the property has been for sale for more than a decade now, this is the seventh time the listing has been removed, according to Zillow.

Click or scroll through to tour the erstwhile love nest, discover what the property looked like when the Trumps were in residence, and find out why it has been such a struggle to sell...

Nestled on a picturesque peninsula jutting out into Long Island Sound, the elegant Georgian Revival mansion, which now boasts a total of 11 bedrooms and 15 bathrooms, was completed in 1939 for hotshot businessman Robert M Hillas, a pioneering auto executive and director of Binney & Smith, the company behind Crayola crayons.

The 45-room manse was christened Haroldlyn House, presumably in memory of Hillas' father-in-law Harold Smith, the co-inventor of the iconic crayons, who died in 1931. Hillas passed away in 1956, but it appears his wife, Bertha, outlived him by many years. In 1982, her prized ceramics collection was auctioned off at Christie's New York, the same year Donald Trump bought the wealthy heiress' 5.8-acre estate.

At the time, the Lifestyles of the Rich and Famous TV show guesstimated the estate's value at $10 million, but in actual fact, Donald paid only $4 million, which translates to $12.6 million in 2022 dollars. Like so many of the property deals the mogul has closed over the years, Haroldlyn House turned out to be a terrific bargain.

Approaching the handsome front door, which is painted a traditional high-gloss pitch black, you can't help but be impressed by the round portico, pristine white brickwork and other attractive architectural details, such as the oculus window that graces the pediment. The Hillases certainly didn't scrimp on the design and construction of their dream home.

During the Trump Years, the plasterwork on the façade was accented with gold. Note the lawn jockey and Grecian-style urns. Back in 1982, the Trumps' sole residence was a relatively compact (albeit plush) Manhattan apartment. However, given their wealth and social status, and with a growing family—Donald Jr was three and Ivanka barely one—snapping up a sprawling estate they could escape to at weekends and over the summer was a no-brainer.

Opening the front door, the stunning entry hall is the first space you encounter, and it most definitely makes a striking impression, something that would have appealed to the flashy Trumps. The highlight of the entryway is, of course, that dramatic, sweeping double bridal staircase. But the archway, columns and bespoke parquet medallion flooring are standouts, too.

This photo of the entry hall was taken in the 1950s. As you can see, the space is decorated with a bold mural, two very decadent-looking Art Deco chaise lounges, statues, a crystal chandelier, and an enormous round carpet. That said, it doesn't look OTT, despite the attention-grabbing fresco and decorative pieces. Then the Trumps worked their magic.

Ivana was revamping New York's Plaza Hotel when Donald bought the manse and decorated it in a similar 'Louis XIV on steroids' style, adding Studio 54-esque gold mirror panels to the entrance hall, along with a busy carpet, frilly velvet curtains and other showy embellishments. Donald Trump is pictured in the room in 1987, posing at the foot of his fabulous double staircase.

The library is the next room we come to. Now serving as a living room, the space's standout feature is its beautifully crafted wooden wall panels. While the room itself is very traditional in style, the furniture gracing it at present is more contemporary, which is probably a shrewd move on the part of the current owners, as we'll discover shortly.

Back in the 1950s, the furniture in the library matched its surroundings to a T, with antique pieces that might now be considered fuddy-duddy scattered throughout the room. Still, the space has a rather relaxed, informal feel, and looks like the perfect spot to curl up with a book, especially if there's a fire blazing in the hearth.

The Trumps luxed up the room with the addition of some sparkly silverware and crystal candelabras, but retained its traditional gentlemen's club ambience. In this snap from 1987, Donald is chilling on one of the room's velvet couches with a copy of the New York Times. Now let's check out the kitchen.

The hub of the home is reassuringly high-end, but some potential buyers may think it looks dated. Others may appreciate the fact that the original cabinetry remains in place—a testament to its quality—and enjoy the old-fashioned feel. The current owners have, however, updated the kitchen with solid marble countertops and an all-white paint job.

The result is a traditional space with ornate details that doesn't look garish or overdone. The stained-glass Tiffany light shade is the only pop of color in the room, which almost verges on minimalist. Needless to say, the kitchen didn't look like this when the Trumps called Haroldlyn House home.

The lower kitchen cabinets were painted in a bold Tiffany green and the space was packed with knick-knacks. Donald and Ivana had a coterie of staff catering to their every whim, including a personal chef, who they are shown with here in 1987. That said, Ivana was fond of cooking and would rustle up meals for the family when she had the time.

Ivana always cooked the Thanksgiving dinner, getting up before dawn to prepare the meal, which included a 25-pound turkey with liver, raisin, and nut stuffing served with mashed potatoes, grilled vegetables, and homemade cranberry sauce, and followed by apple tart and ice cream. Ivana is basting the bird with daughter Ivanka helping with the gravy in this shot from Thanksgiving 1993.

Moving on, we come to the dining room. Again, while the décor is on the dated side, the original features, which include exquisite plasterwork and a ravishing fireplace, are a major selling point. To their credit, the Trumps didn't rip out the interiors, and appeared to have kept the property well-maintained.

Next up is the east porch. Overlooking the yard, the light-filled space is retro indoor/outdoor living at its finest, with some of the windows completely floor-to-ceiling. Like the other parts of the mansion, the original features are thankfully in place, including the wrought-iron latticework that surrounds the exterior.

The porch looked very different in 1956. Instead of the dining table and chairs of today, the room is dotted with cane couches, chairs, and tables. A large checkerboard carpet covers the floor, and outside you can make out a striped awning that would have provided a decent amount of shade on hot, sunny days.

Fast-forward to 1987 and the east porch has been given a proper 1980s makeover, with wicker sunbeds decked out with chintzy cushions, a fussy rug, and that quirky parrot sculpture. Regardless, the room does look like a wonderful place to take in the views of the yard and nearby Long Island Sound.

Now we've arrived in the mansion's living room. Unlike the kitchen and the dining room, this space is contemporary in style and is likely to appeal to a wider range of buyers. Lovely and spacious, the room is one of the best in the property, and those wall panels and the fireplace are simply divine.

The 1950s décor went heavy on the antiques and looks very grand indeed. Sadly, there are no pics available showing how the room was decorated when the Trumps lived at the mansion, though you can bet your bottom dollar it was a lot more garish than it is these days. Now let's have a peek upstairs.

The master bedroom has got plenty of wow factor, from the meticulously carved corner wooden fire surround to the double-aspect shuttered windows, cornices, and hardwood flooring. This is one room in the property that really won't be putting off potential buyers given its multitude of plus points.

On the other hand, this bedroom may be more divisive—or, more specifically, that unusual stencil mural on the wall and the floral fresco. Still, the space is bolstered by the prettiest corner fireplace in white marble and the multiple-aspect windows that bathe the room in light. Now let's stroll downstairs and have a wander outside.

Ivana in particular made the most of the manse's acres of grounds. The green-fingered businesswoman liked nothing better than getting her spade and trowel out and hitting the flower beds. “I absolutely adore gardening,” she told Vanity Fair in 1988. “I go up to the Greenwich, I put the gloves on, and I dig. And I have everything up there—if I do something, I do it big. The garden, it’s from here to China.”

One of the property's major draws is its outdoor pool. Another feature that has been around for decades, it's a no-nonsense old-school rectangular pool with few frills. Even the paving stones that surround it have stuck around, though they have been well looked after, together with the mosaic tiling.

It's the pool's setting that potential buyers will find hard to resist. The tranquil vistas of the yard—not to mention those of nearby Long Island Sound and its cute islets—are absolutely delightful. Local realtors say that estates in the area offering these sorts of views are few and far between, and rarely come on the market.

Posing poolside in happier times, Donald and Ivana look the picture of marital bliss in this shot from 1987, with Mrs. Trump gazing lovingly at her husband. But the union soon hit the rocks, and when Donald's affair with Marla Maples came to light, the couple's relationship was history.

The duo divorced in 1992 and Ivana walked away with the Greenwich estate as part of her settlement. According to the Wall Street Journal, Ivana spent several years attempting to sell it, finally offloading the property in 1998 for $15 million, which works out at $28 million in today's money. The sale price was $3 million under the initial asking price.

The buyers were financier Robert Steinberg and his wife Suzanne. The couple proceeded to treat the manse to a sophisticated makeunder, removing many of the Trumps' design touches. Then, in 2000, they had this guest house constructed. A sensational, amenity-loaded add-on, it boasts some seriously snazzy features.

These include the showstopping great room, with its 20-foot-high beamed ceiling. The capacious room is fitted with a small kitchenette and has a cozy fireplace and homely wood paneling, guaranteed to make any guest lucky enough to be visiting the property feel exceedingly comfortable.

The bedrooms in the guesthouse are just as roomy as their counterparts in the mansion, which is another plus for buyers. Be that as it may, the décor is perhaps an acquired taste—this chintzy creation might have seemed like a good idea, but it could be a turn-off for some buyers.

The guest house lap pool, though, offers the perfect antidote with its minimalist, zen-like feel. We can't imagine a more soothing place to take a morning swim. The Steinbergs' first stab at selling the estate came in 2009, when they put the upgraded property on the market with an asking price of $50 million.

The couple attempted to sell the property again in 2014. Trying, no doubt, to capitalize on the "Trump-mania" supposedly then sweeping America, the Steinbergs raised the asking price to $54 million. But, in spite of reported strong interest, nobody was prepared to pay through the nose for the former Trump residence, even with the additions completed in 2000—which also included this regal home cinema.

The Steinbergs had put in a tennis court, too. But even that didn't sway any would-be buyers. According to Zillow, the price was slashed to $45 million in 2016. Thereafter, the property was successively listed at a reduced price on multiple occasions, most recently with Brown Harris Stevens for a hugely discounted $29.9 million. However, the home has just been taken off the market yet again. So why has the property been so hard to shift?

Realtor.com asked several expert agents this question in 2016. The pros put it down to the manse's outdated décor and antiquated grandeur, though the inflated price would obviously have been a key factor, too. Now that a number of rooms have been given a contemporary update and the asking price has been massively discounted, the Steinbergs might finally find that elusive buyer. You never know, maybe one of the Trump kids will bag it for sentimentality's sake? 

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